Application of Huisgen (3 + 2) cycloaddition reaction: Synthesis of 1-(2,3-dihydrobenzofuran-2-yl-methyl [1,2,3]-triazoles and their antitubercular evaluations

1,4-Disubstituted-1,2,3-triazoles ( 3– 27) have been synthesized by [3+2] cycloaddition of different 2-(azidomethyl)-dihydronaptho(benzo)furans ( 2a, 2b, 2c and 2d) with different alkynes. All the compounds were screened for antitubercular activity against Mycobacterium tuberculosis H 37Rv. Compound...

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Published inEuropean journal of medicinal chemistry Vol. 45; no. 1; pp. 142 - 148
Main Authors Tripathi, Rama P., Yadav, Amit Kumar, Ajay, Arya, Bisht, Surendra Singh, Chaturvedi, Vinita, Sinha, Sudhir Kumar
Format Journal Article
LanguageEnglish
Published ISSY-LES-MOULINEAUX Elsevier Masson SAS 2010
Elsevier
Subjects
1,2,3-Triazoles
[3 + 2] cycloaddition
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antitubercular agents
Antitubercular Agents - chemical synthesis
Antitubercular Agents - chemistry
Antitubercular Agents - pharmacology
Biological and medical sciences
Chemistry, Medicinal
Cuprous iodide
Life Sciences & Biomedicine
Medical sciences
Microbial Sensitivity Tests
Mycobacterium tuberculosis - drug effects
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Science & Technology
Temperature
Triazoles - chemical synthesis
Triazoles - chemistry
Triazoles - pharmacology
1,2,3-Triazoles
Cuprous iodide
Antitubercular agents
[3 + 2] cycloaddition
AZIDES
TRIAZOLE
POLYMER
CLICK
ALKYNES
EFFICIENT
[3+2] cycloaddition
1,3-Dipolar cycloaddition
In vitro
Biological activity
Mycobacterium tuberculosis
Mycobacteriales
Mycobacteriaceae
Bacteria
Actinomycetes
Antituberculous agent
Benzofuran derivatives
Antibacterial agent
Chemical synthesis
Lipophilicity
Physicochemical properties
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Abstract 1,4-Disubstituted-1,2,3-triazoles ( 3– 27) have been synthesized by [3+2] cycloaddition of different 2-(azidomethyl)-dihydronaptho(benzo)furans ( 2a, 2b, 2c and 2d) with different alkynes. All the compounds were screened for antitubercular activity against Mycobacterium tuberculosis H 37Rv. Compounds 2a, 7, 9, 12 and 14 exhibited antitubercular activities with MIC ranging from 12.5 to 3.12 μg/ml. (3 + 2) Cycloaddition reaction of 2-azidomethyldihydrobenzofurans with different acetylenes gave 1-(2,3-dihydrobnzofuran-2-yl-methyl [1,2,3]-triazoles. The compounds were screened for their antitubercular activities. [Display omitted]
AbstractList 1,4-Disubstituted-1,2,3-triazoles (3-27) have been synthesized by [3+2] cycloaddition of different 2-(azidomethyl)-dihydronaptho(benzo)furans (2a, 2b, 2c and 2d) with different alkynes. All the compounds were screened for antitubercular activity against Mycobacterium tuberculosis H37Rv. Compounds 2a, 7, 9, 12 and 14 exhibited antitubercular activities with MIC ranging from 12.5 to 3.12 microg/ml.
1,4-Disubstituted-1,2,3-triazoles (3-27) have been synthesized by [3+2] cycloaddition of different 2-(azidomethyl)-dihydronaptho(benzo)furans (2a, 2b, 2c and 2d) with different alkynes. All the compounds were screened for antitubercular activity against Mycobacterium tuberculosis H(37)Rv. Compounds 2a, 7,9,12 and 14 exhibited antitubercular activities with MIC ranging from 12.5 to 3.12 mu g/ml. (C) 2009 Elsevier Masson SAS. All rights reserved.
1,4-Disubstituted-1,2,3-triazoles ( 3– 27) have been synthesized by [3+2] cycloaddition of different 2-(azidomethyl)-dihydronaptho(benzo)furans ( 2a, 2b, 2c and 2d) with different alkynes. All the compounds were screened for antitubercular activity against Mycobacterium tuberculosis H 37Rv. Compounds 2a, 7, 9, 12 and 14 exhibited antitubercular activities with MIC ranging from 12.5 to 3.12 μg/ml. (3 + 2) Cycloaddition reaction of 2-azidomethyldihydrobenzofurans with different acetylenes gave 1-(2,3-dihydrobnzofuran-2-yl-methyl [1,2,3]-triazoles. The compounds were screened for their antitubercular activities. [Display omitted]
Author Tripathi, Rama P.
Ajay, Arya
Chaturvedi, Vinita
Sinha, Sudhir Kumar
Bisht, Surendra Singh
Yadav, Amit Kumar
Author_xml – sequence: 1
  givenname: Rama P.
  surname: Tripathi
  fullname: Tripathi, Rama P.
  email: rpt.cdri@gmail.com
  organization: Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow 226001, UP, India
– sequence: 2
  givenname: Amit Kumar
  surname: Yadav
  fullname: Yadav, Amit Kumar
  organization: Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow 226001, UP, India
– sequence: 3
  givenname: Arya
  surname: Ajay
  fullname: Ajay, Arya
  organization: Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow 226001, UP, India
– sequence: 4
  givenname: Surendra Singh
  surname: Bisht
  fullname: Bisht, Surendra Singh
  organization: Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow 226001, UP, India
– sequence: 5
  givenname: Vinita
  surname: Chaturvedi
  fullname: Chaturvedi, Vinita
  organization: Division of Drug Target Discovery and Development, Central Drug Research Institute, Lucknow 226001, CSIR, UP, India
– sequence: 6
  givenname: Sudhir Kumar
  surname: Sinha
  fullname: Sinha, Sudhir Kumar
  organization: Division of Drug Target Discovery and Development, Central Drug Research Institute, Lucknow 226001, CSIR, UP, India
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Issue 1
Keywords 1,2,3-Triazoles
Cuprous iodide
Antitubercular agents
[3 + 2] cycloaddition
AZIDES
TRIAZOLE
POLYMER
CLICK
ALKYNES
EFFICIENT
[3+2] cycloaddition
1,3-Dipolar cycloaddition
In vitro
Biological activity
Mycobacterium tuberculosis
Mycobacteriales
Mycobacteriaceae
Bacteria
Actinomycetes
Antituberculous agent
Benzofuran derivatives
Antibacterial agent
Chemical synthesis
Lipophilicity
Physicochemical properties
Language English
License CC BY 4.0
Copyright 2009 Elsevier Masson SAS. All rights reserved.
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SSID ssj0005600
Score 2.3678865
Snippet 1,4-Disubstituted-1,2,3-triazoles ( 3– 27) have been synthesized by [3+2] cycloaddition of different 2-(azidomethyl)-dihydronaptho(benzo)furans ( 2a, 2b, 2c...
1,4-Disubstituted-1,2,3-triazoles (3-27) have been synthesized by [3+2] cycloaddition of different 2-(azidomethyl)-dihydronaptho(benzo)furans (2a, 2b, 2c and...
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SubjectTerms 1,2,3-Triazoles
[3 + 2] cycloaddition
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antitubercular agents
Antitubercular Agents - chemical synthesis
Antitubercular Agents - chemistry
Antitubercular Agents - pharmacology
Biological and medical sciences
Chemistry, Medicinal
Cuprous iodide
Life Sciences & Biomedicine
Medical sciences
Microbial Sensitivity Tests
Mycobacterium tuberculosis - drug effects
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Science & Technology
Temperature
Triazoles - chemical synthesis
Triazoles - chemistry
Triazoles - pharmacology
Title Application of Huisgen (3 + 2) cycloaddition reaction: Synthesis of 1-(2,3-dihydrobenzofuran-2-yl-methyl [1,2,3]-triazoles and their antitubercular evaluations
URI https://dx.doi.org/10.1016/j.ejmech.2009.09.036
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https://www.ncbi.nlm.nih.gov/pubmed/19846238
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Volume 45
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