3,3-ethylenedioxy-5,6-secocholest-6-en-5-one | 207672-39-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,3-ethylenedioxy-5,6-secocholest-6-en-5-one
• CAS: 207672-39-7
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: RAIIMVQBNJOLOM-IUIJGFHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,3-ethylenedioxy-5,6-secocholest-6-en-5-one 在 platinum(IV) oxide 盐酸 、 lithium aluminium tetrahydride 、 氨 、 氢气 、 lithium 、 叔丁醇 作用下， 以 乙酸乙酯 为溶剂， 反应 9.25h， 生成 4α-(2-propenyl)-5,6-secocholestan-3-one
  参考文献：
  名称：

  Synthesis of 4α-(2-propenyl)-5,6-secocholestan-3α-ol, a Novel B-ring Seco Analog of the Hypocholesterolemic Agent 4α-(2-propenyl)-5α-cholestan-3α-ol

  摘要：

  4 alpha-(2-Propenyl)-5 alpha-cholestan-3 alpha-ol (LY295427) Ir as previously identified front a CHO cell-based assay to be a potent LDL receptor up-regulator and had demonstrated to be an effective agent in lowering plasma cholesterol levels in hypercholesterolemic hamsters. In order to investigate the effect of flexibility of the 3 alpha-hydroxy-bearing A-ring on the activity 4 alpha-(2-propenyl)-5,6-secocholestan-3 alpha-ol (II), a B-ring seco analog of LY295427, is thus synthesized from cholest-4-en-3-one. Test results indicate that II is not active in the CHO cell-based LDL receptor/luciferase assay at concentrations rip to 20 mu g/mL. The result underlines the importance of maintaining the A-B-C-D ring rigidity of the 3 alpha-sterols in terms of binding to the putative oxysterol receptor. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00004-x
• 作为产物：
  描述：

  3,3-ethylenedioxy-5-oxo-5,6-secocholestan-6-al 在 sodium tetrahydroborate 、 三丁基膦 、 间氯过氧苯甲酸 、 calcium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 3,3-ethylenedioxy-5,6-secocholest-6-en-5-one
  参考文献：
  名称：

  Synthesis of 4α-(2-propenyl)-5,6-secocholestan-3α-ol, a Novel B-ring Seco Analog of the Hypocholesterolemic Agent 4α-(2-propenyl)-5α-cholestan-3α-ol

  摘要：

  4 alpha-(2-Propenyl)-5 alpha-cholestan-3 alpha-ol (LY295427) Ir as previously identified front a CHO cell-based assay to be a potent LDL receptor up-regulator and had demonstrated to be an effective agent in lowering plasma cholesterol levels in hypercholesterolemic hamsters. In order to investigate the effect of flexibility of the 3 alpha-hydroxy-bearing A-ring on the activity 4 alpha-(2-propenyl)-5,6-secocholestan-3 alpha-ol (II), a B-ring seco analog of LY295427, is thus synthesized from cholest-4-en-3-one. Test results indicate that II is not active in the CHO cell-based LDL receptor/luciferase assay at concentrations rip to 20 mu g/mL. The result underlines the importance of maintaining the A-B-C-D ring rigidity of the 3 alpha-sterols in terms of binding to the putative oxysterol receptor. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00004-x