3β,18,21-trihydroxy-5α-pregnane-20-one 18,21-hemiacetal | 81940-97-8

• 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
• 英文名称: 3β,18,21-trihydroxy-5α-pregnane-20-one 18,21-hemiacetal
• 英文别名: 18,20-epoxy-5α-pregnane-3β,20,21-triol；(1R,2S,5S,9R,12S,13S,16S,18S)-6-(hydroxymethyl)-13-methyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icosane-6,16-diol
• CAS: 81940-97-8
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: MRRYTJCUHFJPKO-WINXUJLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β,18,21-trihydroxy-5α-pregnane-20-one 18,21-hemiacetal 在 sodium periodate 作用下， 生成 3β,18-dihydroxy-5α-androstane-17β-carboxylic acid lactone
  参考文献：
  名称：

  减少18-羟基-11-脱氧皮质酮的代谢物

  摘要：

  描述了使用副纯化梭状芽胞杆菌和化学方法通过微生物转化制备18-羟基-11-脱氧氢化可的松（1a）的二氢（2和6）和四氢衍生物（3、5和7）的条件。产物被充分表征并降解为它们各自的20→18乙内酯。微生物和Δ的化学削减4 -3- ketolactone 8被呈现。

  DOI：

  10.1016/0040-4020(82)80055-0
• 作为产物：
  描述：

  3β,18,21-trihydroxy-5α-pregnane-20-one 18,20-hemiacetal 21-acetate 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 生成 3β,18,21-trihydroxy-5α-pregnane-20-one 18,21-hemiacetal
  参考文献：
  名称：

  Mineralocorticoid properties of potential metabolites of 18-hydroxydeoxycorticosterone and 18-hydroxyprogesterone

  摘要：

  The high secretion rate of 18-hydroxydeoxycorticosterone in hypertensives and the steroids implication as a mineralocorticoid has led to the synthesis of potential di-, tetra-, and hexahydro metabolites of it and 18-hydroxy-progesterone. These potential metabolites have been synthesized by reduction of the double bond and the 3- and 20-ketones, singly or in combination. They have been evaluated for pro- and antimineralocorticoid activity and their affinity for the renal aldosterone receptor. All except one of the potential metabolites either lack or have reduced mineralocorticoid activity and aldosterone receptor binding affinity. The exception is the 3-ketopregn-4-ene-18,20-diol which has high receptor affinity but functions as an aldosterone antagonist.

  DOI：

  10.1021/jm00380a014

文献信息

• Reduced metabolites of 18-hydroxy-11-deoxycorticosterone
  作者：M. Harnik、Y. Aharonowittz、R. Lamed

  DOI：10.1016/0040-4020(82)80055-0

  日期：1982.1

  Conditions are described for the preparation of the dihydro (2 and 6) and tetrahydro derivatives (3, 5 and 7) of 18-hydroxy-11-deoxycortisterone (1a) by microbial transformations using Clostridium parapurificum and chemical methods. The products were fully characterized and degraded into their respective 20 → 18 etiolactones. Microbial and chemical reductions of the Δ4-3-ketolactone 8 are presented.

  描述了使用副纯化梭状芽胞杆菌和化学方法通过微生物转化制备18-羟基-11-脱氧氢化可的松（1a）的二氢（2和6）和四氢衍生物（3、5和7）的条件。产物被充分表征并降解为它们各自的20→18乙内酯。微生物和Δ的化学削减4 -3- ketolactone 8被呈现。
• Mineralocorticoid properties of potential metabolites of 18-hydroxydeoxycorticosterone and 18-hydroxyprogesterone
  作者：John F. Weet、George R. Lenz

  DOI：10.1021/jm00380a014

  日期：1985.2

  The high secretion rate of 18-hydroxydeoxycorticosterone in hypertensives and the steroids implication as a mineralocorticoid has led to the synthesis of potential di-, tetra-, and hexahydro metabolites of it and 18-hydroxy-progesterone. These potential metabolites have been synthesized by reduction of the double bond and the 3- and 20-ketones, singly or in combination. They have been evaluated for pro- and antimineralocorticoid activity and their affinity for the renal aldosterone receptor. All except one of the potential metabolites either lack or have reduced mineralocorticoid activity and aldosterone receptor binding affinity. The exception is the 3-ketopregn-4-ene-18,20-diol which has high receptor affinity but functions as an aldosterone antagonist.