1,326 results match your criteria Journal of combinatorial chemistry[Journal]


Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

J Comb Chem 2010 Nov 5;12(6):765-806. Epub 2010 Oct 5.

Adolor Corporation, 700 Pennsylvania Drive, Exton, Pennsylvania 19341, USA.

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http://pubs.acs.org/doi/abs/10.1021/cc100128w
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http://dx.doi.org/10.1021/cc100128wDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4140011PMC
November 2010
12 Reads

Orthogonality of SFC versus HPLC for small molecule library separation.

J Comb Chem 2010 Nov 5;12(6):877-82. Epub 2010 Oct 5.

Bristol-Myers Squibb Company, Applied Biotechnology Division, PO Box 4000, Princeton, New Jersey 08543, USA.

Preparative HPLC and HPLC-MS are well established as the methods of choice for purification of pharmaceutical library compounds. Recent advances in supercritical fluid chromatography (SFC) have now made SFC a viable alternative to HPLC for this application. One of the potential arguments for using SFC in place of, or in addition to, HPLC is that it may offer different selectivity and thus has the potential for improved separation success rates. Read More

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http://dx.doi.org/10.1021/cc100118yDOI Listing
November 2010
19 Reads

Design, synthesis, and in vitro evaluation of potential West Nile virus protease inhibitors based on the 1-oxo-1,2,3,4-tetrahydroisoquinoline and 1-oxo-1,2-dihydroisoquinoline scaffolds.

J Comb Chem 2010 Nov 30;12(6):836-43. Epub 2010 Sep 30.

Department of Chemistry, Wichita State University, Wichita, Kansas 67260, USA.

The 1-oxo-1, 2, 3, 4-tetrahydroisoquinoline and 1-Oxo-1, 2-dihydroisoquinoline scaffolds were utilized in the design and solution phase synthesis of focused libraries of compounds for screening against West Nile Virus (WNV) protease. Exploratory studies have led to the identification of a WNV protease inhibitor (a 1-oxo-1, 2-dihydroisoquinoline-based derivative, 12j) which could potentially serve as a launching pad for a hit-to-lead optimization campaign. The identified hit was devoid of any inhibitory activity toward a panel of mammalian serine proteases. Read More

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http://dx.doi.org/10.1021/cc100091hDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2975906PMC
November 2010
19 Reads

Synthesis of a solid-phase amino imidazotriazine library via palladium catalyzed direct arylation.

J Comb Chem 2010 Nov 29;12(6):818-21. Epub 2010 Sep 29.

Bayer CropScience GmbH, Werk Höchst, G836, D-65926 Frankfurt am Main, Germany.

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http://dx.doi.org/10.1021/cc1001617DOI Listing
November 2010
10 Reads

S(N)Ar-based, facile synthesis of a library of benzothiaoxazepine-1,1'-dioxides.

J Comb Chem 2010 Nov 29;12(6):850-4. Epub 2010 Sep 29.

Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.

The construction of a library of benzothiaoxazepine-1,1'-dioxides utilizing a one-pot, S(N)Ar diversification-ODCT(50) scavenging protocol is reported. This protocol combines microwave irradiation to facilitate the reaction, in conjunction with a soluble ROMP-derived scavenger (ODCT) to afford the desired products in good overall purity. Utilizing this protocol, a 78-member library was successfully synthesized and submitted for biological evaluation. Read More

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http://dx.doi.org/10.1021/cc1001023DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3098767PMC
November 2010
10 Reads

High-throughput screening method to detect amphiphilic counterions able to solubilize conducting polymers.

J Comb Chem 2010 Nov 23;12(6):814-7. Epub 2010 Sep 23.

Departamento de Química, Universidad Nacional de Río Cuarto, 5800-Río Cuarto, Argentina.

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http://dx.doi.org/10.1021/cc1001428DOI Listing
November 2010
8 Reads

Sequential one-pot combination of multireactions through multicatalysis: a general approach to rapid assembly of functionalized push-pull olefins, phenols, and 2-methyl-2H-chromenes.

J Comb Chem 2010 Nov 21;12(6):855-76. Epub 2010 Sep 21.

School of Chemistry, University of Hyderabad, Central University, Hyderabad 500 046, India.

A general, sustainable and practical process for the sequential cascade one-pot synthesis of library of highly substituted push-pull olefins, phenols and 2-methyl-2H-chromenes was reported through multicatalysis cascade (MCC) reactions. Direct sequential one-pot combination of amine- or amino acid-catalyzed cascade Knoevenagel/Michael/aldol condensation/decarboxylation with other reactions like amine- or amino acid-catalyzed cascade Claisen-Schmidt/iso-aromatization, Claisen-Schmidt/isomerization, Claisen-Schmidt/iso-aromatization/isomerization, Michael addition, Claisen-Schmidt/Michael, ruthenium-base-silica-catalyzed ring closing metathesis/base-induced ring-opening/benzylic oxidation/[1,7]-sigmatropic hydrogen shift, or ruthenium-base-heat-catalyzed ring closing metathesis/base-induced ring-opening/[1,7]-sigmatropic hydrogen shift reactions of alkyl acetoacetates, a variety of aldehydes and alkyl halides furnished the highly functionalized push-pull olefins, phenols and 2-methyl-2H-chromenes with high yields. The yields and regioselectivities were good to excellent. Read More

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http://dx.doi.org/10.1021/cc100104kDOI Listing
November 2010
61 Reads

Characterization of photoelectric properties and composition effect of TiO(2)/ZnO/Fe(2)O(3) composite by combinatorial methodology.

J Comb Chem 2010 Nov 21;12(6):883-9. Epub 2010 Sep 21.

State Key Laboratory of Material Processing and Die & Mold Technology, Department of Materials Science and Engineering, Huazhong University of Science and Technology, Wuhan 430074, PR China.

On the basis of combinatorial methodology and the idea of an equilateral ingredient triangle, the TiO(2)/ZnO/Fe(2)O(3) composite system including 66 ingredient points was designed. The photocurrents under different light sources and bias voltages were measured, and the photocurrent amplitude at 300 s was chosen as a parameter to evaluate the photoelectric response of the composite. To appraise the composition effect of the composite compared with pure materials, the quantitative formula of the composition effect has been provided for the first time in this paper. Read More

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http://dx.doi.org/10.1021/cc100121dDOI Listing
November 2010
13 Reads

Solid-phase synthesis of highly diverse purine-hydroxyquinolinone bisheterocycles.

J Comb Chem 2010 Nov 17;12(6):890-4. Epub 2010 Sep 17.

Department of Organic Chemistry, Faculty of Science, Institute of Molecular and Translational Medicine, University of Palacký, 771 46 Olomouc, Czech Republic.

Solid-phase synthesis of bisheterocyclic compounds that contain purine and the 3-hydroxyquinolin-4(1H)-one skeleton connected with an aliphatic spacer of a different length/structure is described. The reaction sequence started from the primary amines immobilized on aminomethylated polystyrene resin equipped with an acid-labile linker (4-(4-formyl-3-methoxyphenoxy)butyric acid). After the arylation of amines with 2,6-dichloropurine via its C(6), purine N(9) was alkylated and subsequently the chlorine at purine C(2) was substituted with aliphatic diamines. Read More

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http://pubs.acs.org/doi/abs/10.1021/cc100132z
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http://dx.doi.org/10.1021/cc100132zDOI Listing
November 2010
7 Reads

Three-component one-pot approach to synthesize benzopyrano[4,3-d]pyrimidines.

J Comb Chem 2010 Nov 17;12(6):895-9. Epub 2010 Sep 17.

State Key Laboratory of Drug Research Shanghai Institute of Materia Medica,Chinese Academy of Science, 555 Zu Chong Zhi Road, Shanghai 201203, China.

A novel benzopyrano[4,3-d]pyrimidine scaffold was generated via a three-component one-pot reaction from iodochromone, alkyne, and an amidine through a Sonogashira coupling, condensation, and cycloaddition. This combinatorial synthetic approach provides an efficient, easy construction of a diversified heterocyclic compounds library. Read More

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http://pubs.acs.org/doi/abs/10.1021/cc100173b
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http://dx.doi.org/10.1021/cc100173bDOI Listing
November 2010
5 Reads

Multidisciplinary synthetic approach for rapid combinatorial library synthesis of triaza-fluorenes.

J Comb Chem 2010 Sep;12(5):723-32

Department of Chemistry, National Chiao Tung University, Hsinchu 300-10, Taiwan.

A new multidisciplinary synthetic approach comprising polymer-support synthesis, microwave-assisted synthesis, and multicomponent condensation facilitates synthesis of triaza-fluorenes library with a set of advantages such as rapid process, simple purification, and structural diversity in one shot. Microwave-assisted multistep synthetic protocol was used to construct the benzimidazole ring on soluble polymer support using activated aryl-fluorides. The PEG anchored aryl fluoride was condensed with selective primary amines via an ipso-fluoro displacement reaction followed by reduction of nitro group. Read More

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http://dx.doi.org/10.1021/cc1000902DOI Listing
September 2010
5 Reads

Quick access to druglike heterocycles: facile silver-catalyzed one-pot multicomponent synthesis of aminoindolizines.

J Comb Chem 2010 Sep;12(5):696-9

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.

A direct and efficient approach to 1-aminoindolizines through three-component one-pot reaction of heteroaryl aldehydes, secondary amines, and terminal alkynes catalyzed by AgBF(4) has been developed. Desired products were obtained in moderate to excellent yields. Similar aminoindolizines products were afforded from trimethylsilyl protected alkyne substrates as well. Read More

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http://dx.doi.org/10.1021/cc100086hDOI Listing
September 2010
7 Reads

Novel and efficient one-step parallel synthesis of dibenzopyranones via Suzuki-Miyaura cross coupling.

J Comb Chem 2010 Sep;12(5):664-9

Center for Drug Discovery, 360 Huntington Avenue, 116 Mugar Hall, Boston, Massachusetts 02115-5000, USA.

Microwave-promoted novel and efficient one-step parallel synthesis of dibenzopyranones and heterocyclic analogues from bromo arylcarboxylates and o-hydroxyarylboronic acids via Suzuki-Miyaura cross coupling reaction is described. Spontaneous lactonization gave dibenzopyranones and heterocyclic analogues bearing electron-donating and -withdrawing groups on both aromatic rings in good to excellent yields. Read More

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http://dx.doi.org/10.1021/cc100068aDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3921962PMC
September 2010
7 Reads

Fluorous tagged N-hydroxy phthalimide for the parallel synthesis of O-aryloxyamines.

J Comb Chem 2010 Sep;12(5):655-8

Centre de recherches de Gif, Institut de Chimie des Substances Naturelles, UPR 2301-CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.

The parallel synthesis of O-aryloxyamines remains an unfulfilled need in the field of medicinal chemistry and fragment-based approaches. To fill this gap a solution-phase two-step process based on (1) a copper-catalyzed cross-coupling of aryl boronic acids with a fluorous tagged N-hydroxyphthalimide, and (2) a supported aminolysis was designed and optimized using Taguchi's method. A library of O-aryloxyamines was synthesized in high yields with high purity and diversity. Read More

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http://dx.doi.org/10.1021/cc100098vDOI Listing
September 2010
22 Reads

Synthesis of diheterocyclic compounds based on triazolyl methoxy phenylquinazolines via a one-pot four-component-click reaction.

J Comb Chem 2010 Sep;12(5):638-42

Department of Chemistry, Faculty of Science, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran.

A facile and highly efficient method for one-pot four-component synthesis of triazolyl methoxy phenylquinazolines is described. A mixture of aromatic propargylated aldehydes, different azides, 2-aminobenzophenone derivatives, and ammonium acetate were condensed in the presence of catalytic amounts of acidic ionic liquid, 1-methylimidazolium trifluoroacetate, ([Hmim]TFA), and Cu(OAc)(2)/sodium ascorbate to afford the corresponding products in excellent yields. This methodology is highly efficient for structurally diverse azides. Read More

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http://dx.doi.org/10.1021/cc100043zDOI Listing
September 2010
7 Reads
1 Citation

Novel isocyanide-based one-pot multicomponent syntheses of tetrahydrobenzo[b][1,4]oxazepine and malonamide derivatives.

J Comb Chem 2010 Sep;12(5):630-2

Department of Chemistry, Shahid Beheshti University, G. C., P.O. Box 19396-4716, Tehran, Iran.

In this work, a novel one-pot multicomponent reaction of 2-aminophenols, Meldrum's acid, and isocyanides leads to the synthesis of tetrahydrobenzo[b][1,4]oxazepine or malonamide derivatives using 1 or 2 equiv of 2-aminophenols, respectively, in good to excellent yields at ambient temperature. Read More

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http://dx.doi.org/10.1021/cc100032dDOI Listing
September 2010
6 Reads

Synthesis of 5-carboxamide-oxazolines with a Passerini-Zhu/Staudinger-Aza-Wittig two-step protocol.

J Comb Chem 2010 Sep;12(5):613-6

Università degli Studi di Genova, Dipartimento di Chimica e Chimica Industriale, Genova, Italy.

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http://dx.doi.org/10.1021/cc100122nDOI Listing
September 2010
6 Reads

Catalyst-free one-pot four component synthesis of polysubstituted imidazoles in neutral ionic liquid 1-butyl-3-methylimidazolium bromide.

J Comb Chem 2010 Nov 9;12(6):844-9. Epub 2010 Sep 9.

Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran.

A catalyst-free one-pot four component methodology for the synthesis of 1,2,4,5-substituted imidazoles under conventional heating and microwave irradiation using 1-butyl-3-methylimidazolium bromide, [Bmim]Br, as a neutral reaction media is described. A broad range of structurally diverse aldehydes (aromatic aldehydes bearing electron withdrawing and/or electron releasing groups as well as heteroaromatic aldehydes) and primary amines (aromatic and aliphatic) were applied successfully, and corresponding products were obtained in good to excellent yields without any byproduct. Read More

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http://dx.doi.org/10.1021/cc100097mDOI Listing
November 2010
5 Reads
1 Citation

Practical multi-component synthesis of di- or tri-aryl (Heteraryl) substituted 2-(pyridin-2-yl)imidazoles from simple building blocks.

J Comb Chem 2010 Nov 8;12(6):829-35. Epub 2010 Sep 8.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.

A convenient and highly efficient multicomponent protocol has been developed for the synthesis of various poly-substituted 2-(pyridin-2-yl)imidazoles from 2-cyanopyridine, corresponding aromatic aldehydes, and NH(4)OAc/primary amine. Notably, tri-substituted 2-(pyridin-2-yl)imidazoles were highly yielded when aromatic primary amines were used as substrates, but both di- and tri-substituted 2-(pyridin-2-yl)imidazoles were obtained in one pot when some aliphatic primary amines were used as substrates. Read More

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http://pubs.acs.org/doi/abs/10.1021/cc100079b
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http://dx.doi.org/10.1021/cc100079bDOI Listing
November 2010
27 Reads

Synthesis of multicyclic β-lactam derivatives via solid-phase-generated ketenes.

J Comb Chem 2010 Nov 2;12(6):810-3. Epub 2010 Sep 2.

Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, CONICET, Suipacha 531, S2002LRK Rosario, Argentina.

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http://dx.doi.org/10.1021/cc100140rDOI Listing
November 2010
4 Reads

Efficient synthesis of pyrazolopyrimidine libraries.

J Comb Chem 2010 Nov 30;12(6):807-9. Epub 2010 Aug 30.

Department of Chemical Biology & Therapeutics, St Jude Children's Research Hospital, 262 Danny Thomas Place, Memphis, Tennessee 38105, USA.

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http://dx.doi.org/10.1021/cc1001204DOI Listing
November 2010
4 Reads

Direct construction of imino-pyrrolidine-thione scaffold via isocyanide-based multicomponent reaction.

J Comb Chem 2010 Nov 30;12(6):822-8. Epub 2010 Aug 30.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.

A novel and efficient method has been developed for the direct construction of imino-pyrrolidine-thione scaffold via the coupling of isocyanides, heterocyclic thiols, and gem-dicyano olefins. Smiles rearrangement followed by intramolecular cyclization leads directly to formation of the core structure. A water-acceleration effect is observed, promoting most of the reactions to go to completion within a short reaction time. Read More

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http://pubs.acs.org/doi/abs/10.1021/cc100014g
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http://dx.doi.org/10.1021/cc100014gDOI Listing
November 2010
11 Reads

Generation of diverse 2H-isoindol-1-ylphosphonates via three-component reaction of 2-alkynylbenzaldehyde, aniline, and phosphite.

J Comb Chem 2010 Sep;12(5):743-6

Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China.

Diverse 2H-isoindol-1-ylphosphonates as potential HCT-116 inhibitors are easily generated via a FeCl(3) and PdCl(2) cocatalyzed three-component reaction of 2-alkynylbenzaldehyde, aniline, and phosphite. The focused small library is constructed based on parallel diversity-oriented synthesis. Read More

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http://dx.doi.org/10.1021/cc100101aDOI Listing
September 2010
36 Reads

One-pot synthesis of five and six membered N, O, S-heterocycles using a ditribromide reagent.

J Comb Chem 2010 Sep;12(5):754-63

Department of Chemistry, Indian Institute of Technology Guwahati, Assam 781 039, India.

In a one-pot procedure, bromine less brominating reagent 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) has been utilized as an efficient desulfurizing agent for the construction of a library of heterocycles containing N, O, and S starting from aryl/alkyl isothiocyanates. In this approach, aryl/alkyl isothiocyanate reacts with o-phenylenediamine (o-PD), o-aminophenol, and o-aminothiophenol to form their monothiourea which on desulfurization with EDPBT led to the formation of corresponding 2-aminobenzimidazoles, 2-aminobenzoxazoles, and 2-aminobenzothiazoles, respectively. An interesting regioselectivity was observed for unsymmetrical thiourea having a naphthyl moiety on the one side and an ortho amino or an ortho hydroxy phenyl group on the other side giving a completely different product which is mainly dependent on the nature of the nucleophiles (-OH or -NH(2)). Read More

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http://dx.doi.org/10.1021/cc100124qDOI Listing
September 2010
11 Reads
1 Citation

Recycling the versatile Pipecolic linker.

J Comb Chem 2010 Sep;12(5):747-53

IBMM, Institut des Biomolécules Max Mousseron, UMR 5247, Universités Montpellier I and II, CNRS, Faculté de Pharmacie, 15 av. C. Flahault, BP 14491, 34093 Montpellier Cedex 05, France.

The Pipecolic linker is a new highly versatile handle which immobilizes on solid support through a carboxylic acid function a wide range of amines, alcohols, and hydrazines. The anchoring step on pipecolic resin is very easy and efficient, and compounds are released with high purities upon acidic treatment. During this treatment, an oxazolonium intermediate is hydrolyzed, yielding the cleavage of ester or amide bond and the release of free carboxylic acid of the starting linker. Read More

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http://dx.doi.org/10.1021/cc100099zDOI Listing
September 2010
11 Reads

Synthesis of 2,3-dihydroquinazolin-4(1H)-ones by three-component coupling of isatoic anhydride, amines, and aldehydes catalyzed by magnetic Fe(3)O(4) nanoparticles in water.

J Comb Chem 2010 Sep;12(5):643-6

The College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050016, China.

A simple and efficient protocol for one-pot three-component coupling of isatoic anhydride, amines, and aldehydes in water using magnetically recoverable Fe(3)O(4) nanoparticles is reported. This methodology results in the synthesis of a variety of 2,3-dihydroquinazolin-4(1H)-ones in high yields. The catalyst can be recovered and recycled without a significant loss in the catalytic activity. Read More

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http://dx.doi.org/10.1021/cc100047jDOI Listing
September 2010
82 Reads

Efficient assembly of 1-methylene-1H-indenes via palladium-catalyzed tandem reaction of 1-(2,2-dibromovinyl)-2-alkenylbenzene with arylboronic acid.

J Comb Chem 2010 Sep;12(5):670-5

Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China.

Highly efficient palladium-catalyzed reaction of 1-(2,2-dibromovinyl)-2-alkenylbenzene with arylboronic acid is disclosed, which generates the functionalized 1-methylene-1H-indenes in good yields. Tandem Suzuki-Miyaura coupling and Heck reactions are involved in this process. Read More

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http://dx.doi.org/10.1021/cc1000693DOI Listing
September 2010
6 Reads

Analysis of protein-small molecule interactions by microscale equilibrium dialysis and its application as a secondary confirmation method for on-bead screening.

J Comb Chem 2010 Sep;12(5):647-54

BIOTEC/Biophysics, Technische Universität Dresden, Tatzberg 47-51, 01307 Dresden, Germany.

On-bead screening of one-bead one compound (OBOC) libraries is an ultra fast surface based primary high-throughput screening (HTS) method. Typically the binding of a tagged target protein to bead immobilized compounds or its altered enzymatic activity are detected. For an efficient and reliable ligand discovery process secondary assays to confirm on-bead compound activity in homogeneous solution are key to exclude artifacts and weak binders. Read More

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http://dx.doi.org/10.1021/cc100057eDOI Listing
September 2010
7 Reads

Dipeptidyl-quinolone derivatives inhibit hypoxia inducible factor-1α prolyl hydroxylases-1, -2, and -3 with altered selectivity.

J Comb Chem 2010 Sep;12(5):676-86

Chemistry Research & Discovery, Amgen, Inc., One Amgen Center Drive, Thousand Oaks, California 91320, USA.

Intracellular levels of the hypoxia-inducible transcription factor (HIF) are regulated under normoxic conditions by prolyl hydroxylases (PHD1, 2, and 3). Treatment of cells with PHD inhibitors stabilizes HIF-1α, eliciting an artificial hypoxic response that includes the transcription of genes involved in erythropoiesis, angiogenesis, and glycolysis. The different in vivo roles of the three PHD isoforms are not yet known, making a PHD-selective inhibitor useful as a biological tool. Read More

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http://dx.doi.org/10.1021/cc100073aDOI Listing
September 2010
19 Reads

Automated maskless photolithography system for peptide microarray synthesis on a chip.

J Comb Chem 2010 Jul;12(4):463-71

School of Chemical and Biological Engineering and School of Electrical Engineering and Computer Science, Seoul National University, Seoul 151-744, Korea.

Maskless photolithographic peptide synthesis was performed on a glass chip using an automated peptide array synthesizer system. The peptide array synthesizer was built in a closed box, which contained optical and fluidic systems. The conditions for peptide synthesis were fully controlled by a computer program. Read More

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http://dx.doi.org/10.1021/cc100009gDOI Listing
July 2010
25 Reads

Studies toward a library of tetrahydrofurans: click and MCR products of mono- and bis-tetrahydrofurans.

J Comb Chem 2010 Sep;12(5):609-12

Department of Chemistry and Center for Chemical Methodologies & Library Development, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.

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http://dx.doi.org/10.1021/cc1000709DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2954415PMC
September 2010
8 Reads

Regioselective synthesis of novel spiropyrrolidines and spirothiapyrrolizidines through multicomponent 1,3-dipolar cycloaddition reaction of azomethine ylides.

J Comb Chem 2010 Sep;12(5):633-7

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123, PR China.

A series of novel spiropyrrolidines and spirothiapyrrolizidines were synthesized via a three-component 1,3-dipolar cycloaddition reaction of isatin or acenaphthenequinone, sarcosine or thiaproline and 4-hydroxy-6-methyl-3-((E)-3-phenylacryloyl)-2H-pyran-2-ones in refluxing ethanol. Advantages of this method include the availability of starting materials, mild reaction conditions, high yields, and the complete regioselectivity observed. Read More

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http://dx.doi.org/10.1021/cc100035qDOI Listing
September 2010
12 Reads

Positional scanning peptide libraries for kinase substrate specificity determinations: straightforward and reproducible synthesis using pentafluorophenyl esters.

J Comb Chem 2010 Sep;12(5):733-42

Department of Chemistry, Medicinal Chemistry, University of Gothenburg, Göteborg, Sweden.

An efficient method to synthesize positional scanning synthetic combinatorial libraries (PS-SCLs) for studying the specificity of protein kinases is presented. Isokinetic ratios for pentafluorophenyl esters were determined iteratively using a new approach incorporating high performance liquid chromatography (HPLC) quantification and statistical experimental design. In the development process a large amount of work was put in to find efficient ways of screening for new isokinetic mixtures and to optimize the process of PS-SCL synthesis. Read More

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http://dx.doi.org/10.1021/cc100095yDOI Listing
September 2010
8 Reads

Jeffamine derivatized TentaGel beads and poly(dimethylsiloxane) microbead cassettes for ultrahigh-throughput in situ releasable solution-phase cell-based screening of one-bead-one-compound combinatorial small molecule libraries.

J Comb Chem 2010 Sep;12(5):700-12

Department of Biochemistry and Molecular Medicine, Division of Hematology & Oncology, University of California Davis Cancer Center, University of California Davis, 4501 X Street, Sacramento, California 95817, USA.

A method to efficiently immobilize and partition large quantities of microbeads in an array format in microfabricated poly(dimethylsiloxane) (PDMS) cassette for ultrahigh-throughput in situ releasable solution-phase cell-based screening of one-bead-one-compound (OBOC) combinatorial libraries is described. Commercially available Jeffamine triamine T-403 (∼440 Da) was derivatized such that two of its amino groups were protected by Fmoc and the remaining amino group capped with succinic anhydride to generate a carboxyl group. This resulting trifunctional hydrophilic polymer was then sequentially coupled two times to the outer layer of topologically segregated bilayer TentaGel (TG) beads with solid phase peptide synthesis chemistry resulting in beads with increased loading capacity, hydrophilicity, and porosity at the outer layer. Read More

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http://dx.doi.org/10.1021/cc100083fDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3045263PMC
September 2010
7 Reads

Synthesis of a library of 5,6-unsubstituted 1,4-dihydropyridines based on a one-pot 4CR/elimination process and their application to the generation of structurally diverse fused nitrogen heterocycles.

J Comb Chem 2010 Sep;12(5):713-22

Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain.

Indium trichloride is an efficient catalyst for the sequential four-component reaction between aliphatic amines, β-ketoesters, α,β-unsaturated aldehydes, and ethanol to afford 6-ethoxy-1,4,5,6-tetrahydropyridines, which were converted in situ into 5,6-unsubstituted 1,4-dihydropyridines via ethanol elimination in the presence of neutral Al(2)O(3), in a very efficient, one-pot protocol from acyclic, readily available starting materials that involves the generation of two C-N σ and one C-C π bonds. The structural variety of the dihydropyridine library thus generated was extended by base-promoted γ-alkylation of their C-2 position. The application of these 1,4-dihydropyridines to the facile generation of molecular diversity and complexity was demonstrated by employing them as dienophiles for Yb(OTf)(3)-catalyzed imino Diels-Alder (Povarov) reactions leading diastereoselectively to hexahydrobenzo[h][1,6]-naphthyridine derivatives containing three adjacent stereocenters. Read More

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http://dx.doi.org/10.1021/cc100084bDOI Listing
September 2010
7 Reads

Novel, one-pot, three-component route to indol-3-yl substituted spirooxindole derivatives.

J Comb Chem 2010 Sep;12(5):659-63

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.

A simple and efficient approach to the synthesis of a novel series of polysubstituted 6'-(1H-indol-3-yl)-1',7'-dihydrospiro[indoline-3,4'-pyrazolo[3,4-b]pyridine]-2-one derivatives in high yields was developed from a one-pot, three-component reaction of 3-cyanoacetyl indoles, isatins, and 1H-pyrazol-5-amines in H(2)O/HOAc. Read More

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http://dx.doi.org/10.1021/cc100064cDOI Listing
September 2010
12 Reads

One-pot synthesis of new substituted 1,2,3,4-tetrahydrocarbazoles via Petasis reaction.

J Comb Chem 2010 Sep;12(5):617-29

Syngene International Ltd, Biocon Park, Plot No. 2 & 3, Bommasandra IV Phase, Jigani Link Road, Bangalore 560 099, India.

The one-pot synthesis of a new substituted 1,2,3,4-tetrahydrocarbazoles has been described via Petasis reactions. These tetrahydrocarbazoles exhibits various medicinal importance and might be suitable for elaboration into larger peptides at carboxy termini. The scope and limitations of this method have been examined. Read More

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http://dx.doi.org/10.1021/cc900194kDOI Listing
September 2010
5 Reads

Solution phase synthesis of a combinatorial library of chalcones and flavones as potent cathepsin V inhibitors.

J Comb Chem 2010 Sep;12(5):687-95

Departamento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil.

Cathepsin V is a papain-like cysteine protease. It is involved in the control of human T cells (responsible for cell immunity), and presents the largest elastolytic activity among the proteolytic enzymes. Therefore, cathepsin V is a potential molecular target for the treatment of atherosclerosis. Read More

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http://dx.doi.org/10.1021/cc100076kDOI Listing
September 2010
5 Reads

Combinatorial approach to the development of a single mass YVO(4):Bi(3+),Eu(3+) phosphor with red and green dual colors for high color rendering white light-emitting diodes.

J Comb Chem 2010 Jul;12(4):587-94

Department of Chemistry, National Taiwan University, Taipei, Taiwan.

Instead of developing a novel red phosphor individually, this work proposes the production of white light by combining a near-ultraviolet/ultraviolet diode chip with blue and special yellow phosphors: the yellow phosphor includes the red and green components with high color saturation. The availability of this scheme is demonstrated by preparing a white light-emitting diode (WLED) with color rendering index (Ra) up to 90.3. Read More

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http://pubs.acs.org/doi/abs/10.1021/cc100063x
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http://dx.doi.org/10.1021/cc100063xDOI Listing
July 2010
25 Reads

Library of 1,4-disubstituted 1,2,3-triazole analogs of oxazolidinone RNA-binding agents.

J Comb Chem 2010 Jul;12(4):491-6

Department of Chemistry and Biochemistry, Ohio University, Athens, Ohio 45701, USA.

The design and synthesis of small molecules that target RNA is immensely important in antibacterial therapy. We had previously reported on the RNA binding of a series of 4,5-disubstituted 2-oxazolidinones that bind to a highly conserved bulge region of bacterial RNA. This biological target T box antitermination system, which is found mainly in Gram-positive bacteria, regulates the expression of several amino acid related genes. Read More

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http://dx.doi.org/10.1021/cc100029yDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2925680PMC
July 2010
16 Reads

Synthesis of hexahydrobenzo[b]pyrimido[4,5-h][1,6]naphthyridines via an intramolecular hetero-Diels-Alder reaction.

J Comb Chem 2010 Jul;12(4):476-81

The Center for Combinatorial Chemistry and Drug Discovery, School of Pharmaceutical Sciences and College of Chemistry, Jilin University, Changchun, Jilin, PR China.

Method development was completed for a strategy to access a novel pyrimidine-fused heterocyclic scaffold. The key step for this synthetic route entails an intramolecular inverse electron demand hetero-Diels-Alder reaction of imines or iminiums formed in situ from allylaminopyrimidinealdehydes 3 and anilines. The reactions provided exclusively cis-configuration products 6. Read More

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http://dx.doi.org/10.1021/cc100018bDOI Listing
July 2010
5 Reads

Efficient and convenient synthesis of pyrrolo[1,2-a]quinazoline derivatives with the aid of tin(II) chloride.

J Comb Chem 2010 Jul;12(4):582-6

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu, PR China.

An efficient, convenient, one-pot synthesis of 2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazolin-5(1H)-one and 2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazoline-1,5-dione was accomplished in good yields via the novel reductive cyclization of 2-nitrobenzamides with haloketones or keto acids mediated by SnCl(2).2H(2)O system. A variety of substrates can participate in the process with good yields, making this methodology suitable for library synthesis in drug discovery efforts. Read More

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http://dx.doi.org/10.1021/cc100062eDOI Listing
July 2010
9 Reads

Combinatorial syntheses of five-membered ring heterocycles using carbon disulfide and a solid support.

J Comb Chem 2010 Jul;12(4):393-409

Innovative Drug Library Research Center, Department of Chemistry, Dongguk University-Seoul, Jung-gu, Seoul 100-715, Korea.

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http://dx.doi.org/10.1021/cc100049uDOI Listing
July 2010
6 Reads

Simultaneous and orthogonal covalent exchange processes in dynamic combinatorial libraries.

J Comb Chem 2010 Jul;12(4):410-3

Area Farmacognosia, Facultad de Ciencias Bioquimicas y Farmaceuticas, Universidad Nacional de Rosario, CONICET, Rosario, Argentina.

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http://dx.doi.org/10.1021/cc100046rDOI Listing
July 2010
4 Reads

Novel approach to 1,5-benzodiazepine-2-ones containing peptoid backbone via one-pot diketene-based Ugi-4CR.

J Comb Chem 2010 Jul;12(4):497-502

Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran, and Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China.

An efficient and simple route for preparation of substituted 1,5-benzodiazepine-2-one containing peptoid backbone is presented. The classical Ugi reaction is considerably extended by application of o-phenylenediamine and diketene as amine and oxo component. 1,3-Dihydro-1,5-benzodiazepine-2-one is generated in situ from these two building blocks combined with isocyanide and aromatic or aliphatic carboxylic acid to assemble the multifunctionalized titled scaffold in high yields. Read More

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http://dx.doi.org/10.1021/cc100037vDOI Listing
July 2010
9 Reads

Microwave-assisted copper(II)-catalyzed one-pot four-component synthesis of multifunctionalized dihydropyridines.

J Comb Chem 2010 Jul;12(4):577-81

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical, Sciences, Nanyang Technological University, Singapore 637371, Singapore.

A fast and highly efficient copper-catalyzed multicomponent synthesis of 1,4-dihydropyridines under microwave irradiation is described. The protocol utilizes mild reaction conditions with low catalytic loading, leading to high yields. This methodology provides us with biologically active 1,4-dihydropyridine library for medicinal chemistry applications. Read More

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http://dx.doi.org/10.1021/cc100060sDOI Listing
July 2010
11 Reads

Solid-phase synthesis of N-substituted pyrrolidinone-tethered N-substituted piperidines via Ugi reaction.

J Comb Chem 2010 Jul;12(4):566-70

Torrey Pines Institute for Molecular Studies, Port Saint Lucie, Florida 34987, USA.

Starting with resin-bound glutamic acid, an efficient synthesis of N-substituted pyrrolidinones is described, using the Ugi four-component reaction (U-4CR). The same methodology is employed to produce N-substituted pyrrolidinone tethered N-substituted piperidines. Read More

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http://dx.doi.org/10.1021/cc100054uDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2917892PMC
July 2010
6 Reads

One-step synthesis of diarylpyrazolo[3,4-b]pyridines from isoflavones.

J Comb Chem 2010 Jul;12(4):600-3

Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, PR China.

A new concise, facile, and efficient method for the synthesis of 3-hydroxy-5,6-diphenylpyrazolo[3,4-b]pyridine derivatives has been described. The cyclocondensation of isoflavones with 3-amino-5-hydroxypyrazole in the presence of sodium methoxide gave fused heteroaromatic 3-hydroxy-5,6-diphenylpyrazolo[3,4-b]pyridines in moderate to good yields. Read More

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http://dx.doi.org/10.1021/cc1000506DOI Listing
July 2010
5 Reads

Pattern-based sensing with metal-dye complexes: sensor arrays versus dynamic combinatorial libraries.

J Comb Chem 2010 Jul;12(4):595-9

Institut des Sciences et Ingenierie Chimiques, Ecole Polytechnique Federale de Lausanne (EPFL), Lausanne, Switzerland.

The dyes Methyl Calcein Blue, Arsenazo I, and Xylenol Orange, and the metal salts CuCl(2) and NiCl(2) were used to generate colorimetric sensors for peptides. Two different approaches were followed: (1) Sensors based on dynamic combinatorial libraries of metal-dye complexes were created by mixing dyes with metal salts in one pot. The optical response of these libraries was analyzed by measuring the spectral changes of the mixtures upon addition of the peptide analytes at six selected wavelengths. Read More

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http://dx.doi.org/10.1021/cc1000727DOI Listing
July 2010
6 Reads

One-pot synthesis of 4,6-diaryl-2-oxo(imino)-1,2-dihydropyridine-3-carbonitrile; a New Scaffold for p38alpha MAP kinase inhibition.

J Comb Chem 2010 Jul;12(4):559-65

Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Biotechnology, German University in Cairo, Cairo 11835, Egypt.

Two series of new compounds with the general formula 4,6-diaryl-2-oxo-1,2-dihydropyridine-3-carbonitriles and their isosteric 2-imino derivatives were synthesized by the multicomponent reaction of the appropriate acetophenone, aromatic aldehyde, ammonium acetate, and malononitrile or ethyl cyanoacetate. The products were obtained with excellent yields. The prepared compounds were evaluated for their in vitro ability to inhibit p38 alpha-MAP kinase. Read More

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http://dx.doi.org/10.1021/cc1000488DOI Listing
July 2010
5 Reads