Synthesis of novel 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)uracil and -thymine, and their corresponding S-oxidized derivatives

被引：14
作者：
Núñez, MD
Entrena, A
Rodríguez-Serrano, F
Marchal, JA
Aránega, A
Gallo, MA
Espinosa, A
Campos, JM
机构：
[1] Fac Farm, Dept Quim Farmaceut & Organ, Granada 18071, Spain
[2] Fac Ciencias, Dept Biol Celular, Granada 18071, Spain
[3] Fac Ciencias Expt & Salud, Dept Ciencias Salud, Jaen 23071, Spain
[4] Fac Med, Dept Ciencias Morfol, Granada, Spain
来源：
TETRAHEDRON | 2005年 / 61卷 / 43期
关键词：
antitumour compounds; benzoxathiepins; computer-assisted methods; uracils;
D O I：
10.1016/j.tet.2005.07.065
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
On the basis of molecular variations on isosteric replacements from the prototype 1-(2,3-dihydro-5H- 1,4-benzodioxepin-3-yl)-5fluorouracil a series of 3-(2,3-dihydro-5H-4, 1-benzoxathiepin-3-yl)-uracil or -thymine O,N-acetals was prepared. The nature of the cis- and trans-sulfoxide isomers was established by means of their conformational analyses carried out with Sybyl and after comparing the theoretical results with the H-1 NMR responses of the target molecules. (RS)-3-(1,1-Dioxo-2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)thymine and (IS*, 3S*)-1-(1-oxo-3,5-dihydro-2H-4,1-benzoxathiepin-3-yl)thymine were found to be inhibitors of the MCF-7 cell growth. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：10363 / 10369
页数：7
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