1-羟基孕钙化醇 | 58702-12-8

• 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
• 中文名称: 1-羟基孕钙化醇
• 英文名称: (1R,3S)-5-[2-[(1S,3aS,7aR)-1-Ethyl-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexane-1,3-diol
• 英文别名: 1-Hydroxypregnacalciferol；(1R,3S,5Z)-5-[(2E)-2-[(1S,3aS,7aR)-1-ethyl-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• CAS: 58702-12-8
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: XMDLIEZJERQGEY-ZHFUSYIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Acetic acid (1S,3R,9S,10R,13R,14R,17S)-3-acetoxy-17-ethyl-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl ester 生成 1-羟基孕钙化醇
  参考文献：
  名称：

  Structural analogs of lα,25-dihydroxycholecalciferol: Preparation and biologial assay of 1α-hydroxypregnacalciferol

  摘要：

  The synthesis of 1alpha-hydroxypregnacalciferol, a side chain analog of 1alpha,25-dihydroxycholecalciferol (1alpha,25-dihydroxyvitamin D3), is described. Pregnenolone acetate was converted in five steps to 5-pregnen-1alpha,3beta-diol. Conversion of the diol to pregna-5,7-diene-1alpha,3beta diol diacetate followed by ultraviolet irradiation gave the corresponding previtamin derivative. Thermal isomerization, hydrolysis and chromatography then furnished the desired analog, 1alpha-hydroxypregnacalciferol. The compound was tested in vivo for its effect on intestinal calcium transport, serum calcium and phosphate levels and bone calcification, and in vitro for its effect on bone resorption. When given to intact rats, either as a single dose or in repeated daily doses, the analog even at high dose levels, exhibited no biological activity. The compound stimulated bone resorption in vitro, but only at high concentrations.

  DOI：

  10.1016/0039-128x(75)90063-x

文献信息

• Enzymatic production or chemical synthesis and uses for 5,7-dienes and UVB conversion products thereof
  申请人：Slominski Andrzej

  公开号：US20110118228A1

  公开（公告）日：2011-05-19

  Provided herein are steroidal compounds that are androsta-5,7-dienes or a pregna-5,7-dienes and ultraviolet B (UVB) conversion products thereof which includes pharmaceutical compositions of the steroidal compounds as shown in Tables 1 and 2. Also provided is a method for producing hydroxylated metabolites of cholecalciferol or ergocalciferol via the P450scc (CYP11A1) or CYP27B1 enzyme systems where the hydroxylase has an activity to hydroxylate position C20 of a secosteroid or its 5,7-dieneal precursor and the hydroxylated metabolites so produced. In addition, a method for inhibiting proliferation of either a normally or abnormally proliferating cell by contacting the cell with any of the compounds described herein. A related method is provided of treating a condition associated with the proliferating cell such as a cancer, a skin disorder, a defect in cell differentiation, cosmetic, prophylaxsis, or healthy cell maintenance.

  本文提供的是雄甾-5,7-二烯或孕甾-5,7-二烯及其紫外线B（UVB）转化产物的类固醇化合物，其中包括所示的表1和表2的类固醇化合物的药物组成。此外，还提供了一种通过P450scc（CYP11A1）或CYP27B1酶系统产生维生素D3或维生素D2的羟化代谢产物的方法，其中羟化酶具有羟化一个类固醇的C20位置或其5,7-二烯前体的活性，以及所产生的羟化代谢产物。此外，还提供了一种通过接触任何本文所述的化合物来抑制正常或异常增殖细胞增殖的方法。还提供了一种相关的方法，用于治疗与增殖细胞相关的疾病，例如癌症，皮肤疾病，细胞分化缺陷，美容，预防或维持健康的细胞。
• Enzymatic Production or Chemical Synthesis and Uses for 5,7-Dienes and UVB Conversion Products Thereof
  申请人：Slominski Andrzej T.

  公开号：US20140200201A1

  公开（公告）日：2014-07-17

  Provided herein are steroidal compounds that are androsta-5,7-dienes or a pregna-5,7-dienes and ultraviolet B (UVB) conversion products thereof which includes pharmaceutical compositions of the steroidal compounds as shown in Tables 1 and 2. Also provided is a method for producing hydroxylated metabolites of cholecalciferol or ergocalciferol via the P450scc (CYP11A1) or CYP27B1 enzyme systems where the hydroxylase has an activity to hydroxylate position C20 of a secosteroid or its 5,7-dieneal precursor and the hydroxylated metabolites so produced. In addition, a method for inhibiting proliferation of either a normally or abnormally proliferating cell by contacting the cell with any of the compounds described herein. A related method is provided of treating a condition associated with the proliferating cell such as a cancer, a skin disorder, a defect in cell differentiation, cosmetic, prophylaxsis, or healthy cell maintenance.

  本文提供了雄甾-5,7-二烯或孕甾-5,7-二烯及其紫外线B（UVB）转化产物的类固醇化合物，其中包括如表1和表2所示的类固醇化合物的制药组合物。此外，还提供了一种通过P450scc（CYP11A1）或CYP27B1酶系统产生维生素D3或维生素D2的羟基代谢物的方法，其中羟化酶具有羟化一个类固醇或其5,7-二烯前体的C20位置的活性，并产生所述羟基化代谢物。此外，还提供了一种通过将细胞与本文所述的任何化合物接触来抑制正常或异常增殖细胞增殖的方法。还提供了一种相关方法，用于治疗与增殖细胞相关的疾病，例如癌症、皮肤疾病、细胞分化缺陷、美容、预防和健康细胞维护。
• VITAMIN D RECEPTOR AGONISTS TO TREAT DISEASES INVOLVING CXCL12 ACTIVITY
  申请人：Salk Institute for Biological Studies

  公开号：US20160089385A1

  公开（公告）日：2016-03-31

  Provided herein are methods of treating and preventing pancreatitis, such as pancreatitis induced by glucagon-like peptide (GLP) agonists (such as GLP-1 agonists, for example Byetta®), by administration of a vitamin D receptor agonist (such as vitamin D, vitamin D analogs, vitamin D precursors, and vitamin D receptor agonists precursors). In some examples the subject has diabetes, such as type 2 diabetes.