title: Rapid 'one-pot' synthesis of a novel benzimidazole-5-carboxylate and its hydrazone derivatives as potential anti-inflammatory and antimicrobial agents.
abstract: A novel series of N-arylidene-2-(2,4-dichloro phenyl)-1-propyl-1H-benzo[d] imidazole-5-carbohydrazides having different substitution on the arylidene part were synthesized in good yield. The core nucleus benzimidazole-5-carboxylate (5) was efficiently synthesized by 'one-pot' nitro reductive cyclization reaction between ethyl-3-nitro-4-(propylamino)benzoate and 2,4-dichlorobenzaldehyde using sodium dithionite in dimethylsulfoxide. This 'one-pot' reaction was proceeded very smoothly, in short reaction time with an excellent yield. All the compounds (7a-r) were screened for their in vivo anti-inflammatory and in vitro antimicrobial activity. Most of the compounds exhibited remarkable paw-edema inhibition in the initial one hour of administration indicating the higher potentiality of these molecules. In particular, compounds 7a, 7d, 7f and 7g displayed a high level of carrageenan-induced paw edema inhibition compared to that of indomethacin. Compound 7p exhibited very good antibacterial activity and antifungal activity with a MIC of 3.12 μg/mL against most of the tested organisms. Furthermore, compounds 7d, 7f, 7h and 7p found to be good inhibitors of Aspergillus niger with MIC of 3.12 μg/mL. Cytotoxicity of the potent compounds 7d, 7f and 7p was checked using MDA MB-231 breast cancer cell line and are found to be non toxic at the highest concentration used (i.e., 10 μg/mL).
authors.affiliation: Department of Studies in Chemistry, Mangalore University, Mangalagangotri, Karnataka 574 199, India.
authors.forename: Kumar
authors.initials: K
authors.lastname: Vasantha
authors.affiliation: Acharya & B.M. Reddy College of Pharmacy, Soldevanahalli, Chikkabanavara Post, Bangalore 560 090, Karnataka, India.
authors.forename: Guru
authors.initials: G
authors.lastname: Basavarajaswamy
authors.affiliation: Department of Bio-chemistry, Yenepoya University, Deralakatte, Mangalore, Karnataka 575 018, India.
authors.forename: M
authors.initials: M
authors.lastname: Vaishali Rai
authors.affiliation: Department of Studies in Chemistry, Mangalore University, Mangalagangotri, Karnataka 574 199, India. Electronic address: bojapoojary@gmail.com.
authors.forename: Poojary
authors.initials: P
authors.lastname: Boja
authors.affiliation: Department of Bio-chemistry, Yenepoya University, Deralakatte, Mangalore, Karnataka 575 018, India.
authors.forename: Vinitha R
authors.initials: VR
authors.lastname: Pai
authors.affiliation: Department of Studies in Chemistry, Mangalore University, Mangalagangotri, Karnataka 574 199, India.
authors.forename: N
authors.initials: N
authors.lastname: Shruthi
authors.affiliation: Department of Studies in Chemistry, Mangalore University, Mangalagangotri, Karnataka 574 199, India.
authors.forename: Mahima
authors.initials: M
authors.lastname: Bhat
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001234:Aspergillus niger / Q000187:drug effects; D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D002351:Carrageenan; D004305:Dose-Response Relationship, Drug; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy*; D006801:Humans; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010408:Penicillium chrysogenum / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D000935:Antifungal Agents; D001562:Benzimidazoles; D006835:Hydrazones; D002351:Carrageenan
keywords: Anti-inflammatory activity; Antimicrobial activity; Hydrazones; Reductive cyclization; ‘One-pot’ method