OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS
Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues
Kanakapura Narayanaramakrishna Padmavath (1) , Yeriyuru Basavaiah Basavaraju (2,*) , Basavaiah Umesha (3)
(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
(*) Corresponding Author
Received: 27 Dec 2015 | Revised: 04 Apr 2016 | Accepted: 09 Apr 2016 | Published: 30 Jun 2016 | Issue Date: June 2016
Podophyllotoxin has captured the attention of chemists all over the world for its biological activity. It was isolated from many plants of Podophyllum species such as Podophyllum emodi, Podophyllum peltatum and others. It mainly exhibits anticancer, antimitotic, antimalarial, anti-aids and other activities. Its use is restricted due to its toxicity and unfavourable solubility. It was aimed to synthesize some new heterocyclic analogues of podophyllotoxin by changing the substituents by changing lactone ring with pyrazoline ring and substituents in ring C with hydrogen and methoxy group. Chalcones were prepared by Claisen-Schmidt reaction of 1,3-methylene dioxyacetophenone with benzaldehyde and p-anisaldehyde. The reaction of chalcone with trimethylsulphoxonium iodide in presence of sodium hydride gave cyclopropyl ketone. Intramolecular cyclization reaction of cyclopropyl ketone gave tetralone intermediates of podophyllotoxin. They are obtained in good yields. The structure of all the products was confirmed by spectral data.
Links for Article
| | | | | | |
| | | | | | |
| | | |
Article MetricsThis Abstract was viewed 1864 times | PDF Article downloaded 398 times
University Grant Commission (UGC) University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India, Rajiv Gandhi National Fellowship (RGNF), India
. Podwyssotzki, V. Arch. Exp. Pathol. Pharmakol. 1880, 13, 29-52.
. Smissmann, E. S.; Murray, R. J.; McChesneyet, J. D. J. Med. Chem. 1976, 19, 148-153.
. Ward, R. S. Synthesis 1992, 8, 719-730.
. Nencki, M.; Sieber, N. J. Prakt. Chem. 1881, 23, 147-156.
. Lokanatha Rai, K. M.; Anjanamurthy, C.; Radhakrishna, P. M. Synth. Commun. 1990, 20, 1273-1277.
. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Text Book of Practical Organic Chemistry, 5th Edition, ELBS & Longman, 1989.
. Haworth, R. D. J. Chem. Soc. 1942, 1942, 448-456.
. Vyas, D. M.; Skonezhy, M. P.; Jenkins, T. A.; Doyle, T. W. Tetrahedron Lett. 1986, 27, 3099-3102.
. Doyle, M. P.; Hu, W. Adv. Synth. Catal. 2001, 343, 299-302.
. Umesha, B.; Basavaraju, Y. B. Eur. J. Chem. 2013, 4, 235-239.
. Sathisha, A. D.; Hemakumar, K. H.; Basavaraju, Y. B. Ind. J. Heterocycl. Chem. 2007, 17, 15‐18.
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.7.2.192-194.1389
| | | | | | | | |
| | | | | | |
Save to Zotero Save to Mendeley
European Journal of Chemistry 2016, 7(2), 192-194 | doi: https://doi.org/10.5155/eurjchem.7.2.192-194.1389 | Get rights and content
- There are currently no refbacks.
© Copyright 2010 - 2022 • 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 2010-2022 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.