3β-acetoxy-4β,5β-epoxycholestan-6-one | 20951-84-2

• 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: 3β-acetoxy-4β,5β-epoxycholestan-6-one
• 英文别名: [(1S,2R,5S,6S,8R,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-9-oxo-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadecan-5-yl] acetate
• CAS: 20951-84-2
• 化学式: C₂₉H₄₆O₄
• 分子量: 458.682
• InChiKey: AMVVGMABXOSFHO-AADSKDKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-4β,5β-epoxycholestan-6-one 在 吡啶 、 盐酸羟胺 作用下， 以80%的产率得到3β-acetoxy-4β,5β-epoxy-(6E)-hydroxyiminocholestane
  参考文献：
  名称：

  Synthesis and evaluation of new 6-hydroximinosteroid analogs as cytotoxic agents

  摘要：

  Taking into account the structural requirements for cytotoxicity, several new hydroximinosteroid derivatives have been prepared and evaluated for their cytotoxic activity against A-549, HI 16, PSN1, and T98G cultured tumor cell lines in order to obtain further information on the potential pharmacophoric core of this type of compound. The influence of the oxygenated position in the A ring, the presence of an additional oxygenated position at C-7 and C-16, and a fluorinated position at C-5 were considered in order to study the structure-activity relationships. The results reveal the importance of oxygenated positions in the A ring (e.g., 4,5-epoxide showed an IC50 value against HCT-116 under micromolar level) for an increase in cytotoxic activity in this type of compound. Furthermore, they showed an important selectivity toward colon tumor line (HCT-116). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.003
• 作为产物：
  描述：

  乙酸酐 、 4β,5β-epoxy-3β-hydroxycholestan-6-one 在 吡啶 作用下， 反应 24.0h， 以99%的产率得到3β-acetoxy-4β,5β-epoxycholestan-6-one
  参考文献：
  名称：

  Synthesis and evaluation of new 6-hydroximinosteroid analogs as cytotoxic agents

  摘要：

  Taking into account the structural requirements for cytotoxicity, several new hydroximinosteroid derivatives have been prepared and evaluated for their cytotoxic activity against A-549, HI 16, PSN1, and T98G cultured tumor cell lines in order to obtain further information on the potential pharmacophoric core of this type of compound. The influence of the oxygenated position in the A ring, the presence of an additional oxygenated position at C-7 and C-16, and a fluorinated position at C-5 were considered in order to study the structure-activity relationships. The results reveal the importance of oxygenated positions in the A ring (e.g., 4,5-epoxide showed an IC50 value against HCT-116 under micromolar level) for an increase in cytotoxic activity in this type of compound. Furthermore, they showed an important selectivity toward colon tumor line (HCT-116). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.003

文献信息

• Epoxidation and Baeyer–Villiger oxidation of γ-hydroxy-αβ-unsaturated ketones on exposure to m-chloroperbenzoic acid
  作者：Marioara Mendelovici、Erwin Glotter

  DOI：10.1039/p19920001735

  日期：——

  of 6β-and 6α-hydroxy-(acetoxy-)cholest-4-en-3-one with MCPBA gives two types of product, depending on the initial site of the peroxy acid attack. Attack at the carbonyl group gives a Baeyer–Villiger rearrangement leading first to enol lactones and then by epoxidation of the latter to epoxy lactones. Alternatively, attack at the double bond gives epoxy ketones which can subsequently undergo a Baeyer–Villiger

  用MCPBA处理3β-和3α-羟基（乙酰氧基）胆甾4烯-6和6β和6α-羟基（乙酰氧基）胆甾4烯-3产生两种类型的产物，取决于过氧酸侵蚀的初始部位。攻击羰基会产生BAeyer-Villiger重排，首先导致烯醇内酯，然后再将后者环氧化为环氧内酯。另外，对双键的进攻会产生环氧酮，随后会发生拜尔-维利格重排，从而生成环氧内酯。除了一个例外（3α-hydroxycholest-4-en-6-one），烯酮的BAeyer-Villiger氧化是主要过程。在轴向3α-或6β-乙酰氧基的存在下，双键的环氧化被抑制。