Journal
TETRAHEDRON
Volume 66, Issue 29, Pages 5407-5423Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.05.028
Keywords
Vitamin D-3; 14-epi-Previtamin D-3; Osteocalcin; Vitamin D receptor
Categories
Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- Japan Society for the Promotion of Science
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2 alpha- and 2 beta-Substituted analogs of 14-epi-previtamin D-3 were synthesized and isolated after thermal isomerization of 14-epi-vitamin D-3 triene at 80 degrees C. The VDR binding affinity and transactivation activity of osteocalcin promoter in HOS cells were tested, and the 2 alpha-methyl-substituted analog was found to have greater genomic activity than 14-epi-previtamin D-3. We found that modification at the C2 position of the seco-steroidal skeleton afforded interesting effects for biological genomic activity for the previtamin D form as well as the natural vitamin D form. (C) 2010 Elsevier Ltd. All rights reserved.
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