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-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.
Department of Pharmaceutical Chemistry, Bapatla College of Pharmacy, Bapatla, Andra Pradesh, India.
Immadisetty Sri
IS
Krishnanjaneyulu
Department of Pharmaceutical Chemistry, Bapatla College of Pharmacy, Bapatla, Andra Pradesh, India.
Govindaraj
G
Saravanan
Department of Pharmaceutical Chemistry, Bapatla College of Pharmacy, Bapatla, Andra Pradesh, India.
Janga
J
Vamsi
Department of Pharmaceutical Chemistry, Bapatla College of Pharmacy, Bapatla, Andra Pradesh, India.
Pamidipamula
P
Supriya
Department of Pharmaceutical Chemistry, Bapatla College of Pharmacy, Bapatla, Andra Pradesh, India.
Jarugula Udaya
JU
Bhavana
Department of Pharmaceutical Chemistry, Bapatla College of Pharmacy, Bapatla, Andra Pradesh, India.
Mittineni Venkata
MV
Sunil Kumar
Antibacterial; antifungal; chalcone; mannich base; pyrazole