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Synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives

A series of novel N-((1H-benzoimidazol-1-yl) methyl)-4-(1-phenyl-5-substituted-4, 5-dihydro-1-benzoimidazol-1-yl) methyl)-4-(1-phenyl-5-substituted-4, 5-dihydro-1H-pyrazol-3-yl) benzenamine were synthesized by treating various 1-(4-((1H-benzoimidazol-1-yl) methylamino) phenyl)-3-substitutedprop-2-en...

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Autores principales: Krishnanjaneyulu, Immadisetty Sri, Saravanan, Govindaraj, Vamsi, Janga, Supriya, Pamidipamula, Bhavana, Jarugula Udaya, Sunil Kumar, Mittineni Venkata
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Medknow Publications & Media Pvt Ltd 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3960790/
https://www.ncbi.nlm.nih.gov/pubmed/24696814
http://dx.doi.org/10.4103/2231-4040.126983
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author Krishnanjaneyulu, Immadisetty Sri
Saravanan, Govindaraj
Vamsi, Janga
Supriya, Pamidipamula
Bhavana, Jarugula Udaya
Sunil Kumar, Mittineni Venkata
author_facet Krishnanjaneyulu, Immadisetty Sri
Saravanan, Govindaraj
Vamsi, Janga
Supriya, Pamidipamula
Bhavana, Jarugula Udaya
Sunil Kumar, Mittineni Venkata
author_sort Krishnanjaneyulu, Immadisetty Sri
collection PubMed
description A series of novel N-((1H-benzoimidazol-1-yl) methyl)-4-(1-phenyl-5-substituted-4, 5-dihydro-1-benzoimidazol-1-yl) methyl)-4-(1-phenyl-5-substituted-4, 5-dihydro-1H-pyrazol-3-yl) benzenamine were synthesized by treating various 1-(4-((1H-benzoimidazol-1-yl) methylamino) phenyl)-3-substitutedprop-2-en-1-one with phenyl hydrazine in the presence of sodium acetate through a simple ring closure reaction. The starting material, 1-(4-((1H-benzoimidazol-1-yl) methylamino) phenyl)-3-substitutedprop-2-en-1-one,-benzoimidazol-1-yl) methylamino) phenyl)-3-substitutedprop-2-en-1-one, was synthesized from o-phenylenediamine by a multistep synthesis. All the synthesized compounds were characterized by spectroscopic means and elemental analyses. The title compounds were investigated for in vitro antibacterial and antifungal properties against some human pathogenic microorganisms by employing the agar streak dilution method using Ciprofloxacin and Ketoconazole as standard drugs. All title compounds showed activity against the entire strains of microorganism. Structural activity relationship studies reveal that compounds possessing an electron-withdrawing group display better activity than the compounds containing electron-donating groups, whereas the unsubstituted derivatives display moderate activity. Based on the results obtained, N-((1H-benzoimidazol-1-yl) methyl)-4-(1-phenyl-5-(4-(trifluoromethyl) phenyl)-4,5-dihydro-1H-pyrazol-3-yl) benzenamine 5i was found to be very active compared with the rest of the compounds and standard drugs that were subjected to antimicrobial assay.
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spelling pubmed-39607902014-04-02 Synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives Krishnanjaneyulu, Immadisetty Sri Saravanan, Govindaraj Vamsi, Janga Supriya, Pamidipamula Bhavana, Jarugula Udaya Sunil Kumar, Mittineni Venkata J Adv Pharm Technol Res Original Article A series of novel N-((1H-benzoimidazol-1-yl) methyl)-4-(1-phenyl-5-substituted-4, 5-dihydro-1-benzoimidazol-1-yl) methyl)-4-(1-phenyl-5-substituted-4, 5-dihydro-1H-pyrazol-3-yl) benzenamine were synthesized by treating various 1-(4-((1H-benzoimidazol-1-yl) methylamino) phenyl)-3-substitutedprop-2-en-1-one with phenyl hydrazine in the presence of sodium acetate through a simple ring closure reaction. The starting material, 1-(4-((1H-benzoimidazol-1-yl) methylamino) phenyl)-3-substitutedprop-2-en-1-one,-benzoimidazol-1-yl) methylamino) phenyl)-3-substitutedprop-2-en-1-one, was synthesized from o-phenylenediamine by a multistep synthesis. All the synthesized compounds were characterized by spectroscopic means and elemental analyses. The title compounds were investigated for in vitro antibacterial and antifungal properties against some human pathogenic microorganisms by employing the agar streak dilution method using Ciprofloxacin and Ketoconazole as standard drugs. All title compounds showed activity against the entire strains of microorganism. Structural activity relationship studies reveal that compounds possessing an electron-withdrawing group display better activity than the compounds containing electron-donating groups, whereas the unsubstituted derivatives display moderate activity. Based on the results obtained, N-((1H-benzoimidazol-1-yl) methyl)-4-(1-phenyl-5-(4-(trifluoromethyl) phenyl)-4,5-dihydro-1H-pyrazol-3-yl) benzenamine 5i was found to be very active compared with the rest of the compounds and standard drugs that were subjected to antimicrobial assay. Medknow Publications & Media Pvt Ltd 2014 /pmc/articles/PMC3960790/ /pubmed/24696814 http://dx.doi.org/10.4103/2231-4040.126983 Text en Copyright: © Journal of Advanced Pharmaceutical Technology & Research http://creativecommons.org/licenses/by-nc-sa/3.0 This is an open-access article distributed under the terms of the Creative Commons Attribution-Noncommercial-Share Alike 3.0 Unported, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Original Article
Krishnanjaneyulu, Immadisetty Sri
Saravanan, Govindaraj
Vamsi, Janga
Supriya, Pamidipamula
Bhavana, Jarugula Udaya
Sunil Kumar, Mittineni Venkata
Synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives
title Synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives
title_full Synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives
title_fullStr Synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives
title_full_unstemmed Synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives
title_short Synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives
title_sort synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3960790/
https://www.ncbi.nlm.nih.gov/pubmed/24696814
http://dx.doi.org/10.4103/2231-4040.126983
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