Synthesis and antifungal activity of 3-(1,3,4-oxadiazol-5-yl)-indoles and 3-(1,3,4-oxadiazol-5-yl)methyl-indoles

被引：131

作者：

Zhang, Ming-Zhi ^{[1
]}

Mulholland, Nick ^{[2
]}

Beattie, David ^{[2
]}

Irwin, Dianne ^{[2
]}

Gu, Yu-Cheng ^{[2
]}

Chen, Qiong ^{[1
]}

Yang, Guang-Fu ^{[1
]}

Clough, John ^{[2
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China

[2] Syngenta Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 63卷

关键词：

Indole; 1,3,4-Oxadiazole; Synthesis; Antifungal activity; Structure-activity relationships; SULFONE DERIVATIVES; POTENT; INHIBITORS;

D O I：

10.1016/j.ejmech.2013.01.038

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

On the basis of the principle of combination of active structural moieties, a modified and efficient synthetic method for three series of novel indole-based 1,3,4-oxadiazoles is described. Bioassays conducted at Syngenta showed that several of the synthesized compounds exhibit higher antifungal activity than pimprinine, the natural product which inspired this synthesis. Two main structural-alterations were found to broaden the spectrum of biological activity in most cases. Compounds 3g, 6c, 6e, 6h, 9d, 9e, 9h and 9m (Fig. 1) were identified as the most active on the biological assays, and will be studied further. (c) 2013 Elsevier Masson SAS. All rights reserved.

引用

页码：22 / 32

页数：11

共 30 条

[1] Studies with azoles and benzoazoles: A novel simple approach for synthesis of 3-functionally substituted 3-acylindoles [J].

Abdel-Motaleb, Ramadan Maawad ;

Makhloof, Abdel-Moneim Abdel-Salam ;

Ibrahim, Hamada Mohamed ;

Elnagdi, Mohamed Hilmy .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (01) :109-114

[2] Novel 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives: Promising anticancer agents [J].

Aboraia, AS ;

Abdel-Rahman, HM ;

Mahfouz, NM ;

El-Gendy, MA .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (04) :1236-1246

[3] SYNTHESIS AND FUNCTIONALIZATION OF THE 3-(1,3,4-OXADIAZOL-2-YL)-1H-INDOLES [J].

Alyab'ev, S. B. ;

Kravchenko, D. V. ;

Ivashchenko, A. V. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (10) :1270-1275

[4] Catalytic Functionalization of Indoles in a New Dimension [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644

[5] Oxadiazoles in Medicinal Chemistry [J].

Bostrom, Jonas ;

Hogner, Anders ;

Llinas, Antonio ;

Wellner, Eric ;

Plowright, Alleyn T. .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (05) :1817-1830

[6] Reserpine: A challenge for total synthesis of natural products [J].

Chen, FE ;

Huang, J .

CHEMICAL REVIEWS, 2005, 105 (12) :4671-4706

[7] Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(I-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones [J].

El-Emam, AA ;

Al-Deeb, OA ;

Al-Omar, M ;

Lehmann, J .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (19) :5107-5113

[8]

Farghaly ARAH, 2004, J CHIN CHEM SOC-TAIP, V51, P147

[9] Synthesis and antimicrobial studies of a new series of 2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-5-substituted-1,3,4-oxadiazoles [J].

Gaonkar, S. L. ;

Rai, K. M. L. ;

Prabhuswamy, B. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (07) :841-846

[10] A Practical Synthesis of 5-Lipoxygenase Inhibitor MK-0633 [J].

Gosselin, Francis ;

Britton, Robert A. ;

Davies, Ian W. ;

Dolman, Sarah J. ;

Gauvreau, Danny ;

Hoerrner, R. Scott ;

Hughes, Gregory ;

Janey, Jacob ;

Lau, Stephen ;

Molinaro, Carmela ;

Nadeau, Christian ;

O'Shea, Paul D. ;

Palucki, Michael ;

Sidler, Rick .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (12) :4154-4160

← 1 2 3 →