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7H-苯并[h]色烯并[2,3-d]嘧啶和14H-苯并[h]色烯并[3,2-e][1,2,4]三唑并[1,5-c]嘧啶衍生物的结构表征及抗菌活性

Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives.

作者信息

Okasha Rawda M, Albalawi Fawzia F, Afifi Tarek H, Fouda Ahmed M, Al-Dies Al-Anood M, El-Agrody Ahmed M

机构信息

Chemistry Department, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi Arabia.

Chemistry Department, Faculty of Science, King Khalid University, Abha 61413, P.O. Box 9004, Saudi Arabia.

出版信息

Molecules. 2016 Nov 1;21(11):1450. doi: 10.3390/molecules21111450.

Abstract

Three new series of chromene molecules have been synthesized in order to explore their antimicrobial activity. The series encompass 2-substituted 14-(4-halophenyl)-12-methoxy-14-benzo[]chromeno[3,2-][1,2,4]-triazolo[1,5-]pyrimidines -, 9-benzylideneamino-7-(4-halo-phenyl)-5-methoxy-8-imino-7-benzo-[]chromeno[2,3-]pyrimidines - and 3-ethoxycarbonyl-14-(4-halophenyl)-12-methoxy-14-benzo-[]chromeno[3,2-][1,2,4]triazolo[1,5-]pyrimidine-2-one derivatives -. The structure of these novel compounds were confirmed using IR, ¹H- and C-NMR as well as MS spectroscopy. The new compounds were evaluated in vitro for their antimicrobial activity and it was demonstrated that 7-benzochromenopyrimidine and derivatives of 14-benzochromenotriazolopyrimidine exhibited the most promising antibacterial activities compared to the reference antimicrobial agents. The structure activity relationship (SAR) studies of the target compounds agreed with the in vitro essays and confirmed higher potent antimicrobial activity against some of the tested microorganisms.

摘要

为了探索其抗菌活性,已合成了三个新系列的色烯分子。该系列包括2-取代的14-(4-卤苯基)-12-甲氧基-14-苯并[]色烯并[3,2-][1,2,4]-三唑并[1,5-]嘧啶 -、9-亚苄基氨基-7-(4-卤苯基)-5-甲氧基-8-亚氨基-7-苯并[]色烯并[2,3-]嘧啶 - 和3-乙氧羰基-14-(4-卤苯基)-12-甲氧基-14-苯并[]色烯并[3,2-][1,2,4]三唑并[1,5-]嘧啶-2-酮衍生物 -。使用红外光谱、¹H-和C-NMR以及质谱对这些新型化合物的结构进行了确证。对新化合物的抗菌活性进行了体外评估,结果表明,与参考抗菌剂相比,7-苯并色烯嘧啶和14-苯并色烯三唑嘧啶的衍生物表现出最有前景的抗菌活性。目标化合物的构效关系(SAR)研究与体外试验结果一致,并证实对一些受试微生物具有更高的强效抗菌活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b151/6273467/70a975411cc1/molecules-21-01450-sch001.jpg

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