(E)-17β-[(guanidinoimino)methyl]-5β-androstane-3β,17β-diol hydrochloride

• 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: (E)-17β-[(guanidinoimino)methyl]-5β-androstane-3β,17β-diol hydrochloride
• 英文别名: 2-[(E)-[(3S,5R,8R,9S,10S,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]methylideneamino]guanidine;hydrochloride
• 化学式: C₂₁H₃₆N₄O₂*ClH
• 分子量: 413.003
• InChiKey: SOFDZPRCQCTSKO-AUABOCDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  117
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-17β-[(guanidinoimino)methyl]-5β-androstane-3β,17β-diol hydrochloride 在 二氧化铂 盐酸 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以to give 0.30 g of the title compound (I-aa) as a white solid, hydrochloride的产率得到17β-[2-(Amidino)]hydrazinomethyl-5β-androstane-3β,14β-diol
  参考文献：
  名称：

  Hydrazino and hydroxyamino-14-.beta.-hydroxyandrostane derivatives

  摘要：

  该发明描述了具有一般式（I）的肼基和羟肼基-14.beta.-羟基雄烷衍生物：##STR1## 其中符号表示.alpha.或.beta.构型，A、B、R.sup.1、R.sup.2、R.sup.3和R.sup.4的含义如描述中所给，并且它们在治疗心血管疾病如心力衰竭和高血压中的应用。

  公开号：

  US05599806A1
• 作为产物：
  描述：

  3β,14β-dihydroxy-5β-androstane-17β-carboxaldehyde 、 氨基胍碳酸氢盐 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以61%的产率得到(E)-17β-[(guanidinoimino)methyl]-5β-androstane-3β,17β-diol hydrochloride
  参考文献：
  名称：

  Synthesis and Quantitative Structure−Activity Relationships of 17β-(Hydrazonomethyl)-5β-androstane-3β,14β-diol Derivatives That Bind to Na⁺,K⁺-ATPase Receptor

  摘要：

  A series of 17 beta-(hydrazonomethyl)-5 beta-androstane-3 beta,14 beta-diol derivatives was synthesized and evaluated in the displacement of [H-3]ouabain binding from Na+,K+-ATPase. The data were explored with multiple linear regression and partial least-squares to find possible quantitatives structure-activity relationships. Good correlations were found between binding to the receptor and van der Waals volumes or molar refractivities of the 17 beta-hydrazonomethyl substituents and pK(a) values of the compounds. Equivalent results were obtained using the proton affinity (calculated using MOPAC) of the hydrazone residues instead of experimental pK(a). As basicity or related electronic factors of the substituents explain a significant portion of the observed changes in the activity, an ion-pair interaction between a carboxylate residue of the enzyme and the protonated 17 beta-hydrazonomethyl group, as postulated by Thomas, plays an important role in the interaction of the ligand to the Na+,K+-ATPase receptor.

  DOI：

  10.1021/jm950806n

文献信息

• New hydrazino and hydroxyamino-14beta-hydroxyandrostane derivatives active on the cardio-vascular system, processes for their preparation and pharmaceutical compositions containing same
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0688786B1

  公开（公告）日：1997-08-06
• US5599806A
  申请人：——

  公开号：US5599806A

  公开（公告）日：1997-02-04