阿马夫隆 | 50588-47-1

• 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
• 中文名称: 阿马夫隆
• 中文别名: 阿马复龙
• 英文名称: 3α-Amino-5α-androstan-2β-ol-17-one
• 英文别名: amafalone；Amafolone；(2S,3S,5S,8R,9S,10S,13S,14S)-3-amino-2-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
• CAS: 50588-47-1
• 化学式: C₁₉H₃₁NO₂
• 分子量: 305.461
• InChiKey: QPRBHGIRKWZUFJ-PPMYXAGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  阿马夫隆 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 Gly-amafalone hydrochloride
  参考文献：
  名称：

  Peptidyl aminosteroids as potential new antiarrhythmic agents

  摘要：

  The synthesis of peptidyl derivatives of the aminosteroid, amafalone (Am), is described. Six analogs were synthesized: the hydrochloride salts of Gly-Am (2) Ala-Gly-Am (3), D-Ala-Gly-Am (4), Pro-Am (6), Pro-Pro-Am (7), and D-Ala-Pro-Am (8). The peptide bonds were formed by the polymeric reagent method using polymeric hydroxybenzotriazole as the activating polymer. Peptidyl aminosteroids 2, 6, 7, and 8, when administered to rats intravenously, had protective antiarrhythmic effects similar to those of amafalone. By the oral route, less marked protection, in comparison to amafalone, was observed with 6, while 7 and 8 were disappointingly inactive.

  DOI：

  10.1016/0039-128x(90)90098-v
• 作为产物：
  描述：

  5alpha-雄甾-2-烯-17-酮 在 氢氧化钾 、 高氯酸 、 1,3-二溴-5,5-二甲基海因 、 氨 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 11.0h， 生成 阿马夫隆
  参考文献：
  名称：

  Synthesis and antiarrhythmic activity of 3 α-amino-5-α-androstan-2 β-ol-17-one

  摘要：

  DOI：

  10.1007/bf00758562

文献信息

• GYLLENHAAL O.; VESSMAN J., J. CHROMATOGR., 395,(1987) 445-453
  作者：GYLLENHAAL O.、 VESSMAN J.

  DOI：——

  日期：——
• US4393226A
  申请人：——

  公开号：US4393226A

  公开（公告）日：1983-07-12
• US4542153A
  申请人：——

  公开号：US4542153A

  公开（公告）日：1985-09-17
• Synthesis and antiarrhythmic activity of 3 α-amino-5-α-androstan-2 β-ol-17-one
  作者：S. D. Shuvalova、N. I. Men'shova、G. S. Grinenko、K. A. Zaitseva、M. D. Mashkovskii

  DOI：10.1007/bf00758562

  日期：1986.3
• Peptidyl aminosteroids as potential new antiarrhythmic agents
  作者：Michael Mokotoff、Ming Zhao、Richard J. Marshall、Eileen Winslow、Lan K. Wong、Qing-Jiang Liao

  DOI：10.1016/0039-128x(90)90098-v

  日期：1990.9

  The synthesis of peptidyl derivatives of the aminosteroid, amafalone (Am), is described. Six analogs were synthesized: the hydrochloride salts of Gly-Am (2) Ala-Gly-Am (3), D-Ala-Gly-Am (4), Pro-Am (6), Pro-Pro-Am (7), and D-Ala-Pro-Am (8). The peptide bonds were formed by the polymeric reagent method using polymeric hydroxybenzotriazole as the activating polymer. Peptidyl aminosteroids 2, 6, 7, and 8, when administered to rats intravenously, had protective antiarrhythmic effects similar to those of amafalone. By the oral route, less marked protection, in comparison to amafalone, was observed with 6, while 7 and 8 were disappointingly inactive.