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Catalytic asymmetric synthesis and anticancer effects of the novel non-calcemic analog of vitamin D, 2α-fluoro-19-nor-22-oxa-1α,25-dihydroxyvitamin D3 in metastatic lung carcinoma
- Source :
- Journal of Fluorine Chemistry. 128:654-667
- Publication Year :
- 2007
- Publisher :
- Elsevier BV, 2007.
-
Abstract
- 1α,25-Dihydroxyvitamin D 3 (1α,25-D 3 ) has potent antiproliferative and anti-invasive properties in vitro in cancer cells. However, the major limitation to its clinical use is that it causes hypercalcemia. Therefore, vitamin D analogs with potent cell regulatory effects but with weaker calcemic effects than 1α,25-D 3 are required. Among them, 22-oxa-1α,25-D 3 and 19-nor-1α,25-D 3 have anti-cancer effects with relatively low calcemic effects. Modifications at the C-2α position of the A-ring also produced analogs with a unique biological profile. Not only the side-chain but also the A-ring modification thus generates a unique analog with potent cell regulatory effects and low calcemic activity as well. We report here that the hybrid 1α,25-D 3 analog, synthesized via the highly regio- and stereo-selective ring opening 2α-fluorination and catalytic asymmetric carbonyl-ene cyclization, with 2α-fluoro, 19-nor, and 22-oxa modification exhibits unique cell regulatory activities against the development of metastatic lung carcinoma.
- Subjects :
- Chemistry
Organic Chemistry
Cell
Enantioselective synthesis
medicine.disease
Biochemistry
In vitro
Metastasis
Inorganic Chemistry
medicine.anatomical_structure
Cancer cell
medicine
Cancer research
Carcinoma
Vitamin D and neurology
Environmental Chemistry
Physical and Theoretical Chemistry
Lung cancer
Subjects
Details
- ISSN :
- 00221139
- Volume :
- 128
- Database :
- OpenAIRE
- Journal :
- Journal of Fluorine Chemistry
- Accession number :
- edsair.doi...........d9e49e4e3d3b7173060051b11325ed8c