新型金刚烷基查尔酮：合成、抗菌及抗癌活性

New Adamantyl Chalcones: Synthesis, Antimicrobial and Anticancer Activities.

作者信息

Tabbi Aouatef, Tebbani Dahmane, Caporale Angelamaria, Saturnino Carmela, Nabavi S F, Giuseppe Palma, Arra Claudio, Canturk Zerrin, Turan-Zitouni Gulhan, Merazig Hocine, Sobarzo-Sanchez Eduardo, Rastrelli Luca

机构信息

Department of chemistry, Faculty of sciences, Mentouri University, 25000 Constantine, Algeria.

出版信息

Curr Top Med Chem. 2017;17(4):498-506. doi: 10.2174/1568026616666160824121935.

DOI:10.2174/1568026616666160824121935

PMID:27558673

Abstract

BACKGROUND

A new variety of adamantyl chalcones (2, 3a-o) were efficiently prepared by Claisen-Schmidt reaction of 4-adamantyl acetophenone 2 with a serie of aromatic aldehydes in good yields. Their structures were confirmed by spectroscopic data, and the relative configuration of 3d was confirmed by X-ray crystallography. All synthesized chalcones were tested against a panel of Grampositive and Gram-negative bacteria and pathogenic fungus and displayed strong antibacterial activity against Enterococcus faecali 29212, Pseudomonas aeruginosa ATCC27853, Escherichia coli and interesting antifungal activity against Candida glabrata ATCC 90030.

RESULT

The effect of these compounds was also tested in vitro as antitumor on Miapaca2 cells. Compounds also showed anticancer activity against human pancreas cancer cell MiaPaca2.

摘要

背景

通过4-金刚烷基苯乙酮2与一系列芳香醛的克莱森-施密特反应高效制备了一种新型金刚烷基查耳酮（2, 3a-o），产率良好。通过光谱数据确认了它们的结构，并且通过X射线晶体学确认了3d的相对构型。对所有合成的查耳酮针对一组革兰氏阳性和革兰氏阴性细菌以及致病真菌进行了测试，结果显示其对粪肠球菌29212、铜绿假单胞菌ATCC27853、大肠杆菌具有较强的抗菌活性，并且对光滑念珠菌ATCC 90030具有有趣的抗真菌活性。