Počet záznamů: 1
Microwave-assisted synthesis, molecular docking and antitubercular activity of 1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives
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SYSNO ASEP 0385875 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Microwave-assisted synthesis, molecular docking and antitubercular activity of 1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives Tvůrce(i) Mohan, S. B. (IN)
Kumar, B. V. V. R. (IN)
Dinda, S. C. (IN)
Naik, D. (IN)
Seenivasan, S. P. (IN)
Kumar, V. (IN)
Rana, D. N. (IN)
Brahmkshatriya, Pathik (UOCHB-X)Celkový počet autorů 8 Zdroj.dok. Bioorganic and Medicinal Chemistry Letters. - : Elsevier - ISSN 0960-894X
Roč. 22, č. 24 (2012), s. 7539-7542Poč.str. 4 s. Jazyk dok. eng - angličtina Země vyd. GB - Velká Británie Klíč. slova antitubercular ; binding interactions ; luciferase reporter phage (LRP) assay ; microwave-assisted ; molecular docking Vědní obor RIV CC - Organická chemie CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000311425500051 DOI https://doi.org/10.1016/j.bmcl.2012.10.032 Anotace Based on bioisosteric similarities with isoniazid, a series of 1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives has been designed. The target compounds have been synthesized by multicomponent reaction which involves one-pot organic reactions using ethylcyanoacetate, urea/thiourea and arylaldehydes in presence of ethanolic K2CO3. Two methodologies, conventional and microwave-assisted, have been adopted for the synthesis. The later strategy gave high yields in less than 10 min as compared to long hours using the former approach. Molecular docking of the target compounds into the enzyme Mycobacterium tuberculosis enoyl reductase (InhA) revealed important structural information on the plausible binding interactions. Major binding interactions were found to be of dispersion type (residues Tyr158, Ile215, Met103 and Met199) and a hydrogen bond with Tyr158. Binding poses of the all the compounds were energetically favorable and showed good interactions with the active site residues. Few selected compounds were also evaluated for antitubercular activity in vitro against drug-sensitive M. tuberculosis H37Rv strain and clinically isolated S, H, R and E resistant M. tuberculosis by luciferase reporter phage (LRP) assay method. Some compounds displayed promising antimycobacterial activity comparable or less than the standard drugs isoniazid and rifampicin. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Rok sběru 2013
Počet záznamů: 1