Abstract
A series of 1,2,3-triazolyl quinolines possessing substituents like –CH2OAr (Ar = aryl) moiety on the triazolyl ring were synthesized via a multi-step sequence consisting of copper-catalyzed azide-alkyne cycloaddition (CuAAC) of 3- (azidomethyl)-quinoline derivative with terminal alkynes as a key step. This step was found to be remarkably faster in pure water and completed within 10-45 min. The robustness of this step was demonstrated by synthesizing a large number of compounds some of which showed promising antibacterial activities when tested in vitro. The crystal structure analysis of a representative compound along with hydrogen bonding patterns and molecular arrangement present within the molecule is described.
Keywords: Quinoline, 1, 2, 3-Triazole, Cycloaddition, Antibacterial agents, Copper, Water
Letters in Drug Design & Discovery
Title:A Remarkably Faster Approach Towards 1,2,3-Triazolyl Quinolines Via CuAAC in Water: Their Crystal Structure Analysis and Antibacterial Activities
Volume: 10 Issue: 4
Author(s): Jyoti Mareddy, Koduru Sri Shanthi Praveena, Nallapati Suresh, Anireddy Jayashree, Soma Roy, Dandela Rambabu, Nandula Yadagiri Sreenivasa Murthy and Sarbani Pal
Affiliation:
Keywords: Quinoline, 1, 2, 3-Triazole, Cycloaddition, Antibacterial agents, Copper, Water
Abstract: A series of 1,2,3-triazolyl quinolines possessing substituents like –CH2OAr (Ar = aryl) moiety on the triazolyl ring were synthesized via a multi-step sequence consisting of copper-catalyzed azide-alkyne cycloaddition (CuAAC) of 3- (azidomethyl)-quinoline derivative with terminal alkynes as a key step. This step was found to be remarkably faster in pure water and completed within 10-45 min. The robustness of this step was demonstrated by synthesizing a large number of compounds some of which showed promising antibacterial activities when tested in vitro. The crystal structure analysis of a representative compound along with hydrogen bonding patterns and molecular arrangement present within the molecule is described.
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Mareddy Jyoti, Sri Shanthi Praveena Koduru, Suresh Nallapati, Jayashree Anireddy, Roy Soma, Rambabu Dandela, Yadagiri Sreenivasa Murthy Nandula and Pal Sarbani, A Remarkably Faster Approach Towards 1,2,3-Triazolyl Quinolines Via CuAAC in Water: Their Crystal Structure Analysis and Antibacterial Activities, Letters in Drug Design & Discovery 2013; 10 (4) . https://dx.doi.org/10.2174/1570180811310040008
DOI https://dx.doi.org/10.2174/1570180811310040008 |
Print ISSN 1570-1808 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-628X |
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