کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1405075 | 1501707 | 2016 | 7 صفحه PDF | دانلود رایگان |
• Isoxazoline hetero rings were introduced into ring D of the sterane core.
• Intermolecular alkene−nitrile oxide cycloadditions were carried out.
• The stereo- and regioselectivity of the ring-closures were investigated.
• The structures of all novel compounds were confirmed by NMR measurements.
• Antiproliferative effects were determined in vitro on 4 malignant human cell lines.
Efficient syntheses of some pregnane-fused isoxazolines from 16-dehydropregnenolone acetate with different arylnitrile oxides were carried out by 1,3-dipolar cycloadditions. The intermolecular ring-closures occurred in a highly regio- and stereoselective manner permitting the formation of a single 16α,17α-condensed diastereomer in which the O terminus of the nitrile oxide dipole is attached to C-17 of the sterane core. The conversions were found to be affected significantly by the electronic character of the substituents on the aromatic moiety of the 1,3-dipoles. Deacetylation of the primary products resulted in the corresponding 3β-OH analogs. All of the synthesized compounds were subjected to in vitro pharmacological studies for the determination of their antiproliferative effects on four breast cancer cell lines (MCF7, T47D, MDA-MB-231 and MDA-MB-361).
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Journal: Journal of Molecular Structure - Volume 1110, 15 April 2016, Pages 143–149