Synthesis and antimicrobial activity of novel tetrahydrobenzothienopyrimidines.
Due to the rapidly growing number of resistant strains of bacteria, the search for antibacterial agents with new modes of action will always remain an important and challenging task. Thus, the reaction of 2-substituted or unsubstituted-4-(4-acetylanilino)-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidine derivatives 1-3 with the hydrazine derivatives, semi and/or thiosemicarbazides, provided the corresponding hydrazones 4-6 and semi and/or thiosemicarbazones 7-9. Claisen-Schmidt condensation of compounds 1 or 2 with the appropriate aldehyde yielded the chalcones 10, 11 which, when treated with hydroxylamine hydrochloride gave rise to the isoxazoline-containing compounds 12, 13. Furthermore, reacting the respective chalcones 10, 11 with different hydrazines, urea and/or thiourea, furnished compounds 14, 15, 16, and 17 respectively. Representative compounds were tested for their antimicrobial activity against Candida albicans and certain gram-positive and gram-negative bacteria. Their MICs were then determined. Compound 15e, showed a broad spectrum of activity while most of the other compounds showed varying antimicrobial activity.
Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University, Kasr El Aini Street, Cairo 11562, Egypt. phd_amalabdelhaleem@hotmail.com
Amal Abdel Haleem Mohamed
AA
Eissa
Ashraf Ahmed
AA
Moneer
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects / Q000254:growth & development; D008826:Microbial Sensitivity Tests / Q000706:statistics & numerical data; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects / Q000254:growth & development
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D011743:Pyrimidines; C476003:thienopyrimidine