Journal
MOLECULAR DIVERSITY
Volume 19, Issue 3, Pages 511-527Publisher
SPRINGER
DOI: 10.1007/s11030-015-9593-3
Keywords
Steroid; [3+2] Cycloaddition; Lewis acid; Stereoselectivity; Arylpyrazoline; Antiproliferative effect
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Funding
- Hungarian Scientific Research Fund [OTKA K-109107, OTKA K-109293]
- European Union
- State of Hungary
- European Social Fund [TAMOP 4.2.4. A/2-11/1-2012-0001]
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Novel androstenoarylpyrazolines were synthesized stereoselectively by the -induced intramolecular 1,3-dipolar cycloaddition of alkenyl hydrazones obtained from a steroidal D-seco-aldehyde with differently substituted arylhydrazines. The reaction rates were observed to be affected significantly by the electronic character of the substituents on the aromatic moiety. The cyclizations are assumed to follow a stepwise rather than a pure concerted mechanism, to afford arylpyrazolidines as primary products. Spontaneous oxidation of the saturated ,-heterocycles under the reaction conditions led to pyrazoline derivatives in good to excellent yields. In in vitro antiproliferative studies on a panel of breast cancer cells (MCF7, T47D, MDA-MB-231, and MDA-MB-361), some of the 3-deacetylated cycloadducts exerted marked growth inhibitory activities, with values in the range 3.56-9.32 , which are comparable to that for the reference agent cisplatin.
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