Practical and efficient synthesis of pyrano[3,2-c]pyridone, pyrano[4,3-b]pyran and their hybrids with nucleoside as potential antiviral and antileishmanial agents

被引：130

作者：

Fan, Xuesen ^{[1
]}

Feng, Dong ^{[1
]}

Qu, Yingying ^{[1
]}

Zhang, Xinying ^{[1
]}

Wang, Jianji ^{[1
]}

Loiseau, Philippe M. ^{[2
]}

Andrei, Graciela ^{[3
]}

Snoeck, Robert ^{[3
]}

De Clercq, Erik ^{[3
]}

机构：

[1] Henan Normal Univ, Sch Chem & Environm Sci, Henan Key Lab Environm Pollut Control, Xinxiang 453007, Henan, Peoples R China

[2] Univ Paris 11, CNRS, UMR 8076, F-92290 Chatenay Malabry, France

[3] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Leuven, Belgium

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 03期

基金：

中国国家自然科学基金;

关键词：

Pyrano[3,2-c]pyridone; Pyrano[4,3-b]pyran; Pyrimidine nucleoside; Hybrid compounds; Ionic liquids; Antivirals; Antileishmanial agents; THROUGHPUT SCREENING ASSAY; REVERSE-TRANSCRIPTASE INHIBITORS; ANTI-ORTHOPOXVIRUS ACTIVITY; BIOACTIVE NATURAL-PRODUCTS; IONIC LIQUIDS; STRUCTURAL SIMPLIFICATION; MULTICOMPONENT SYNTHESIS; LEISHMANIA-DONOVANI; GREEN PREPARATION; IN-VITRO;

D O I：

10.1016/j.bmcl.2009.12.102

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A highly practical and efficient preparation of pyrano[3,2-c]pyridone and pyrano[4,3-b]pyran derivatives was developed via an ionic liquid mediated and promoted multi-component reaction of aldehyde (1), 4-hydroxy-pyridin-2(1H)-one or 4-hydroxy-2-pyranone (2), and malononitrile (3). As an application, a series of pyrimidine nucleoside-pyrano[3,2-c]pyridone or pyrano[4,3-b]pyran hybrids were efficiently obtained. These hybrid compounds were evaluated as potential antiviral and antileishmanial agents and showed encouraging biological activities. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：809 / 813

页数：5

共 28 条

[1] Efficient catalyst reuse by simple dissolution in non-conventional media [J].

Afonso, Carlos A. M. ;

Branco, Luis C. ;

Candeias, Nuno R. ;

Gois, Pedro M. P. ;

Lourenco, Nuno M. T. ;

Mateus, Nuno M. M. ;

Rosa, Joao N. .

CHEMICAL COMMUNICATIONS, 2007, (26) :2669-2679

[2] An overview of diazine nucleoside analogues [J].

Agrofoglio, LA .

CURRENT ORGANIC CHEMISTRY, 2006, 10 (03) :333-362

[3] VINYLOGOUS CARBINOLAMINE TUMOR INHIBITORS .24. SYNTHESIS, CHEMISTRY, AND ANTINEOPLASTIC ACTIVITY OF ALPHA-HALOPYRIDINIUM SALTS - POTENTIAL PYRIDONE PRODRUGS OF ACYLATED VINYLOGOUS CARBINOLAMINE TUMOR INHIBITORS [J].

ANDERSON, WK ;

DEAN, DC ;

ENDO, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) :1667-1675

[4] CHEMICAL AND BIOACTIVE CONSTITUENTS FROM ZANTHOXYLUM SIMULANS [J].

CHEN, IS ;

WU, SJ ;

TSAI, IL ;

WU, TS ;

PEZZUTO, JM ;

LU, MC ;

CHAI, H ;

SUH, N ;

TENG, CM .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (09) :1206-1211

[5] Perspectives of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection [J].

De Clercq, E .

FARMACO, 1999, 54 (1-2) :26-45

[6] LEISHMANIA-DONOVANI - INVITRO GROWTH-INHIBITION OF PROMASTIGOTES BY A CARBOCYCLIC ANALOG OF 2'-DEOXYGUANOSINE [J].

DONG, Z ;

ZHU, B ;

JEFFREY, AM .

EXPERIMENTAL PARASITOLOGY, 1992, 75 (02) :257-258

[7] Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 6. Structure-activity studies of orally bioavailable, 2-pyridone-containing peptidomimetics [J].

Dragovich, PS ;

Prins, TJ ;

Zhou, R ;

Brown, EL ;

Maldonado, FC ;

Fuhrman, SA ;

Zalman, LS ;

Tuntland, T ;

Lee, CA ;

Patick, AK ;

Matthews, DA ;

Hendrickson, TF ;

Kosa, MB ;

Liu, B ;

Batugo, MR ;

Gleeson, JPR ;

Sakata, SK ;

Chen, LJ ;

Guzman, MC ;

Meador, JW ;

Ferre, RA ;

Worland, ST .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (08) :1607-1623

[8] InCl3•4H2O-promoted green preparation of xanthenedione derivatives in ionic liquids [J].

Fan, XS ;

Hu, XY ;

Zhang, XY ;

Wang, JJ .

CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (01) :16-20

[9] Ionic liquid promoted Knoevenagel and Michael reactions [J].

Fan, XS ;

Hu, XY ;

Zhang, XY ;

Wang, JJ .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2004, 57 (11) :1067-1071

[10] Toward orthopoxvirus countermeasures: A novel heteromorphic nucleoside of unusual structure [J].

Fan, Xuesen ;

Zhang, Xinying ;

Zhou, Longhu ;

Keith, Kathy A. ;

Prichard, Mark N. ;

Kern, Earl R. ;

Torrence, Paul F. .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (14) :4052-4054

← 1 2 3 →