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Crystal structures and biological activity of 1,1,4-triphenyl-substituted 1,3-enyne compounds.
Acta Crystallographica Section C ( IF 0.8 ) Pub Date : 2019-12-12 , DOI: 10.1107/s2053229619016127
Leslie W Pineda 1 , María Laura Arias 2 , Jorge A Cabezas 1
Affiliation  

1,3-Enyne structural motifs are versatile building blocks in organic synthesis and occur widely in various natural products with many of them being highly active as cytotoxic macrolides and antitumour antibiotics. This article presents the crystal structure of three 1,1,4-triphenyl-substituted 1,3-enynes, viz. 4-(2-methylphenyl)-1,1-diphenylbut-1-en-3-yne, C23H18 (1), 4-(2-methoxyphenyl)-1,1-diphenylbut-1-en-3-yne, C23H18O (2), and 4-(4-nitrophenyl)-1,1-diphenylbut-1-en-3-yne, C22H15NO2 (3). The benzene ring at position 4 of the but-1-en-3-yne group bears a weakly activating methyl group in compound 1, a moderately activating methoxy group in 2 and a strongly deactivating nitro group in 3. The crystal structures of 1 and 3 both have monoclinic symmetry, while that of 2 is orthorhombic, and all of them have one molecule in the asymmetric unit. All three compounds were investigated for their antibacterial and antifungal activities. Interestingly, enyne 2 is the only compound tested that inhibited the growth of Aspergillus niger.

中文翻译:

1,1,4-三苯基取代的1,3-烯炔化合物的晶体结构和生物学活性。

1,3-烯炔结构基序是有机合成中的通用构建基块,广泛存在于各种天然产物中,其中许多作为细胞毒性大环内酯类和抗肿瘤抗生素具有很高的活性。本文介绍了三个1,1,4-三苯基取代的1,3-烯炔的晶体结构。4-(2-甲基苯基)-1,1-二苯基丁-1-烯-3-炔,C23H18(1),4-(2-甲氧基苯基)-1,1-二苯基丁-1-烯-3-炔,C23H18O (2)和4-(4-硝基苯基)-1,1-二苯基丁-1-烯-3-炔,C22H15NO2(3)。but-1-en-3-yne基团第4位的苯环在化合物1中具有弱活化甲基,在2中具有中等活化甲氧基,在3中具有强烈失活硝基。1和1的晶体结构3个均具有单斜对称性,而2个均具有斜方对称性,并且它们的不对称单元均具有一个分子。研究了这三种化合物的抗菌和抗真菌活性。有趣的是,烯炔2是唯一测试的抑制黑曲霉生长的化合物。
更新日期:2019-12-12
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