European Journal of Chemistry 2014, 5(3), 424-429. doi:10.5155/eurjchem.5.3.424-429.1020

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


Santhekasalagere Basavaiah Shivakumar (1) , Yeriyur Basavaiah Basavaraju (2,*) , Basavaiah Umesha (3) , Mudeenahally Hucchegowda Krishna (4) , Ningegowda Mallesha (5)

(1) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India
(2) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India
(3) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India
(4) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India
(5) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India
(*) Corresponding Author

Received: 20 Jan 2014, Accepted: 25 Mar 2014, Published: 30 Sep 2014

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.


Keywords


Ketones; Itaconic acids; Tetralone acids; Antimitotic activity; Stobbe condensation; Catalytic hydrogenation

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.5.3.424-429.1020

Get Citation | Scilit | GrowKudos | ResearchGate | Publons | Microsoft Academic

WorldCat | Dimensions | SemanticScholar | PlumX Metrics | Kopernio | Zotero | Mendeley

Article Metrics


This Abstract was viewed 498 times | PDF Article downloaded 352 times


Citations

/


[1]. Haruyasu Asahara, Keita Arikiyo, Nagatoshi Nishiwaki
Development of variously functionalized nitrile oxides
Beilstein Journal of Organic Chemistry  11, 1241, 2015
DOI: 10.3762/bjoc.11.138
/


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.


How to cite


Shivakumar, S.; Basavaraju, Y.; Umesha, B.; Krishna, M.; Mallesha, N. Eur. J. Chem. 2014, 5(3), 424-429. doi:10.5155/eurjchem.5.3.424-429.1020
Shivakumar, S.; Basavaraju, Y.; Umesha, B.; Krishna, M.; Mallesha, N. Synthesis and evaluation of antimitotic activity of new tetralone acid analogues of podophyllotoxin. Eur. J. Chem. 2014, 5(3), 424-429. doi:10.5155/eurjchem.5.3.424-429.1020
Shivakumar, S., Basavaraju, Y., Umesha, B., Krishna, M., & Mallesha, N. (2014). Synthesis and evaluation of antimitotic activity of new tetralone acid analogues of podophyllotoxin. European Journal of Chemistry, 5(3), 424-429. doi:10.5155/eurjchem.5.3.424-429.1020
Shivakumar, Santhekasalagere, Yeriyur Basavaiah Basavaraju, Basavaiah Umesha, Mudeenahally Hucchegowda Krishna, & Ningegowda Mallesha. "Synthesis and evaluation of antimitotic activity of new tetralone acid analogues of podophyllotoxin." European Journal of Chemistry [Online], 5.3 (2014): 424-429. Web. 6 Dec. 2019
Shivakumar, Santhekasalagere, Basavaraju, Yeriyur, Umesha, Basavaiah, Krishna, Mudeenahally, AND Mallesha, Ningegowda. "Synthesis and evaluation of antimitotic activity of new tetralone acid analogues of podophyllotoxin" European Journal of Chemistry [Online], Volume 5 Number 3 (30 September 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.3.424-429.1020

| | | | |

| | | | | |

.

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.