(17β-Acetoxyandrostano<2,3-b>)cholestano<2,3-e>pyrazine | 144303-53-7

• 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: (17β-Acetoxyandrostano<2,3-b>)cholestano<2,3-e>pyrazine
• 英文别名: (17β-Acetoxyandrostano[2,3-b])cholestano[2,3-e]pyrazine；[(5S,6S,9S,10S,13S,14R,17S,23S,24S,27R,28R,31S,32R,35S)-5,9,23,27-tetramethyl-28-[(2R)-6-methylheptan-2-yl]-2,20-diazanonacyclo[19.15.0.03,19.05,17.06,14.09,13.023,35.024,32.027,31]hexatriaconta-1(21),2,19-trien-10-yl] acetate
• CAS: 144303-53-7
• 化学式: C₄₈H₇₄N₂O₂
• 分子量: 711.128
• InChiKey: DFKRKZIUOHQDNV-FGGVITHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.7
• 重原子数：
  52
• 可旋转键数：
  7
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (17β-Acetoxyandrostano<2,3-b>)cholestano<2,3-e>pyrazine 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 以82%的产率得到(17β-Hydroxyandrostano<2,3-b>)cholestano<2,3-e>pyrazine
  参考文献：
  名称：

  Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1

  摘要：

  A mild, high-yielding synthesis of symmetrical steroidal pyrazines was achieved from the dimerization of 2-amino-3-ketosteroids, which were produced in situ from the triphenylphosphine-water reduction of the corresponding alpha-azido ketone. 2-Azidocholestan-3-one gave the dimeric steroidal pyrazine very cleanly, and two known dimeric pyrazines based on androstanone were also made using this methodology. Both C-2-symmetric geometric isomers of the dimeric steroidal pyrazine derived from cholestane were prepared by reaction of 2,3-diaminocholestane with cholestane-2,3-dione. A route to unsymmetrical bis-steroidal pyrazines was based on the observation that alpha-acetoxy ketones react with alpha-amino oximes directly with no need for oxidation of intermediate dihydropyrazines. Heating either 2 beta,17 beta-dihydroxyandrostan-3-one diacetate or 2 beta,17 beta-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyiminocholestane in toluene at 145 degrees C gave the corresponding unsymmetrical pyrazine in moderate yield. Five of the steroidal pyrazines were evaluated in the National Cancer Institute's new in vitro, disease-oriented antitumor screen, but none showed sufficient activity to warrant in vivo investigation.

  DOI：

  10.1021/jo00101a052
• 作为产物：
  描述：

  Cholestan-3-one, 2-azido-, O-methyloxime, (2a,5a)- 在 水 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.0h， 生成 (17β-Acetoxyandrostano<2,3-b>)cholestano<2,3-e>pyrazine
  参考文献：
  名称：

  A convenient procedure for the synthesis of bis-steroidal pyrazines: models for the cephalostatins

  摘要：

  Efficient routes have been developed for both symmetrical and unsymmetrical bis-steroidal pyrazines from readily available precursors.

  DOI：

  10.1021/jo00050a002