IRREVERSIBLE ENZYME INHIBITORS .147. CANDIDATE ACTIVE-SITE-DIRECTED IRREVERSIBLE INHIBITORS OF XANTHINE OXIDASE DERIVED FROM 9-(P-ACYLAMIDOALKOXYPHENYL)GUANINES BEARING A TERMINAL SULFONYL FLUORIDE

被引：20

作者：

BAKER, BR

WOOD, WF

机构：

[1] Department of Chemistry, University of California, Sania Barbara

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1969年 / 12卷 / 02期

关键词：

D O I：

10.1021/jm00302a004

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Twelve candidate irreversible inhibitors of xanthine oxidase were synthesized from 9-(p-aminoethoxyphenvl )-guanine (23a) and 9-(p-aminopropoxyphenyl (guanine (23b) by connection to a benzenesulfonyl fluoride wit It an amide (24) or urea (25) bridge. Reversible inhibition results indicated the benzenesulfonyl fluoride moiety of 1 he inhibitors was in contact with the enzyme surface within the enzyme-inhibitor complex; nevertheless, none of the twelve compounds was an irreversible inhibitor. © 1969, American Chemical Society. All rights reserved.

引用

收藏

页码：214 / &

相关论文

共 14 条

[1] THE CHEMOTHERAPY OF SCHISTOSOMIASIS .3. N-PARA-AMINOPHENOXYALKYL-AMIDES, N-PARA-AMINOPHENOXYALKYL-IMIDES, AND N-PARA-AMINOPHENOXYALKYL-SULPHONAMIDES [J].

ASHLEY, JN ;

COLLINS, RF ;

DAVIS, M ;

SIRETT, NE .

JOURNAL OF THE CHEMICAL SOCIETY, 1959, (DEC) :3880-3894

[2] IRREVERSIBLE ENZYME INHIBITORS .109. CANDIDATE IRREVERSIBLE INHIBITORS OF DIHYDROFOLIC REDUCTASE DERIVED FROM 4,6-DIAMINO-1,2-DIHYDRO-2,2-DIMETHYL-1-PHENYL-S-TRIAZINE .3. [J].

BAKER, BR ;

LOURENS, GJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (01) :26-&

[3] IRREVERSIBLE ENZYME INHIBITORS .123. CANDIDATE IRREVERSIBLE INHIBITORS OF GUANINE DEAMINASE AND XANTHINE OXIDASE DERIVED FROM 9-PHENYLGUANINE SUBSTITUTED WITH A TERMINAL SULFONYL FLUORIDE [J].

BAKER, BR ;

WOOD, WF .

JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (04) :650-&

[4] IRREVERSIBLE ENZYME INHIBITORS .156. ACTIVE-SITE-DIRECTED IRREVERSIBLE INHIBITORS OF XANTHINE OXIDASE DERIVED FROM 9-(ACYLAMIDOPHENYL)GUANINES SUBSTITUTED WITH A TERMINAL SULFONYL FLUORIDE [J].

BAKER, BR ;

WOOD, WF .

JOURNAL OF MEDICINAL CHEMISTRY, 1969, 12 (02) :211-&

[5] IRREVERSIBLE ENZYME INHIBITORS .122. ON NATURE AND DIMENSIONS OF HYDROPHOBIC BONDING REGION OF GUANINE DEAMINASE AND XANTHINE OXIDASE [J].

BAKER, BR ;

WOOD, WF .

JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (04) :644-&

[6]

BAKER BR, 1968, J MED CHEM, V11, P666, DOI 10.1021/jm00310a007

[7] IRREVERSIBLE ENZYME INHIBITORS .102. ON MODE OF PHENYL BINDING OF 9-PHENYLGUANINE TO GUANINE DEAMINASE AND XANTHINE OXIDASE [J].

BAKER, BR ;

WOOD, WF .

JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (06) :1101-&

[8] IRREVERSIBLE ENZYME INHIBITORS . 0142 . FURTHER STUDIES ON ACTIVE-SITE-DIRECTED IRREVERSIBLE INHIBITORS OF DIHYDROFOLIC REDUCTASE DERIVED FROM 5-(P-AMINOPHENOXYPROPYL)-2,4,6-TRIAMINOPYRIMIDINE BEARING A TERMINAL SULFONYL FLUORIDE [J].

BAKER, BR ;

MEYER, RB .

JOURNAL OF MEDICINAL CHEMISTRY, 1969, 12 (01) :104-&

[9]

BAKER BR, 1969, J MED CHEM, V12, P74, DOI 10.1021/jm00301a019

[10] IRREVERSIBLE ENZYME INHIBITORS . 135 . EFFECT OF RING SUBSTITUTION ON SELECTIVE IRREVERSIBLE INHIBITION OF DIHYDROFOLIC REDUCTASE FROM L1210 MOUSE LEUKEMIA AND LIVER BY 2,4-DIAMINO-5-(3,4-DICHLOROPHENYL)-6-(P-(P-FLUOROSULFONYLPHENYLUREIDO)PHENOXYMETHYL)PYRIMIDINE [J].

BAKER, BR ;

VERMEULEN, NM .

JOURNAL OF MEDICINAL CHEMISTRY, 1969, 12 (01) :79-+