Synthesis and antimicrobial evaluation of 1-(benzofuran-2-yl)-4-nitro-3-arylbutan-1-ones and 3-(benzofuran-2-yl)-4,5-dihydro-5-aryl-1-[4-(aryl)-1,3-thiazol-2-yl]-1H-pyrazoles.
2-Acetylbenzofuran 1 on treatment with substituted aldehydes affords the corresponding chalcones 2a-c. Treatment of the chalcones with nitromethane under Michael addition condition furnished the corresponding Michael adducts 3a-c. Cyclocondensation of the chalcones 2a and 2b with thiosemicarbazide under basic refluxing conditions gave 3-(benzofuran-2-yl)-5-(4-aryl)-4,5-dihydropyrazole-1-carbothioamides 4a,b. The pyrazolines 7a-d were synthesized by treating 4a,b with phenacyl bromides in refluxing ethanol. All the synthesized compounds were screened for their antibacterial and antifungal activities at 100 microg concentration. Some of our compounds showed excellent antimicrobial activities than control drugs.
Abdel-Wahab
Bakr F
BF
Applied Organic Chemistry Department, National Research Center, Dokki, Giza, Egypt. bakrfatehy@yahoo.com
Abdel-Aziz
Hatem A
HA
Ahmed
Essam M
EM
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001234:Aspergillus niger / Q000187:drug effects; D001412:Bacillus subtilis / Q000187:drug effects; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D047188:Chalcones / Q000737:chemistry; D003500:Cyclization; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013854:Thioamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001572:Benzofurans; D047188:Chalcones; D011720:Pyrazoles; D013854:Thioamides