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1.
Acta Crystallogr C Struct Chem ; 72(Pt 9): 670-8, 2016 Sep 01.
Article in English | MEDLINE | ID: mdl-27585930

ABSTRACT

Hydrazone derivatives exhibit a wide range of biological activities, while pyrazolo[3,4-b]quinoline derivatives, on the other hand, exhibit both antimicrobial and antiviral activity, so that all new derivatives in these chemical classes are potentially of value. Dry grinding of a mixture of 2-chloroquinoline-3-carbaldehyde and 4-methylphenylhydrazinium chloride gives (E)-1-[(2-chloroquinolin-3-yl)methylidene]-2-(4-methylphenyl)hydrazine, C17H14ClN3, (I), while the same regents in methanol in the presence of sodium cyanoborohydride give 1-(4-methylphenyl)-4,9-dihydro-1H-pyrazolo[3,4-b]quinoline, C17H15N3, (II). The reactions between phenylhydrazinium chloride and either 2-chloroquinoline-3-carbaldehyde or 2-chloro-6-methylquinoline-3-carbaldehyde give, respectively, 1-phenyl-1H-pyrazolo[3,4-b]quinoline, C16H11N3, (III), which crystallizes in the space group Pbcn as a nonmerohedral twin having Z' = 3, or 6-methyl-1-phenyl-1H-pyrazolo[3,4-b]quinoline, C17H13N3, (IV), which crystallizes in the space group R\overline{3}. The molecules of compound (I) are linked into sheets by a combination of N-H...N and C-H...π(arene) hydrogen bonds, and the molecules of compound (II) are linked by a combination of N-H...N and C-H...π(arene) hydrogen bonds to form a chain of rings. In the structure of compound (III), one of the three independent molecules forms chains generated by C-H...π(arene) hydrogen bonds, with a second type of molecule linked to the chains by a second C-H...π(arene) hydrogen bond and the third type of molecule linked to the chain by multiple π-π stacking interactions. A single C-H...π(arene) hydrogen bond links the molecules of compound (IV) into cyclic centrosymmetric hexamers having \overline{3} (S6) symmetry, which are themselves linked into a three-dimensional array by π-π stacking interactions.

2.
Eur J Med Chem ; 89: 616-27, 2015 Jan 07.
Article in English | MEDLINE | ID: mdl-25462270

ABSTRACT

New anti-tubercular agents, imidazo[1,2-a]pyridine-2-carboxamide derivatives (5a-q) have been designed and synthesized. The structural considerations of the designed molecules were further supported by the docking study with a long-chain enoyl-acyl carrier protein reductase (InhA). The chemical structures of the new compounds were characterized by IR, (1)H NMR, (13)C NMR, HRMS and elemental analysis. In addition, single crystal X-ray diffraction has also been recorded for compound 5f. Compounds were evaluated in vitro against Mycobacterium tuberculosis H37Rv, and cytotoxicity against HEK-293T cell line. Amongst the tested compounds 5j, 5l and 5q were emerged as good anti-tubercular agents with low cytotoxicity. The structure-anti TB activity relationship of these derivatives was explained by molecular docking.


Subject(s)
Antitubercular Agents/chemical synthesis , Antitubercular Agents/pharmacology , Imidazoles/chemistry , Molecular Docking Simulation , Mycobacterium tuberculosis/drug effects , Pyridines/chemistry , Antitubercular Agents/chemistry , Cell Proliferation/drug effects , Crystallography, X-Ray , Dose-Response Relationship, Drug , HEK293 Cells , Humans , Imidazoles/pharmacology , Models, Molecular , Molecular Structure , Pyridines/pharmacology , Structure-Activity Relationship
3.
Eur J Med Chem ; 77: 288-97, 2014 Apr 22.
Article in English | MEDLINE | ID: mdl-24657565

ABSTRACT

New antimicrobial agents, imidazo[4,5-c]pyridine derivatives have been synthesized. We have developed a new synthetic protocol for the final reaction, an efficient microwave-assisted synthesis of imidazo[4,5-c]pyridines from substituted 3,4-diaminopyridine and carboxylic acids in presence of DBU mediated by T3P. The chemical structures of the new compounds were characterized by IR, (1)H NMR, (13)C NMR, mass spectral analysis and elemental analysis. In addition, single crystal X-ray diffraction has also been recorded for compound 9c. The in vitro antimicrobial activities of the compounds were conducted against various Gram-negative, Gram-positive bacteria and fungi. Amongst the tested compounds 9c, 9e, 9g, 9k and 9l displayed promising antimicrobial activity. The molecular docking of GlcN-6-P synthase with newly synthesized compounds was carried out.


Subject(s)
Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Imidazoles/pharmacology , Molecular Docking Simulation , Pyridines/pharmacology , Anti-Bacterial Agents/chemical synthesis , Antifungal Agents/chemical synthesis , Bacteria/drug effects , Crystallography, X-Ray , Dose-Response Relationship, Drug , Fungi/drug effects , Humans , Imidazoles/chemical synthesis , Imidazoles/chemistry , Microbial Sensitivity Tests , Molecular Structure , Pyridines/chemical synthesis , Pyridines/chemistry , Structure-Activity Relationship
4.
Acta Crystallogr C ; 64(Pt 8): o423-5, 2008 Aug.
Article in English | MEDLINE | ID: mdl-18682647

ABSTRACT

The crystal and molecular structure of the title compound, C(15)H(26)O(4)Si(2), reveals a self-assembly facilitated via the rare co-existence of dimeric and catemeric patterns, which is attributed to the influence of the trimethylsilyl groups. The structure is dicussed in the context of a database search and subsequent analysis of structures of cis-1,2-dicarboxylic acids.

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