17β-(N-formyl-N-methylamino)estra-1,3,5(10)-triene-3,16α-diol | 80177-54-4

• 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: 17β-(N-formyl-N-methylamino)estra-1,3,5(10)-triene-3,16α-diol
• 英文别名: 17β-(N-formyl-N-methylamino)-oestra-1,3,5(10)-triene-3,16α-diol；17beta-(N-Formyl-N-methylamino)-oestra-1,3,5(10)-triene-3,16alpha-diol；N-[(8R,9S,13S,14S,16R,17R)-3,16-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-N-methylformamide
• CAS: 80177-54-4
• 化学式: C₂₀H₂₇NO₃
• 分子量: 329.439
• InChiKey: USNCTZPTLYGDDX-NADOGSGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17β-(N-formyl-N-methylamino)estra-1,3,5(10)-triene-3,16α-diol 在 氢氧化钾 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 176.0h， 生成 3-<<2-hydroxy-3-(tert-butylamino)propyl>oxy>-17β-(N-methylamino)estra-1,3,5(10)-trien-16β-ol
  参考文献：
  名称：

  Antiarrhythmic activity of 17.beta.-aminoestratrienes. Comparison of 3-ols and 3-acetates with the corresponding 3-(3-amino-2-hydroxypropyl) ethers

  摘要：

  The antiarrhythmic efficacy of 17 beta-amino- and 17 beta-amino-16 alpha-hydroxyestratrien-3-ols and 3-acetates (group 1) was compared with the efficacy of corresponding 3-[2-hydroxy-3-(isopropylamino)propyl] and 3-[2-hydroxy-3-(tert-butylamino)propyl] ethers (group II), substituents which are usually associated with beta-adrenoceptor blocking activity. Group I compounds exerted potent antiarrhythmic activity against both aconitine-induced arrhythmias in mice and ischemia-induced arrhythmias in rats and reduced the maximum following frequency of isolated guinea pig atria. Electrophysiological studies indicated that their mechanism of action is due to an ability to reduce the fast inward sodium current in cardiac cells (class I antiarrhythmic action). Group II compounds were inactive in the aconitine and atrial tests and electrophysiological studies confirmed that they were devoid of class I activity. However, these compounds, like both class I antiarrhythmic and beta-adrenoceptor blocking drugs, were active against ischemia-induced arrhythmias. Group II compounds, unlike group I compounds, exerted nonspecific beta-adrenoceptor blocking actions, which may account for their activity in the rat test. It was concluded that introduction of the 3-substituted ether group did not confer any advantage over the parent 3-ol or 3-acetate compounds.

  DOI：

  10.1021/jm00152a013
• 作为产物：
  描述：

  17β-(methylamino)estra-1,3,5(10)-triene-3,16α-diol 在 sodium 作用下， 以 甲醇 、 乙醇 、 甲酸乙酯 为溶剂， 生成 17β-(N-formyl-N-methylamino)estra-1,3,5(10)-triene-3,16α-diol
  参考文献：
  名称：

  Novel 17-amino-16-hydroxy steroids of the androstane and oestrane series

  摘要：

  本发明揭示了具有以下化学式I的雄烷和雌烷系列的新型、药理学上有用的17-氨基-16-羟基类固醇，以及其药学上可接受的无毒酸盐，其中：R.sub.1 = H或含有1至6个碳原子的烃基（优选为较低的烷基，如甲基）；R.sub.2 = H或含有1至6个碳原子的烃基（优选为较低的烷基，如甲基）；R.sub.3 = 自由、酯化或醚化的羟基基团；环A包括碳原子6和9具有以下配置之一：其中R.sub.4 = 自由、酯化或醚化的羟基基团；R.sub.5 = O或H(R.sub.7)，其中R.sub.7是自由、酯化或醚化的羟基基团；R.sub.6 = H或甲基；虚线代表4,5-或5,6-位的可选双键；以及这些类固醇的对映体和拉氏体。这些新型化合物具有抗心律失常的特性。

  公开号：

  US04330539A1

文献信息

• Novel 17-amino-16-hydroxy steroids of the androstane and oestrane series and derivatives thereof, processes for their preparation and pharmaceutical compositions
  申请人：AKZO N.V.

  公开号：EP0033561A1

  公开（公告）日：1981-08-12

  New and pharmacologically useful 17-amino-16-hydroxy-steroids of the androstane and oestrane series are disclosed having the formula I: and pnarmaceutically acceptable non-toxic acid addition salts thereof, wherein: R, = H or hydrocarbyl of one to six carbon atoms (preferably lower alkyl , such as methyl); R2 = H or hydrocarbyl of one to six carbon atoms (preferably lower alkyl, such as methyl); R3 = a free, esterified or etherified hydroxyl group; ring A inclusive carbon atoms 6 and 9 has one of the following configurations: in which R4 = a free, esterified or etherified hydroxyl group; R5 = O or H(R7), wherein R7 is a free, esterified or etherified hydroxyl group; R6 = H or methyl; and the dotted lines represent an optional double bond in 4,5- or 5,6-position; as well as the enantiomers and racemates of these steroids. The novel compounds have antiarrhythmic properties.

  本研究公开了具有式 I 的新的药理作用的雄烷和雌烷系列 17-氨基-16-羟基类固醇： 及其药学上可接受的无毒酸加成盐，其中 R，＝H 或一至六个碳原子的烃基（最好是低级烷基，如甲基）； R2 = H 或一至六个碳原子的烃基（最好是低级烷基，如甲基）； R3 = 自由的、酯化的或醚化的羟基； 包含碳原子 6 和 9 的环 A 具有下列构型之一： 其中 R4 = 自由、酯化或醚化羟基； R5 = O 或 H(R7)，其中 R7 是游离的、酯化的或醚化的羟基； R6 = H 或甲基；以及 虚线代表 4,5- 位或 5,6- 位的任选双键； 以及这些类固醇的对映体和外消旋体。 这些新型化合物具有抗心律失常的特性。
• US4330539A
  申请人：——

  公开号：US4330539A

  公开（公告）日：1982-05-18