两种（E,E）-和（Z,E）-噻唑-5-基戊-2,4-二烯酮。

Two (E,E)- and (Z,E)-thiazol-5-ylpenta-2,4-dienones.

作者信息

Breydo Leonid, Barnes Charles L, Gates Kent S

机构信息

Department of Chemistry, University of Missouri-Columbia, Columbia, MO 65211, USA.

出版信息

Acta Crystallogr C. 2002 Aug;58(Pt 8):o447-9. doi: 10.1107/s0108270102007503. Epub 2002 Jul 12.

DOI:10.1107/s0108270102007503

PMID:12154296

Abstract

In order to characterize the structural elements that might play a role in non-covalent DNA binding by the antitumor antibiotic leinamycin, we have solved the crystal structures of the two leinamycin analogs, methyl (R)-5-[2-[1-(tert-butoxycarbonylamino)ethyl]thiazol-4-yl]penta-(E,E)-2,4-dienoate, C(16)H(22)N(2)O(4)S, (II), and 2-methyl-8-oxa-16-thia-3,17-diazabicyclo[12.2.1]heptadeca-(Z,E)-1(17),10,12,14-tetraene-4,9-dione, C(14)H(16)N(2)O(3)S, (III). The penta-2,4-dienone moiety in both of these analogs adopts a conformation close to planarity, with the thiazole ring twisted out of the plane by 12.9 (2) degrees in (II) and by 21.4 (4) degrees in (III).

摘要

为了表征可能在抗肿瘤抗生素链黑菌素与DNA的非共价结合中发挥作用的结构元件，我们解析了两种链黑菌素类似物的晶体结构，即（R）-5-[2-[1-（叔丁氧羰基氨基）乙基]噻唑-4-基]戊-（E，E）-2,4-二烯酸甲酯，C(16)H(22)N(2)O(4)S，（II），以及2-甲基-8-氧杂-16-硫杂-3,17-二氮杂双环[12.2.1]十七碳-（Z，E）-1(17),10,12,14-四烯-4,9-二酮，C(14)H(16)N(2)O(3)S，（III）。这两种类似物中的戊-2,4-二烯酮部分均采取接近平面的构象，噻唑环在（II）中偏离平面12.9（2）度，在（III）中偏离平面21.4（4）度。