(3beta,20S)-20-甲基-孕甾-5-烯-3,21-二醇3-乙酸酯21-对甲苯磺酰基 | 120664-97-3

• 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
• 中文名称: (3beta,20S)-20-甲基-孕甾-5-烯-3,21-二醇3-乙酸酯21-对甲苯磺酰基
• 英文名称: 3β-acetoxy-22-O-(p-toluenesulfonyl)-5-cholen-22-ol
• 英文别名: 3β-acetoxy-22-toluenesolfonyloxy-23,24-bisnorchol-5-ene；3β-acetoxy-23,24-bisnor-chol-5-en-22-yl p-toluenesulfonate；3β-acetoxy-22-(toluene-4-sulfonyloxy)-23,24-dinor-chol-5-ene；3β-Acetoxy-22-(toluol-4-sulfonyloxy)-23,24-dinor-chol-5-en；(3beta,20S)-20-Methyl-pregn-5-ene-3,21-diol 3-Acetate 21-Tosyl；[(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(2S)-1-(4-methylphenyl)sulfonyloxypropan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 120664-97-3
• 化学式: C₃₁H₄₄O₅S
• 分子量: 528.753
• InChiKey: YJIVKCVTWWRTED-CIMDZAPNSA-N

物化性质

• 溶解度：
  溶于二氯甲烷、乙醚、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3beta,20S)-20-甲基-孕甾-5-烯-3,21-二醇3-乙酸酯21-对甲苯磺酰基 在 xylene 作用下， 生成 3B-羟基-D5-胆烯酸
  参考文献：
  名称：

  Hayatsu, Pharmaceutical Bulletin, 1957, vol. 5, p. 452,457

  摘要：

  DOI：
• 作为产物：
  描述：

  3β-acetoxy-23,24-dinorchol-5-en-22-oyl chloride 在 吡啶 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 (3beta,20S)-20-甲基-孕甾-5-烯-3,21-二醇3-乙酸酯21-对甲苯磺酰基
  参考文献：
  名称：

  A mechanism-based fluorogenic probe for the cytochrome P-450 cholesterol side chain cleavage enzyme

  摘要：

  The rate-limiting step of steroid biosynthesis is the enzymatic conversion of cholesterol to pregnenolone by cytochrome P-450scc (side chain cleavage) located in the inner mitochondrial membrane of all steroid producing cells. We report here the synthesis and application of a fluorogenic probe which is a cholene-based steroid with a fluorogenic moiety (resorufin) strategically located at the site of side chain cleavage. Synthesis of the probe required four steps starting from 3-beta-acetoxy-22,23-bisnor-5-cholenic acid and resorufin. Reaction of the probe with P-450scc yields pregnenolone and the highly fluorescent resorufin, thus providing a sensitive fluorescent signal representative of enzyme activity. The fluorescence quantum yield of this probe is approximately 40-fold lower (phi = 0.006) than resorufin (phi = 0.23) and is essentially nonfluorescent at wavelengths used to excite resorufin. The utility of the probe is demonstrated biochemically by incubation with mitochondria known to contain the P-450scc enzyme, and its specificity for this enzyme is shown by regulation of the enzyme activity with inhibitors and through the use of a nonspecific substrate.

  DOI：

  10.1021/jo00018a036

文献信息

• Preparation of (25)- and (25)-26-functionalized steroids as tools for biosynthetic studies of cholic acids
  作者：V KHRIPACH、V ZHABINSKII、O KONSTANTINOVA、N KHRIPACH、A ANTONCHICK、A ANTONCHICK、B SCHNEIDER

  DOI：10.1016/j.steroids.2005.02.014

  日期：2005.7

  new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3beta-hydroxy-Delta(5)- or a Delta(4)-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3beta-acetoxy-pregn-5-en-20-carboxylic acid. The obtained compounds are useful as standards for studies of cholic acids. Construction of the side chain was achieved by linkage of steroidal 23-iodides

  从豆甾醇或 (20S) 开始，描述了在环 A 中含有 3β-羟基-Delta(5)-或 Delta(4)-3-酮基官能团的 26-胆甾烷酸和 26-醇的差向异构形式的新合成)-3β-乙酰氧基-pregn-5-en-20-羧酸。所得化合物可用作研究胆酸的标准品。侧链的构建是通过将甾体 23-碘化物连接到由 (2R)- 和 (2S)-3-羟基-2-甲基丙酸酯制备的砜来实现的。使用由 TEMPO 和漂白剂催化的亚氯酸钠，将中间体 26-醇氧化成相应的羧酸，确保保留 C-25 的立体化学和环状部分的官能团。
• Preparation of transition-state analogues of sterol 24-methyl transferase as potential anti-parasitics
  作者：Silvia Orenes Lorente、Carmen Jimenez Jimenez、Ludovic Gros、Vanessa Yardley、Kate de Luca-Fradley、Simon L. Croft、Julio A. Urbina、Luis M. Ruiz-Perez、Dolores Gonzalez Pacanowska、Ian H. Gilbert

  DOI：10.1016/j.bmc.2005.06.012

  日期：2005.9

  There is an urgent need for new drugs to treat leishmaniasis and Chagas disease. One important drug target in these organisms is sterol biosynthesis. In these organisms the main endogenous sterols are ergosta- and stigmata-like compounds in contrast to the situation in mammals, which have cholesterol as the sole sterol. In this paper we discuss the design, synthesis and evaluation of potential transition state analogues of the enzyme Delta(24(25))-methyltransferase (24-SMT). This enzyme is essential for the biosynthesis of ergosterol, but not required for the biosynthesis of cholesterol. A series of compounds were successfully synthesised in which mimics of the S-adenosyl methionine co-factor were attached to the sterol nucleus. Compounds were evaluated against recombinant Leishmania major 24-SMT and the parasites L. donovani and Trypanosoma cruzi in vitro, causative organisms of leishmaniasis and Chagas disease, respectively. Some of the-compounds showed inhibition of the recombinant Leishmania major 24-SMT and induced growth inhibition of the parasites. Some compounds also showed anti-parasitic activity against L. donovani and T cruzi, but no inhibition of the enzyme. In addition, some of the compounds had anti-proliferative activity against the bloodstream forms of Trypanosoma brucei rhodesiense, which causes African trypanosomiasis. (c) 2005 Published by Elsevier Ltd.