Synthesis of antitumor 6-alkylidenepenicillanate sulfones and related 3-alkylidene-2-azetidinones.
6-alkylidenepenicillanate sulfoxides and sulfones were synthesized on the base of 6-oxopenicillanate esters. The targeted splitting of their thiazolidine ring led to the formation of 3-alkylidene substituted 4-heteryldithio and 4-methylsulfonyl azetidin-2-ones. Some of mono and bicyclic beta-lactams revealed potent cytotoxic properties towards monolayer tumor cells in <10-microM concentrations.
Veinberg
Grigory
G
Latvian Institute of Organic Synthesis, 21 Aizkraukles Street, Riga, LV 1006, Latvia. veinberg@osi.lv
Shestakova
Irina
I
Vorona
Maxim
M
Kanepe
Iveta
I
Lukevics
Edmunds
E
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology; D001384:Azetidines / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D045744:Cell Line, Tumor; D006224:Cricetinae; D006801:Humans; D051379:Mice; D010406:Penicillins / Q000138:chemical synthesis* / Q000494:pharmacology
C116379:2-azetidinone; D000903:Antibiotics, Antineoplastic; D001384:Azetidines; D010406:Penicillins