Investigations of regio- and stereoselectivities in the synthesis of cytotoxic isoxazolidines through 1,3-dipolar cycloadditions of nitrones to dipolarophiles bearing an allylic oxygen |
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Authors: | Rajinder Singh A.K. Sexana Abdul Faruk |
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Affiliation: | a Bio-organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar 143 005, Punjab, India b Pharmacology Division, Regional Research Laboratory, Jammu 184 001, J & K, India |
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Abstract: | Regio- and stereoselectivities in cycloadditions of nitrones to dipolarophiles bearing an allylic oxygen, which furnishes substituted-isoxazolidine analogs of the furanose ring of nucleosides, have been investigated. Although the obtained regioselectivities are anticipated, a rationalization of the preferred formation of endo-cycloadducts necessitates the involvement of an allylic oxygen in secondary interaction. The obtained isoxazolidines display cytotoxic activities against a number of human cancer cell lines. |
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Keywords: | Cycloadditions Nitrone Stereoselectivities Secondary interactions Isoxazolidines Anticancer activity |
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