Abstract
A series of novel flavone incorporated semicarbazides (Y2a–Y2j) was synthesized and characterized by elemental analyses, 1H NMR, 13C NMR, and mass spectral studies. The newly synthesized compounds were screened for their anticonvulsant activity against maximal electroshock seizure model in male wistar rats and compared with the standard drug phenytoin. Compound Y2g i.e., with dimethylamino substitution was found to be most active compound as comparable to standard drug phenytoin and free from in silico neurotoxicity.
Similar content being viewed by others
References
Alam O, Mullick P, Verma SP, Gilani SJ, Khan SA, Siddiqui N, Ahsan W (2010) Synthesis, anticonvulsant and toxicity screening of newer pyrimidine semicarbazone derivatives. Eur J Med Chem 45:2467–2472
Andurkar SV, Beguin C, Stables JP, Kohn H (2001) Synthesis and structural studies of aza analogues of functionalized amino Acids: new anticonvulsant agents. J Med Chem 44:1475–1478
Bhat MA, Siddiqui N, Khan SA (2008) Synthesis of novel 3-(4-acetyl-5H/methyl-5-substituted phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2H-chromen-2-ones as potential anticonvulsant agents. Acta Pol Pharm Drug Res 65(2):235–239
Deckers CLP, Genton P, Sills GJ, Schmidt D (2003) Current limitations of antiepileptic drug therapy: a conference review. Epilepsy Res 53:1–5
Dimmock JR, Sidhu KK, Thayer RS, Mack P, Duffy MJ, Reid RS, Quail JW, Pugazhenthi U, Ong A (1993) Anticonvulsant activities of some arylsemicarbazones displaying potent oral activity in the maximal electroshock screen in rats accompanied by high protection indices. J Med Chem 36:2243–2252
Dimmock JR, Vashishtha SV, Stables JP (2000) Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones and semicarbazones derived from aromatic and unsaturated carbonyl compounds. Eur J Med Chem 35:241–248
Ertl P, Rohde B, Selzer P (2000) Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 43:3714–3717
Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR (1989) Vogel’s textbook of practical organic chemistry, 5th edn. Wiley, New York, pp 964–965
Ilaria M, Marcello I, Alessio C, Marilene S, Niccolo C, Anna MB (2009) Development of QSAR models for predicting hepatocarcinogenic toxicity of chemicals. Eur J Med Chem 44:3658–3664
Lipinski CA, Lombardo L, Dominy BW, Feeney PJ (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 46:3–26
Martin YC, Kutter E, Austel V (1989) The medicinal chemist’s approach, in modern drug research. Path to better and safer Drugs. Marcel Dekker, New York
Masereel B, Lambert DM, Dogné JM, Poupaert JH, Delarge J (1997) Anticonvulsant activity of pyrid-3-yl-sulfonyl ureas and thioureas. Epilepsia 38:334–337
Murti Y, Agrawal T, Pathak D (2010) Synthesis and Anticonvulsant activity of substituted benzaldehyde-4-aryl-thiosemicarbazones. Indian Drugs 47(10):19–27
Pallas 3.1.1.2, ADME-Tox software, CompuDrug International Inc., U.S.A., 2000
Pandeya SN (2012) Semicarbazone—a versatile therapeutic pharmacophore for fragment based anticonvulsant drug design. Acta Pharm 62:263–286
Sameem S, Kumar N, Pathak D (2012) Synthesis and anticonvulsant activity of some newer semicarbazone derivatives. IJPSDR 4(3):195–198
Sharma CS, Nema RK, Sharma VK (2009) Synthesis, anticonvulsant activity and in silico study of some novel amino acids incorporated bicyclo compounds. S J Pharm Sci 2:42–47
Singh HP, Chauhan CS, Pandeya SN, Sharma CS, Srivastava B, Singhal M (2010) Design, synthesis, analgesic and anti-inflammatory activity of some novel chalconesemicarbazone derivatives. Der Pharm Lett 2:460–472
Smith DA (1994) Design of drugs through a consideration of drug metabolism and pharmacokinetics. Eur J Drug Metab Pharm 3:193–199
Vogel HG, Vogel WH (1997) Drug discovery and evaluation. Pharmacological Assays, Springer, Berlin
Molinspiration Cheminformatics, Bratislava, Slovak Republic, Available from: http://www.molinspiration.com/services/properties.html (accessed 16 feb 2013)
Yogeeshwari P, Thirumurgan R, Kavya R, Samuel JS, Stables J (2004) Sriram D. 3-Chloro-2-methylphenyl-substituted semicarbazones: synthesis and anticonvulsant activity. Eur J Med Chem 39:729–734
Yogeeswari P, Sriram D, Suniljit LRJ, Kumar SS, Stables JP (2002) Anticonvulsant and neurotoxicity evaluation of some 6-chlorobenzothiazolyl-2-thiosemicarbazones. Eur J Med Chem 37:231–236
Zhao YH, Abraham MH, Le J, Hersey A, Luscombe CN, Beck G (2002) Rate-limited steps of human oral absorption and QSAR studies. Pharm Res 19:1446–1457
Acknowledgments
The authors are thankful to the BN College of Pharmacy, Udaipur, India for providing laboratory facility for carrying out research work. The authors also deeply appreciate the Punjab University, Punjab, India for providing the spectral studies.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Sharma, C.S., Verma, T., Singh, H.P. et al. Synthesis, characterization and preliminary anticonvulsant evaluation of some flavanone incorporated semicarbazides. Med Chem Res 23, 4814–4824 (2014). https://doi.org/10.1007/s00044-014-1040-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-014-1040-y