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C-20 cyclopropyl vitamin D3 analogs.
- Source :
-
Current topics in medicinal chemistry [Curr Top Med Chem] 2006; Vol. 6 (12), pp. 1289-96. - Publication Year :
- 2006
-
Abstract
- The formal C-20 methylation of 1,25-dihydroxy vitamin D3 (calcitriol) and bridging of two methyl groups produces spiro[cyclopropane-1, 20'-calcitriol], colloquially referred to as C-20 cyclopropylcalcitriol, which is much more active in MLR for suppression of interferon-gamma release than calcitriol, and hypercalcemia in mice is elicited at a ten-fold lower dose when compared to calcitriol. Introduction of the Delta16,17-double bond, modification of the side chain by 23-unsaturation and replacement of the methyl groups at C-26 and C-27 with trifluoromethyl moieties create a highly active series of vitamin D analogs. As previously observed in the calcitriol series, the presence of the C-16 double bond in the cyclopropyl analogs also arrests metabolic side-chain oxidation in the at the C-24 oxo level in UMR 106 cells. The enhanced biological activity is ascribed, at least in part, to the improved resistance toward metabolic degradation.
- Subjects :
- Animals
Antineoplastic Agents chemistry
Cell Line, Tumor
Cholecalciferol chemistry
Cholecalciferol therapeutic use
Humans
Male
Mice
Mice, Nude
Molecular Structure
Neoplasms, Experimental
Prostatic Neoplasms drug therapy
Rats
Structure-Activity Relationship
Antineoplastic Agents therapeutic use
Cholecalciferol analogs & derivatives
Subjects
Details
- Language :
- English
- ISSN :
- 1568-0266
- Volume :
- 6
- Issue :
- 12
- Database :
- MEDLINE
- Journal :
- Current topics in medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 16848742
- Full Text :
- https://doi.org/10.2174/156802606777864962