Di(cholestano<2,3-b:3',2'-e>)pyrazine | 160381-46-4

• 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: Di(cholestano<2,3-b:3',2'-e>)pyrazine
• 英文别名: di(5α-cholestano[2,3-b:3',2'-e])pyrazine；Di(cholestano[2,3-b:3',2'-e])pyrazine；(5S,6S,9R,10R,13S,14R,17S,23S,26R,27S,30R,31R,34S,35S)-5,9,31,35-tetramethyl-10,30-bis[(2R)-6-methylheptan-2-yl]-2,20-diazanonacyclo[19.15.0.03,19.05,17.06,14.09,13.023,35.026,34.027,31]hexatriaconta-1,3(19),20-triene
• CAS: 160381-46-4
• 化学式: C₅₄H₈₈N₂
• 分子量: 765.306
• InChiKey: DVLGABIKQCBQIF-KAKCLIIISA-N

物化性质

• 密度：
  0.987±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  18.3
• 重原子数：
  56
• 可旋转键数：
  10
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Di(cholestano<2,3-b:3',2'-e>)pyrazine 在 偶氮二异丁腈 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 四氯化碳 、 氯仿 为溶剂， 反应 145.0h， 生成 1α-methoxy-di(5α-cholestano[2,3-b:3',2'-e])pyrazine
  参考文献：
  名称：

  Functionalization of Dimeric Cholestanopyrazines at the quasi-Benzylic Position

  摘要：

  Two isomeric di-5 alpha-cholestanopyrazines were brominated with NBS/AIBN at the quasi-benzylic positions (1 alpha or 4 alpha). The nucleophilic displacement of bromides with methanol afforded the corresponding methoxy derivatives. Both pyrazines gave mono- or di-N-oxides upon oxidation with m-chloroperoxybenzoic acid.

  DOI：

  10.1007/s007060050007
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 在 potassium tert-butylate 、 氧气 作用下， 以 甲苯 、 叔丁醇 为溶剂， 反应 24.0h， 生成 Di(cholestano<2,3-b:3',2'-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

文献信息

• A Facile Synthesis of Symmetrical Dimeric Steroid-pyrazines
  作者：Zenon Łotowski、Agnieszka Gryszkiewicz、Jolanta B. Borowiecka、Agnieszka Nikitiuk、Jacek W. Morzycki

  DOI：10.1039/a905508h

  日期：——

  The reaction of steroidal 2α-bromo-3-ketones (e.g. 2α-bromocholestan-3-one 2) with ammonia followed by hydrolysis and air-oxidation affords the easily separable mixture of the trans and cis dimeric steroid-pyrazines (3 and 4, respectively).

  类固醇 2α-溴-3-酮（如 2α-溴胆烷-3-酮 2）与氨反应，然后进行水解和空气氧化，可得到易于分离的反式和顺式二聚类固醇吡嗪混合物（分别为 3 和 4）。
• Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1
  作者：Clayton H. Heathcock、Stephen C. Smith

  DOI：10.1021/jo00101a052

  日期：1994.11

  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.
• Functionalization of Dimeric Cholestanopyrazines at the quasi-Benzylic Position
  作者：Zenon Łotowski、Eligiusz N. Dubis、Jacek W. Morzycki

  DOI：10.1007/s007060050007

  日期：2000.1.15

  Two isomeric di-5 alpha-cholestanopyrazines were brominated with NBS/AIBN at the quasi-benzylic positions (1 alpha or 4 alpha). The nucleophilic displacement of bromides with methanol afforded the corresponding methoxy derivatives. Both pyrazines gave mono- or di-N-oxides upon oxidation with m-chloroperoxybenzoic acid.