Synthesis of novel 5-fluorouracil derivatives with 1,4-oxaheteroepane moieties

被引：12

作者：

Gómez, JA ^{[1
]}

Trujillo, MA ^{[1
]}

Campos, J ^{[1
]}

Gallo, MA ^{[1
]}

Espinosa, A ^{[1
]}

机构：

[1] Fac Farm, Dept Quim Organ, Granada 18071, Spain

来源：

TETRAHEDRON | 1998年 / 54卷 / 43期

关键词：

D O I：

10.1016/S0040-4020(98)00815-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of new ring-expanded isosteres (1,4-oxaheteroepanes) of Ftorafur [1-(2-tetrahydrofuranyl)-5-fluorouracil] has been synthesized. The branching of C-3 of the seven-membered cycloacetal and the electronegativity of the Y group on the 3-YCH2 moities (Y being H, I and Cl), respectively, seem to direct their regiochemical and stereochemical outcome. The more electronegative the group Y is (and favouring accordingly the formation of an external ion pair), the more diastereoselectivity that is reached. The in vitro cytotoxicity versus HT-29 has been tested, showing that cis-3g was the only moderately active compound. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：13295 / 13312

页数：18

相关论文

共 50 条

[31] CONVENIENT SYNTHESIS OF 5-FLUOROURACIL [J].

BARTON, DHR ;

TOH, HT ;

HESSE, RH ;

PECHET, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (02) :329-&

[32] 5-fluorouracil derivatives .22. Synthesis and antitumor activities of 1-carbamoyl-5-fluorouracils [J].

Ozaki, S ;

Kong, XZ ;

Watanabe, Y ;

Hoshiko, T ;

Koga, T ;

Ogasawara, T ;

Takizawa, T ;

Fujisawa, H ;

Iigo, M ;

Hoshi, A .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1997, 45 (08) :1372-1375

[33] A SIMPLE SYNTHESIS OF 5-FLUOROURACIL BY A NOVEL RING TRANSFORMATION REACTION [J].

CHUNG, WK ;

CHUNG, JH ;

WATANABE, KA .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (02) :457-457

[34] SYNTHESIS AND PROPERTIES OF NOVEL CODRUGS OF 5-FLUOROURACIL WITH ANTIINFLAMMATORY AGENTS [J].

CYNKOWSKA, G ;

CYNKOWSKI, T ;

GUO, H ;

ASHTON, P ;

CROOKS, PA .

ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 :182-MEDI

[35] The synthesis of comb-like polymeric prodrugs of 5-fluorouracil derivatives [J].

Qiu, Fei ;

Yan, Hui ;

Wei, Lin ;

Diao, Yong .

ADVANCED DESIGN TECHNOLOGY, 2012, 421 :35-38

[36] SYNTHESIS OF O-GLYCOSIDIC DERIVATIVES OF 5-FLUOROURACIL AND THEIR ANTITUMOUR ACTIVITIES [J].

KANEKO, M ;

KIMURA, M ;

TANAKA, H ;

SHIMIZU, F ;

ARAKAWA, M ;

SHIMIZU, B .

NUCLEIC ACIDS RESEARCH, 1977, :S35-S38

[37] Synthesis and Antitumor Activities of the Diacid Solanesyl 5-Fluorouracil Esters Derivatives [J].

Xiao, Keyi ;

Dai, Ya ;

Shi, Wanqi ;

Li, Jianzhong ;

Li, Ying ;

Yin, Shufan .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (01) :169-173

[38] Synthesis and evaluation of new 5-fluorouracil antitumor cell differentiating derivatives [J].

Domínguez, JF ;

Marchal, JA ;

Correa, A ;

Carrillo, E ;

Boulaiz, H ;

Aránega, A ;

Gallo, MA ;

Espinosa, A .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (03) :315-323

[39] Synthesis and Insecticidal Activities of Novel 1,3,4-Thiadiazole 5-Fluorouracil Acetamides Derivatives: An RNA Interference Insecticide [J].

Wan, Rong ;

Zhang, Jian-Qiang ;

Han, Fen ;

Wang, Peng ;

Yu, Peng ;

He, Qiu .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2011, 30 (04) :280-292

[40] Synthesis and preliminary biological assessments of a new class of amphiphilic telomers bearing 5-fluorouracil moieties [J].

Contino, C ;

Maurizis, JC ;

Pucci, B .

MACROMOLECULAR CHEMISTRY AND PHYSICS, 1999, 200 (06) :1351-1355

← 1 2 3 4 5 →