Synthesis and in vitro anti-HIV activity of certain 2-(1H-benzimidazol-2-ylamino)pyrimidin-4(3H)-ones and related derivatives

被引：13

作者：

Badawey, ESAM ^{[1
]}

Kappe, T ^{[1
]}

机构：

[1] KARL FRANZENS UNIV GRAZ,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA

来源：

ARCHIV DER PHARMAZIE | 1997年 / 330卷 / 03期

关键词：

2-(1H-benzimidazol-2-ylamino)pyrimidines; beta-keto esters; 2-acetyl-butyrolactone; anti-HIV activity;

D O I：

10.1002/ardp.19973300304

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In an ongoing effort to develop novel non-nucleoside human immunodeficiency virus inhibitors, a series of substituted 2-(1H-benzimidazol-2-ylamino)pyrimidin-4(3H)-ones and related derivatives were synthesized via cyclocondensation of 2-guanidino-1H-benzimidazole with diethyl ethoxymethylenemalonate, substituted diethyl malonates, some beta-keto esters and 2-acetylbutyrolactone. From these series of compounds, 2-(1H-benzimidazol-2-ylamino) 2-(1H-benzimidazol-2-ylamino)-6-hydroxy-5-phenylpyrimidin-4(3H)-ones (5f, NSC 666286) was confirmed to have a moderate in vitro anti-HIV activity.

引用

页码：59 / 62

页数：4

共 15 条

[1] ASSESSMENT OF ANTI-HIV ACTIVITY OF SOME BENZIMIDAZOLYLTHIAZOLES [J].

BADAWEY, EAM ;

HAZZAA, AA ;

RIDA, SM ;

FAHMY, HTY .

ARCHIV DER PHARMAZIE, 1992, 325 (09) :565-567

[2] SYNTHESIS OF NEW BENZIMIDAZOLE DERIVATIVES AS POTENTIAL ANTIMICROBIAL AGENTS [J].

BADAWEY, ESAM ;

HASSAN, AMM ;

KAPPE, T .

ARCHIV DER PHARMAZIE, 1991, 324 (06) :355-357

[3]

CHIMIRRI A, 1991, FARMACO, V46, P925

[4] CARDIOTONIC AGENTS - SYNTHESIS AND CARDIOVASCULAR PROPERTIES OF NOVEL 2-ARYLBENZIMIDAZOLES AND AZABENZIMIDAZOLES [J].

GUNGOR, T ;

FOUQUET, A ;

TEULON, JM ;

PROVOST, D ;

CAZES, M ;

CLOAREC, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (23) :4455-4463

[5] AMINO-ACID AMIDES OF 2-[(2-AMINOBENZYL)SULFINYL]BENZIMIDAZOLE AS ACID-STABLE PRODRUGS OF POTENTIAL INHIBITORS OF H+/K+ ATPASE [J].

HIRAI, K ;

KOIKE, H ;

ISHIBA, T ;

UEDA, S ;

MAKINO, I ;

YAMADA, H ;

ICHIHASHI, T ;

MIZUSHIMA, Y ;

ISHIKAWA, M ;

ISHIHARA, Y ;

HARA, Y ;

HIROSE, H ;

SHIMA, N ;

DOTEUCHI, M .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1991, 26 (02) :143-158

[6] SYNTHESIS AND EVALUATION OF 2-PYRIDINONE DERIVATIVES AS HIV-1-SPECIFIC REVERSE-TRANSCRIPTASE INHIBITORS .4. 3-[2-(BENZOXAZOL-2-YL)ETHYL]-5-ETHYL-6-METHYLPYRIDIN-2(1H)-ONE AND ANALOGS [J].

HOFFMAN, JM ;

SMITH, AM ;

ROONEY, CS ;

FISHER, TE ;

WAI, JS ;

THOMAS, CM ;

BAMBERGER, DL ;

BARNES, JL ;

WILLIAMS, TM ;

JONES, JH ;

OLSON, BD ;

OBRIEN, JA ;

GOLDMAN, ME ;

NUNBERG, JH ;

QUINTERO, JC ;

SCHLEIF, WA ;

EMINI, EA ;

ANDERSON, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (08) :953-966

[7]

IEMURA R, 1989, CHEM PHARM BULL, V37, P967

[8] REACTION OF N-CYANOFORMIMIDATES WITH SOME HETEROCYCLIC-COMPOUNDS - A NEW SYNTHESIS OF 5-AZAADENINE AND RELATED-COMPOUNDS [J].

LALEZARI, I ;

NABAHI, S .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (05) :1121-1123

[9]

REYNOLD JEF, 1993, MARTINDALE EXTRA PHA, pP896

[10] SYNTHESIS AND BIOLOGICAL INVESTIGATIONS OF SOME NEW THIAZOLYLBENZIMIDAZOLES AND BENZIMIDAZOLYLTHIAZOLO[3,2-ALPHA]PYRIDINES [J].

RIDA, SM ;

HABIB, NS ;

BADAWEY, EAM ;

FAHMY, HTY ;

GHOZLAN, HA .

ARCHIV DER PHARMAZIE, 1995, 328 (04) :325-328

← 1 2 →