Synthesis and in vitro activity of 6-amino-2,9-diarylpurines for Mycobacterium tuberculosis

被引：22

作者：

Correia, Carla ^{[1
]}

Carvalho, M. Alice ^{[1
]}

Proenca, M. Fernanda ^{[1
]}

机构：

[1] Univ Minho, Dept Quim, P-4710057 Braga, Portugal

来源：

TETRAHEDRON | 2009年 / 65卷 / 34期

关键词：

Purine; Antimicrobial agent; Tuberculosis; ANTIMYCOBACTERIAL ACTIVITY; SIDEROPHORE BIOSYNTHESIS; BIOLOGICAL-ACTIVITY; INHIBITORY-ACTIVITY; FACILE SYNTHESIS; PURINES; 6-CYANOPURINES; ANALOGS; SAR; NUCLEOSIDES;

D O I：

10.1016/j.tet.2009.06.065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild method was developed to synthesize 6-amino-2-phenolic-9-alkyl and 9-arylpurines. The new compounds were screened for antibacterial activity against Mycobacterium tuberculosis strain H(37)Rv. The 9-tolyl derivatives with a dimethylamino or a piperidine substituent in C6 and the 3-hydroxyphenyl or 4-hydroxyphenyl substituent in C2 were highly active against the bacilli. (C) 2009 Elsevier Ltd. All rights reserved.

引用

收藏

页码：6903 / 6911

页数：9

相关论文

共 42 条

[1] Facile synthesis of 6-cyano-9-substituted-9H-purines and their ring expansion to 8-(arylamino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidines [J].

Al-Azmi, A ;

Booth, BL ;

Carpenter, RA ;

Carvalho, A ;

Marrelec, E ;

Pritchard, RG ;

Proença, MFJRP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (20) :2532-2537

[2]

Alves M.J., 1993, J. Chem. Research (M), P2701

[3] A new approach to the synthesis of NN-dialkyladenine derivatives [J].

Alves, M. Jose ;

Carvalho, M. Alice ;

Carvalho, Silvia ;

Dias, Alice M. ;

Fernandes, Francisco H. ;

Proenca, M. Fernanda .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (29) :4881-4887

[4] SYNTHESIS OF 4-DISUBSTITUTED AND 5-DISUBSTITUTED 1-BENZYLIMIDAZOLES, IMPORTANT PRECURSORS OF PURINE ANALOGS [J].

ALVES, MJ ;

PROENCA, MFJRP ;

BOOTH, BL .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (02) :345-350

[5]

ALVES MJ, 1993, J CHEM RES-S, P402

[6] (Z)-N3-(2-AMINO-1,2-DICYANOVINYL)FORMAMIDRAZONE - A PRECURSOR IN THE SYNTHESIS OF 1,5-DIAMINOIMIDAZOLES AND 6-CARBAMOYL-1,2-DIHYDROPURINES [J].

ALVES, MJ ;

BOOTH, BL ;

FREITAS, AP ;

PROENCA, MFJRP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (07) :913-917

[7] Synthesis of 6-cyanopurines and the isolation and X-ray structure of novel 2H-pyrroles [J].

Alves, MJ ;

Carvalho, MA ;

Proenca, MFJRP ;

Booth, BL ;

Pritchard, RG .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (03) :739-743

[8]

[Anonymous], 2008, Global tuberculosis control - surveillance, planning, financing

[9] 9-benzylpurines with inhibitory activity against Mycobacterium tuberculosis [J].

Bakkestuen, AK ;

Gundersen, LL ;

Langli, G ;

Liu, FS ;

Nolsoe, JMJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (11) :1207-1210

[10] Synthesis, biological activity, and SAR of antimycobacterial 9-aryl-, 9-arylsulfonyl-, and 9-benzyl-6-(2-furyl)purines [J].

Bakkestuen, AK ;

Gundersen, LL ;

Utenova, BT .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (07) :2710-2723

← 1 2 3 4 5 →