(8S,20S)-des-A,B-8-benzoyloxy-20-[(4'S)-(tertbutyldimethylsilyl)oxy-pent-(1'E)-en-yl]-pregnane | 1016232-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (8S,20S)-des-A,B-8-benzoyloxy-20-[(4'S)-(tertbutyldimethylsilyl)oxy-pent-(1'E)-en-yl]-pregnane
• 英文别名: (8S,20S)-de-A,B-8-benzoyloxy-20-[(4S)-tert-butyldimethylsilyloxy-pent-(1E)-enyl]pregnane；[(1R,3aR,4S,7aR)-1-[(E,2S,6S)-6-[tert-butyl(dimethyl)silyl]oxyhept-3-en-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate
• CAS: 1016232-58-8
• 化学式: C₃₀H₄₈O₃Si
• 分子量: 484.795
• InChiKey: PWJFLQLNCAIJQI-NLOHRDEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.42
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8S,20S)-des-A,B-8-benzoyloxy-20-[(4'S)-(tertbutyldimethylsilyl)oxy-pent-(1'E)-en-yl]-pregnane 在 sodium hydroxide 、 乙醇 作用下， 反应 18.0h， 以72%的产率得到(8S,20S)-de-A,B-20-[(4S)-tert-butyldimethylsilyloxy-pent-(1E)-en-yl]pregnan-8-ol
  参考文献：
  名称：

  2-Methylene-(20S,25S)-19,27-Dinor-(22E)-Vitamin D Analogs

  摘要：

  本发明披露了2-甲烯基-(20S,25S)-19,27-二去-(22E)-维生素D类似物，特别是2-甲烯基-(20S,25S)-19,27-二去-(22E)-1α,25-二羟基维生素D3及其药物用途。该化合物表现出明显的抑制未分化细胞增殖和诱导其分化为单核细胞的活性，因此可用作抗癌剂和治疗诸如银屑病等皮肤疾病以及皮肤状况，如皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足。该化合物也几乎没有钙代谢活性，因此可用于治疗人类的自身免疫性疾病或炎症性疾病以及肾性骨营养不良。该化合物还可用于治疗或预防肥胖症。

  公开号：

  US20080081799A1
• 作为产物：
  描述：

  维生素D2 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 pyridine-SO3 complex 、 四丁基氢氧化铵 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 67.83h， 生成 (8S,20S)-des-A,B-8-benzoyloxy-20-[(4'S)-(tertbutyldimethylsilyl)oxy-pent-(1'E)-en-yl]-pregnane
  参考文献：
  名称：

  2-Methylene-(20S,25S)-19,27-Dinor-(22E)-Vitamin D Analogs

  摘要：

  本发明披露了2-甲烯基-(20S,25S)-19,27-二去-(22E)-维生素D类似物，特别是2-甲烯基-(20S,25S)-19,27-二去-(22E)-1α,25-二羟基维生素D3及其药物用途。该化合物表现出明显的抑制未分化细胞增殖和诱导其分化为单核细胞的活性，因此可用作抗癌剂和治疗诸如银屑病等皮肤疾病以及皮肤状况，如皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足。该化合物也几乎没有钙代谢活性，因此可用于治疗人类的自身免疫性疾病或炎症性疾病以及肾性骨营养不良。该化合物还可用于治疗或预防肥胖症。

  公开号：

  US20080081799A1

文献信息

• 26-Desmethyl-2-methylene-22-ene-19-nor-1α,25-dihydroxyvitamin D3 compounds selectively active on intestine
  作者：Grazia Chiellini、Pawel Grzywacz、Lori A. Plum、Margaret Clagett-Dame、Hector F. DeLuca

  DOI：10.1016/j.steroids.2014.01.012

  日期：2014.5

  Six new analogs of 2-methylene-19-nor-1 alpha,25-dihydroxyvitamin D-3, 6-7 and 8a,b-9a,b, have been synthesized. All compounds are characterized by a trans double bond located in the side chain between C-22 and C-23. While compounds 6 and 7 possess C-26 and C-27 methyls, compounds 8a,b and 9a,b lack one of these groups. A Lythgoe-based synthesis, employing the Wittig-Horner reaction was used for these preparations. Two different types of Delta E-22-25-hydroxy Grundmann's ketone, having either only one stereogenic center located at position C-20 (20 and 21), or two stereogenic centers located at 20- and 25-positions (24a,b-25a,b) were obtained by a multi-step procedure from commercial vitamin D-2. The introduction of a double bond at C-22 appeared to lower biological activity in vitro and in vivo. Further removal of a 26-methyl in these analogs had little effect on receptor binding, HL-60 differentiation and CYP24A expression but markedly diminished or eliminated in vivo activity on bone calcium mobilization while retaining activity on intestinal calcium transport. (C) 2014 Elsevier Inc. All rights reserved.
• 2-Methylene-(20S,25S)-19,27-Dinor-(22E)-Vitamin D Analogs
  申请人：DeLuca F. Hector

  公开号：US20080081799A1

  公开（公告）日：2008-04-03

  This invention discloses 2-methylene-(20S,25S)-19,27-dinor-(22E)-vitamin D analogs, and specifically 2-methylene-(20S,25S)-19,27-dinor-(22E)-1α,25-dihydroxyvitamin D 3 , and pharmaceutical uses therefor. This compound exhibits pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also has little, if any, calcemic activity and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.

  本发明披露了2-甲烯基-(20S,25S)-19,27-二去-(22E)-维生素D类似物，特别是2-甲烯基-(20S,25S)-19,27-二去-(22E)-1α,25-二羟基维生素D3及其药物用途。该化合物表现出明显的抑制未分化细胞增殖和诱导其分化为单核细胞的活性，因此可用作抗癌剂和治疗诸如银屑病等皮肤疾病以及皮肤状况，如皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足。该化合物也几乎没有钙代谢活性，因此可用于治疗人类的自身免疫性疾病或炎症性疾病以及肾性骨营养不良。该化合物还可用于治疗或预防肥胖症。