Synthesis and preliminary biological screening of sterol analogues as new antifungal agents against plant pathogens

被引：23

作者：

Alonso, Fernando

Cirigliano, Adriana M.

Cabrera, Gabriela M.

Ramirez, Javier A. ^{[1
]}

机构：

[1] Univ Buenos Aires, Dept Quim Organ, Buenos Aires, DF, Argentina

来源：

STEROIDS | 2010年 / 75卷 / 10期

关键词：

Antifungal; Azasterols; Plant pathogens; Ugi reaction; CHEMISTRY;

D O I：

10.1016/j.steroids.2010.04.002

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

In this paper we report the synthesis of a new family of sterol analogues that have two amidic bonds on the side chain. These azasterols were obtained by a straightforward procedure including an Ugi condensation that allows the facile attachment of a polyfunctionalized side chain into the steroidal framework. Some of the new compounds showed an interesting inhibitory effect on the growth of two pathogenic fungi involved in plant diseases. (C) 2010 Elsevier Inc. All rights reserved.

引用

收藏

页码：659 / 664

页数：6

相关论文

共 14 条

[1]

Synthesis of 4-azasteroids by an intramolecular Ugi reaction [J].

Alonso, Fernando ;

Acebedo, Sofia L. ;

Bruttomesso, Andrea C. ;

Ramirez, Javier A. .

STEROIDS, 2008, 73 (12) :1270-1276

[2]

[Anonymous], [No title captured]

[3]

Synthesis and antifungal activity of oxygenated cholesterol derivatives [J].

Brunel, JM ;

Loncle, C ;

Vidal, N ;

Dherbomez, M ;

Letourneux, Y .

STEROIDS, 2005, 70 (13) :907-912

[4]

Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry [J].

Bruttomesso, Andrea C. ;

Eiras, Javier ;

Ramirez, Javier A. ;

Galagovsky, Lydia R. .

TETRAHEDRON LETTERS, 2009, 50 (28) :4022-4024

[5]

Azasteroids as antifungals [J].

Burbiel, J ;

Bracher, F .

STEROIDS, 2003, 68 (7-8) :587-594

[6]

Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[7]

Ernst E.J., 2005, Antifungal Agents: Methods and Protocols

[8]

Evaluation of azasterols as anti-parasitics [J].

Gros, Ludovic ;

Lorente, Silvia Orenes ;

Jimenez, Carmen Jimenez ;

Yardley, Vanessa ;

Rattray, Lauren ;

Wharton, Hayley ;

Little, Susan ;

Croft, Simon L. ;

Ruiz-Perez, Luis M. ;

Gonzalez-Pacanowska, Dolores ;

Gilbert, Ian H. .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (20) :6094-6103

[9]

Rationale and perspectives on the development of fungicides [J].

Knight, SC ;

Anthony, VM ;

Brady, AM ;

Greenland, AJ ;

Heaney, SP ;

Murray, DC ;

Powell, KA ;

Schulz, MA ;

Spinks, CA ;

Worthington, PA ;

Youle, D .

ANNUAL REVIEW OF PHYTOPATHOLOGY, 1997, 35 :349-372

[10]

SATO Y, 1980, CHEM PHARM BULL, V28, P1150