Novel molecular hybrids of cinnamic acids and guanylhydrazones as potential antitubercular agents.
In an attempt to identify potential new agents active against tuberculosis, 20 novel phenylacrylamide derivatives incorporating cinnamic acids and guanylhydrazones were synthesized using microwave assisted synthesis. Activity of the synthesized compounds was evaluated using resazurin microtitre plate assay (REMA) against Mycobacterium tuberculosis H37Rv. Based on empirical structure-activity relationship data it was observed that both steric and electronic parameters play major role in the activity of this series of compounds. Compound 7s (2E)-N-((-2-(3,4-dimethoxybenzylidene) hydrazinyl) (imino) methyl)-3-(4-methoxyphenyl) acrylamide showed MIC of 6.49microM along with good safety profile of >50-fold in VERO cell line. Thus, this compound could act as a potential lead for further antitubercular studies.
Bairwa
Ranjeet
R
Institute of Chemical Technology, Nathalal Parikh Marg, Matunga, Mumbai 400 019, India.
Kakwani
Manoj
M
Tawari
Nilesh R
NR
Lalchandani
Jaya
J
Ray
M K
MK
Rajan
M G R
MG
Degani
Mariam S
MS
D020106:Acrylamide / Q000737:chemistry; D000178:Acrylamides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000818:Animals; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002522:Chlorocebus aethiops; D002934:Cinnamates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D015195:Drug Design; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008872:Microwaves; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014709:Vero Cells
D000178:Acrylamides; D000995:Antitubercular Agents; D002934:Cinnamates; D006835:Hydrazones; C549576:N-((2-(3,4-dimethoxybenzylidene)hydrazinyl)(imino)methyl)-3-(4-methoxyphenyl)acrylamide; C029010:cinnamic acid; D020106:Acrylamide