Direct C(1) hydroxylation of vitamin D3 and related compounds

Moriarty

JNCI Journal of the National Cancer Institute

et al. 1997

106

Section: Synthesis Of 1␣(oh)dmentioning

confidence: 99%

Prevention of Preneoplastic Mammary Lesion Development by a Novel Vitamin D Analogue, 1 -Hydroxyvitamin D5

Moriarty

JNCI Journal of the National Cancer Institute

et al. 1997

106

“…日清キョーリン製薬株式会社創薬研究所（〒356 8511 埼玉県ふじみ野市鶴ヶ岡 5 3 1) e-mail: tachibanay＠nk-pharm.co.jp ルスルホン誘導体（25a, 25b, 31b, 33b）を用いて C22-C23 に二重結合を有する 9, 10, 11, 13 を合成した（Scheme 5）． 26,27) Table 3. Neurite Outgrowth Activity of Dictyosterol and Related Compounds (c：1 mg/ml) …”

unclassified

ステロールを用いる生物活性化合物の合成と構造活性相関

Tachibana¹

2006

YAKUGAKU ZASSHI

Sterols are widely and abundantly distributed in nature. It is convenient to utilize them for the preparation of useful compounds such as pharmaceuticals with steroid and secosteroid skeletons. This paper describes the synthesis and structure-activity relationships of naturally occurring active forms of vitamin D analogues, sterols having neurite outgrowth activity, and liver X receptor agonist. The active form of vitamin D 4 showed similar biological activities but had higher a‹nity to the vitamin D-binding protein compared with the corresponding vitamins D 2 and D 3 . This shows that the active form of vitamin D 4 is a good candidate for an agent to replace the active forms of vitamins D 2 and D 3 . In the course of screening for low molecular-weight compounds that exhibit neurite outgrowth activity in the culture broth, we found that the natural product dictyosterol showed strong activity. From screening of the analogues, it was found that the double bond between C22 and C23 in the side chain of the sterol is essential for its activity. Ergost-22-ene-1a,3b-diol was found to serve as a stronger liver X receptor agonist than 24(S), 25-epoxycholesterol, which regulates the expression of genes involved in lipid metabolism. Structure-function study showed that the 1a-hydroxyl group, the saturated steroid structure, and the double bond between C22 and C23 are needed to function as a liver X receptor agonist. しかし，1 はその強い毒性（カルシウム上昇作

“…Proton NMR data were consistent with those reported in the literature. 7 See Supporting Information.…”

Section: ■ Conclusionmentioning

confidence: 99%

Development of an Improved Process for Doxercalciferol via a Continuous Photochemical Reaction

Anderson

Bauta

Cantrell

2012

Org. Process Res. Dev.

Doxercalciferol (1α-hydroxyvitamin D2) is a commercially approved vitamin D derivative used to treat chronic kidney disease (CKD) patients whose kidneys cannot metabolically introduce a hydroxyl group at C1. A new process for the production of doxercalciferol from ergocalciferol was developed using a continuous photoisomerization of a known vitamin D intermediate as the key step, thus circumventing the limitations of batch photoisomerization processes. Doxercalciferol is produced in an overall yield of about 10% from ergocalciferol.