期刊
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
卷 45, 期 12, 页码 6120-6126出版社
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2010.09.051
关键词
Cycloaddition; Azomethine ylide; Spiroheterocycle; Oxindolopyrrolizidines; Antibacterial activity; Antifungal activity
Reaction of (E)-3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones with azomethine ylide (generated in situ via decarboxylative condensation of isatin with L-proline) in refluxing methanol afforded 1'-(aryl)-2'-(2-thienylcarbonyl)-spiro[3H-indole-3,3'-[3H]pyrrolizin]-2-ones as the sole product in a regiospecific manner. The synthesized compounds have been characterized by their elemental, analytical and spectral studies. The synthesized compounds were screened for their antibacterial and antifungal activities against a spectrum of microbial organisms. These studies proved that compounds 1'-(p-chlorophenyl)-2'-(2-thienylcarbonyl)-spiro[3H-indole-3,3'-[3H]pyrrolizin]-2-one (4b), 1'-(p-fluorophenyl)-2'-(2-thienylcarbonyl)-spiro[3H-indole-3,3'-[3H] pyrrolizin]-2-one (4d) and 1'-(p-methoxyphenyl)-2'-(2-thienylcarbonyl)-spiro[3H-indole-3,3'[3H] pyrrolizin]-2-one (4h) against Staphylococcus aureus, 1'-(p-chlorophenyl)-2'-(2-thienylcarbonyl)-spiro[3H-indole-3,3'[3H]pyrrolizin]-2-one (4b), 1'-(p-methylphenyl)-2'-(2-thienylcarbonyl)-spiro[3H-indole-3,3'-[3H]pyrrolizin]-2-one (4c) and 1'-(p-fluorophenyl)-2'-(2-thienylcarbonyl)-spiro[3H-indole-3,3'[3H]pyrrolizin]-2-one (4d) against Salmonella typhi show maximum inhibition potency at low concentration (6.25 mu g/mL) whereas 4d against Candida albicans and 4b and 4d against Rhizopus sp. showed beneficial antifungal activity at minimum concentration. (C) 2010 Elsevier Masson SAS. All rights reserved.
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