(S)-1-[(1R,3aS,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-2-((1R,5R)-2-methylene-bicyclo[3.1.0]hex-1-yl)-5-(tetrahydro-pyran-2-yloxy)-pentan-2-ol | 244291-45-0

• 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: (S)-1-[(1R,3aS,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-2-((1R,5R)-2-methylene-bicyclo[3.1.0]hex-1-yl)-5-(tetrahydro-pyran-2-yloxy)-pentan-2-ol
• CAS: 244291-45-0
• 化学式: C₃₅H₅₈O₃
• 分子量: 526.844
• InChiKey: DQMQETCUIUBPLH-KPOPLBGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.0
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-1-[(1R,3aS,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-2-((1R,5R)-2-methylene-bicyclo[3.1.0]hex-1-yl)-5-(tetrahydro-pyran-2-yloxy)-pentan-2-ol 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 6-<3-(hydroxypropyl)>vitamin D₃-acetate
  参考文献：
  名称：

  C-6 functionalized analogs of 25-hydroxyvitamin D3 and 1α,25-dihydroxyvitamin D3: synthesis and binding analysis with vitamin D-binding protein and vitamin D receptor11Note: Stereochemistries of the 3- and 1-hydroxyl groups of vitamin D sterols are designated according to cholesterol nomenclature.

  摘要：

  In this article, we describe the development of a general synthetic strategy to functionalize the C-6 position of vitamin D-3 and its biologically important metabolites, i.e. 25-hydroxyvitamin D-3 (25-OH-D-3) and 1 alpha,25-dihydroxyvitamin D-3 [1,25(OH)(2)D-3]. We employed Mazur's cyclovitamin D method to synthesize vitamin D-3 analogs with several functionalities at the C-6 position. In addition, we synthesized 6-(3-hydroxypropyl) and 6-[(2-bromoacetoxy)propyl] derivatives of 25-OH-D-3 15 and 16, respectively, and 6-(3-hydroxypropyl) derivative of 1,25(OH)(2)D-3 17. Competitive binding assays of 15-17 with human serum vitamin D-binding protein showed that all these analogs specifically bound to this protein, although with significantly lower affinity than the 25-OH-D-3, the strongest natural binder. but with comparable affinity with 1,25(OH)(2)D-3, the hormone. On the other hand, 6-[3-hydroxypropyl], 1 alpha,25-dihydroxyvitamin D-3 17 did not show any specific binding for recombinant nuclear vitamin D receptor. These results indicated that the region containing the C-6 position of che parent seco-steroid [1,25(OH)(2)D-3] may be an important recognition marker towards vitamin D receptor binding. Information, delineated in this article, will be important for evaluating structure-activity relationship in synthetic analogs of vitamin D and its metabolites. (C) 1999 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00009-4
• 作为产物：
  描述：

  2-(3-溴丙氧基)四氢-2H-吡喃 、 6-oxo-3,5-cyclovitamin D₃ 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 以78.5%的产率得到(S)-1-[(1R,3aS,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-2-((1R,5R)-2-methylene-bicyclo[3.1.0]hex-1-yl)-5-(tetrahydro-pyran-2-yloxy)-pentan-2-ol
  参考文献：
  名称：

  C-6 functionalized analogs of 25-hydroxyvitamin D3 and 1α,25-dihydroxyvitamin D3: synthesis and binding analysis with vitamin D-binding protein and vitamin D receptor11Note: Stereochemistries of the 3- and 1-hydroxyl groups of vitamin D sterols are designated according to cholesterol nomenclature.

  摘要：

  In this article, we describe the development of a general synthetic strategy to functionalize the C-6 position of vitamin D-3 and its biologically important metabolites, i.e. 25-hydroxyvitamin D-3 (25-OH-D-3) and 1 alpha,25-dihydroxyvitamin D-3 [1,25(OH)(2)D-3]. We employed Mazur's cyclovitamin D method to synthesize vitamin D-3 analogs with several functionalities at the C-6 position. In addition, we synthesized 6-(3-hydroxypropyl) and 6-[(2-bromoacetoxy)propyl] derivatives of 25-OH-D-3 15 and 16, respectively, and 6-(3-hydroxypropyl) derivative of 1,25(OH)(2)D-3 17. Competitive binding assays of 15-17 with human serum vitamin D-binding protein showed that all these analogs specifically bound to this protein, although with significantly lower affinity than the 25-OH-D-3, the strongest natural binder. but with comparable affinity with 1,25(OH)(2)D-3, the hormone. On the other hand, 6-[3-hydroxypropyl], 1 alpha,25-dihydroxyvitamin D-3 17 did not show any specific binding for recombinant nuclear vitamin D receptor. These results indicated that the region containing the C-6 position of che parent seco-steroid [1,25(OH)(2)D-3] may be an important recognition marker towards vitamin D receptor binding. Information, delineated in this article, will be important for evaluating structure-activity relationship in synthetic analogs of vitamin D and its metabolites. (C) 1999 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00009-4