1α,25-dihydroxy-19-nor-vitamin D3, a novel vitamin D-related compound with potential therapeutic activity

✍ Scribed by Kato L. Perlman; Rafal R. Sicinski; Heinrich K. Schnoes; Hector F. DeLuca

• Book ID: 104228947
• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 89 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)98795-1

✦ Synopsis

l~,25-Dihydroxy-19-nor-vitamin D 3 has been synthesized via oxidative degradation of the l~-hydroxycylcovitamin intermediate.

Preliminary studies indicate that the new analog induces the differentiation of human leukemia HL-60 cells, with little or no calcemic activity.

The hormone, l~,25-dihydroxyvitamin D 3 (!), is known to be a highly potent regulator of calcium homeostasis in animals and more recently, its activity in cellular 2 differentiation has also been established.

Many structural analogs have been prepared

and tested and found to exhibit a highly promising dichotomy between cell differentiation and calcium regulation. This difference in activity may be useful in the treatment of some cancers or osteoporosis. 3 In our systematic investigation of structure activity relationship of the vitamin D molecule, we chose to investigate the potency of the 19-nor analogs, i.e. compounds in which the ring A exocyclic methylene group (carbon 19), typical of the vitamin D system, has been removed and replaced by two hydrogen atoms (2).

In this paper we describe the synthesis of la,25-dihydroxy-19-nor-vitamin D 3.