NOVEL IMMUNOSUPPRESSIVE BUTENAMIDES

被引：15

作者：

AXTON, CA ^{[1
]}

BILLINGHAM, MEJ ^{[1
]}

BISHOP, PM ^{[1
]}

GALLAGHER, PT ^{[1
]}

HICKS, TA ^{[1
]}

KITCHEN, EA ^{[1
]}

MULLIER, GW ^{[1
]}

OWTON, WM ^{[1
]}

PARRY, MG ^{[1
]}

SCOTT, S ^{[1
]}

STEGGLES, DJ ^{[1
]}

机构：

[1] ELI LILLY & CO,LILLY RES CTR LTD,WINDLESHAM GU20 6PH,SURREY,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 17期

关键词：

D O I：

10.1039/p19920002203

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-[4-(1,1-Dimethylethyl)phenyl]thiophene 12 was carboxylated using butyllithium and carbon dioxide to give 5-[4-(1,1-dimethylethyl)phenyl]thiophene-2-carboxylic acid 13. Conversion of the acid 13 using diphenyl phosphazidate and triethylamine gave 5-[4-(1,1-dimethylethyl)phenyl]thiophene-2-carbonyl azide 14, which was rearranged in toluene at 110-degrees-C with loss of nitrogen to give the isocyanate 15; this in turn was treated with sodium 1-cyanoprop-1-ene 2-oxide 16 in tetrahydrofuran to give 2-cyano-N-{5-[4-(1,1-dimethylethyl)phenyl]thiophen-2-yl}-3-hydroxybut-2-enamide 17. Analogous chemistry has been utilised to synthesize both phenylheteroarylbutenamides and phenylbutenamides which display immunosuppressive activity towards proliferating concanavalin A-stimulated T-lymphocytes.

引用

页码：2203 / 2213

页数：11

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