کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1361588 | 981467 | 2007 | 10 صفحه PDF | دانلود رایگان |
Novel fluorinated sulfone analogs of the hormone 1α,25-dihydroxyvitamin D3 have been designed and synthesized in order to study the biological effects of fluorine incorporation at the terminus of the C,D-ring side chain. Although biologically active 26,27-hexafluorinated 1α,25-dihydroxyvitamin D3 analogs have been synthesized previously, this investigation reports the first successful fluorinated series in which trifluoromethyl sulfone analogs present a favorable biological profile. This study shows that two new analogs featuring incorporation of a synthetically simple single trifluoromethyl sulfone group have significantly increased antiproliferative activity while causing desirably low in vivo calciuria relative to that of calcitriol. Incorporation of additional fluorines, as in a perfluorobutyl analog, results in a loss of antiproliferative activity.
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Journal: Bioorganic & Medicinal Chemistry - Volume 15, Issue 16, 15 August 2007, Pages 5509–5518