Efficient synthesis, antitubercular and antimicrobial evaluation of 1,4-disubstituted 1,2,3-triazoles with amide functionality

被引：17

作者：

Kaushik, C. P. ^{[1
]}

Pahwa, Ashima ^{[1
]}

Singh, Dharmendra ^{[2
]}

Kumar, Krishan ^{[1
]}

Luxmi, Raj ^{[1
]}

机构：

[1] Guru Jambheshwar Univ Sci & Technol, Dept Chem, Hisar, Haryana, India

[2] IPCA Lab Ltd, Ctr Res & Dev, Mumbai, Maharashtra, India

来源：

MONATSHEFTE FUR CHEMIE | 2019年 / 150卷 / 06期

关键词：

Click reaction; Heterocycles; 1,4-Disubstituted; 1,2,3-Triazoles; Alkynes; One-pot synthesis; Biological activity; LINKED COUMARINYL TRIAZOLES; CLICK CHEMISTRY; ANTIMALARIAL; CYCLOADDITION; DERIVATIVES;

D O I：

10.1007/s00706-019-2361-9

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of 21 amide linked 1,4-disubstituted-1,2,3-triazoles were achieved via one-pot synthesis through Cu(I) catalyzed click reaction between terminal alkynes and 2-azido-N-substituted acetamides. Newly formed triazoles were characterized by various spectroscopic techniques (FT-IR, H-1 NMR, C-13 NMR spectroscopy, and HRMS) and investigated for in vitro antitubercular evaluation against bacteria, i.e., Mycobacterium tuberculosis and antimicrobial evaluation against Bacillus subtilis, Staphylococcus epidermidis, Escherichia coli, Pseudomonas aeruginosa, Candida albicans, and Aspergillus niger. Some of the synthesized triazole derivatives were found to exhibit moderate inhibitory activity against the tested antitubercular strain, whereas one compound displayed a significant inhibitory activity against most of the tested microbial strains.

引用

页码：1127 / 1136

页数：10

共 50 条

[41] 'Green' synthesis of 1,4-disubstituted 5-iodo-1,2,3-triazoles under neat conditions, and an efficient approach of construction of 1,4,5-trisubstituted 1,2,3-triazoles in one pot
Wang, Dong
Chen, Si
Chen, Baohua
TETRAHEDRON LETTERS, 2014, 55 (51) : 7026 - 7028
[42] Synthesis, antimalarial and antioxidant activity of coumarin appended 1,4-disubstituted 1,2,3-triazoles
Kaushik, C. P.
Chahal, Manisha
MONATSHEFTE FUR CHEMIE, 2021, 152 (08): : 1001 - 1012
[43] A novel class of 1,4-disubstituted 1,2,3-triazoles: Regioselective synthesis, antimicrobial activity and molecular docking studies
Kella, Chennakesava Rao
Balachandran, Chandrasekar
Arun, Yuvaraj
Kaliyappan, Easwaramoorthi
Mahalingam, Sakkarapalayam M.
Ignacimuthu, Savarimuthu
Arumugam, Natarajan
Almansour, Abdulrahman, I
Kumar, Raju Suresh
Perumal, Paramasivan T.
ARABIAN JOURNAL OF CHEMISTRY, 2020, 13 (12) : 9047 - 9057
[44] A facile and regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles using click chemistry
Kumar, Dalip
Reddy, V. Buchi
Varma, Rajender S.
TETRAHEDRON LETTERS, 2009, 50 (18) : 2065 - 2068
[45] 1,4-Disubstituted 1,2,3-Triazoles as Amide Bond Surrogates for the Stabilisation of Linear Peptides with Biological Activity
Recnik, Lisa-Maria
Kandioller, Wolfgang
Mindt, Thomas L.
MOLECULES, 2020, 25 (16):
[46] Facile synthesis, characterization, and antimicrobial studies of some disubstituted 1,2,3-triazoles with sulfonamide functionality
Kaushik, C. P.
Pahwa, Ashima
Kumar, Ashwani
Singh, Dharmendra
Kumar, Krishan
SYNTHETIC COMMUNICATIONS, 2017, 47 (16) : 1485 - 1494
[47] A Green Ultrasound Synthesis, Characterization and Antibacterial Evaluation of 1,4-Disubstituted 1,2,3-Triazoles Tethering Bioactive Benzothiazole Nucleus
Rezki, Nadjet
MOLECULES, 2016, 21 (04):
[48] Recent developments in copper nanoparticle-catalyzed synthesis of 1,4-disubstituted 1,2,3-triazoles in water
Lal, Kashmiri
Rani, Poonam
ARKIVOC, 2016, : 307 - 341
[49] Synthesis of 1,4-Disubstituted 1,2,3-Triazoles by Use of Copper(I) and Amino Acids Ionic Liquid Catalytic System
Yan, Jincan
Wang, Lei
SYNTHESIS-STUTTGART, 2010, (03): : 447 - 452
[50] Efficient synthesis of allylic azides and one-pot regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles from homoallyl alcohols
Reddy, P. Surendra
Ravi, V.
Sreedhar, B.
TETRAHEDRON LETTERS, 2010, 51 (31) : 4037 - 4041

← 1 2 3 4 5 →