Reactions with pyrrolidine-2,4-diones, III (1). Synthesis of some substituted 3-pyrrolin-2-ones and 4-hydrazonopyrrolidin-2-ones as potential antineoplastic and antimicrobial agents.
The syntheses of 3-bromo-, 3-substituted aminomethyl-, and 3-(4-substituted sulfamylphenylazo)-4-hydroxy-1,5-diphenyl-pyrrolin-2-ones 4,6 and 8 from 1,5-diphenylpyrrolidine-2,4-dione 3 via bromination aminomethylation and diazocoupling, respectively, are described. The preparation of some 1,5-diphenyl-4-(substituted thiosemicarbazono) pyrrolidin-2-ones 10 and their conversion either to 1,5-diphenyl-4-(substituted thiazol-2-ylhydrazono)pyrrolidin-2-ones 12 or to 1,5-diphenyl-4-(3,4-disubstituted-4-thiazolin-2-ylidenehydrazon o)pyrrolidin-2- ones 13, is also reported. Nine compounds were screened against P-388 lymphocytic leukemia in mice but were inactive. Two compounds (6a and 6b) exhibited in vitro activities against some Gram-positive bacteria.
el-Dine
S A
SA
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Alexandria, Egypt.
Kassem
M G
MG
Soliman
F S
FS
Saudi
M N
MN
Kader
O
O
D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002175:Candida / Q000187:drug effects; D006835:Hydrazones / Q000138:chemical synthesis* / Q000494:pharmacology; D007941:Leukemia P388 / Q000188:drug therapy; D051379:Mice; D008826:Microbial Sensitivity Tests; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D006835:Hydrazones; D011759:Pyrrolidines