European Journal of Chemistry

Synthesis and evaluation of antimitotic activity of new tetralone acid analogues of podophyllotoxin

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Published: Sep 30, 2014
DOI: https://doi.org/10.5155/eurjchem.5.3.424-429.1020
Keywords:
Ketones, Itaconic acids, Tetralone acids, Antimitotic activity, Stobbe condensation, Catalytic hydrogenation
Section
Research Article
Issue
Vol. 5 No. 3 (2014): September 2014
Dates
Received 2014-01-20
Accepted 2014-03-08
Published 2014-09-30


Main Article Content

Santhekasalagere Basavaiah Shivakumar
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India
Yeriyur Basavaiah Basavaraju
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India
Basavaiah Umesha
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India
Mudeenahally Hucchegowda Krishna
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India
Ningegowda Mallesha
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India

Abstract

The new tetralone acids (7a-e) were synthesized as analogues of podophyllotoxin. They were prepared by replacing 3,4,5-trimethoxyphenyl ring with cyclohexyl group in podophyllotoxin and 1,3-methylene dioxy ring with methoxy, hydrogen, methyl, thiomethyl, and fluorine atoms. The analogues of podophyllotoxin were synthesized using Gensler’s method with some changes in reagents and experimental procedure. The structures of the synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, mass spectra and elemental analysis data. The synthesized tetralones acids were screened for their antimitotic activity. It is noteworthy that compound 7b possessed excellent antimitotic activity, 7c and 7e showed considerable activity and remaining 7a and 7d possessed low activity.


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Shivakumar, S. B.; Basavaraju, Y. B.; Umesha, B.; Krishna, M. H.; Mallesha, N. Synthesis and Evaluation of Antimitotic Activity of New Tetralone Acid Analogues of Podophyllotoxin. Eur. J. Chem. 2014, 5, 424-429.

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References

[1]. Podwyssotzki, V. Arch. Expt. Path. U. Pharmakol. 1880, 13, 29-52.
http://dx.doi.org/10.1007/BF01833268

[2]. Jardine, I. Anticancer Agents Based on Natural Product Models, Cassady, J. M.; Douros, J. D. Eds., Academic Press, New York, 1980, pp. 319-351.

[3]. Hartwell, J. L.; Schrecker, A. W. Fortschr. Chem. Org. Naturst. 1958, 13, 83-166.

[4]. Smissman, E. E.; Murray, R. J.; McChesney, J. D.; Houston, L. L.; Pazdernik, T. L. J. Med. Chem. 1976, 19, 148-153.
http://dx.doi.org/10.1021/jm00223a025

[5]. Schreir, E. A. 152nd National Meeting of the American Chemical Society, New York, 1966, pp. 34.

[6]. Anjanamurthy, C.; Lokanatha Rai, K. M. Indian J. Chem. Sect. B. 1987, 26, 131-135.

[7]. Ward, R. S. Chem. Soc. Rev. 1982, 11, 003-004.

[8]. Basavaraju, Y. B.; Anjanamurthy, C. Indian J. Chem. Sect. B. 2003, 42, 876-880.

[9]. Gensler, W. J.; Samour, C. M.; Wand, S. Y.; Johnson, F. J. Am. Chem. Soc. 1960, 82, 1714-1727.
http://dx.doi.org/10.1021/ja01492a047

[10]. Lokanatha, R. K. M.; Basavaraju, Y. B.; Sadashivamurthy, B. Indian J. Pharm. Sci. 2007, 69, 116-118.
http://dx.doi.org/10.4103/0250-474X.32122

[11]. Fissceja, G. Hereditas. 1985, 102, 099-112.

[12]. Levan, A. Hereditas. 1938, 24, 471-486.
http://dx.doi.org/10.1111/j.1601-5223.1938.tb03221.x

[13]. Hakala, T. R.; Lange, P. A.; Fraley, E. F. Estimation of Human Cell Mediated Cytotoxicity by Lymphocyte Titration and Automated Image Analysis. In: In Vitro Methods in Cell-Mediated Immunity, VII, Bloom, B. R.; David, J. R., Eds., Academic Press, New York, 1976, pp. 451-460.

[14]. Hemakumar, K. H.; Sathisha, A. D.; Basavaraju, Y. B. E-J. Chem. 2008, 5, 114-119.

[15]. Daub, G. H.; Johnso, W. S. The Stobbe Condensation with Sodium Hydride, Organic reactions, John Wiley and Sons, New York, 1950, pp. 501-504.

[16]. Siegel, S.; Dunkel, M.; Smith, G. V.; Halpern, W.; Cozort, J. J. Org. Chem. 1966, 31, 2802-2806.
http://dx.doi.org/10.1021/jo01347a016

[17]. Gault, F. G.; Rooney, J. J.; Kemball, C. J. Catal. 1962, 1, 255-274.
http://dx.doi.org/10.1016/0021-9517(62)90054-4

[18]. Gensler, W. J.; Murthy, C. D.; Trammell M. H. J. Med. Chem. 1977, 20, 635-644.
http://dx.doi.org/10.1021/jm00215a004

[19]. Gensler, W. J.; Gatsonis, C. D. J. Med. Chem. 1966, 31, 4004-4008.

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