(8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pentyl]-pregnane | 1166898-12-9

• 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'R)-hydroxy-pentyl]-pregnane
• 英文别名: (8S,20S)-des-A,B-8-benzoyloxy-20-[(4R)-hydroxy-pentyl]pregnane；[(1R,3aR,4S,7aR)-1-[(2S,6R)-6-hydroxyheptan-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate
• CAS: 1166898-12-9
• 化学式: C₂₄H₃₆O₃
• 分子量: 372.548
• InChiKey: TWUXUAHTOFFUTE-WLUDWXDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 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-[(4'R)-hydroxy-pentyl]-pregnane 在 2,6-二甲基吡啶 、 乙醇 、 苯基锂 、 N-甲基吗啉氧化物 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 二丁醚 为溶剂， 反应 41.75h， 生成 (20S,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethylsilyl)oxy]-19,26-dinorvitamin D3 tert-butyldimethylsilyl ether
  参考文献：
  名称：

  2alpha-Methyl and 2beta-Methyl Analogs of 19,26-Dinor-1alpha,25-Dihydroxyvitamin D3 and Their Uses

  摘要：

  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。

  公开号：

  US20120283228A1
• 作为产物：
  描述：

  (20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al 在 palladium 10% on activated carbon 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 39.0h， 生成 (8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pentyl]-pregnane
  参考文献：
  名称：

  2alpha-Methyl and 2beta-Methyl Analogs of 19,26-Dinor-1alpha,25-Dihydroxyvitamin D3 and Their Uses

  摘要：

  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。

  公开号：

  US20120283228A1

文献信息

• 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。
• Removal of the 26-Methyl Group from 19-nor-1α,25-Dihydroxyvitamin D₃ Markedly Reduces in Vivo Calcemic Activity without Altering in Vitro VDR Binding, HL-60 Cell Differentiation, and Transcription
  作者：Pawel Grzywacz、Grazia Chiellini、Lori A. Plum、Margaret Clagett-Dame、Hector F. DeLuca

  DOI：10.1021/jm1010447

  日期：2010.12.23

  Twelve new analogues of 19-nor-1 alpha,25-dihydroxyvitamin D-3 (5-16) were prepared by convergent syntheses, employing the Wittig-Horner reaction. The necessary Grundmann type ketones (45-48), possessing fixed configurations of the hydroxyl group at C-25, were obtained by a multistep procedure from commercial vitamin D-2 and enantiomers of 1,3-butanediol (23 and 24). We have examined the influence of removal of one of the methyl groups located at C-25 on the biological in vitro and in vivo activity. The in vivo tests showed that the synthesized vitamin D compounds (5-16) exhibit reduced calcemic activity both in bone and in the intestine. However, in vitro potency of 2-methylene and 2 alpha-methyl compounds (5-10, 13, and 14) remained similar or enhanced as compared to that of 1 alpha,25-(OH)(2)D-3.