1,1-dicyclopropyl-N-(oxiran-2-ylmethoxy)methanimine | 90941-24-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,1-dicyclopropyl-N-(oxiran-2-ylmethoxy)methanimine
• CAS: 90941-24-5
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: MSBDBYMKCPGIFC-UHFFFAOYSA-N

物化性质

• 沸点：
  275.2±32.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-二甲氧基苯甲胺 、 1,1-dicyclopropyl-N-(oxiran-2-ylmethoxy)methanimine 以 乙醇 为溶剂， 反应 24.0h， 以48%的产率得到Dicyclopropyl-methanone O-[3-(2,4-dimethoxy-benzylamino)-2-hydroxy-propyl]-oxime
  参考文献：
  名称：

  New β-adrenoceptor-blocking agents derived from dicyclopropyl ketone oxime: influence of amino substituents on in vivo activity

  摘要：

  A series of oximinopropanolamines derived from dicyclopropyl ketone, in which the amine substituents were alkyl, cycloalkyl, aryl and aralkyl groups, has been synthesized. The beta-adrenergic blocking properties were determined on anaesthetized rats. Two N-aralkyl derivatives were found to be as potent as propranolol and compound 11 was twice as active as propranolol. Some structure-activity relationships are discussed.

  DOI：

  10.1016/0223-5234(94)90128-7
• 作为产物：
  描述：

  二环丙基甲酮肟 、 环氧溴丙烷 在 sodium hydride 作用下， 生成 1,1-dicyclopropyl-N-(oxiran-2-ylmethoxy)methanimine
  参考文献：
  名称：

  具有强力β-肾上腺素阻断特性的新型手性和异构环丙基酮肟丙醇胺衍生物。

  摘要：

  描述了O- [3-叔丁基氨基）-2-羟丙基]环丙基甲基酮肟（氟林醇）的R-（+）和S-（-）异构体的合成。法林特洛的顺式和反式异构体是从环丙基甲基酮肟或法林特洛以两种不同方式获得的。为了比较，还制备了二环丙基酮肟衍生物的对映体。描述了构效关系。

  DOI：

  10.1021/jm00145a008

文献信息

• Synthesis and .beta.-adrenergic blocking activity of new aliphatic and alicyclic oxime ethers
  作者：Mohamed Bouzoubaa、Gerard Leclerc、Nicole Decker、Jean Schwartz、Guy Andermann

  DOI：10.1021/jm00376a011

  日期：1984.10

  We describe the synthesis and pharmacological properties of two new series of aliphatic and alicyclic beta-adrenergic blockers, most of them containing a cyclopropyl ring. They belong either to 2-hydroxy-3-(tert-butylamino)propyl ether A or 2-hydroxy-3-tert-(butylamino)propyl ketoxime ether B derivatives. The O-[2-hydroxy-3-(tert-butylamino)propyl] dicyclopropyl ketoxime 5 exhibited a beta-adrenergic

  我们描述了两个新系列的脂肪族和脂环族β-肾上腺素能阻滞剂的合成和药理性质，其中大多数含有环丙基环。它们属于2-羟基-3-（叔丁基氨基）丙基醚A或2-羟基-3-叔-（丁基氨基）丙基酮肟醚B衍生物。O- [2-羟基-3-（叔丁基氨基）丙基]二环丙基酮肟5表现出与普萘洛尔相当的β-肾上腺素能拮抗剂活性。发现酮肟醚B通常显示出比相应的醚A更高的效力。我们证实，芳香核的存在对于β-肾上腺素活性不是至关重要的。讨论了这些系列之间的构效关系。
• Synthesis and Adrenergic Activity of a New Series of <i>N</i>-Aryl Dicyclopropyl Ketone Oxime Ethers: SAR and Stereochemical Aspects
  作者：Madeleine Blanc、Abderrafii Tamir、Silvère Aubriot、Marie Claude Michel、Mohamed Bouzoubaa、Gérard Leclerc、Pierre Demenge

  DOI：10.1021/jm970338c

  日期：1998.5.1

  A novel series of 31 N-aryl dicyclopropyl ketone oxime ethers were synthesized and tested for their activity at alpha- and beta-adrenergic receptors. All of the compounds showed greater affinity for beta-than for alpha1-receptor sites. Some compounds had pure antagonist effects whereas some were partial agonists. Several compounds had an antagonist effect matching that of propranolol in in vitro (binding

  合成了一系列新颖的31种N-芳基二环丙基酮肟醚，并测试了它们在α-和β-肾上腺素能受体上的活性。所有这些化合物对β的亲和力都比对α1受体的更大。一些化合物具有纯的拮抗作用，而另一些则是部分激动剂。几种化合物在体外（在大鼠心室匀浆和豚鼠上的结合数据和pA2值分别自发地击败右和电驱动的左心房分离制剂）具有与普萘洛尔相当的拮抗作用，并且在体内试验中（拮抗对异丙肾上腺素诱导的麻醉性大鼠心动过速）。此外，所有化合物均显示出β1肾上腺素选择性（β2亲和力> 1500 nM）。
• Derivatized alkanolamines as cardiovascular agents
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0358284A2

  公开（公告）日：1990-03-14

  Novel derivatized alkanolamines of the following structural formula are described as useful cardiovascular agents. Most especially described is their usefulness as cardiovascular agents exhibiting an antiarrhythmic effect. Said antiarrhythmic effect is of a combination Class II/Class III variety. Pharmaceutical formulations containing such compounds are also described.

  结构式如下的新型衍生化烷醇胺 被描述为有用的心血管制剂。尤其是它们作为心血管药剂具有抗心律失常的作用。所述抗心律失常作用为 II 类/III 类联合作用。还描述了含有此类化合物的药物制剂。
• Synthesis of novel (aryloxy)propanolamines and related compounds possessing both class II and class III antiarrhythmic activity
  作者：Randall Lis、Thomas K. Morgan、Anthony J. Marisca、Robert P. Gomez、Joan M. Lind、David D. Davey、Gary B. Phillips、Mark E. Sullivan

  DOI：10.1021/jm00172a033

  日期：1990.10

  Several (aryloxy)propanolamines and related compounds (i.e. 5-13, 16-18, 20-24, 27-33, 35, 37-39, 41, and 42) were synthesized and investigated for their class III electrophysiological activity and class II (beta-blocking) effects with use of in vitro and in vivo models. Structure-activity relationships are discussed for a series of 30 compounds. A number of these compounds prolonged the action potential duration at 95% repolarization of isolated canine cardiac Purkinje fibers by 20% (C20APD95) at concentrations of less than 1.0 microM, with no significant effects on cardiac conduction. beta-Adrenergic receptor binding studies showed that some of these compounds were 2-20 times more potent for cardiac beta 1 receptors than for beta 2 receptors. In particular, compounds 32, 41, 1, and especially (S)-1 were found to be orally active class III agents in anesthetized mongrel dogs (1 or 3 mg/kg, id) and efficacious at suppressing programmed electrical stimulation induced arrhythmias in halothane-anesthetized dogs. The profile of these compounds was similar to that found for sotalol. Compound (S)-1, which was more potent than sotalol in the PES study and equieffective in the halothane/epinephrine dog model, is being investigated further as a combined class III/II antiarrhythmic agent.
• Bouzoubaa; Leclerc; Ehrhardt, Bulletin de la Societe Chimique de France, 1985, vol. NO. 6, # 6, p. 1230 - 1236
  作者：Bouzoubaa、Leclerc、Ehrhardt、Andermann

  DOI：——

  日期：——