Publications by authors named "Moha Taourirte"

19 Publications

  • Page 1 of 1

An Insight into Saponins from Quinoa ( Willd): A Review.

Molecules 2020 Feb 27;25(5). Epub 2020 Feb 27.

Laboratory of Natural Resources Valorization, Department of AgroBioSciences, Mohammed VI Polytechnic University Benguerir, Ben Guerir 43150, Morocco.

Saponins are an important group found in . They represent an obstacle for the use of quinoa as food for humans and animal feeds because of their bitter taste and toxic effects, which necessitates their elimination. Several saponins elimination methods have been examined to leach the saponins from the quinoa seeds; the wet technique remains the most used at both laboratory and industrial levels. Dry methods (heat treatment, extrusion, roasting, or mechanical abrasion) and genetic methods have also been evaluated. The extraction of quinoa saponins can be carried out by several methods; conventional technologies such as maceration and Soxhlet are the most utilized methods. However, recent research has focused on technologies to improve the efficiency of extraction. At least 40 saponin structures from quinoa have been isolated in the past 30 years, the derived molecular entities essentially being phytolaccagenic, oleanolic and serjanic acids, hederagenin, 3β,23,30 trihydroxy olean-12-en-28-oic acid, 3β-hydroxy-27-oxo-olean-12en-28-oic acid, and 3β,23,30 trihydroxy olean-12-en-28-oic acid. These metabolites exhibit a wide range of biological activities, such as molluscicidal, antifungal, anti-inflammatory, hemolytic, and cytotoxic properties.
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http://dx.doi.org/10.3390/molecules25051059DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7179108PMC
February 2020

Surface modification of α-chitin using an acidic treatment followed by ultrasonication: Measurements of their sorption properties.

Int J Biol Macromol 2020 May 19;151:492-498. Epub 2020 Feb 19.

Laboratory of Bioorganic and Macromolecular Chemistry, Department of Chemistry, Faculty of Sciences and Technology, Cadi Ayyad University, 40000 Marrakesh, Morocco.

The biopolymer α-chitin is a promising raw source that can be used as a low-cost material for environmental applications. Nevertheless, its low surface properties and high crystallinity limit its use. Recent developments include surface modification as one of the most promising strategies for the application of α-chitin. To this end, we used an acidic treatment, followed by ultrasonication, to modify the α-chitin surface and improve its sorption characteristics to achieve the above goal. Structural analysis and measurement of the physicochemical properties (chemical structure and thermal degradation) of α-chitin, before and after surface modification, indicated no significant changes. However, specific surface area, morphology, surface charge, crystallinity and study of the sorption of methylene blue (MB) from aqueous solution demonstrated surface modification. It was established that the S of modified α-chitin increased to 110.7 m/g and the crystallinity index decreased to 48%. Interestingly, the modified α-chitin could easily adsorb organic dye from an aqueous solution. The experimental adsorption capacity of the resulting α-chitin after surface modification reached the value of about 95 mg/g.
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http://dx.doi.org/10.1016/j.ijbiomac.2020.02.204DOI Listing
May 2020

Foliar Application of Chitosan Increases Tomato Growth and Influences Mycorrhization and Expression of Endochitinase-Encoding Genes.

Int J Mol Sci 2020 Jan 14;21(2). Epub 2020 Jan 14.

Department of Cell and Metabolic Biology, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), Germany.

Nowadays, applying bio-organic fertilizer (e.g., chitosan, Ch) or integrating beneficial microorganisms (e.g., arbuscular mycorrhizal fungi, AMF) are among the successful strategies to promote plant growth. Here, the effect of two application modes of Ch (foliar spray or root treatment) and Ch-derived nanoparticles (NPs) on tomato plants colonized with the AMF were analyzed, thereby focusing on plant biomass, flowering and mycorrhization. An increase of shoot biomass and flower number was observed in arbuscular mycorrhizal (AM) plants sprayed with Ch. The interaction with AMF, however, was reduced as shown by decreased mycorrhization rates and AM-specific gene expression. To get insights into Ch effect on mycorrhization, levels of sugars, jasmonates, abscisic acid, and the expression of two chitinase-encoding genes were determined in mycorrhizal roots. Ch had no effect on sugar and phytohormone levels, but the reduced mycorrhization was correlated with down- and upregulated expression of and , respectively. In contrast, application of NPs to leaves and Ch applied to the soil did not show any effect, neither on mycorrhization rate nor on growth of mycorrhizal plants. Concluding, Ch application to leaves enhanced plant growth and flowering and reduced interaction with AMF, whereas root treatment did not affect these parameters.
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http://dx.doi.org/10.3390/ijms21020535DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7013828PMC
January 2020

Uptake of Pb(II) onto nanochitosan/sodium alginate hybrid beads: Mechanism and kinetics study.

Water Environ Res 2019 Mar 28;91(3):239-249. Epub 2019 Jan 28.

Laboratory of Bioorganic and Macromolecular Chemistry, Department of Chemistry, Faculty of Sciences and Technologies, Cadi Ayyad University, Marrakesh, Morocco.

Nanochitosan/sodium alginate (NCS/SA) beads were prepared using nanochitosan and alginate as a high-performance absorbent for Pb(II) removal from aqueous solution. The morphology, structure, thermal stability, surface area, and elements present in the NCS/SA beads before and after adsorption were characterized using instrumental techniques like SEM, FTIR, TGA, BET, and EDX analysis, respectively. Various adsorption parameters were studied. The results indicated that the equilibrium adsorption data were fitted to Langmuir isotherms and the maximum Langmuir monolayer capacity of Pb(II) was 178.57 mg/g at 45°C. The adsorption process was in good agreement with pseudo-first-order kinetic model. Mechanism studies showed that electrostatic interaction and ion exchange were the major mechanisms for lead (II) removal by the NCS/SA beads. The results of this study indicate that NCS/SA beads could be used as an effective adsorbent for the elimination of lead (II) present in aqueous solution. PRACTITIONER POINTS: Nanochitosan/sodium alginate beads were synthesized using Ca as a crosslinking agent. NCS/SA beads were used to remove Pb(II) for the first time and working parameters were optimized. Adsorption monolayer capacity of NCS/SA adsorbent towards Pb (II) was found to be 178.57 mg/g.
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http://dx.doi.org/10.1002/wer.1050DOI Listing
March 2019

Bioinspired Synthesis of Pygmaeocins and Related Rearranged Abietane Diterpenes: Synthesis of Viridoquinone.

Org Lett 2018 09 13;20(18):5666-5670. Epub 2018 Sep 13.

Departamento de Química Orgánica , Facultad de Ciencias, Universidad de Granada , 18071 Granada , Spain.

A bioinspired synthesis of rearranged abietane diterpenes, related to pygmaeocins, is described. In this process, the key step is the 1,2-migration of the C-20 angular methyl to the C-5 position of the abietane skeleton, which occurs when a C6-C7 unsaturated dehydroabietane derivative is treated with SeO in dioxane under reflux (19 examples for this rearrangement are described). Utilizing this reaction, an enantiospecific synthesis of pygmaeocin C and the first synthesis of viridoquinone, starting from the abietane phenol ferruginol, are reported. A tentative mechanism for this reaction and a possible biosynthetic pathway for this family of metabolites are postulated.
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http://dx.doi.org/10.1021/acs.orglett.8b02395DOI Listing
September 2018

Dihydropyrimidinone/1,2,3-triazole hybrid molecules: Synthesis and anti-varicella-zoster virus (VZV) evaluation.

Eur J Med Chem 2018 Jul 13;155:772-781. Epub 2018 Jun 13.

Laboratory of Biomolecular and Medicinal Chemistry, Department of Chemistry, Faculty of Sciences Semlalia (FSSM), Marrakesh, Morocco. Electronic address:

By combining the structural features of dihydropyrimidinone and 1,2,3-triazole heterocycles, novel hybrid compounds were synthesized using a simple and convenient method. A series of novel mono and bis 1,2,3-triazole was synthesized via copper-catalyzed Huisgen azide-alkyne cycloadditions (CuAAC) under microwave irradiation. The newly synthesized compounds were evaluated for their antiviral activity against varicella-zoster virus (VZV). Compounds 6aa, 7ab, 6ba and 6da showed valuable antiviral activities, with EC values ranging from 3.6 to 11.3 μM against TK+ and TK- VZV and without measurable cell-growth inhibition.
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http://dx.doi.org/10.1016/j.ejmech.2018.06.028DOI Listing
July 2018

Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3-Triazolylbenzyl-aminophosphonates.

Arch Pharm (Weinheim) 2016 Jan 17;349(1):30-41. Epub 2015 Nov 17.

Department of Chemistry, Faculty of Sciences Semlalia, Laboratory of Biomolecular and Medicinal Chemistry, Marrakesh, Morocco.

A novel series of ribonucleosides of 1,2,3-triazolylbenzyl-aminophosphonates was synthesized through the Kabachnik-Fields reaction using I2 as catalyst followed by copper-catalyzed cycloaddition of the azide-alkyne reaction (CuAAC). All structures of the newly prepared compounds were characterized by (1) H NMR, (13) C NMR, and HRMS spectra. The structures of 2e, 2f, 3d, and 3g were further confirmed by X-ray diffraction analysis. These compounds were tested against various strains of DNA and RNA viruses; compounds 4b and 4c showed a modest inhibitory activity against respiratory syncytial virus (RSV) and compound 4h displayed modest inhibitory activity against Coxsackie virus B4.
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http://dx.doi.org/10.1002/ardp.201500292DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4832832PMC
January 2016

Crystal structure of 2-benzamido-N-(2,2-di-eth-oxy-eth-yl)benzamide.

Acta Crystallogr E Crystallogr Commun 2015 Mar 28;71(Pt 3):o214-5. Epub 2015 Feb 28.

Institut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany.

In the title compound, C20H24N2O4, both peptide bonds adopt a trans configuration with respect to the -N-H and -C=O groups. The dihedral angle between the aromatic rings is 53.58 (4)°. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. The crystal packing is characterized by zigzag chains of N-H⋯O hydrogen-bonded mol-ecules running along the b-axis direction.
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http://dx.doi.org/10.1107/S2056989015003370DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4350703PMC
March 2015

Benzimidazole-1,2,3-triazole hybrid molecules: synthesis and evaluation for antibacterial/antifungal activity.

Arch Pharm (Weinheim) 2014 Oct 4;347(10):748-55. Epub 2014 Aug 4.

Laboratory of Bioorganic and Macromolecular Chemistry, Department of Chemistry, Faculty of Sciences and Technology Gueliz (FSTG), Marrakesh, Morocco; Laboratory of Biomolecular and Medicinal Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, Marrakesh, Morocco; Institute for Organic Chemistry and Chemical Biology, Goethe-University Frankfurt am Main, Frankfurt am Main, Germany.

A novel series of hybrid molecules 4a-i and 5a-i were prepared by condensation of 4-(trimethylsilylethynyl)benzaldehyde 1 with substituted o-phenylenediamines. These in turn were reacted with 2-(azidomethoxy)ethyl acetate in a Cu alkyne-azide cycloaddition (CuAAC) to generate the 1,2,3-triazole pharmacophore under microwave assistance. The newly synthesized compounds were examined for their in vitro antimicrobial activities against Gram-positive and Gram-negative bacteria and the phytopathogenic fungi Verticillium dahliae and Fusarium oxysporum f. sp. albedinis. 2-((4-(4-(5-Trifluoromethyl benzimidazol-2-yl)phenyl)-1,2,3-triazol-1-yl)methoxy)ethanol 5e showed a moderate inhibition of 30% in the Foa sporulation test.
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http://dx.doi.org/10.1002/ardp.201400142DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4225497PMC
October 2014

Synthesis of new 1,2,3-triazol-4-yl-quinazoline nucleoside and acyclonucleoside analogues.

Molecules 2014 Mar 24;19(3):3638-53. Epub 2014 Mar 24.

Laboratory of Biomolecular and Medicinal Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, Marrakech 40000, Morocco.

In this study, we describe the synthesis of 1,4-disustituted-1,2,3-triazolo-quinazoline ribonucleosides or acyclonucleosides by means of 1,3-dipolar cycloaddition between various O or N-alkylated propargyl-quinazoline and 1'-azido-2',3',5'-tri-O-benzoylribose or activated alkylating agents under microwave conditions. None of the compounds selected showed significant anti-HCV activity in vitro.
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http://dx.doi.org/10.3390/molecules19033638DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271638PMC
March 2014

Four related diethyl [(arylamino)(4-ethynylphenyl)methyl]phosphonates.

Acta Crystallogr C 2013 Oct 6;69(Pt 10):1157-63. Epub 2013 Sep 6.

Laboratory of Bioorganic and Macromolecular Chemistry, Department of Chemistry, Faculty of Sciences and Technology Guéliz (FSTG), BP 549, Marrakech, Morocco.

Crystal structures are reported for four related diethyl [(arylamino)(4-ethynylphenyl)lmethyl]phosphonate derivatives, namely diethyl [(4-bromoanilino)(4-ethynylphenyl)methyl]phosphonate, C19H21BrNO3P, (I), diethyl ((4-chloro-2-methylanilino){4-[2-(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, C23H31ClNO3PSi, (II), diethyl ((4-fluoroanilino){4-[2-(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, C22H29FNO3PSi, (III), and diethyl [(4-ethynylphenyl)(naphthalen-2-ylamino)methyl]phosphonate, C23H24NO3P, (IV). The conformation of the anilinobenzyl group is very similar in all four compounds. The P-C bond has an approximately staggered conformation, with the aniline and ethynylphenyl groups in gauche positions with respect to the P=O double bond. The two six-membered rings are almost perpendicular. The sums of the valence angles about the N atoms vary from 344 (2) to 351 (2)°. In the crystal structures, molecules of (I), (III) and (IV) are arranged as centrosymmetric or pseudocentrosymmetric dimers connected by two N-H···O=P hydrogen bonds. The molecules of (II) are arranged as centrosymmetric dimers connected by C(methyl)-H···O=P hydrogen bonds. The N-H bond of (II) is not involved in hydrogen bonding.
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http://dx.doi.org/10.1107/S0108270113022981DOI Listing
October 2013

Methyl 2-(3-chloro-benzamido)-benzoate.

Acta Crystallogr Sect E Struct Rep Online 2012 Dec 24;68(Pt 12):o3400-1. Epub 2012 Nov 24.

Laboratoire de Chimie Bio-organique et Macromoléculaire, Faculté des Sciences et Techniques Guéliz, Marrakech, Morocco.

In the mol-ecule of the title compound, C15H12ClNO3, the chloro-benzamide and benzoate units are almost co-planar, with a dihedral angle between the six-membered rings of 2.99 (10)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, each mol-ecule is linked to a symmetry-equivalent counterpart across a twofold rotation axis by weak C-H⋯O and C-H⋯Cl hydrogen bonds, forming dimers. The packing is stabilized through weak π-π stacking along the b-axis direction, leading to π-stacked columns of inversion-related mol-ecules, with an inter-planar distance of 3.46 (2) Å and a centroid-centroid vector of 3.897 (2) Å.
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http://dx.doi.org/10.1107/S1600536812046934DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588991PMC
December 2012

Attempts to separate (-)-α-thujone, (+)-β-thujone epimers from camphor enantiomers by enantioselective HPLC with polarimetric detection.

J Sep Sci 2013 Mar 4;36(5):832-9. Epub 2013 Feb 4.

Bioorganic and Macromolecular Chemistry Laboratory, FST, Cadi Ayyad University, Marrakech, Morocco.

In a first step, 26 chiral stationary phases (CSPs) have been screened for the separation of (-)-α-thujone, (+)-β-thujone epimers and camphor enantiomers by LC. The separations were monitored by a polarimeter detector. None of these CSPs provided a noticeable resolution for camphor enantiomers. The three components of a test mixture were clearly baseline separated on Chiralpak AS-H, Chiralpak AZ-H and TCI-MBS (poly(N-alpha-(S)-methylbenzylmaleimide) coated on silica gel) in a mobile phase composed of hexane/2-PrOH (99:1 v/v). Interestingly, for a preparative application, the three CSPs produced different elution orders for the three constituents of the mixture. In a second step, it is shown that the use of online polarimetric detection constitutes an unprecedented method to reveal the occurrence and the relative content of thujone epimers and the chirality of the major camphor enantiomer in crude essential oils. A proof of concept is illustrated on crude essential oils from Rosmarinus tournefortii, Artemisia herba alba and A. arborescens, which grow in Morocco and have several traditional uses there. In a third step, pure (+)-β-thujone was quantitatively collected from A. arborescens crude oil by semi-preparative HPLC on Chiralpak AZ-H monitored by a polarimeter.
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http://dx.doi.org/10.1002/jssc.201200907DOI Listing
March 2013

3-{[1-(2,3,5-Tri-O-benzoyl-β-d-ribofur-an-os-1-yl)-1H-1,2,3-triazol-4-yl]meth-yl}quin-a-zolin-4(3H)-one.

Acta Crystallogr Sect E Struct Rep Online 2012 Nov 20;68(Pt 11):o3166. Epub 2012 Oct 20.

Laboratoire de Chimie Bio-organique et Macromoléculaire, Faculté des Sciences et Techniques Guéliz, Marrakech, Morocco.

In the compound, C(37)H(29)N(5)O(8), the quinazoline residue forms a dihedral angle of 72.90 (9)° with the triazole ring. The furan ring adopts a twist conformation. In the crystal, the mol-ecules are linked by non-classical C-H⋯N and C-H⋯O hydrogen bonds, building an infinite three-dimensional network.
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http://dx.doi.org/10.1107/S1600536812042778DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515260PMC
November 2012

2-({4-[4-(1H-Benzimidazol-2-yl)phen-yl]-1H-1,2,3-triazol-1-yl}meth-oxy)ethanol.

Acta Crystallogr Sect E Struct Rep Online 2012 Jun 26;68(Pt 6):o1908. Epub 2012 May 26.

In the title molecule, C(18)H(17)N(5)O(2), the dihedral angle between the benzene plane and the benzimidazole plane is 19.8 (1)° and the angle between the benzene plane and the triazole plane is 16.7 (1)°. In the crystal, mol-ecules are connected by O-H⋯N hydrogen bonds, forming zigzag chains along the c-axis direction. The chains are connected by bifurcated N-H⋯(N,N) hydrogen bonds into layers parallel to (100). These layers are connected along the a-axis direction by weak C-H⋯O contacts, forming a three-dimensional network.
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http://dx.doi.org/10.1107/S1600536812023410DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379465PMC
June 2012

Synthesis of 1,4-disubstituted mono and bis-triazolocarbo-acyclonucleoside analogues of 9-(4-hydroxybutyl)guanine by Cu(I)-catalyzed click azide-alkyne cycloaddition.

Molecules 2011 Dec 27;17(1):179-90. Epub 2011 Dec 27.

Laboratoire de Chimie Bioorganique et Macromoléculaire, Faculté des Sciences et Techniques-Guéliz, 40000, Marrakech, Maroc.

A series of novel mono-1,2,3-triazole and bis-1,2,3-triazole acyclonucleoside analogues of 9-(4-hydroxybutyl)guanine was prepared via copper(I)-catalyzed 1,3-dipolar cycloaddition of N-9 propargylpurine, N-1-propargylpyrimidines/as-triazine with the azido-pseudo-sugar 4-azidobutylacetate under solvent-free microwave conditions, followed by treatment with K(2)CO(3)/MeOH, or NH(3)/MeOH. All compounds studied in this work were screened for their antiviral activities [against human rhinovirus (HRV) and hepatitis C virus (HCV)] and antibacterial activities against a series of Gram positive and negative bacteria.
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http://dx.doi.org/10.3390/molecules17010179DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6269037PMC
December 2011

4-{4-[(4-Oxoquinazolin-3-yl)meth-yl]-1H-1,2,3-triazol-1-yl}butyl acetate.

Acta Crystallogr Sect E Struct Rep Online 2011 Dec 5;67(Pt 12):o3191. Epub 2011 Nov 5.

In the heterocyclic title compound, C(17)H(19)N(5)O(3), the quinazolinone ring system forms a dihedral angle of 67.22 (7)° with the triazole ring. The butyl acetate group has a non-linear conformation, with an alternation of synclinal and anti-periplanar torsion angles [N-C-C-C = 58.5 (2)°, C-C-C-C = 170.72 (19)° and C-C-C-O = -65.9 (3)°]. The crystal structure features inter-molecular C-H⋯N and C-H⋯O non-classical hydrogen bonds, building an infinite one-dimensional network along the [100] direction.
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http://dx.doi.org/10.1107/S1600536811045600DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3238858PMC
December 2011

Efficient microwave-assisted synthesis, antibacterial activity and high fluorescence of 5 benzimidazolyl-2'-deoxyuridines.

Bioorg Med Chem 2012 Jan 25;20(1):480-6. Epub 2011 Oct 25.

Laboratoire de Chimie Bioorganique et Macromoléculaire, Faculté des Sciences et Techniques-Guéliz, 40000 Marrakech, Morocco.

A series of novel C-5 benzimidazolyl-2'-deoxyuridines was synthesized in good yields under solvent-free conditions and microwave irradiation from 5-formyl-2'-deoxyuridine and arylenediamine derivatives in the presence of NaHSO(3) as catalyst. Their absorption and fluorescence spectra were measured. They showed intense fluorescence around 400-500nm with quantum yields between 0.3 and 0.5. All compounds studied in this work were screened for their antibacterial activities against a series of Gram positive and negative bacteria. The trifluoromethyl substituted benzimidazole derivatives showed some antibacterial activity.
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http://dx.doi.org/10.1016/j.bmc.2011.10.041DOI Listing
January 2012

4-(4-{[(2-Phenyl-quinazolin-4-yl)-oxy]methyl}-1H-1,2,3-triazol-1-yl)butan-1-ol hemihydrate.

Acta Crystallogr Sect E Struct Rep Online 2011 Aug 13;67(Pt 8):o2029-30. Epub 2011 Jul 13.

The title compound, C(21)H(21)N(5)O(2)·0.5H(2)O, has two fused six-membered rings linked to a benzene ring and to a triazole ring, which is connected to a butanol group. The quinazoline ring forms a dihedral angle of 7.88 (8)° with the benzene ring, while the triazole ring is approximately perpendicular to the benzene ring and to the quinazoline system, making dihedral angles of 84.38 (10) and 76.55 (8)°, respectively. The stereochemical arrangement of the butanol chain, with a C-C-C-C torsion angle of 178.34 (19)°, corresponds to an anti-periplanar conformation. However the position of the -OH group is split into two very close [O-O = 0.810(3) Å] positions of equal occupancy. The crystal structure features O-H⋯N and O-H⋯O hydrogen bonds, building an infinite three-dimensional network. The water molecule is located on a half-filled general position.
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http://dx.doi.org/10.1107/S1600536811027280DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3213479PMC
August 2011
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