(8S,20S)-des-A,B-8-benzoyloxy-20-(hydroxymethyl)-pregnane | 66774-70-7

• 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-(hydroxymethyl)-pregnane
• 英文别名: (8S,20S)-des-A,B-8-benzoyloxy-20-(hydroxymethyl)pregnane；(8S,20S)-de-A,B-8-benzoyloxy-20-(hydroxymethyl)pregnane；des-A,B-8β-(benzoyloxy)-23,24-dinorcholane-22-ol；[(1R,3aR,4S,7aR)-1-[(2S)-1-hydroxypropan-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate
• CAS: 66774-70-7
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: YDGDTMZQDFVDCD-RDGCENLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8S,20S)-des-A,B-8-benzoyloxy-20-(hydroxymethyl)-pregnane 在 四丁基氢氧化铵 、 三氧化硫吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 17.0h， 生成 (20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al
  参考文献：
  名称：

  [EN] 2-METHYLENE-19,26-NOR-(20S)-1a-HYDROXYVITAMIN D3
  [FR] 2-MÉTHYLÈNE-19,26-NOR-(20S)-1?-HYDROXYVITAMINE D3

  摘要：

  提供了化学式I的化合物，其中X1和X2可以独立地选择为H或羟基保护基团。这些化合物可用于制备药物组合物，并在治疗各种生物状况方面具有用处。

  公开号：

  WO2011066506A1
• 作为产物：
  描述：

  维生素D2 在 4-二甲氨基吡啶 吡啶 、 臭氧 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 27.83h， 生成 (8S,20S)-des-A,B-8-benzoyloxy-20-(hydroxymethyl)-pregnane
  参考文献：
  名称：

  [EN] 2-METHYLENE-19,26-NOR-(20S)-1a-HYDROXYVITAMIN D3
  [FR] 2-MÉTHYLÈNE-19,26-NOR-(20S)-1?-HYDROXYVITAMINE D3

  摘要：

  提供了化学式I的化合物，其中X1和X2可以独立地选择为H或羟基保护基团。这些化合物可用于制备药物组合物，并在治疗各种生物状况方面具有用处。

  公开号：

  WO2011066506A1

文献信息

• Gold(I)-Catalyzed Synthesis of Unsymmetrical Ethers Using Alcohols as Alkylating Reagents
  作者：Yongxiang Liu、Xiaoyu Wang、Yanshi Wang、Chuan Du、Hui Shi、Shengfei Jin、Chongguo Jiang、Jianyong Xiao、Maosheng Cheng

  DOI：10.1002/adsc.201401097

  日期：2015.3.23

  microwave‐irradiated alcohol‐protecting strategy based on gold catalysis utilizing benzyl alcohol, tert‐butyl alcohol and triphenylmethanol as alkylating reagents has been developed. This protecting strategy has wide functional group tolerance with satisfactory yields for the majority of the selected alcohols. The mechanism of this transformation was probed with oxygen‐18 isotope labelled alcohols assisted by

  基于苄基醇，叔丁醇和三苯甲醇作为烷基化试剂的金催化的微波辐射醇保护策略已经被开发出来。对于大多数选定的醇，该保护策略具有宽泛的官能团耐受性和令人满意的产率。在GC-MS技术和化学动力学实验的辅助下，用氧18同位素标记的醇探索了这种转变的机理。该策略为有机合成中的苄基，叔丁基和三苯甲基醚的制备提供了一种有效，直接和替代的方法。
• Vitamin D analogs for obesity prevention and treatment
  申请人：DeLuca F. Hector

  公开号：US20050119242A1

  公开（公告）日：2005-06-02

  Methods for treating and preventing obesity, inhibiting adipocyte differentiation, inhibiting increased SCD-1 gene transcription, and/or reducing body fat in a subject include administering at least one analog of 1α,25-dihydroxyvitamin D 3 or 1α,25-dihydroxyvitamin D 2 or a pharmaceutical composition that includes such an analog to a subject in need thereof. The analog may be a 19-nor vitamin D analog such as a compound of formula IA, a compound of formula IB, or a mixture thereof where the variables R 1 , R 2 , and R 3 have the values described herein.

  治疗和预防肥胖的方法，抑制脂肪细胞分化，抑制增加的SCD-1基因转录，和/或减少受试者体脂肪的方法包括向需要的受试者施用至少一种1α,25-二羟基维生素D3或1α,25-二羟基维生素D2的类似物或包含这种类似物的药物组合物。该类似物可以是19-去甲基维生素D类似物，如式IA的化合物，式IB的化合物，或其中的混合物，其中变量R1、R2和R3具有此处描述的值。
• 2alpha-Methyl and 2beta-Methyl Analogs of 19,26-Dinor-1alpha,25-Dihydroxyvitamin D3 and Their Uses
  申请人：DeLuca Hector F.

  公开号：US20120283228A1

  公开（公告）日：2012-11-08

  This invention discloses 2α-methyl and 2β-methyl analogs of 19,26-dinor-1α,25-dihydroxyvitamin D 3 and pharmaceutical uses therefor. These compounds exhibit in vitro biological activities 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. These compounds have little, if any, in vivo calcemic activity and therefore may be used to treat autoimmune disorders in humans as well as secondary hyperparathyroidism and renal osteodystrophy.

  这项发明揭示了19,26-去甲基-1α,25-二羟基维生素D3的2α-甲基和2β-甲基类似物以及其药用。这些化合物在体外表现出生物活性，可作为抗癌剂以及治疗银屑病等皮肤疾病，以及皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足等皮肤状况的用途。这些化合物在体内几乎没有钙调节活性，因此可用于治疗人类的自身免疫性疾病，以及继发性甲状旁腺功能亢进和肾性骨病。
• 2-Methylene-(20S,25S)-19,26-Dinor-Vitamin D Analogs
  申请人：DeLuca Hector F.

  公开号：US20090170821A1

  公开（公告）日：2009-07-02

  This invention discloses 2-methylene-(20S,25S)-19,26-dinor-vitamin D analogs, and specifically 2-methylene-(20S,25S)-19,26-dinor-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.

  这项发明披露了2-亚甲基-(20S,25S)-19,26-二诺尔维生素D类似物，具体为2-亚甲基-(20S,25S)-19,26-二诺尔-1α,25-二羟基维生素D3，以及其药用。该化合物在阻止未分化细胞增殖和诱导它们向单核细胞分化方面表现出显著活性，因此可作为抗癌剂以及用于治疗银屑病等皮肤疾病以及皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足等皮肤状况的药物。该化合物在钙代谢方面几乎没有活性，因此可用于治疗人类的自身免疫性疾病或炎症性疾病，以及肾性骨病。此外，该化合物还可用于肥胖的治疗或预防。
• 2-Methylene-(20S,25R)-19,26-Dinor-Vitamin D Analogs
  申请人：DeLuca Hector F.

  公开号：US20090170820A1

  公开（公告）日：2009-07-02

  This invention discloses 2-methylene-(20S,25R)-19,26-dinor-vitamin D analogs, and specifically 2-methylene-(20S,25R)-19,26-dinor-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.

  该发明揭示了2-亚甲基-(20S,25R)-19,26-双去-维生素D类似物，具体为2-亚甲基-(20S,25R)-19,26-双去-1α,25-二羟基维生素D3，以及其药用。该化合物在抑制未分化细胞增殖和诱导它们分化为单核细胞方面表现出显著活性，因此可作为抗癌剂以及用于治疗银屑病等皮肤疾病以及皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足等皮肤状况的药物。该化合物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病。该化合物还可用于治疗或预防肥胖。