Synthesis and Antitubercular Activity of 2‐(substituted phenyl/benzyl‐amino)‐6‐(4‐chlorophenyl)‐5‐(methoxycarbonyl)‐4‐methyl‐3,6‐dihydropyrimidin‐1‐ium Chlorides
Синтез и противотуберкулёзная активность хлоридов 2-(замещённого фенила/бензиламино)-6-(4-хлорфенил)-5-(метоксикарбонил)-4-метил-3,6-дигидропиримидин-1-ия
2012-11-14
SCID: 54.1/agjjraan
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Antitubercular activityDihydropyrimidinium chloridesMultidrug-resistant tuberculosisMycobacterium tuberculosis H37RvSingle-crystal X-ray crystallography
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Abstract (AI)
A series of 2-(substituted phenyl/benzyl-amino)-6-(4-chlorophenyl)-5-(methoxycarbonyl)-4-methyl-3,6-dihydropyrimidin-1-ium chlorides 7-13 and 15 was synthesized in their hydrochloride salt form. The title compounds were characterized by FT-IR, NMR ((1)H and (13)C) and elemental analysis. They were evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv, multidrug resistance tuberculosis and extensively drug resistance tuberculosis by agar diffusion method and tested for the cytotoxic action on peripheral blood mononuclear cells by MTT assay. Among all the tested compounds in the series, compounds 7 and 11 emerged as promising antitubercular agents at 16 μg/mL against multidrug resistance tuberculosis and over 64 μg/mL against extensively drug resistance tuberculosis. The conformational features and supramolecular assembly of the promising compounds 7 and 11 were determined by single crystal X-ray study.
Key Findings
1
A series of hydrochloride salts, compounds 7–13 and 15, was synthesized with substituted phenyl or benzyl amino groups.
2
Compounds 7 and 11 exhibited antitubercular activity at concentrations above 64 μg/mL against extensively drug-resistant tuberculosis.
3
Compounds 7 and 11 showed promising antitubercular activity at 16 μg/mL against multidrug-resistant Mycobacterium tuberculosis.
4
The conformations and supramolecular assemblies of promising compounds 7 and 11 were determined by single-crystal X-ray diffraction, while cytotoxicity was assessed using peripheral blood mononuclear cells.
5
The synthesized compounds were structurally characterized using FT-IR, 1H and 13C NMR spectroscopy, and elemental analysis.
Research Object
2-(substituted phenyl/benzyl-amino)-6-(4-chlorophenyl)-5-(methoxycarbonyl)-4-methyl-3,6-dihydropyrimidin-1-ium chloride compounds (7–13 and 15)
Research Subject
The in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv, multidrug-resistant tuberculosis, and extensively drug-resistant tuberculosis, together with cytotoxicity toward peripheral blood mononuclear cells
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2012-11-14
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