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lüll Low-calcemic, highly antiproliferative, 23-oxa ether analogs of the natural hormone 1 alpha,25-dihydroxyvitamin D3: design, synthesis, and preliminary biological evaluation Petersen KS; Dolan PM; Kensler TW; Peleg S; Posner GHJ Med Chem 2007[Nov]; 50 (23): 5824-32Eight new side-chain allylic, benzylic, and propargylic ether analogs of the natural hormone calcitriol have been rationally designed and easily synthesized. Three of these 23-oxa ether analogs lacking the typical side-chain OH group are more antiproliferative in vitro and desirably less calcemic in vivo than the natural hormone. One of these three 23-oxa analogs has transcriptional potency almost as high as that of calcitriol, even though it binds to the human vitamin D receptor only about 1% as well as calcitriol.|Alkynes/chemical synthesis/pharmacology[MESH]|Allyl Compounds/chemical synthesis/pharmacology[MESH]|Animals[MESH]|Benzyl Compounds/chemical synthesis/pharmacology[MESH]|Binding, Competitive[MESH]|Calcitriol/*analogs & derivatives/*chemical synthesis/pharmacology[MESH]|Calcium Channels/biosynthesis/genetics[MESH]|Calcium/*urine[MESH]|Cell Line[MESH]|Cell Proliferation/*drug effects[MESH]|Duodenum/metabolism[MESH]|Female[MESH]|Humans[MESH]|Keratinocytes/cytology/drug effects[MESH]|Mice[MESH]|Mice, Inbred C57BL[MESH]|Rats[MESH]|Receptors, Calcitriol/metabolism[MESH]|Stereoisomerism[MESH]|Steroid Hydroxylases/biosynthesis/genetics[MESH]|Structure-Activity Relationship[MESH]|TRPV Cation Channels/biosynthesis/genetics[MESH]|Transcription, Genetic/drug effects[MESH]|Vitamin D3 24-Hydroxylase[MESH] |