2α,3α-Diaminocholestane | 160381-48-6

• 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: 2α,3α-Diaminocholestane
• 英文别名: 2α,3α-Diaminocholestan；(2R,3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-2,3-diamine
• CAS: 160381-48-6
• 化学式: C₂₇H₅₀N₂
• 分子量: 402.707
• InChiKey: GICFUTHUAIMVCB-ZEQHCUNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2α,3α-Diaminocholestane 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 48.0h， 生成 Di(cholestano<2,3-b:2',3'-e>)pyrazine bis-N-oxide
  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：

  2α-azido-5α-cholestan-3-one 在 吡啶 、 硼烷 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 55.33h， 生成 2α,3α-Diaminocholestane
  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

• Steroide, 32. Stereospezifische Darstellung stickstoffhaltiger Steroide aus Aziridinen und vicinalen Azidoalkohol‐methansulfonaten
  作者：Kurt Ponsold、Dieter Klemm

  DOI：10.1002/cber.19721050827

  日期：1972.8

  3α-(6a) und 2β.3β-Diamino-cholestan (3a) werden aus den entsprechenden trans-diaxialen Azidoalkohol-sulfonaten (4, 1) über die cis-Diazide 5 und 2 synthetisiert. Das trans-diaxiale 2β.3α-Diamino-cholestan (9a) wird durch Ringöffnung von 2α.3α- und 2β.3β-Imino-cholestan und nachfolgende Reduktion der erhaltenen Azido-amine 8a und 11a dargestellt. Die Umsetzung der isomeren N-Benzoyl-aziridine 12 und 14 mit

  2α.3α-（6a）和2β.3β-二氨基胆甾醇（3a）werden aus den entsprechenden trans -diaxialen Azidoalholhol-sulfonaten（4，1，）顺式-Diazide 5和2合成。Das反式双轴2β.3α-二氨基胆甾醇（9a）与durchRingöffnungvon2α.3α-和2β.3β-Imino-cholestanund nachfolgende Reduktion der halhaltenen Azido-amine 8a和11a dargestellt。死于异构体的N-苯甲酰基-氮丙啶12和14 mit Natriumazid wird untersucht。
• 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.