2β,3β-dihydroxy-5α-cholestan-6-one | 7674-78-4

• 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: 2β,3β-dihydroxy-5α-cholestan-6-one
• 英文别名: 2β,3β-Dihydroxy-5α-cholestan-6-on；2β,3β-Dihydroxy-5α-cholestan-6on；2β,3β-Dihydroxy-5α-cholestanon-6；(2S,3R,5S,8S,9S,10R,13R,14S,17R)-2,3-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 7674-78-4
• 化学式: C₂₇H₄₆O₃
• 分子量: 418.66
• InChiKey: KIKODPSBQXENPH-KHFLUYKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2β,3β-dihydroxy-5α-cholestan-6-one 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 2β,3β-Dihydroxy-5β-cholestan-6-on
  参考文献：
  名称：

  Velgova,H. et al., Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 1015 - 1034

  摘要：

  DOI：
• 作为产物：
  描述：

  2β,3β-Diacetoxy-5α-cholestan-6-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 2β,3β-dihydroxy-5α-cholestan-6-one
  参考文献：
  名称：

  On steroids CIII. Molting deficiencies produced by some sterol derivatives in an insect (Pyrrhocoris apterus L.)

  摘要：

  DOI：

  10.1016/0039-128x(66)91017-8

文献信息

• Zur Synthese des Ecdysons. II. Mitteilung über Insektenhormone Synthesen von 2β, 3β-Dihydroxy-6-keto-A|B-<i>cis</i>-Steroiden
  作者：R. Wiechert、U. Kerb、P. Hocks、A. Furlenmeier、A. Fürst、A. Langemann、G. Waldvogel

  DOI：10.1002/hlca.19660490517

  日期：——

  Experiments towards a synthesis of ecdysone (1) ([22R]-2β, 3β, 14, 22, 25-pentahydroxy-5β, 14α-cholest-7-en-6-one) have led to 2β, 3β-dihydroxy-6-keto-5α-steroids. These could be epimerized to the corresponding 5β-series. The proposed configurational assignments are supported by physical data and chemical correlation.

  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。
• Synthesis of ecdysone.II.Synthesis of and Stereochemistry of 2β, 3β-Dihydroxycholestan-6-ones and Their Derivatives
  作者：Hiromu Mori、Kiyoshi Tsuneda、Kenyu Shibata、Masanobu Sawai

  DOI：10.1248/cpb.15.466

  日期：——

  2β, 3β-Dihydroxycholestan-6-ones and their derivatives were prepared and their stereo chemistry was studied. In 2β, 3β-dihydroxy-or 2β, 3β-diacetoxycholestan-6-ones, equilibrium mixture consisted of 5α-and 5β-compound at the ratioof 3 : 2. On the other hand, 5α-compound was found to be exclusively stable in 2β, 3β-dihydroxycholestan-6-one acetonides.

  制备了2β,3β-二羟基胆甾坦-6-酮及其衍生物并研究了它们的立体化学。在 2β, 3β-二羟基-或 2β, 3β-二乙酰氧基胆甾烷-6-酮中，平衡混合物由 5α-和 5β-化合物以 3:2 的比例组成。另一方面，发现 5α-化合物在2β，3β-二羟基胆甾烷-6-酮丙酮化合物。
• Synthesis of analogs of α-ecdysone. A simplified synthesis of 2β,3β,14α-trihydroxy-7-en-6-one-5β-steroids
  作者：Malcolm J. Thompson、William E. Robbins、John N. Kaplanis、Charles F. Cohen、Stanton M. Lancaster

  DOI：10.1016/s0039-128x(70)80099-x

  日期：1970.7
• Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies
  作者：Victoria Richmond、Ana P. Murray、Marta S. Maier

  DOI：10.1016/j.steroids.2013.08.003

  日期：2013.11

  Disulfated and trisulfated steroids have been synthesized from cholesterol and their acetylcholinesterase inhibitory activity has been evaluated. In our studies we have found that the activity was not only dependent on the location of the sulfate groups but on their configurations. 2 beta,3 alpha,6 alpha-trihydroxy-5 alpha-cholestan-6-one trisulfate (18) was the most active steroid with an IC50 value of 15.48 mu M comparable to that of 2 beta,3 alpha-dihydroxy-5 alpha-cholestan-6-one disulfate (1). Both compounds were found to be less active than the reference compound eserine. The butyrylcholinesterase activity of 1 and 18 was one magnitude lower than that against acetylcholinesterase revealing a selective inhibitor profile. (C) 2013 Elsevier Inc.
• Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids
  作者：Victoria Richmond、Valeria P. Careaga、Paula Sacca、Juan C. Calvo、Marta S. Maier

  DOI：10.1016/j.steroids.2014.03.001

  日期：2014.6

  Four new 6E-hydroximinosteroids (1, 2a, 3 and 4) have been synthesized from the corresponding ketones, 2 beta,3 beta-dihydroxy-5 alpha-cholestan-6-one (5), 2 alpha,3 alpha-dihydroxy-5 alpha-cholestan-6-one (6), 2 beta,3 alpha-dihydroxy-5 alpha-cholestan-6-one (7) and 2 beta,3 alpha-dihydroxy-5 alpha-cholestan-6-one-disulfate (8). The cytotoxic activity of the steroidal oxirnes was evaluated against two prostate carcinoma cell lines (PC-3 and LNCaP) and compared with that of five polyhydroxylated sulfated analogs (8-12). Oxime 3 and trisulfated analog 11 were the most active compounds with IC50 values of 10.8 mu M (PC-3) and 7.9 mu M (LNCaP), respectively. (C) 2014 Elsevier Inc. All rights reserved.