Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 17, Issue 15, Pages 5627-5631Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2009.06.033
Keywords
1 alpha,25-Dihydroxyvitamin D-3; Sulfone; Calcitriol; Trifluoromethyl; Antiproliferative
Funding
- NCI NIH HHS [R01 CA093547, R01 CA093547-05] Funding Source: Medline
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The replacement of a t-butyl group with a trifluoromethyl group has profound effects on the biological profile of 1 alpha,25-dihydroxyvitamin D-3 sulfone analogs. Investigation of whether the improved biological activities are due to steric and electronic factors of the trifluoromethyl group led to the design, synthesis and biological evaluation of two analogous alkyl sulfone molecules, methyl sulfone (AU-16-ene-25-SO2-CH3) and isopropyl sulfone (AU-16-ene-25-SO2-i-Pr). These alkyl sulfones are sterically comparable to, but electronically very different from a trifluoromethyl group. The syntheses, antiproliferative activities and calcemic activities of these new alkyl sulfones are presented herein. In comparing the in vitro antiproliferative profiles of the new alkyl sulfone 1 alpha,25-dihydroxyvitamin D-3 analogs with the trifluoromethylsulfone and an analogous t-butyl sulfone, the activities increase in the following order: CH3
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