Synthesis, anticancer, and anti-inflammatory activity evaluation of methanesulfonamide and amidine derivatives of 3,4-diaryl-2-imino-4-thiazolines.
Condensation of 3,4-diaryl-2-imino-4-thiazoli-nes 1a-j with methanesulfonyl chloride gave methanesulfonamide derivatives 2a-j. Condensation of 2-cyanopyrazine, 4-cyanopyridine, and 2-cyanopyridine with 3,4-diaryl-2- imino-4-thiazolines 1h-m in the presence of sodium methoxide afforded amidine derivatives 3a-j. Compounds 2a-j and 3a-j were screened against various human cancer cell lines (COLO-205, HEP-2, A-549, IMR-32) and their percentage growth inhibition profile determined at 1 x 10(-5)M. The anti-inflammatory activity of these compounds was assessed using the carrageenan-induced paw edema model. Compound 2i exhibited 34.7% anti-inflammatory activity at 50 mg/kg p.o., which is comparable to standard care drug phenyl butazone (37% activity at 50 mg/kg p.o.).
Sondhi
Sham M
SM
Department of Chemistry, Indian Institute of Technology-Roorkee, Roorkee 247667, UA, India. sondifcy@iitr.ernet.in
Rani
Reshma
R
Gupta
P P
PP
Agrawal
S K
SK
Saxena
A K
AK
D000578:Amidines / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D002351:Carrageenan; D045744:Cell Line, Tumor; D004195:Disease Models, Animal; D004354:Drug Screening Assays, Antitumor; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D005260:Female; D006801:Humans; D008297:Male; D011247:Pregnancy; D051381:Rats; D013449:Sulfonamides / Q000138:chemical synthesis / Q000494:pharmacology*; D013844:Thiazoles / Q000138:chemical synthesis / Q000494:pharmacology*
D000578:Amidines; D000893:Anti-Inflammatory Agents; D000970:Antineoplastic Agents; D013449:Sulfonamides; D013844:Thiazoles; C036871:methanesulfonamide; D002351:Carrageenan