Synthesis, structure-activity relationship of iodinated-4-aryloxymethyl-coumarins as potential anti-cancer and anti-mycobacterial agents.
A series of new iodinated-4-aryloxymethylcoumarins 6, 8 and 10 have been obtained from the reaction of various 4-bromomethylcoumarins 4 with 2-iodophenol 5, 3-iodophenol 7 and 4-iodophenol 9 respectively. All the title compounds were screened for anticancer activity against two cancer cell lines (MDA-MB human adenocarcinoma mammary gland and A-549 human lung carcinoma) and two mycobacterial strains (Mycobacterium tuberculosis H₃₇ RV and Mycobacterium phlei). The SAR results indicate that nine compounds are potent, among these 10h and 10i having chlorine are most effective. This is the first report assigning in vitro anti-mycobacterial, anticancer and structure-activity relationship for this new class of iodinated-4-aryloxymethyl-coumarins.
P.G. Department of Chemistry, P.C. Jabin Science College, Hubli 580031, Karnataka, India. Electronic address: mahanteshachem@gmail.com.
Mahantesha
M
Basanagouda
P.G. Department of Chemistry, P.C. Jabin Science College, Hubli 580031, Karnataka, India.
Vishwanath B
VB
Jambagi
P.G. Department of Chemistry, P.C. Jabin Science College, Hubli 580031, Karnataka, India.
Nivedita N
NN
Barigidad
P.G. Department of Studies and Research in Polymer Science, Sir, M.V. PG Centre, Mandya 571402, University of Mysore, Karnataka, India.
Sandeep S
SS
Laxmeshwar
Department of Physics, L.V.D. College, Raichur 584103, Karnataka, India.
Venkatesh
V
Devaru
Department of Chemistry, L.V.D. College, Raichur 584103, Karnataka, India.
Narayanachar
D000970:Antineoplastic Agents / Q000494:pharmacology*; D000995:Antitubercular Agents / Q000494:pharmacology*; D045744:Cell Line, Tumor; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D007455:Iodine / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D000995:Antitubercular Agents; D003374:Coumarins; D007455:Iodine
Anti-mycobacterial; Anticancer; Coumarin; Heterocycles; Iodine; SAR