An expeditious synthesis and anticancer activity of novel 4-(3'-indolyl)oxazoles.
A series of 4-(3'-indolyl)oxazole congeners have been synthesized and studied for their cytotoxicity against six cancer cell lines. Reaction of 3-acetyl-1'-benzenesulfonylindole with [hydroxy(tosyloxy)iodo]benzene afforded pure 3-tosyloxyacetyl-1'-benzenesulfonylindole. Microwave-accelerated neat reaction of 3-tosyloxyacetyl-1-benzenesulfonylindole with amides resulted in the exclusive formation of 4-(1'-benzenesulfonylindol-3'-yl)-2-substituted oxazoles (4) in very good yield. Treatment of 4 with aqueous sodium hydroxide under refluxing conditions afforded pure 4-(3'-indolyl)-2-substituted oxazoles (5) in excellent yield. The 4-(3'-indolyl)oxazoles 5d and 11 were found to be most cytotoxic and selective against various cancer cell lines. Compounds 5g, 5j and 5l showed moderate anticancer activity.
Kumar
Dalip
D
Chemistry Group, Birla Institute of Technology and Science, Pilani 333031, Rajasthan, India. dalipk@bits-pilani.ac.in
Kumar
N Maruthi
NM
Sundaree
Swapna
S
Johnson
Emmanuel O
EO
Shah
Kavita
K
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy; D010080:Oxazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D007211:Indoles; D010080:Oxazoles