methyl (20S)-3,6-dioxo-5α-pregnane-20-carboxylate | 7674-82-0

• 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: methyl (20S)-3,6-dioxo-5α-pregnane-20-carboxylate
• 英文别名: 20S-3,6-Dioxo-5α-pregnan-20-carbonsaeure-methylester；3,6-dioxo-23,24-dinor-5α-cholanoic acid-(22)-methyl ester；3,6-Dioxo-23,24-dinor-5α-cholansaeure-(22)-methylester；3.6-Dioxo-20β_F-methyl-5α-pregnansaeure-(21)-methylester；methyl (2S)-2-[(5S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3,6-dioxo-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoate
• CAS: 7674-82-0
• 化学式: C₂₃H₃₄O₄
• 分子量: 374.521
• InChiKey: RDDUZOVSWADKSS-HICXXYTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  0.87
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (20S)-3,6-dioxo-5α-pregnane-20-carboxylate 在 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 乙醚 、 正庚烷 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 (24S)-[26,27-2H6]3,6-(dioxolan-2-yl)-23-phenylsulfonyl-24-methyl-5α-cholestan-22-one
  参考文献：
  名称：

  由23,24-双降胆固醇酸甲酯合成[26,27-2H6]油菜素类固醇。

  摘要：

  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。

  DOI：

  10.1016/j.steroids.2004.05.014
• 作为产物：
  描述：

  3,3-ethanediyldioxy-20β_F-methyl-pregn-5-en-21-oic acid methyl ester 生成 methyl (20S)-3,6-dioxo-5α-pregnane-20-carboxylate
  参考文献：
  名称：

  用于合成蜕皮激素。II。关于2β，3β-二羟基-6-酮-A | B-顺式-类固醇的昆虫激素合成的信息†

  摘要：

  合成蜕皮激素（1）（[22 R ]-2β，3β，14，22，25-五羟基-5β，14α-胆甾-7-en-6-one）的实验已导致2β，3β-二羟基- 6-酮5α-类固醇。这些可以差向异构为相应的5β系列。物理数据和化学相关性为所建议的构型分配提供了支持。

  DOI：

  10.1002/hlca.19660490517

文献信息

• Methyl esters of 23,24-Dinor-5α-cholan-22-oic acids as brassinosteroid Analogues. Synthesis, evaluation of plant growth promoting activity and Molecular docking
  作者：P. Franco Cimino、G. María Núñez、Anielka Rosado-Abón、Ángel Amesty、Ana Estévez-Braun、Katy Díaz、C. Luis Espinoza、Martín A. Iglesias-Arteaga

  DOI：10.1016/j.steroids.2023.109248

  日期：2023.8

  Five new brassinosteroid analogues were synthetized from 3β-acetoxy-23,24-dinorchol-4-en-22-oic acid. All the obtained compound showed significant activity in the Rice Lamina Inclination Test. Interestingly the effects of the methyl ester of 3β-hydroxy-6-oxo-23,24-dinorcholan-22-oic acid (14) at concentrations of 1 x 10-7 and 1 x 10-6 M proved to be higher than those produced by brassinolide. In silico

  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。
• 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.
• ZHOU, WEI-SHAN;JIANG, LI-ZHONG;TIAN, WEI-SHENG;ZHAO, XU-YANG;ZHENG, HU, XUASYUEH SYUEHBAO, 46,(1988) N2, S. 1212-1218
  作者：ZHOU, WEI-SHAN、JIANG, LI-ZHONG、TIAN, WEI-SHENG、ZHAO, XU-YANG、ZHENG, HU

  DOI：——

  日期：——