Publications by authors named "Bohari M Yamin"

97 Publications

Hexaferrocenium tri[hexa(isothiocyanato)iron(III)] trihydroxonium complex as a new DNA intercalator for electrochemical DNA biosensor.

Sci Rep 2021 Apr 12;11(1):7883. Epub 2021 Apr 12.

Department of Chemical Sciences, Faculty of Science and Technology, Universiti Kebangsaan Malaysia (UKM), 43600, Bangi, Selangor Darul Ehsan, Malaysia.

Ferrocene or ferrocenium has been widely studied in the field of organometallic complexes because of its stable thermodynamic, kinetic and redox properties. Novel hexaferrocenium tri[hexa(isothiocyanato)iron(III)]trihydroxonium (HexaFc) complex was the product from the reaction of ferrocene, maleic acid and ammonium thiocyanate and was confirmed by elemental analysis CHNS, FTIR and single crystal X-ray crystallography. In this study, HexaFc was used for the first time as an electroactive indicator for porcine DNA biosensor. The UV-Vis DNA titrations with this compound showed hypochromism and redshift at 250 nm with increasing DNA concentrations. The binding constant (K) for HexaFc complex towards CT-DNA (calf-thymus DNA) was 3.1 × 10 M, indicated intercalator behaviour of the complex. To test the usefulness of this complex for DNA biosensor application, a porcine DNA biosensor was constructed. The recognition probes were covalently immobilised onto silica nanospheres (SiNSs) via glutaraldehyde linker on a screen-printed electrode (SPE). After intercalation with the HexaFc complex, the response of the biosensor to the complementary porcine DNA was measured using differential pulse voltammetry. The DNA biosensor demonstrated a linear response range to the complementary porcine DNA from 1 × 10 to 1 × 10 µM (R = 0.9642) with a limit detection of 4.83 × 10 µM and the response was stable up to 23 days of storage at 4 °C with 86% of its initial response. The results indicated that HexaFc complex is a feasible indicator for the DNA hybridisation without the use of a chemical label for the detection of porcine DNA.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1038/s41598-021-86939-zDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8041802PMC
April 2021

In silico studies, nitric oxide, and cholinesterases inhibition activities of pyrazole and pyrazoline analogs of diarylpentanoids.

Arch Pharm (Weinheim) 2021 Jan 4;354(1):e2000161. Epub 2020 Sep 4.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, Bangi, Selangor, Malaysia.

A new series of pyrazole, phenylpyrazole, and pyrazoline analogs of diarylpentanoids (excluding compounds 3a, 4a, 5a, and 5b) was pan-assay interference compounds-filtered and synthesized via the reaction of diarylpentanoids with hydrazine monohydrate and phenylhydrazine. Each analog was evaluated for its anti-inflammatory ability via the suppression of nitric oxide (NO) on IFN-γ/LPS-activated RAW264.7 macrophage cells. The compounds were also investigated for their inhibitory capability toward acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), using a modification of Ellman's spectrophotometric method. The most potent NO inhibitor was found to be phenylpyrazole analog 4c, followed by 4e, when compared with curcumin. In contrast, pyrazole 3a and pyrazoline 5a were found to be the most selective and effective BChE inhibitors over AChE. The data collected from the single-crystal X-ray diffraction analysis of compound 5a were then applied in a docking simulation to determine the potential binding interactions that were responsible for the anti-BChE activity. The results obtained signify the potential of these pyrazole and pyrazoline scaffolds to be developed as therapeutic agents against inflammatory conditions and Alzheimer's disease.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1002/ardp.202000161DOI Listing
January 2021

Synthesis, characterization, quantum chemical calculations and anticancer activity of a Schiff base NNOO chelate ligand and Pd(II) complex.

PLoS One 2020 14;15(4):e0231147. Epub 2020 Apr 14.

Faculty of Applied Sciences, Universiti Teknologi MARA, Shah Alam, Selangor, Malaysia.

This paper reports the synthesis, characterization, anticancer screening and quantum chemical calculation of a tetradentate Schiff base 2,2'-((1E,1'E)-((2,2-dimethylpropane-1,3-diyl)bis- (azanylylidene))bis(methanylylidene))bis(4-fluorophenol) (L2F) and its Pd (II) complex (PdL2F). The compounds were characterized via UV-Visible, NMR, IR spectroscopy and single crystal x-ray diffraction. Density Functional Theory (DFT) and time-dependent DFT calculations in gas and solvent phases were carried out using B3LYP, B3P86, CAM-B3LYP and PBE0 hybrid functionals combined with LanL2DZ basis set. Complexation of L2F to form PdL2F was observed to cause a bathochromic shift of the maximum absorption bands of n-π* from 327 to 410 nm; an upfield shift for δ (HC = N) from 8.30 to 7.96 ppm and a decreased wavenumber for ν(C = N) from 1637 to 1616 cm-1. Overall, the UV-Vis, NMR and IR spectral data are relatively well reproduced through DFT and TD-DFT methods. L2F and PdL2F showed IC50 of 90.00 and 4.10 μg/mL, respectively, against human colorectal carcinoma (HCT116) cell lines, signifying increased anticancer activity upon complexation with Pd (II).
View Article and Find Full Text PDF

Download full-text PDF

Source
http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0231147PLOS
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7156068PMC
July 2020

A comparative study of the metal binding behavior of alanine based bis-thiourea isomers.

Chem Cent J 2017 Aug 4;11(1):76. Epub 2017 Aug 4.

School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM, Bangi, Selangor, Malaysia.

Two new symmetrical bis-thiourea, 2,2'-[{(terephthaloylbis(azanediyl)bis(carbonothioyl) bis(azanediyl)}dipropanoic acid] (1A) and 3,3'-[{(terephthaloylbis(azanediyl)bis (carbonothioyl)bis(azanediyl)} dipropanoic acid] (1B) were synthesized by the reaction of terephthaloyl chloride with α- and β-alanine in good yields. Their binding properties were investigated with various metal cations using UV-Vis titration experiments. Both isomers exhibited effective binding with Ag, Cu, Hg, Pb, Fe and Fe cations. However, in the presence of other cations, such as Na, Ni, Co, Cd, Zn, Mn, Mg, Ca, Sn, Al, and anions tetrabutylammonium Cl and HPO, no interaction occurred. Both isomers displayed similar trends towards binding with metal cations.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1186/s13065-017-0304-2DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5544659PMC
August 2017

3,4-Dimethoxybenzohydrazide derivatives as antiulcer: Molecular modeling and density functional studies.

Bioorg Chem 2017 12 7;75:235-241. Epub 2017 Oct 7.

H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.

3,4-Dimethoxybenzohydrazide derivatives (1-25) have been synthesized and evaluated for their urease inhibitory potential. Among the series, compounds 2, 3, 4 and 5 with IC values 12.61 ± 0.07, 18.24 ± 0.14, 19.22 ± 0.21, and 8.40 ± 0.05 µM, respectively, showed excellent urease inhibitory potentials when compared with standard thiourea (IC value 21.40 ± 0.21 µM). Compounds 1, 6, 8, 18, 19 and 20 also showed good to moderate inhibition, while the remaining compounds were found to be completely inactive. The structures of compounds 6 and 25 were confirmed through X-ray crystallography while the structures of remaining compounds were confirmed through ESI-MS and H NMR. Molecular docking studies were performed understand the binding interactions with enzyme active site. The synthesized compounds were evaluated for cytotoxicity and found to be nontoxic.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.bioorg.2017.10.004DOI Listing
December 2017

Characterisation of fucoidan extracted from Malaysian Sargassum binderi.

Food Chem 2016 Oct 18;209:267-73. Epub 2016 Apr 18.

School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia. Electronic address:

Fucoidan is a sulphated polysaccharide that consists mainly of fucose, normally found in brown seaweeds. In this study, fucoidan was extracted from Sargassum binderi (Fsar) from Malaysia and subsequently characterised. The chemical characteristics of Fsar were found to be different than those of commercial food grade fucoidan (Fysk) and those of previously studied fucoidans. NMR analysis proposed that the main structure of Fsar is →3)fuc-2-OSO3(-)(1→3)fuc(1→. The molecular weight (47.87kDa) and degree of sulphation (0.20) of Fsar were higher than those of Fysk, at 27.98kDa and 0.15, respectively. However, Fsar's polydispersity index (1.12) and fucose content (34.50%) were lower than those of Fysk, at 1.88 and 43.30%, respectively. Both Fsar and Fysk showed similar thermo-gravimetric properties with four mass losses, amorphous in nature and negative optical rotations. Results show that Fsar has fundamental characteristics of fucoidan with different structural conformation i.e. variation in glycosidic linkages and sulphate group orientation.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.foodchem.2016.04.058DOI Listing
October 2016

Synthesis of unsymmetrical monocarbonyl curcumin analogues with potent inhibition on prostaglandin E2 production in LPS-induced murine and human macrophages cell lines.

Bioorg Med Chem Lett 2016 05 26;26(10):2531-2538. Epub 2016 Mar 26.

Drug and Herbal Research Centre, Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abdul Aziz, 50300 Kuala Lumpur, Malaysia. Electronic address:

The syntheses and bioactivities of symmetrical curcumin and its analogues have been the subject of interest by many medicinal chemists and pharmacologists over the years. To improve our understanding, we have synthesized a series of unsymmetrical monocarbonyl curcumin analogues and evaluated their effects on prostaglandin E2 production in lipopolysaccharide-induced RAW264.7 and U937 cells. Initially, compounds 8b and 8c exhibited strong inhibition on the production of PGE2 in both LPS-stimulated RAW264.7 (8b, IC50=12.01μM and 8c, IC50=4.86μM) and U937 (8b, IC50=3.44μM and 8c, IC50=1.65μM) cells. Placing vanillin at position Ar2 further improved the potency when both compounds 15a and 15b significantly lowered the PGE2 secretion level (RAW264.7: 15a, IC50=0.78μM and 15b, IC50=1.9μM while U937: 15a, IC50=0.95μM and 15b, IC50=0.92μM). Further experiment showed that compounds 8b, 8c, 15a and 15b did not target the activity of downstream inflammatory COX-2 mediator. Finally, docking simulation on protein targets COX-2, IKK-β, ERK, JNK2, p38α and p38β were performed using the conformation of 15a determined by single-crystal XRD.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.bmcl.2016.03.092DOI Listing
May 2016

Crystal structure of 2-amino-3-ethyl-4,5-di-hydro-1,3-thia-zol-3-ium 3-chloro-benzo-ate.

Acta Crystallogr E Crystallogr Commun 2015 Jun 7;71(Pt 6):o378. Epub 2015 May 7.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor D.E., Malaysia.

The title salt, C5H11N2S(+)·C7H4ClO2 (-), comprises a 2-amino-3-ethyl-4,5-di-hydro-1,3-thia-zol-3-ium cation in which the five-membered ring adopts an envelope conformation with the methyl-ene C adjacent to the S atom being the flap, and a planar 3-chloro-benzoate anion (r.m.s. deviation for the 10 non-H atoms = 0.021 Å). The most prominent feature of the crystal packing are N-H⋯O hydrogen bonds whereby the two amine H atoms bridge two carboxyl-ate O atoms resulting in the formation of a centrosymmetric 12-membered {⋯HNH⋯OCO}2 synthon involving two cations and two anions. These aggregates are linked by C-H⋯O inter-actions to form a supra-molecular chain along the a-axis direction.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S2056989015008385DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4459344PMC
June 2015

Synthesis, X-ray, NMR, FT-IR, UV/vis, DFT and TD-DFT studies of N-(4-chlorobutanoyl)-N'-(2-, 3- and 4-methylphenyl)thiourea derivatives.

Spectrochim Acta A Mol Biomol Spectrosc 2015 Jun 21;144:115-24. Epub 2015 Feb 21.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43650 Bangi, Selangor, Malaysia. Electronic address:

A new isomers of thiourea derivatives, namely N-(4-chlorobutanoyl)-N'-(2-methylphenyl)-thiourea (1a), N-(4-chlorobutanoyl)-N'-(3-methylphenyl)thiourea (1b) and N-(4-chlorobutanoyl)-N'-(4-methylphenyl)thiourea (1c) have been synthesized by refluxing mixture of equimolar amounts of 4-chlorobutanoylisothiocyanate with 2, 3 or 4-toluidine, respectively. The three isomers were characterized by spectroscopic (UV/vis, FT-IR and NMR) and X-ray crystallography techniques. To investigate the isomerization effect on spectroscopic data, DFT and TD-DFT calculations have been carried out using five hybrid functionals (B3LYP, B3P86, CAM-B3LYP, M06-2X and PBE0) to predict UV/vis absorption bands (n→π∗ and π→π∗), (1)H and (13)C NMR chemical shifts, FT-IR vibration modes and X-ray parameters (bonds, bond angles and torsion angles) for 1a, 1b and 1c isomers. The results showed that the isomerization effect is significant on λ(MAX) absorption bands, while for IR and NMR the effect is negligible. In accordance with previous studies, B3LYP, B3P86 and PBE0 gave the most reliable to predict the excitation energies of thiourea derivatives.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.saa.2015.01.092DOI Listing
June 2015

Crystal structure of 4-cyclo-hexyl-1-(propan-2-yl-idene)thio-semicarbazide.

Acta Crystallogr Sect E Struct Rep Online 2014 Oct 13;70(Pt 10):o1109. Epub 2014 Sep 13.

Department of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan Serawak, Malaysia.

In the title compound, C10H19N3S, the cyclo-hexyl group adopts a chair conformation and adopts a position approximately syn to the thione S atom. The CN2S thio-urea moiety makes dihedral angle of 13.13 (10)° with the propan-2-yl-idene-amino group. An intra-molecular N-H⋯N hydrogen bond is noted. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R (2) 2(8) loops.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S160053681402025XDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4257229PMC
October 2014

Crystal structure of 4-fluoro-N-[2-(4-fluoro-benzo-yl)hydra-zine-1-carbono-thio-yl]benzamide.

Acta Crystallogr Sect E Struct Rep Online 2014 Sep 1;70(Pt 9):o915-6. Epub 2014 Aug 1.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.

In the title compound, C15H11F2N3O2S, the dihedral angle between the fluoro-benzene rings is 88.43 (10)° and that between the central semithiocarbazide grouping is 47.00 (11)°. The dihedral angle between the amide group and attached fluoro-benzene ring is 50.52 (11)°; the equivalent angle between the carbonyl-thio-amide group and its attached ring is 12.98 (10)°. The major twists in the mol-ecule occur about the C-N-N-C bonds [torsion angle = -138.7 (2)°] and the Car-Car-C-N (ar = aromatic) bonds [-132.0 (2)°]. An intra-molecular N-H⋯O hydrogen bond occurs, which generates an S(6) ring. In the crystal, the mol-ecules are linked by N-H⋯O and N-H⋯S hydrogen bonds, generating (001) sheets. Weak C-H⋯O and C-H⋯F inter-actions are also observed.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536814015761DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4186173PMC
September 2014

Crystal structure of (E)-N'-benzyl-idene-2-meth-oxy-benzohydrazide.

Acta Crystallogr Sect E Struct Rep Online 2014 Sep 30;70(Pt 9):o1071-2. Epub 2014 Aug 30.

Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D.E., Malaysia ; Faculty of Pharmacy, Universiti Tecknologi MARA, Puncak Alam, 42300 Selangor, Malaysia.

In the title benzoyl-hydrazide derivative, C15H14N2O2, the dihedral angle between the planes of the two phenyl rings is 12.56 (9)°. The azomethine double bond adopts an E configuration stabilized by an N-H⋯O hydrogen bond. In the crystal, the components are linked by C-H⋯O inter-actions to form chains along the b axis.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536814019011DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4186185PMC
September 2014

(E)-3-Chloro-N'-(2-fluoro-benzyl-idene)thio-phene-2-carbohydrazide.

Acta Crystallogr Sect E Struct Rep Online 2014 Jul 4;70(Pt 7):o751. Epub 2014 Jun 4.

Faculty of Applied Sciences, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor D.E., Malaysia ; Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E., Malaysia.

The title compound, C12H8ClFN2OS, is a hydrazide derivative adopting an E conformation with an azomethine N=C double bond length of 1.272 (2) Å. The mol-ecular skeleton is approximately planar; the terminal five- and six-membered rings form a dihedral angle of 5.47 (9)°. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds into zigzag chains propagating in [100].
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536814011568DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120552PMC
July 2014

Inhibition of prostaglandin E(2) production by synthetic minor prenylated chalcones and flavonoids: synthesis, biological activity, crystal structure, and in silico evaluation.

Bioorg Med Chem Lett 2014 Aug 27;24(16):3826-34. Epub 2014 Jun 27.

Drugs and Herbal Research Centre, Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abdul Aziz, 50300 Kuala Lumpur, Malaysia. Electronic address:

The discovery of potent inhibitors of prostaglandin E2 (PGE2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a vast array of biological signals and physiological events that contributes to inflammatory diseases such as rheumatoid arthritis, atherosclerosis, cancer, and pain. In this Letter, we report the synthesis of a series of minor prenylated chalcones and flavonoids which was found to be significantly active in suppressing the PGE2 production secreted by lipopolysaccharide-induced mouse macrophage cells (RAW 264.7). Among the compounds tested, 14b showed a dose-response inhibition of PGE2 production with an IC50 value of 2.1 μM. The suppression upon PGE2 secretion was not due to cell death since 14b did not reduce the cell viability in close proximity to the PGE2 inhibition concentration. The obtained atomic coordinates for the single-crystal XRD of 14b was then applied in the docking simulation to determine the potential important binding interactions with murine COX-2 and mPGES-1 putative binding sites.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.bmcl.2014.06.061DOI Listing
August 2014

3-[3-(2-Fluoro-benzo-yl)thio-ureido]propionic acid.

Acta Crystallogr Sect E Struct Rep Online 2014 Jun 24;70(Pt 6):o705. Epub 2014 May 24.

Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia ; Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E., Malaysia.

In the title compound, C10H11FN3O3S, the 2-fluoro-benzoyl and proponic acid groups maintain a trans-cis conformation with respect to the thiono C=S bond across their C-N bonds. The propionic acid group adopts an anti conformation about the C-C bond, with an N-C-C-C torsion angle of 173.8 (2)°. The amino groups are involved in the formation of intra-molecular N-H⋯O and N-H⋯F hydrogen bonds. In the crystal, pairs of O-H⋯O hydrogen bonds link mol-ecules into inversion dimers.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536814011404DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4051025PMC
June 2014

1-(4-Bromo-phen-yl)-3-(3-chloro-propan-oyl)thio-urea.

Acta Crystallogr Sect E Struct Rep Online 2014 Jun 21;70(Pt 6):o685. Epub 2014 May 21.

Faculty of Applied Sciences, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor D.E. , Malaysia.

The title compound, C10H10BrClN2OS, adopts a trans-cis conformation with respect to the position of the 3-chloro-propanoyl and 4-bromo-phenyl groups, respectively, against the thiono C=S bond across their C-N bonds. The benzene ring makes a dihedral angle of 9.55 (16)° with the N2CS thio-urea moiety. Intra-molecular N-H⋯O and C-H⋯S hydrogen bonds occur. In the crystal, mol-ecules are linked into chains along the c-axis direction by N-H⋯S, C-H⋯S and C-H⋯O hydrogen bonds.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536814011209DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4051006PMC
June 2014

1-(4-Chloro-butano-yl)-3-(3-chloro-phen-yl)thio-urea.

Acta Crystallogr Sect E Struct Rep Online 2014 Jun 17;70(Pt 6):o675. Epub 2014 May 17.

Faculty of Applied Sciences, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor D.E., Malaysia.

The two independent mol-ecules in the asymmetric unit of the title compound, C11H12Cl2N2OS, exhibit different conformations, with the benzene ring and the N2CS thio-urea group forming dihedral angles of 87.40 (18) and 69.42 (15)°. An intra-molecular N-H⋯O hydrogen bond is present in each mol-ecule. Two further N-H⋯O hydrogen bonds link the independent mol-ecules into a dimer. In the crystal, the dimers are linked by N-H⋯S and C-H⋯S hydrogen bonds, forming chains parallel to the c axis.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536814009295DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4051110PMC
June 2014

N-[Eth-yl(2-hy-droxy-eth-yl)carbamo-thio-yl]-2-methyl-benzamide.

Acta Crystallogr Sect E Struct Rep Online 2014 May 26;70(Pt 5):o602. Epub 2014 Apr 26.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.

The title compound, C13H18N2O2S, adopts a cis conformation between the methyl-benzoyl and thiono groups across their thio-urea C-N bond. However, the methyl-benzoyl group and N2CS thio-urea moiety are twisted by 15.03 (3)°. In the molecule there is an N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by O-H⋯O inter-actions, generating chains extending along the c-axis direction.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536814008952DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4011282PMC
May 2014

N-[Eth-yl(2-hy-droxy-eth-yl)carbamo-thio-yl]-3-fluoro-benzamide.

Acta Crystallogr Sect E Struct Rep Online 2014 May 18;70(Pt 5):o570. Epub 2014 Apr 18.

Low Carbon Research Group, School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.

In the title compound, C12H15FN2O2S, the mol-ecule adopts a cis configuration of the fluoro-benzoyl group with respect to the thiono group about their C-N bond. The dihedral angle between the fluoro-benzoyl group and the thio-urea N2CS fragment is 69.60 (11)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, mol-ecules form chains along the b-axis direction via O-H⋯S and C-H⋯O hydrogen bonds.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536814008174DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4011211PMC
May 2014

4,4'-({[(Pyridine-2,6-di-yl)bis-(methyl-ene)]bis-(-oxy)}bis-(methyl-ene))dibenzo-nitrile.

Acta Crystallogr Sect E Struct Rep Online 2014 Feb 11;70(Pt 2):o132. Epub 2014 Jan 11.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.

The complete title molecule, C23H19N3O2, is generated by a twofold axis passing through the central ring. The two oxymethyl-benzo-nitrile arms are attached at the meta positions of the central pyridine ring. The dihedral angle between the pyridine ring and benzene ring of both arms is 84.55 (6)° while the benzene rings make a dihedral angle of 46.07 (7)°. In the crystal, weak C-H⋯π inter-actions link the molecules sheets parallel to the ac plane.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536814000245DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998298PMC
February 2014

N-(2-Chloro-5-nitro-phen-yl)-N'-(3-chloro-propion-yl)thio-urea.

Acta Crystallogr Sect E Struct Rep Online 2014 Jan 11;70(Pt 1):o34. Epub 2013 Dec 11.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.

The title compound, C10H9Cl2N3O3S, adopts a trans-cis conformation with respect to the position of chloropropionyl and chloronitrobenzene groups respectively, against the thiono about their C-N bonds. The conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. In the crystal, there is a short Cl⋯Cl contact with a distance of 3.386 (13) Å.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536813032662DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3914079PMC
January 2014

2,4-Di-chloro-N-[eth-yl(2-hy-droxy-eth-yl)carbamo-thio-yl]benzamide.

Acta Crystallogr Sect E Struct Rep Online 2014 Jan 11;70(Pt 1):o33. Epub 2013 Dec 11.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.

In the title compound, C12H14Cl2N2O2S, the mol-ecule adopts a cis conformation with respect to the di-chloro-benzoyl group against the thiono group about the C-N bond. However, the di-chloro-benzene group and the thio-urea moiety are twisted by 75.41 (8)°. An intra-molecular N-H⋯O hydrogen bond occurs between the amido H atom and hydroxyl O atom. In the crystal, O-H⋯S and O-H⋯O hydrogen bonds link the molecules, forming chains along the b-axis direction.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536813032881DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3914078PMC
January 2014

1-(4-Chlorophenyl)-3-(3-chloro-pro-pionyl)thio-urea.

Acta Crystallogr Sect E Struct Rep Online 2013 Oct 23;69(Pt 11):o1696. Epub 2013 Oct 23.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.

In the title compound, C10H10Cl2N2OS, the mol-ecule adopts a trans-cis conformation with respect to the position of the carbonyl group and the chloro-phenyl groups relative to the thiono group across the C-N bonds. The mol-ecule is stabilized by an N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by N-H⋯S and C-H⋯O hydrogen bonds, forming zigzag chains along the b-axis direction. C-H⋯π inter-actions are also present.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536813028511DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3884346PMC
October 2013

(4-Fluoro-phen-yl)thio-urea-1,10-phenanthroline (1/1).

Acta Crystallogr Sect E Struct Rep Online 2013 23;69(Pt 9):o1468. Epub 2013 Aug 23.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.

Refluxing a mixture of 1,10-phenanthroline, (4-fluoro-phen-yl)thio-urea and cadmium(II) chloride did not produce the expected mixed-ligand complex but formed a co-crystal of the two ligands, C12H8N2·C7H7FN2S. The asymmetric unit consists of two pairs of the co-crystal mol-ecules. In each (4-fluoro-phen-yl)thio-urea mol-ecule, the planes of the N2CS thio-urea units are almost perpendicular to the corresponding fluoro-benzene rings, subtending angles of 76.53 (7) and 85.25 (7)°. In the crystal, N-H⋯N and N-H⋯S hydrogen bonds form inversion dimers from the co-crystal pairs. A weak π-π inter-action between the phenanthroline rings [centroid-centroid distance = 3.7430 (15)Å] is also observed.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536813023222DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3884412PMC
January 2014

Synthesis, structure and theoretical investigation into a homoleptic tris(dithiolene) tungsten.

Spectrochim Acta A Mol Biomol Spectrosc 2014 16;120:208-15. Epub 2013 Oct 16.

Fuel Cell Institute, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia; School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia. Electronic address:

A new homoleptic dithiolene tungsten complex, tris-{1,2-bis(3,5-dimethoxyphenyl)-1,2-ethylenodithiolene-S,S'}tungsten, was successfully synthesized via a reaction of the thiophosphate ester and sodium tungstate. The thiophosphate ester was prepared from 3,5-dimethoxybenzaldehyde via benzoin condensation to produce the intermediate 1,2-bis-(3,5-dimethoxyphenyl)-2-hydroxy-ethanone compound, followed by a reaction of the intermediate with phosphorus pentasulfide. FTIR, UV-Vis spectroscopy, 1H NMR and 13C NMR and elemental analysis confirmed the product as tris{1,2-bis-(3,5-dimethoxyphenyl)-1,2-ethylenodithiolene-S,S'}tungsten with the molecular formula of C54H54O12S6W. Crystals of the product adopted a monoclinic system with space group of P2(1)/n, where a=12.756(2) Å, b=21.560(3) Å, c=24.980(4) Å and β=103.998(3)°. Three thioester ligands were attached to the tungsten as bidentate chelates to form a distorted octahedral geometry. Density functional theory calculations were performed to investigate the molecular properties in a generalized-gradient approximation framework system using Perdew-Burke-Ernzerhof functions and a double numeric plus polarization basis set. The HOMO was concentrated on the phenyl ligands, while the LUMO was found along the W(S2C2)3 rings. The theoretical optical properties showed a slight blue shift in several low dielectric solvents. The solvatochromism effect was insignificant for high polar solvents.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.saa.2013.09.069DOI Listing
September 2014

Synthesis, characterization, X-ray structure and biological activities of C-5-bromo-2-hydroxyphenylcalix[4]-2-methyl resorcinarene.

Molecules 2013 Oct 29;18(11):13369-84. Epub 2013 Oct 29.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, Bangi 43600, Selangor, Malaysia.

C-5-bromo-2-hydroxyphenylcalix[4]-2-methylresorcinarene (I) was synthesized by cyclocondensation of 5-bromo-2-hydroxybenzaldehyde and 2-methylresorcinol in the presence of concentrated HCl. Compound I was characterized by infrared and nuclear magnetic resonance spectroscopic data. X-ray analysis showed that this compound crystallized in a triclinic system with space group of Pī, a = 15.9592(16)Å, b = 16.9417(17)Å, c = 17.0974(17)Å, α = 68.656(3)°, β = 85.689(3)°, γ = 81.631(3)°, Z = 2 and V = 4258.6(7)Å3. The molecule adopts a chair (C2h) conformation. The thermal properties and antioxidant activity were also investigated. It was strongly antiviral against HSV-1 and weakly antibacterial against Gram-positive bacteria. Cytotoxicity testing on Vero cells showed that it is non-toxic, with a CC50 of more than 0.4 mg/mL.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.3390/molecules181113369DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270492PMC
October 2013

1-(2-Chloro-phen-yl)-3-(2-ethyl-hexa-noyl)thio-urea.

Acta Crystallogr Sect E Struct Rep Online 2013 10;69(Pt 8):o1220. Epub 2013 Jul 10.

Department of Physics, Government Arts College for Women (Autonomous), Pudukkottai 622 001, India.

In the title compound, C15H21ClN2OS, the central chromophore moiety (C2N2OS) is approximately planar, with a maximum deviation of -0.027 (1) Å, and is oriented at a dihedral angle of 86.7 (1)° with respect to the chloro-phenyl ring. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation. In the crystal, mol-ecules associate via N-H⋯S hydrogen bonds, forming inversion dimers with motif R 2 (2)(8). These dimers are further connected by N-H⋯O hydrogen bonds, forming R 2 (2)(12) dimers. As a result, hydrogen-bonded chains running along [110] are formed. C-H⋯S inter-actions also occur. The terminal two C atoms of the butyl chain are disordered over two positions with an occupancy ratio of 0.54:0.46.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S160053681301828XDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3793726PMC
October 2013

3-Chloro-N-[N-(furan-2-carbon-yl)hydrazinocarbo-thio-yl]benzamide.

Acta Crystallogr Sect E Struct Rep Online 2013 21;69(Pt 10):o1567. Epub 2013 Sep 21.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.

In the title compound C13H10ClN3O3S, the benzoyl group maintains its trans conformation against the thiono group about the C-N bond and the intra-molecular hydrogen bond between the benzoyl O atom and thio-amide H atom. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules, forming chains along the b-axis direction. In addition, C-H⋯π inter-actions occur between a phenyl H atom and the furan ring.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S1600536813025440DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3790427PMC
October 2013

A study on dispersion and characterisation of α-mangostin loaded pH sensitive microgel systems.

Chem Cent J 2013 16;7:85. Epub 2013 May 16.

School of Chemical Sciences & Food Technology, Faculty Science and Technology, Universiti Kebangsaan Malaysia, Bangi, Selangor 43600, Malaysia.

Background: α-Mangostin was extracted with methanol from the rind of mangosteen fruit and purified by using silica gel column chromatography technique. The compound is characterised using infrared, (13)C and (1)H NMR as well as UV-vis spectroscopy. The α-mangostin dispersion in colloidal systems was studied by incorporating it with an ionic microgel, poly (N-Isopropylacrylamide)-co-2VP at different pH.

Result: The DLS result showed the size of microgel-α-mangostin mixture declined from 548 nm to 200 nm upon the increment of the pH. Moreover, it was found the morphology of loaded compound depended largely on the nature of the continuous phase of the microgel system. Interestingly, by manipulating the pH, α-mangostin tends to form crystal at extremely low pH and transforms into spherical shapes at pH 6.

Conclusion: This research shows different structures of the α-mangostin particle that are attributed by adjusting the pH using microgel systems as a template.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1186/1752-153X-7-85DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3662622PMC
May 2014

4-Chloro-anilinium thio-cyanate.

Acta Crystallogr Sect E Struct Rep Online 2012 Jul 2;68(Pt 7):o1988. Epub 2012 Jun 2.

School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.

In the title compound, C(6)H(7)ClN(+)·NCS(-), the benzene ring and the protonated amine and chloro substituents are nearly planar, with a maximum deviation of 0.002 (2) Å for the N atom. In the crystal, the mol-ecules are linked by N-H⋯N and N-H⋯S hydrogen bonds into a chain along the b axis.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1107/S160053681202377XDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3393264PMC
July 2012