Synthesis of Novel Symmetrical 1,4-Disubstituted 1,2,3-Bistriazole Derivatives via 'Click Chemistry' and Their Biological Evaluation

被引：14

作者：

Dugdu, Esra ^{[1
]}

Unluer, Dilek ^{[1
]}

Celik, Fatih ^{[1
]}

Sancak, Kemal ^{[1
]}

Karaoglu, Sengul Alpay ^{[2
]}

Ozel, Arzu ^{[3
]}

机构：

[1] Karadeniz Tech Univ, Dept Chem, TR-61080 Trabzon, Turkey

[2] Recep Tayyip Erdogan Univ, Dept Biol, TR-53100 Rize, Turkey

[3] Karadeniz Tech Univ, Fac Pharm, TR-61080 Trabzon, Turkey

来源：

MOLECULES | 2016年 / 21卷 / 05期

关键词：

1,2,3-triazole; 1,3-dipolar cycloaddition; antioxidant activity; antimicrobial activity; 1,2,3-TRIAZOLES; ANTIOXIDANT; CYCLOADDITION;

D O I：

10.3390/molecules21050659

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of symmetric bis-1,2,3-triazole compounds 2-5(a-f) were synthesized as potential antioxidant agents via click chemistry. Their structures were confirmed by H-1-NMR and C-13-NMR. All of the synthesized compounds were subjected to antioxidant and antimicrobial assays. The antioxidant activity of these compounds (AChE inhibition, DPPH and SOD activities) was evaluated. Compound 2f was found to show the highest AChE inhibition activity of all compounds, while compound 3b showed a strong inhibitory effect on DPPH radical and compound 2a was the most effective of all compounds for SOD activity. All synthesized compounds were found to possess moderate antibacterial activity against the bacteria E. coli and Y. pseudotuberculosis.

引用

页数：13

共 27 条

[1] Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].

Agalave, Sandip G. ;

Maujan, Suleman R. ;

Pore, Vandana S. .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718

[2] Screening of some Indian medicinal plants for their antimicrobial properties [J].

Ahmad, I ;

Mehmood, Z ;

Mohammad, F .

JOURNAL OF ETHNOPHARMACOLOGY, 1998, 62 (02) :183-193

[3] Synthesis and Antiprotozoal Activity of Cationic 1,4-Diphenyl-1H-1,2,3-triazoles [J].

Bakunov, Stanislav A. ;

Bakunova, Svetlana M. ;

Wenzler, Tanja ;

Ghebru, Maedot ;

Werbovetz, Karl A. ;

Brun, Reto ;

Tidwell, Richard R. .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (01) :254-272

[4] ANTIOXIDANT DETERMINATIONS BY THE USE OF A STABLE FREE RADICAL [J].

BLOIS, MS .

NATURE, 1958, 181 (4617) :1199-1200

[5] Novel 1,2,3-Triazole Derivatives for Use against Mycobacterium tuberculosis H37Rv (ATCC 27294) Strain [J].

Boechat, Nubia ;

Ferreira, Vitor F. ;

Ferreira, Sabrina B. ;

Ferreira, Maria de Lourdes G. ;

da Silva, Fernando de C. ;

Bastos, Monica M. ;

Costa, Marilia dos S. ;

Lourenco, Maria Cristina S. ;

Pinto, Angelo C. ;

Krettli, Antoniana U. ;

Aguiar, Anna Caroline ;

Teixeira, Brunno M. ;

da Silva, Nathalia V. ;

Martins, Priscila R. C. ;

Bezerra, Flavio Augusto F. M. ;

Camilo, Ane Louise S. ;

da Silva, Gerson P. ;

Costa, Carolina C. P. .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (17) :5988-5999

[6] Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity [J].

D'hooghe, Matthias ;

Vandekerckhove, Stephanie ;

Mollet, Karen ;

Vervisch, Karel ;

Dekeukeleire, Stijn ;

Lehoucq, Liesbeth ;

Lategan, Carmen ;

Smith, Peter J. ;

Chibale, Kelly ;

De Kimpe, Norbert .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :1745-1752

[7] A NEW AND RAPID COLORIMETRIC DETERMINATION OF ACETYLCHOLINESTERASE ACTIVITY [J].

ELLMAN, GL ;

COURTNEY, KD ;

ANDRES, V ;

FEATHERSTONE, RM .

BIOCHEMICAL PHARMACOLOGY, 1961, 7 (02) :88-&

[8]

Fan W.-Q., 1996, COMPREHENSIVE HETERO, V4, P1, DOI DOI 10.1016/B978-008096518-5.00079-4

[9] Synthesis, characterization, and antifungal activity of biaryl-based bis(1,2,3-triazoles) using click chemistry [J].

Gaur, Manoj ;

Goel, Mayurika ;

Sridhar, L. ;

Ashok, Tara Devi S. ;

Prabhakar, S. ;

Dureja, P. ;

Raghunathan, P. ;

Eswaran, S. V. .

MONATSHEFTE FUR CHEMIE, 2012, 143 (02) :283-288

[10] Synthesis, antimalarial and antitubercular activity of acetylenic chalcones [J].

Hans, Renate H. ;

Guantai, Eric M. ;

Lategan, Carmen ;

Smith, Peter J. ;

Wan, Baojie ;

Franzblau, Scott G. ;

Gut, Jiri ;

Rosenthal, Philip J. ;

Chibale, Kelly .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (03) :942-944

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