Synthesis and characterization of diaza analogues of podophyllotoxin

Basavaraju, Y. B.; Umesha, Basavaiah

doi:10.5155/eurjchem.4.3.235-239.782

Eur. J. Chem.

2013

DOI: 10.5155/eurjchem.4.3.235-239.782

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Synthesis and characterization of diaza analogues of podophyllotoxin

Y. B. Basavaraju

Basavaiah Umesha

Abstract: KEYWORDSIn 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. Chalcones Tetralones Ethylformate Sodium hydride Hydrazine hydrate Cyclopropyl ketones

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Cited by 3 publications

References 14 publications

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1-(3,4-Dimethoxyphenyl)-3-phenylprop-2-en-1-one

et al. 2014

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In the title compound, C17H16O3, the dihedral angle between the mean planes of the benzene rings is 57.1 (1)°. The mean plane of the ketone group is twisted by 10.0 (5)° from that of the dimethoxyphenyl ring. The two dimethoxyphenyl groups are twisted slighly from the mean plane of the phenyl ring, with C—O—C—C torsion angles of 6.4 (2) and −7.9 (2)° [r.m.s. deviations = 0.15 (3) and 0.18 (3) Å for the two methoxy C atoms]. In the crystal, weak centroid–centroid π–π stacking interactions, with intercentroid distances of 3.8939 (11) and 3.9430 (10) Å are observed.

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1-(3,4-Dimethoxyphenyl)-3-phenylprop-2-en-1-one

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Synthesis and study of antimicrobial activity of new tetralone esters

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Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues

2016

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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.

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Synthesis and characterization of diaza analogues of podophyllotoxin

Cited by 3 publications

References 14 publications

1-(3,4-Dimethoxyphenyl)-3-phenylprop-2-en-1-one

1-(3,4-Dimethoxyphenyl)-3-phenylprop-2-en-1-one

Synthesis and study of antimicrobial activity of new tetralone esters

Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues

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