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






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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

Abstract


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.


Keywords


Synthesis; Chalcones; Tetralones; Acetophenone; Podophyllotoxin; Cyclopropyl ketones

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DOI: 10.5155/eurjchem.7.2.192-194.1389

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Funding information


University Grant Commission (UGC) University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India, Rajiv Gandhi National Fellowship (RGNF), India

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How to cite


Padmavath, K.; Basavaraju, Y.; Umesha, B. Eur. J. Chem. 2016, 7(2), 192-194. doi:10.5155/eurjchem.7.2.192-194.1389
Padmavath, K.; Basavaraju, Y.; Umesha, B. Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues. Eur. J. Chem. 2016, 7(2), 192-194. doi:10.5155/eurjchem.7.2.192-194.1389
Padmavath, K., Basavaraju, Y., & Umesha, B. (2016). Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues. European Journal of Chemistry, 7(2), 192-194. doi:10.5155/eurjchem.7.2.192-194.1389
Padmavath, Kanakapura, Yeriyuru Basavaiah Basavaraju, & Basavaiah Umesha. "Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues." European Journal of Chemistry [Online], 7.2 (2016): 192-194. Web. 2 Jun. 2020
Padmavath, Kanakapura, Basavaraju, Yeriyuru, AND Umesha, Basavaiah. "Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues" European Journal of Chemistry [Online], Volume 7 Number 2 (30 June 2016)

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DOI Link: https://doi.org/10.5155/eurjchem.7.2.192-194.1389

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