A short entry to alpha-substituted gamma-alkylidene pentenolides. Synthesis and preliminary biological evaluation of novel gelastatin analogues.
Biologically interesting 2-substituted 4-alkylidene pentenolides were prepared with complete control of regio- and stereoselectivity from 2-iodo allylic alcohols via an array of Pd-catalyzed processes, including alkynylation with methyl propiolate, tributyltin hydride addition, and alpha-functionalization. Some of the compounds possess selective cytostatic activity against ovarian carcinoma HeLa S3 and leukemia CCRF-CEM cell lines.
Pavlík
Jan
J
Centre for New Antivirals and Antineoplastics, Department of Inorganic and Organic Chemistry, Charles University, Faculty of Pharmacy, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic.
Snajdr
Ivan
I
Kunes
Jirí
J
Spulák
Marcel
M
Pour
Milan
M
D000475:Alkenes / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001555:Benzene Derivatives / Q000737:chemistry; D002384:Catalysis; D045744:Cell Line, Tumor; D006801:Humans; D020128:Inhibitory Concentration 50; D051379:Mice; D010165:Palladium / Q000737:chemistry; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000475:Alkenes; D000970:Antineoplastic Agents; D001555:Benzene Derivatives; D011422:Propionates; D010165:Palladium