Azide-enolate 1,3-dipolar cycloaddition in the synthesis of novel triazole-based miconazole analogues as promising antifungal agents

被引：43

作者：

Gonzalez-Calderon, Davir ^{[1
]}

Mejia-Dionicio, Maria G. ^{[1
]}

Morales-Reza, Marco A. ^{[1
]}

Ramirez-Villalva, Alejandra ^{[1
]}

Morales-Rodriguez, Macario ^{[2
]}

Jauregui-Rodriguez, Bertha ^{[2
]}

Diaz-Torres, Eduardo ^{[1
]}

Gonzalez-Romero, Carlos ^{[1
]}

Fuentes-Benites, Aydee ^{[1
]}

机构：

[1] Univ Autonoma Estado Mexico, Fac Quim, Dept Quim Organ, Paseo Colon Paseo Tollocan S-N, Toluca 50120, Estado De Mexic, Mexico

[2] Univ Autonoma Estado Mexico, Fac Quim, Dept Microbiol, Paseo Colon Paseo Tollocan S-N, Toluca 50120, Estado De Mexic, Mexico

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2016年 / 112卷

关键词：

Miconazole analogs; 1,2,3-Triazole derivatives; Antifungal activity; Azide-enolate cycloaddition; POTENTIAL ANTICANCER AGENTS; ALKYNE CLICK CHEMISTRY; MOLECULAR DOCKING; ANTIMALARIAL EVALUATION; ANTITUBERCULAR AGENTS; CONJUGATES SYNTHESIS; CANDIDA-ALBICANS; FACILE SYNTHESIS; DRUG-RESISTANCE; 1,2,3-TRIAZOLES;

D O I：

10.1016/j.ejmech.2016.02.013

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Seven miconazole analogs involving 1,4,5-tri and 1,5-disubstituted triazole moieties were synthesized by azide-enolate 1,3-dipolar cycloaddition. The antifungal activity of these compounds was evaluated in vitro against four filamentous fungi, including Aspergillus fumigatus, Trichosporon cutaneum, Rhizopus oryzae, and Mucor hiemalis as well as three species of Candida spp. as yeast specimens. These pre-clinical studies suggest that compounds 4b, 4d and 7b can be considered as drug candidates for future complementary biological studies due to their good/excellent antifungal activities. (C) 2016 Elsevier Masson SAS. All rights reserved.

引用

页码：60 / 65

页数：6

共 69 条

[51]

National Committee for Clinical Laboratory Standards Institute (CLSI), 2002, DOC M38 A2 REF METH

[52] Click chemistry inspired structural modification of azole antifungal agents to synthesize novel 'drug like' molecules [J].

Pericherla, Kasiviswanadharaju ;

Khedar, Poonam ;

Khungar, Bharti ;

Kumar, Anil .

TETRAHEDRON LETTERS, 2012, 53 (50) :6761-6764

[53] The Chemistry of Griseofulvin [J].

Petersen, Asger B. ;

Ronnest, Mads H. ;

Larsen, Thomas O. ;

Clausen, Mads H. .

CHEMICAL REVIEWS, 2014, 114 (24) :12088-12107

[54]

Pfaller Michael A., 2012, AM J MED, V125, pS3

[55] 1H-1,2,3-Triazole-tethered isatin-7-chloroquinoline and 3-hydroxy-indole-7-chloroquinoline conjugates: Synthesis and antimalarial evaluation [J].

Raj, Raghu ;

Gut, Jiri ;

Rosenthal, Philip J. ;

Kumar, Vipan .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (03) :756-759

[56] Enamine/Enolate-Mediated Organocatalytic Azide-Carbonyl [3+2] Cycloaddition Reactions for the Synthesis of Densely Functionalized 1,2,3-Triazoles [J].

Ramasastry, Sripada S. V. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (52) :14310-14312

[57] A facile synthesis of novel miconazole analogues and the evaluation of their antifungal activity [J].

Ramirez-Villalva, Alejandra ;

Gonzalez-Calderon, Davir ;

Gonzalez-Romero, Carlos ;

Morales-Rodriguez, Macario ;

Jauregui-Rodriguez, Bertha ;

Cuevas-Yanez, Erick ;

Fuentes-Benites, Aydee .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 :275-279

[58]

Schwalbe R., 2007, An overview of the Clinical and Laboratory Standards Institute (CLSI) and its impact on antimicrobial susceptibility tests, P1, DOI [10.1201/9781420014495/ANTIMICROBIAL-SUSCEPTIBILITY-TESTINGPROTOCOLS-RICHARD-SCHWALBE-LYNN-STEELE-MOORE, DOI 10.1201/9781420014495.CH1]

[59] Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: Their anti-inflammatory and anti-nociceptive activities [J].

Shafi, Syed ;

Alam, Mohammad Mahboob ;

Mulakayala, Naveen ;

Mulakayala, Chaitanya ;

Vanaja, G. ;

Kalle, Arunasree M. ;

Pallu, Reddanna ;

Alam, M. S. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 49 :324-333

[60] 1,2,3-Triazole derivatives as antitubercular agents: synthesis, biological evaluation and molecular docking study [J].

Shaikh, Mubarak H. ;

Subhedar, Dnyaneshwar D. ;

Nawale, Laxman ;

Sarkar, Dhiman ;

Khan, Firoz A. Kalam ;

Sangshetti, Jaiprakash N. ;

Shingate, Bapurao B. .

MEDCHEMCOMM, 2015, 6 (06) :1104-1116

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