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).
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Authors | Kumar Vasantha, Guru Basavarajaswamy, M Vaishali Rai, Poojary Boja, Vinitha R Pai, N Shruthi, Mahima Bhat |
Journal | Bioorganic & medicinal chemistry letters
(Bioorg Med Chem Lett)
Vol. 25
Issue 7
Pg. 1420-6
(Apr 01 2015)
ISSN: 1464-3405 [Electronic] England |
PMID | 25765910
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Copyright | Copyright © 2015 Elsevier Ltd. All rights reserved. |
Chemical References |
- Anti-Inflammatory Agents, Non-Steroidal
- Antifungal Agents
- Benzimidazoles
- Hydrazones
- Carrageenan
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Topics |
- Animals
- Anti-Inflammatory Agents, Non-Steroidal
(chemical synthesis, chemistry, pharmacology)
- Antifungal Agents
(chemical synthesis, chemistry, pharmacology)
- Aspergillus niger
(drug effects)
- Benzimidazoles
(chemical synthesis, chemistry, pharmacology)
- Candida albicans
(drug effects)
- Carrageenan
- Dose-Response Relationship, Drug
- Edema
(chemically induced, drug therapy)
- Humans
- Hydrazones
(chemical synthesis, chemistry, pharmacology)
- Mice
- Microbial Sensitivity Tests
- Molecular Structure
- Penicillium chrysogenum
(drug effects)
- Structure-Activity Relationship
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