European Journal of Chemistry 2013, 4(3), 235-239. doi:10.5155/eurjchem.4.3.235-239.782

Synthesis and characterization of diaza analogues of podophyllotoxin


Yeriyur Basavaiah Basavaraju (1,*) , Basavaiah Umesha (2)

(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
(*) Corresponding Author

Received: 23 Mar 2013, Accepted: 07 May 2013, Published: 30 Sep 2013

Abstract


In an attempt to synthesize the novel diaza analogues of podophyllotoxin (7a-d) in five step reactions. The synthesis of title compounds has been achieved from tetralones, which were formylated with ethylformate; prepared via cyclization with hydrazine hydrate. Furthermore, these newly synthesized compounds were characterized by spectral and elemental analysis data.

4_3_235_239

Keywords


Chalcones; Tetralones; Ethylformate; Sodium hydride; Hydrazine hydrate; Cyclopropyl ketones

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.4.3.235-239.782

Article Metrics


This Abstract was viewed 520 times | PDF Article downloaded 308 times

Citations

/


[1]. Basavaiah Umesha, Yeriyur Basavaiah Basavaraju, Manpreet Kaur, Hemmige S. Yathirajan, Jerry P. Jasinski
1-(3,4-Dimethoxyphenyl)-3-phenylprop-2-en-1-one
Acta Crystallographica Section E Structure Reports Online  70(3), o368, 2014
DOI: 10.1107/S160053681400378X
/


[2]. Krishna Mudeenahally Hucchegowda, Basavaraju Yeriyur Basavaiah, Umesha Basavaiah, Shivakumar Santhekasalagere Basavaiah
Synthesis and study of antimicrobial activity of new tetralone esters
European Journal of Chemistry  5(4), 584, 2014
DOI: 10.5155/eurjchem.5.4.584-587.1093
/


[3]. Kanakapura Narayanaramakrishna Padmavath, Yeriyuru Basavaiah Basavaraju, Basavaiah Umesha
Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues
European Journal of Chemistry  7(2), 192, 2016
DOI: 10.5155/eurjchem.7.2.192-194.1389
/


References

[1]. Shi-Wu, C.; Yun-Hua, W.; Yan, J.; Xuan, T.; Yong-Tang, Z.; Du-Qiang, L.; Yong-Qiang, T. Bioorg. Med. Chem. Lett. 2007, 17, 2091- 2095.
http://dx.doi.org/10.1016/j.bmcl.2006.11.070
PMid:17317161

[2]. Mohammed, M. M. D.; Chen, M.; Zhai, L.; Ibrahim, N. A. Eur. J. Chem. 2010, 1(2), 110-114.
http://dx.doi.org/10.5155/eurjchem.1.2.110-114.74

[3]. Zhu, X. K.; Guan, J.; Xiao, Z.; Cosentino, M.; Lee, K. H. Bioorg. Med. Chem. 2004, 12, 4267-4273.
http://dx.doi.org/10.1016/j.bmc.2004.04.048
PMid:15246103

[4]. Lee, K. H. ACS Symp. Ser. 1993, 170-190.
http://dx.doi.org/10.1021/bk-1993-0534.ch012

[5]. MacRae, W. D.; Hudson, J. B.; Towers, B. H. N. Planta Med. 1993, 55, 531-535.
http://dx.doi.org/10.1055/s-2006-962087
PMid:2559420

[6]. Imbert, T. F. Biochimie. 1998, 80, 207-222.
http://dx.doi.org/10.1016/S0300-9084(98)80004-7

[7]. Hemakumar, K. H.; Sathisha, A. D.; Basavaraju, Y. B. E-Journal Chem. 2008, 5, 114-119.
http://dx.doi.org/10.1155/2008/314724

[8]. Jardine, I.; Carrady, J. M.; Dourous, J. D. Anticancer agents Based on Natural Product Models, Eds., Academic press, New York. 1980, pp. 319-351.

[9]. Lee, K. H.; Beers, S. A.; Mori, M.; Wang, Z. Q.; Kuo, Y. H.; Li, L.; Liu, S. Y.; Chang, J. Y.; Han, F. S.; Chang, Y. C. J. Med. Chem. 1990, 33, 1365-1368.
http://dx.doi.org/10.1021/jm00167a013

[10]. Stehlin, H.; Von Wartburg, A. Prog. Drug Res. 1989, 33, 169-266.
http://dx.doi.org/10.1007/978-3-0348-9146-2_8

[11]. Ahmad, K.; Ashwin, K. B.; Paidakula, S.; Nagula, S.; Shiva, K. M. Bioorg. Med. Chem. Lett. 2011, 21, 350-353.
http://dx.doi.org/10.1016/j.bmcl.2010.11.002
PMid:21144748

[12]. Kelly, M. G.; Hart Well, J. L. Natl. J. Cancer Ins. 1954, 14, 967-1010.

[13]. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogels text book of practical organic chemistry, 5th edition, ELBS with Longman, 1989.
PMCid:PMC1216650

[14]. Rai, K. M. L.; Murthy, C. V.; Radhakrishna, P. M. Synthetic Comm. 1990, 20, 1273-1277.
http://dx.doi.org/10.1080/00397919008052837

[15]. Doyle, M. P.; Hu, W. Adv. Synth. Catal. 2001, 343, 299-302.
http://dx.doi.org/10.1002/1615-4169(20010330)343:3<299::AID-ADSC299>3.0.CO;2-Y

[16]. Davies, H. M. L.; Calvo, R. L.; Townsend, R. J.; Ren, P.; Churchill, R. M. J. Org. Chem. 2000, 65, 4261-4268.
http://dx.doi.org/10.1021/jo991959b

[17]. Sadashiva, M. B.; Basavaraju, Y. B. Bulg. Chem. Comm. 2005, 37, 135-139.

[18]. Anjana, M. C.; Basavaraju, Y. B. Ind. J. Hetero. Chem. 1998, 7, 177-180.

[19]. Padmavathi, V.; Mohan, R. B. J.; Balaiah, A.; Venugopal, R. K.; Bhaskar, R. D. Molecules. 2000, 5, 1281-1286.
http://dx.doi.org/10.3390/51201281


How to cite


Basavaraju, Y.; Umesha, B. Eur. J. Chem. 2013, 4(3), 235-239. doi:10.5155/eurjchem.4.3.235-239.782
Basavaraju, Y.; Umesha, B. Synthesis and characterization of diaza analogues of podophyllotoxin. Eur. J. Chem. 2013, 4(3), 235-239. doi:10.5155/eurjchem.4.3.235-239.782
Basavaraju, Y., & Umesha, B. (2013). Synthesis and characterization of diaza analogues of podophyllotoxin. European Journal of Chemistry, 4(3), 235-239. doi:10.5155/eurjchem.4.3.235-239.782
Basavaraju, Yeriyur, & Basavaiah Umesha. "Synthesis and characterization of diaza analogues of podophyllotoxin." European Journal of Chemistry [Online], 4.3 (2013): 235-239. Web. 23 Jan. 2019
Basavaraju, Yeriyur, AND Umesha, Basavaiah. "Synthesis and characterization of diaza analogues of podophyllotoxin" European Journal of Chemistry [Online], Volume 4 Number 3 (30 September 2013)

DOI Link: https://doi.org/10.5155/eurjchem.4.3.235-239.782

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2018  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 2018 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.