3α,6α-dihydroxy-23,24-dinor-5β-cholanoic acid-(22)-methyl ester | 121822-10-4

• 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: 3α,6α-dihydroxy-23,24-dinor-5β-cholanoic acid-(22)-methyl ester
• 英文别名: 3β,6β-dihydroxy-23,24-dinor-5α-cholanoic acid-(22)-methyl ester；3β,6β-Dihydroxy-23,24-dinor-5α-cholansaeure-(22)-methylester；3β.6β-Dihydroxy-20β_F-methyl-5α-pregnansaeure-(21)-methylester
• CAS: 121822-10-4
• 化学式: C₂₃H₃₈O₄
• 分子量: 378.552
• InChiKey: YEMRFOKPXWEDMV-PCQRDADSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3α,6α-dihydroxy-23,24-dinor-5β-cholanoic acid-(22)-methyl ester 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 以79.9 %的产率得到methyl (20S)-3β-hydroxy-6-oxo-5α-pregnan-20-carboxylate
  参考文献：
  名称：

  23,24-Dinor-5α-cholan-22-oic Acids 甲酯作为油菜素类固醇类似物。植物促生长活性的合成、评价及分子对接

  摘要：

  由 3β-acetoxy-23,24-dinorchol-4-en-22-oic 酸合成了五种新的油菜素类固醇类似物。所有获得的化合物在水稻叶片倾斜试验中都显示出显着的活性。有趣的是，浓度为 1 x 10 -7和 1 x 10 -6 M的 3β-羟基-6-氧代-23,24-dinorcholan-22-oic 酸甲酯(14)的效果被证明比那些浓度更高由油菜素内酯产生。对具有最高生物活性数据的化合物进行了计算机分子对接和诱导拟合对接（IFD）模拟，以研究进入油菜素内酯结合槽的结合模式相互作用，结果表明化合物14具有高结合能值和良好的结合能。亲和力。

  DOI：

  10.1016/j.steroids.2023.109248
• 作为产物：
  描述：

  methyl 3β-hydroxy-23-bisnorchol-5-en-22-oate 在 甲醇 、 sodium tetrahydroborate 、 Jones reagent 、 溶剂黄146 、 锌 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 3.17h， 生成 3α,6α-dihydroxy-23,24-dinor-5β-cholanoic acid-(22)-methyl ester
  参考文献：
  名称：

  23,24-Dinor-5α-cholan-22-oic Acids 甲酯作为油菜素类固醇类似物。植物促生长活性的合成、评价及分子对接

  摘要：

  由 3β-acetoxy-23,24-dinorchol-4-en-22-oic 酸合成了五种新的油菜素类固醇类似物。所有获得的化合物在水稻叶片倾斜试验中都显示出显着的活性。有趣的是，浓度为 1 x 10 -7和 1 x 10 -6 M的 3β-羟基-6-氧代-23,24-dinorcholan-22-oic 酸甲酯(14)的效果被证明比那些浓度更高由油菜素内酯产生。对具有最高生物活性数据的化合物进行了计算机分子对接和诱导拟合对接（IFD）模拟，以研究进入油菜素内酯结合槽的结合模式相互作用，结果表明化合物14具有高结合能值和良好的结合能。亲和力。

  DOI：

  10.1016/j.steroids.2023.109248

文献信息

• Interactions between GABAergic and aminoacidergic pathways in the control of gonadotropin and GH secretion in pre-pubertal female rats
  作者：L. Pinilla、L. C. González、M. Tena-Sempere、Enrique Aguilar

  DOI：10.1007/bf03343970

  日期：2002.2

  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.