1-[1,3-bis-(tert-butyldimethylsilanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanol | 103909-74-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 1-[1,3-bis-(tert-butyldimethylsilanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanol
• 英文别名: 1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-hydroxypregna-5,7-diene；1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-hydroxypregna-5 7-diene；1α,3β-bis(t-butyldimethylsilyloxy)-20S-hydroxy-5,7-pregnadiene；(1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)-pregna-5,7-dien-20-ol；(1S,3R,20S)-1,3-bis(t-butyldimethylsilyloxy)-pregna-5,7-dien-20-ol；1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20(S)-hydroxypregna-5,7-diene；(1S)-1-[(1S,3R,9S,10R,13S,14R,17S)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanol
• CAS: 103909-74-6
• 化学式: C₃₃H₆₀O₃Si₂
• 分子量: 561.009
• InChiKey: WBYQKQDJKQQCRT-WJYMXFQBSA-N

物化性质

• 沸点：
  558.2±50.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.26
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[1,3-bis-(tert-butyldimethylsilanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanol 在 cerium(III) chloride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 1α,3β-bis(tertbutyldimethylsilyloxy)-20α-(3-oxobutyloxy)-5,7-pregnadiene
  参考文献：
  名称：

  从醇中实际形成 γ-酮或 γ-羟基醚键1

  摘要：

  摘要描述了从醇中形成 γ-酮或 γ-羟基醚键的实用方法，用于构建 1α, 25-二羟基-22-氧维生素 D3 (OCT) 的侧链。

  DOI：

  10.1080/00397919708004097
• 作为产物：
  描述：

  以 various solvent(s) 为溶剂， 反应 2.5h， 以87%的产率得到1-[1,3-bis-(tert-butyldimethylsilanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanol
  参考文献：
  名称：

  An improved procedure for retro-cycloaddition of adducts from steroidal 5,7-dienes and 4-phenyl-1,2,4-triazoline-3,5-dione

  摘要：

  DOI：

  10.1021/jo00044a045

文献信息

• Vitamin d derivatives
  申请人：——

  公开号：US20040019023A1

  公开（公告）日：2004-01-29

  The object of the present invention is to provide vitamin D derivatives that have excellent physiological activities as medicines, particularly as therapeutic agents for skin diseases such as psoriasis, and that have a reduced hypercalcemic effect. The present invention provides a vitamin D derivative of Formula (1): 1 wherein X represents an oxygen atom or a sulfur atom; m represents a number of 1 to 3; R 1 and R 2 each represent a hydrogen atom or an alkyl group; R 4 and R 5 each represent a hydrogen atom or a hydroxyl group, etc.; R 3 represents —YR 8 , etc.; R 6 represents a hydrogen atom, etc.; and R 7 represents a hydrogen atom, etc.

  本发明的目的是提供作为药物的维生素D衍生物，特别是作为治疗银屑病等皮肤疾病的治疗剂，并且具有减少高钙血症作用的维生素D衍生物。 本发明提供了化学式（1）的维生素D衍生物： 1 其中 X代表氧原子或硫原子； m代表1至3的数字； R 1 和R 2 分别代表氢原子或烷基； R 4 和R 5 分别代表氢原子或羟基等； R 3 代表—YR 8 等； R 6 代表氢原子等；以及 R 7 代表氢原子等。
• Synthetic Studies of Vitamin D Analogues. XVII.Synthesis and Differentiation-Inducing Activity of 1α, 24-Dihydroxy-22-oxavitamin D<SUB>3</SUB> Analogues and Their 20(R)-Epimers
  作者：Noboru KUBODERA、Hiroyoshi WATANABE、Katsuhito MIYAMOTO、Masahiko MATSUMOTO、Setsu MATSUOKA、Takehiko KAWANISHI

  DOI：10.1248/cpb.41.1659

  日期：——

  Four vitamin D3 analogues, 1α, 24(S)-and 1α, 24(R)-dihydroxy-22-oxavitamin D3 (5 and 6) and their 20(R)-epimers (7 and 8) were synthesized from the 20(S)-alcohol (10). In tests of activity to induce differentiation of human myeloid leukemia cells (HL-60) to macrophages, 5 showed comparable activity to 1α, 25-dihydroxy-22-oxavitamin D3 (OCT) (2), and the other three analogues (6, 7 and 8) were less active than OCT (2). The binding properties of these analogues to the chick embryonic intestinal 1α, 25-dihydroxyvitamin D3 (1) receptor were evaluated. Furthermore, 20(R)-OCT (9) was synthesized and its biological properties were compared with those of OCT (2) and the 20(R)-epimers (7 and 8).

  合成了四种维生素D3类似物，1α、24(S)-和1α、24(R)-二羟基-22-氧维生素D3（5和6）及其20(R)-表异构体（7和8），它们均来源于20(S)-醇（10）。在诱导人类骨髓白血病细胞（HL-60）向巨噬细胞分化的活性测试中，5表现出与1α、25-二羟基-22-氧维生素D3（OCT）（2）相当的活性，而其他三个类似物（6、7和8）的活性均低于OCT（2）。评估了这些类似物与小鸡胚胎肠道1α、25-二羟基维生素D3（1）受体的结合特性。此外，合成了20(R)-OCT（9），并将其生物特性与OCT（2）和20(R)-表异构体（7和8）的特性进行了比较。
• Synthetic Studies of Vitamin D Analogs. XXII. Synthesis and Antiproliferation Activity of Putative Metabolites of 1.ALPHA.,25-Dihydroxy-22-oxavitamin D3.
  作者：Hiroyoshi WATANABE、Susumi HATAKEYAMA、Kazuki TAZUMI、Seiichi TAKANO、Sonoko MASUDA、Toshio OKANO、Tadashi KOBAYASHI、Noboru KUBODERA

  DOI：10.1248/cpb.44.2280

  日期：——

  As putative metabolites of 1 alpha,25-dihydroxy-22-oxavitamin D3 (OCT), 24-hydroxylated OCT in 24(R) and 24(S) forms, 24-ketoOCT, 26-hydroxylated OCT in 25(S) and 25(R) forms, pentanorOCT and pentanor-ketoOCT were synthesized from the steroidal 20(S)-alcohol. Their antiproliferation activities towards human promyelocytic leukemia cells (HL-60 cells) are also reported. Oxidized derivatives at the C-24

  作为1 alpha，25-dihydroxy-22-oxavitamin D3（OCT）的推定代谢产物，以24（R）和24（S）形式形成24-羟基OCT，以25（S）和25形式形成24-ketoOCT，26-羟基OCT。 （R）形式的pentanorOCT和pentanor-ketoOCT由甾族20（S）-醇合成。还报道了它们对人早幼粒细胞白血病细胞（HL-60细胞）的抗增殖活性。C-24位的氧化衍生物，24-酮基OCT，24（R）-羟基化的OCT和24（S）-羟基化的OCT，其活性与OCT相当或略弱，而26-羟基化的OCT的活性却比OCT弱10月。在10（-7）-10（-10）M时，截短的OCT，pentanor OCT和pentanor-ketoOCT无效。
• Synthetic Studies of Vitamin D Analogues. XI. Synthesis and Differentiation-Inducing Activity of 1.ALPHA.,25-Dihydroxy-22-oxavitamin D3 Analogues.
  作者：Noboru KUBODERA、Hiroyoshi WATANABE、Takehiko KAWANISHI、Masahiko MATSUMOTO

  DOI：10.1248/cpb.40.1494

  日期：——

  Six analogues of 1α, 25-dihydroxy-22-oxavitamin D3 (OCT) (2), 26, 27-dimethyl OCT (5), 26, 27-diethyl OCT (6), 24-norOCT (7), 24-homoOCT (8), 24-dihomoOCT (9), and 24-trihomoOCT (10) were synthesized from the 20(S)-alcohol (11) as the common starting material. In the activity inducing differentiation of human myeloid leukemia cells (HL-60) into macrophages, 26, 27-dimethyl OCT (5) and 24-homoOCT (8) showed the highest activities. The binding properties of these analogues to the chick embryonic intestinal 1α, 25-dihydroxyvitamin D3 (1) receptor are also described.

  1α, 25-二羟基-22-奥沙维他命 D3 (OCT) (2)、26, 27-二甲基 OCT (5)、26, 27-二乙基 OCT (6)、24-norOCT (7)、24-homoOCT 的六种类似物(8)、24-dihomoOCT (9) 和 24-trihomoOCT (10) 由 20(S)-醇 (11) 作为共同起始原料合成。在诱导人骨髓性白血病细胞（HL-60）向巨噬细胞分化的活性中，26, 27-二甲基OCT（5）和24-homoOCT（8）表现出最高活性。还描述了这些类似物与鸡胚肠道 1α, 25-二羟基维生素 D3 (1) 受体的结合特性。
• Vitamin D derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US07985744B2

  公开（公告）日：2011-07-26

  The object of the present invention is to provide vitamin D derivatives that have excellent physiological activities as medicines, particularly as therapeutic agents for skin diseases such as psoriasis, and that have a reduced hypercalcemic effect. The present invention provides a vitamin D derivative of Formula (1): wherein X represents an oxygen atom or a sulfur atom; m represents a number of 1 to 3; R1 and R2 each represent a hydrogen atom or an alkyl group; R4 and R5 each represent a hydrogen atom or a hydroxyl group, etc.; R3 represents —YR8, etc.; R6 represents a hydrogen atom, etc.; R7 represents a hydrogen atom, etc.

  本发明的目的是提供具有出色生理活性的维生素D衍生物作为药物，特别是作为治疗银屑病等皮肤疾病的治疗剂，并具有减少高钙血症作用。本发明提供了一种式为（1）的维生素D衍生物：其中X表示氧原子或硫原子；m表示1到3的数字；R1和R2分别表示氢原子或烷基；R4和R5分别表示氢原子或羟基等；R3表示-YR8等；R6表示氢原子等；R7表示氢原子等。