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Sulfur‐Assisted Deprotection of Methylene Nitrile Group: One‐Pot Synthesis of 4‐Substituted‐2 H ‐1,2,3‐triazoles
Author(s) -
Nagesh Hunsur Nagendra,
Singireddi Srinivasarao,
Suresh Amaroju,
Nizalapur Shashidhar,
Murugesan Sankaranarayanan,
Kanneboina Kumar,
Kumar Naresh,
Sekhar Kondapalli Venkata Gowri Chandra
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801075
Subject(s) - nitrile , methylene , chemistry , amide , functional group , sulfur , in vitro , combinatorial chemistry , organic chemistry , biochemistry , polymer
An operationally simpler one‐pot synthesis of 4‐substituted‐2 H ‐1,2,3‐triazole is demonstrated by unusual deprotection of methylene nitrile group using elemental sulfur. The strategy involves click reaction followed by deprotection of methylene nitrile group using elemental sulfur. Broad functional group tolerance with good to excellent yielding method has been developed. Also, N ‐acyl‐cyclopentyl and hexyl amide 1,2,3‐triazole derivatives 6 m and 6 n were evaluated for their in vitro quorum sensing inhibition (QSI) activity against P. aeruginosa . Compounds 6 m and 6 n exhibited significant QSI activity with 49.7% and 50.7% in P. aeruginosa MH602 at 250 μM, respectively. We also report in vitro toxicity of these compounds against human embryonic kidney cell line. 6 m and 6 n are found to be less toxic in HEK 293 cell line.