Microwave-assisted synthesis of N-alkylated benzotriazole derivatives: Antimicrobial studies

S. Nanjunda Swamy, Basappa, G. Sarala, B. S. Priya, S. L. Gaonkar, J. Shashidhara Prasad, K. S. Rangappa

Research output: Contribution to journalArticle

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Abstract

Synthesis and characterization of N-alkylated benzotriazole derivatives 2(a-g) bearing pharmaceutically important bioactive substituents and their antimicrobial studies in vitro are described. The syntheses of the compounds were achieved by N-alkylation of the benzotriazole with different bioactive alkyl halides in presence of powdered K2CO3 in DMF solution and by microwave irradiation method with good yield compared to conventional method. The crystal structure analysis shows that compound 4′-benzotriazol-1-yl-methyl-biphenyl-2-carbonitrile 2a crystallizes in the space group P1 with cell parameters a = 8.526 (3) Å, b = 12.706 (3) Å, c = 7.966 (2) Å, α = 100.89 (2)°, β = 101.63 (3)°, γ = 102.20(2)°, Volume = 801.7(4) Å3, Z = 2 and the final R factor is 0.0559 for 6130 reflections with 218 parameters and zero restraint. This structure exhibits intermolecular hydrogen bonding. Compounds 2e, 2a showed significant antimicrobial activity.

Original languageEnglish
Pages (from-to)999-1004
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume16
Issue number4
DOIs
Publication statusPublished - 15-02-2006

Fingerprint

Microwaves
Bearings (structural)
Derivatives
Microwave irradiation
R Factors
Alkylation
Hydrogen Bonding
Hydrogen bonds
Crystal structure
benzotriazole
diphenyl
potassium carbonate
In Vitro Techniques

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Nanjunda Swamy, S. ; Basappa ; Sarala, G. ; Priya, B. S. ; Gaonkar, S. L. ; Shashidhara Prasad, J. ; Rangappa, K. S. / Microwave-assisted synthesis of N-alkylated benzotriazole derivatives : Antimicrobial studies. In: Bioorganic and Medicinal Chemistry Letters. 2006 ; Vol. 16, No. 4. pp. 999-1004.
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Nanjunda Swamy, S, Basappa, Sarala, G, Priya, BS, Gaonkar, SL, Shashidhara Prasad, J & Rangappa, KS 2006, 'Microwave-assisted synthesis of N-alkylated benzotriazole derivatives: Antimicrobial studies', Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 4, pp. 999-1004. https://doi.org/10.1016/j.bmcl.2005.10.084

Microwave-assisted synthesis of N-alkylated benzotriazole derivatives : Antimicrobial studies. / Nanjunda Swamy, S.; Basappa; Sarala, G.; Priya, B. S.; Gaonkar, S. L.; Shashidhara Prasad, J.; Rangappa, K. S.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 16, No. 4, 15.02.2006, p. 999-1004.

Research output: Contribution to journalArticle

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T1 - Microwave-assisted synthesis of N-alkylated benzotriazole derivatives

T2 - Antimicrobial studies

AU - Nanjunda Swamy, S.

AU - Basappa,

AU - Sarala, G.

AU - Priya, B. S.

AU - Gaonkar, S. L.

AU - Shashidhara Prasad, J.

AU - Rangappa, K. S.

PY - 2006/2/15

Y1 - 2006/2/15

N2 - Synthesis and characterization of N-alkylated benzotriazole derivatives 2(a-g) bearing pharmaceutically important bioactive substituents and their antimicrobial studies in vitro are described. The syntheses of the compounds were achieved by N-alkylation of the benzotriazole with different bioactive alkyl halides in presence of powdered K2CO3 in DMF solution and by microwave irradiation method with good yield compared to conventional method. The crystal structure analysis shows that compound 4′-benzotriazol-1-yl-methyl-biphenyl-2-carbonitrile 2a crystallizes in the space group P1 with cell parameters a = 8.526 (3) Å, b = 12.706 (3) Å, c = 7.966 (2) Å, α = 100.89 (2)°, β = 101.63 (3)°, γ = 102.20(2)°, Volume = 801.7(4) Å3, Z = 2 and the final R factor is 0.0559 for 6130 reflections with 218 parameters and zero restraint. This structure exhibits intermolecular hydrogen bonding. Compounds 2e, 2a showed significant antimicrobial activity.

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