(20S)-3,6-dioxo-5α-pregnane-20-carboxylic acid | 824397-20-8

• 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: (20S)-3,6-dioxo-5α-pregnane-20-carboxylic acid
• 英文别名: 3.6-dioxo-23.24-dinor-5α-cholanoic acid-(22)；3.6-Dioxo-23.24-dinor-5α-cholansaeure-(22)；3.6-Dioxo-20β_F-methyl-5α-pregnansaeure-(21)
• CAS: 824397-20-8
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: ODMMBWUOEVHVKX-DIZJHOEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  71.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (20S)-3,6-dioxo-5α-pregnane-20-carboxylic acid 在 乙醚 、 溶剂黄146 、 铂 作用下， 生成 3α,6α-dihydroxy-23,24-dinor-5β-cholanoic acid-(22)-methyl ester
  参考文献：
  名称：

  Interactions between GABAergic and aminoacidergic pathways in the control of gonadotropin and GH secretion in pre-pubertal female rats

  摘要：

  Present experiments were carried out in 23-day-old female rats to analyze the interaction between excitatory amino acids (EAAs) and gamma-aminobutyric acid (GABA) in the control of gonadotropin and GH secretion. For this purpose, serum concentrations of LH, FSH and GH were measured after injection of different agonists of EAA receptor subtypes [N-methyl-D-aspartate (NMDA); kainic acid (KA), +/--alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA)], antagonists of GABA receptors (bicuculline, phaclofen) or the combined administration of both types of drugs. The results obtained indicated that: 1) GABA has a minor physiological role in the control of LH and GH secretion, since neither LH nor GH serum concentrations changed after administration of bicuculline (antagonist of GABA(A) receptors) or phaclofen (antagonist of GABA(B) receptors); 2) GABA has a sex-specific physiological role in the control of FSH secretion in female rats, in which FSH secretion increases after phaclofen administration; 3) GH secretion was enhanced after administration of NMDA, KA and AMPA, while LH increased only after activation of NMDA receptors; 4) the stimulatory effect of NMDA on LH secretion was counteracted by administration of phaclofen; and 5) bicuculline and phaclofen reduced the ability of NMDA and AMPA to stimulate GH secretion. In conclusion, present experiments evidenced a physiological role of GABA, mediated by GABA(B) receptors, in the control of FSH secretion and a cross-talk between excitatory and inhibitory amino acids in the control of anterior pituitary secretion. (C) 2002, Editrice Kurtis.

  DOI：

  10.1007/bf03343970
• 作为产物：
  描述：

  3α,6α-dihydroxy-23,24-dinor-5β-cholanoic acid-(22) 在 chromium(VI) oxide 、 盐酸 、 溶剂黄146 作用下， 生成 (20S)-3,6-dioxo-5α-pregnane-20-carboxylic acid
  参考文献：
  名称：

  Interactions between GABAergic and aminoacidergic pathways in the control of gonadotropin and GH secretion in pre-pubertal female rats

  摘要：

  Present experiments were carried out in 23-day-old female rats to analyze the interaction between excitatory amino acids (EAAs) and gamma-aminobutyric acid (GABA) in the control of gonadotropin and GH secretion. For this purpose, serum concentrations of LH, FSH and GH were measured after injection of different agonists of EAA receptor subtypes [N-methyl-D-aspartate (NMDA); kainic acid (KA), +/--alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA)], antagonists of GABA receptors (bicuculline, phaclofen) or the combined administration of both types of drugs. The results obtained indicated that: 1) GABA has a minor physiological role in the control of LH and GH secretion, since neither LH nor GH serum concentrations changed after administration of bicuculline (antagonist of GABA(A) receptors) or phaclofen (antagonist of GABA(B) receptors); 2) GABA has a sex-specific physiological role in the control of FSH secretion in female rats, in which FSH secretion increases after phaclofen administration; 3) GH secretion was enhanced after administration of NMDA, KA and AMPA, while LH increased only after activation of NMDA receptors; 4) the stimulatory effect of NMDA on LH secretion was counteracted by administration of phaclofen; and 5) bicuculline and phaclofen reduced the ability of NMDA and AMPA to stimulate GH secretion. In conclusion, present experiments evidenced a physiological role of GABA, mediated by GABA(B) receptors, in the control of FSH secretion and a cross-talk between excitatory and inhibitory amino acids in the control of anterior pituitary secretion. (C) 2002, Editrice Kurtis.

  DOI：

  10.1007/bf03343970

文献信息

• Synthesis of [26,27-2H6]brassinosteroids from 23,24-bisnorcholenic acid methyl ester
  作者：Andrey P. Antonchick、Bernd Schneider、Vladimir N. Zhabinskii、Vladimir A. Khripach

  DOI：10.1016/j.steroids.2004.05.014

  日期：2004.9

  23R-diol function were prepared starting from 23,24-bisnorcholenic acid methyl ester for biosynthetic studies. Synthesis of the cyclic part was accomplished via the initial hydroboration-oxidation of Delta(5)-double bond. The key step in the synthesis of the side chain involved addition of (2S)-[3,4-(2)H(6)]2,3-dimethylbutylphenyl sulfone to the corresponding C-22 aldehydes.

  从23,24-双降胆固醇酸甲酯开始，制备了许多在C-22处具有羟基或22R，23R-二醇官能团的六氘代油菜素类固醇（BS），用于生物合成研究。环状部分的合成是通过Delta（5）-双键的初始硼氢化-氧化反应完成的。合成侧链的关键步骤涉及将（2S）-[3,4-（2）H（6）] 2,3-二甲基丁基苯基砜加成到相应的C-22醛中。
• Sterols. CXXX. 3,6-Diketo Sterols and their Reduction Products^*
  作者：Russell E. Marker、Harry M. Crooks、Eldon M. Jones、Emerson L. Wittbecker

  DOI：10.1021/ja01254a006

  日期：1942.2