17(Z)-1α,25-dihydroxy-17(20)-ene-2-methylene-19,21-dinorvitamin D3 | 1204213-19-3

• 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: 17(Z)-1α,25-dihydroxy-17(20)-ene-2-methylene-19,21-dinorvitamin D3
• 英文别名: (1R,3R)-5-[(2E)-2-[(1Z,3aS,7aS)-1-(5-hydroxy-5-methylhexylidene)-7a-methyl-2,3,3a,5,6,7-hexahydroinden-4-ylidene]ethylidene]-2-methylidenecyclohexane-1,3-diol
• CAS: 1204213-19-3
• 化学式: C₂₆H₄₀O₃
• 分子量: 400.602
• InChiKey: ROBWDHHBRICTRR-CTIJHLJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [(1R,3R)-5-[(2E)-2-[(1Z,3aS,7aS)-7a-methyl-1-(5-methyl-5-triethylsilyloxyhexylidene)-2,3,3a,5,6,7-hexahydroinden-4-ylidene]ethylidene]-3-[tert-butyl(dimethyl)silyl]oxy-2-methylidenecyclohexyl]oxy-tert-butyl-dimethylsilane 在 四丁基氟化铵 作用下， 以70%的产率得到17(Z)-1α,25-dihydroxy-17(20)-ene-2-methylene-19,21-dinorvitamin D3
  参考文献：
  名称：

  2-Methylene-(17Z)-17(20)-Dehydro-19,21-Dinor-Vitamin D Analogs

  摘要：

  本发明公开了2-亚甲基-(17Z)-17(20)-去氢-19,21-二诺-维生素D类似物，具体包括2-亚甲基-(17Z)-17(20)-去氢-19,21-二诺-1α,25-二羟基维生素D3，以及其药用用途。该化合物表现出相对较高的转录活性，以及在阻止未分化细胞增殖和诱导它们分化为单核细胞方面的显著活性，因此表明可用作抗癌剂以及用于治疗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。该化合物在体内也具有显著的钙代谢活性，其骨钙动员活性和肠钙转运活性与天然激素1α,25-二羟基维生素D3相当，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。

  公开号：

  US20100009942A1

文献信息

• 2-METHYLENE-(17Z)-17(20)-DEHYDRO-19,21-DINOR-VITAMIN D ANALOGS
  申请人：Wisconsin Alumni Research Foundation

  公开号：EP2313368B1

  公开（公告）日：2014-09-17
• US7893043B2
  申请人：——

  公开号：US7893043B2

  公开（公告）日：2011-02-22
• [EN] 2-METHYLENE-(17Z)-17(20)-DEHYDRO-19,21-DINOR-VITAMIN D ANALOGS<br/>[FR] ANALOGUES DE LA 2-MÉTHYLÈNE-(17Z)-17(20)-DÉSHYDRO-19,21-DINOR-VITAMINE D
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2010006135A2

  公开（公告）日：2010-01-14

  This invention discloses 2-methylene-(17Z)-17(20)-dehydro-19,21 -dinor-vitamin D analogs, and specifically 2-methylene-(17Z)-17(20)-dehydro-19,21-dinor-1α,25-dihydroxyvitamin D3, and pharmaceutical uses therefor. This compound exhibits relatively high transcription activity as well as 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 significant calcemic activity in vivo having about the same bone calcium mobilization activity and intestinal calcium transport activity as the native hormone 1α,25-dihydroxyvitamin D3, 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.