Efficient Green Chemistry Approach for the Synthesis of 1,2,3-Triazoles Using Click Chemistry through Cycloaddition Reaction: Synthesis and Cytotoxic Study

被引:13
作者
Gondaliya, Bhumit L. [1 ]
Kapadiya, Khushal M. [1 ]
机构
[1] RK Univ, Sch Sci, Dept Chem, Biores & Characterizat Ctr, Rajkot 360020, Gujarat, India
关键词
Green synthesis approach; click chemistry; 1; 2; 3-triazoles; methylene-linkers; NCI-60 cell-line cancer study; CATALYST-FREE; AZIDE; NITROGEN;
D O I
10.1080/10406638.2021.2019804
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we reported the synthesis of diverse N-(substituted phenyl)-2-(4-((dibenzylamino)methyl)-1H-1,2,3-triazol-1-yl)acetamide (6a-6j) through a green chemistry approach using water and eco-friendly catalysts using copper catalyzed click chemistry approach. The optimization of the reaction toward the greener way was discussed through applying the choline azide and ecological suitable solvent/reagent systems. The biological potency of the adducts was described against NCI-60 cancer cell lines in nine cancer panels and four scaffolds with halogens as phenyl ring substituents were found to be most active with negative GI(50) values. Supplemental data for this article is available online at
引用
收藏
页码:686 / 698
页数:13
相关论文
共 39 条
[1]  
Abdelilah E.H\, 2010, MOLECULES, V15, P9354, DOI DOI 10.3390/molecules15129354
[2]   Structure-activity relationship (SAR) study and design strategies of nitrogen-containing heterocyclic moieties for their anticancer activities [J].
Akhtar, Jawaid ;
Khan, Ahsan Ahmed ;
Ali, Zulphikar ;
Haider, Rafi ;
Yar, M. Shahar .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 125 :143-189
[3]   Green Chemistry: Principles and Practice [J].
Anastas, Paul ;
Eghbali, Nicolas .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312
[4]  
Araya-Maturana R, 2017, J CHEM-NY, V2017, P1
[5]   "Clicking" Polymers or Just Efficient Linking: What Is the Difference? [J].
Barner-Kowollik, Christopher ;
Du Prez, Filip E. ;
Espeel, Pieter ;
Hawker, Craig J. ;
Junkers, Tanja ;
Schlaad, Helmut ;
Van Camp, Wim .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (01) :60-62
[6]   Highly Active Dinuclear Copper Catalysts for Homogeneous Azide-Alkyne Cycloadditions [J].
Berg, Regina ;
Straub, Johannes ;
Schreiner, Ella ;
Mader, Steffen ;
Rominger, Frank ;
Straub, Bernd F. .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (18) :3445-3450
[7]   1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview [J].
Bozorov, Khurshed ;
Zhao, Jiangyu ;
Aisa, Haji A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (16) :3511-3531
[8]   Harnessing pyrrolidine iminosugars into dimeric structures for the rapid discovery of divalent glycosidase inhibitors [J].
Carmona, Ana T. ;
Carrion-Jimenez, Sebastian ;
Pingitore, Valeria ;
Moreno-Clavijo, Elena ;
Robina, Inmaculada ;
Moreno-Vargas, Antonio J. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 151 :765-776
[9]   Solvent-Free N-Alkylation of Amides with Alcohols Catalyzed by Nickel on Silica-Alumina [J].
Charvieux, Aubin ;
Le Moigne, Louis ;
Borrego, Lorenzo G. ;
Duguet, Nicolas ;
Metay, Estelle .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (40) :6842-6846
[10]  
DEESPANES EM, 1946, P SOC EXP BIOL MED, V63, P195