Rapid 'one-pot' synthesis of a novel benzimidazole-5-carboxylate and its hydrazone derivatives as potential anti-inflammatory and antimicrobial agents

Bioorganic & Medicinal Chemistry Letters
Kumar VasanthaMahima Bhat

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 7...Continue Reading

References

Nov 17, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hakan GökerSulhiye Yildiz
Dec 5, 2009·European Journal of Medicinal Chemistry·Zahra Garkani-Nejad, Behzad Ahmadi-Roudi
Jan 13, 2011·ACS Medicinal Chemistry Letters·David CarcacheRalf Glatthar

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Citations

May 6, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Valentina OnnisJan Balzarini
Sep 23, 2016·Future Medicinal Chemistry·Syed Nasir Abbas BukhariNoorsaadah Abd Rahman
Dec 13, 2016·European Journal of Medicinal Chemistry·Wasim AkhtarM Mumtaz Alam
Jan 10, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ahmet Çağrı KaraburunZafer Asım Kaplancıklı
Sep 25, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ernestine Nicaise DjuidjeAnna Baldisserotto
Apr 13, 2021·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Venkatasamy MeenatchiLiang Cheng

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