Abstract
A series of substituted-N′-[(1E)-substituted-phenylmethylidene]benzohydrazide analogs were synthesized and authenticated by TLC, UV–Visible, FTIR, and NMR spectroscopic techniques. The physicochemical similarity of the new analogs with standard drugs was assessed by calculating from a set of ten physicochemical properties using software programs. The information so obtained can be related to prediction of biological activity for important targets. All the target compounds 4a–n were evaluated for their antioxidant, anti-inflammatory, and antimicrobial activity using different in vitro models. The test compounds demonstrated good similarity values with respect to the standard drugs. The compounds 4c, 4d, and 4e have emerged as important lead compounds showing potential anti-inflammatory; and 4b, 4f, and 4c having antioxidant profile. While studying MIC against bacterial strains 4c, 4f, 4i, 4k, and 4m were most active among all the target compounds. All compounds were found to have very good antifungal activity. The compounds having nitro substitution at the arylidene moiety i.e., 4c and 4f showed the most potent antifungal as well as antibacterial activities. While studying total antioxidant activity, all target compounds were found to have good antioxidant activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Atlan V, El Kaim L, Supiot C (2000) New versatile approach to α-hydrazonoesters and aminoacids derivatives through a modified Japp–Klingemann reaction. Chem Commun 15:1385–1386
Belkheiri N, Bouguerne B, Bedos-Belval F, Duran H, Bernis C, Salvayre R, Negre-Salvayre A, Baltas M (2010) Synthesis and antioxidant activity evaluation of a syringic hydrazones family. Eur J Med Chem 45:3019–3026
Chanda S, Dave R (2009) In vitro models for antioxidant activity evaluation and some medicinal plants possessing antioxidant properties: an overview. Afr J Microbiol Res 3(13):981–996
Corey E (1976) Applications of N,N-dimethylhydrazones to synthesis. Use in efficient, positionally and stereochemically selective C–C bond formation; oxidative hydrolysis to carbonyl compounds. Tetrahedron Lett 17:3–6
Corey EJ, Enders D (1976) Synthetic routes to polyfunctional molecules via mutilated N,N-dimethylhydrazones. Tetrahedron Lett 17:11–14
Eissa AAM, Farag NAH, Soliman GAH (2009) Synthesis, biological evaluation and docking studies of novel benzopyranone congeners for their expected activity as anti-inflammatory, analgesic and antipyretic agents. Bioorg Med Chem 17:5059–5070
Elassar AA, Dib HH, Al-Awadi NA, Elnagdi MH (2007) Chemistry of carbofunctionally substituted hydrazones. ARKIVOC 2:272–315
Kurumbail RG, Stevens AM, Gierse JK, McDonald JJ, Stegeman RA, Pak JY, Gildehaus D, Miyashiro JM, Penning TD, Seibert K, Isakson PC, Stallings WC (1996) Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 384:644–648
Lingnert H, Vallentin K, Eriksson CE (1979) Measurement of antioxidative effect in model system. J Food Process Preserv 3:87–103
Melnyk P, Leroux V, Sergheraerta C, Grellier P (2006) Design, synthesis and in vitro antimalarial activity of an acylhydrazone library. Bioorg Med Chem Lett 16:31–35
Mizushima Y, Kobayashi M (1968) Interaction of anti-inflammatory drugs with serum proteins, especially with some biologically active proteins. J Pharm Pharmacol 20:169–173
Nikolova N, Jaworska J (2003) Approaches to measure chemical similarity: a review. QSAR Comb Sci 22:1006
Panneerselvam P, Reddy RS, Murali K, Kumar NR (2010) Synthesis, analgesic, anti-inflammatory and antimicrobial activities of some novel Schiff’s bases of 5-substituted isatin. Der Pharma Chem 2(1):28–37
Picot D, Loll PJ, Garavito RM (1994) The X-ray crystal structure of the membrane protein prostaglandin H2 synthase-1. Nature 367:243
Prieto P, Pineda M, Aguilar M (1999) Spectrophotometric quantitation of antioxidant capacity through the formation of a phosphomolybdenum complex: specific application to the determination of vitamin E. Anal Biochem 269:337–341
Radwan MAA, Ragab EA, Sabrya NM, El-Shenawy SM (2007) Synthesis and biological evaluation of new 3-substituted indole derivatives as potential anti-inflammatory and analgesic agents. Bioorg Med Chem 15:3832–3841
Rajput AP, Rajput SS (2009) Synthesis of benzaldehyde substituted phenyl carbonyl hydrazones and their formylation using Vilsmeier–Haack reaction. IJPRIF 1(4):1605–1611
Rao DS, Jayachandran E, Sreenivasa GM, Shivakumar B (2005) Inhibition of albumin denaturation and anti-inflammatory activity of 2-[N-p-Tolyl sulphon hydrazino]-6-fluoro-7-substituted (1,3) benzothiazoles. Orient J Chem 21(1):113–116
Rollas S, Kucukguzel G (2007) Biological activities of hydrazone derivatives. Molecules 12:1910–1939
Ruch RJ, Cheng SJ, Klaunig JE (1989) Prevention of cytotoxicity and inhibition of intercellular communication by antioxidant catechins isolated from Chinese green tea. Carcinogenesis 10:1003–1008
Sies H (1991) Oxidative stress; from basic research to clinical applications. Am J Med 91:31S–38S
Singh V, Srivastava VK, Palit G, Shanker K (1992) Coumarin congeners as antidepressants. Arzneim-Forsch Drug Res 42:993–996
Sreenivasa GM, Jayachandran E, Rao DS, Kumar KJ, Ramachandra Setty (2009) Synthesis of bioactive molecule fluoro benzothiazole comprising potent heterocyclic moieties for anti-inflammatory activity. Int J Pharm Sci 1(1):219–229
Sriram D, Yogeeswari P, Vyas DRK, Senthilkumar P, Bhat P, Srividya M (2010) 5-Nitro-2-furoic acid hydrazones: design, synthesis and in vitro antimycobacterial evaluation against log and starved phase cultures. Bioorg Med Chem Lett 20:4313–4316
Stocker R (1999) Dietary and pharmacological antioxidants in atherosclerosis. Curr Opin Lipidol 10:589–597
Sunil LH, Vikas GR, Pravin P, Priyanka SH, Sampat DN, Sandip TA, Anand AS (2010) Synthesis, characterization and anti-microbial evaluation of some 2-iodo-N’-[(1E)-substituted phenylmethylidene]benzohydrazide analogues. IJPSDR 2(2):134–136
Chem 3D Ultra (2012) Molecular modelling and analyses, version 7.0.3. Cambridge Software, Cambridge
Acknowledgments
Authors are thankful to M. M. College of Pharmacy, M. M. University, Mullana, Ambala for providing support and facility to carry out research.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Bala, S., Uppal, G., Kamboj, S. et al. Design, characterization, computational studies, and pharmacological evaluation of substituted-N′-[(1E) substituted-phenylmethylidene]benzohydrazide analogs. Med Chem Res 22, 2755–2767 (2013). https://doi.org/10.1007/s00044-012-0270-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-012-0270-0