cis-(2-phenylcyclopropyl)methylamine | 936-95-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: cis-(2-phenylcyclopropyl)methylamine
• 英文别名: (+/-)-cis-1-Aminomethyl-2-phenyl-cyclopropan；Cis-(2-phenylcyclopropyl)methanamine；[(1R,2S)-2-phenylcyclopropyl]methanamine
• CAS: 936-95-8；936-96-9；15639-87-9
• 化学式: C₁₀H₁₃N
• 分子量: 147.22
• InChiKey: ATTLDOZXPZCOGK-VHSXEESVSA-N

物化性质

• 沸点：
  118 °C(Press: 22 Torr)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-(2-phenylcyclopropyl)methylamine 在 盐酸 作用下， 以 乙醚 、 水 为溶剂， 反应 1.25h， 以26.8 mg的产率得到cis-(2-phenylcyclopropyl)methylamine hydrochlorie
  参考文献：
  名称：

  Selective 5-Hydroxytryptamine 2C Receptor Agonists Derived from the Lead Compound Tranylcypromine: Identification of Drugs with Antidepressant-Like Action

  摘要：

  We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT2C agonist, a series of 1-aminomethyl-2-phenylcyclopropanes was investigated as 5-HT2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyl-trans-cyclopropyl side chain attached to a substituted benzene ring. Among the tested compounds, several were potent and efficacious 5-HT2C receptor agonists with selectivity over both 5-HT2A and 5-HT2B receptors in functional assays. The most promising compound is 37, with 120- and 14-fold selectivity over 5-HT2A and 5-HT2B, respectively (EC50 = 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.

  DOI：

  10.1021/jm801354e
• 作为产物：
  描述：

  顺式-2-苯基环丙烷-1-羧酸 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 cis-(2-phenylcyclopropyl)methylamine
  参考文献：
  名称：

  Dupin,C.; Fraisse-Jullien,R., Bulletin de la Societe Chimique de France, 1964, p. 1993 - 2000

  摘要：

  DOI：

文献信息

• Fluorinated Phenylcyclopropylamines. 1. Synthesis and Effect of Fluorine Substitution at the Cyclopropane Ring on Inhibition of Microbial Tyramine Oxidase
  作者：Shinichi Yoshida、Oliver G. J. Meyer、Thomas C. Rosen、Günter Haufe、Song Ye、Milton J. Sloan、Kenneth L. Kirk

  DOI：10.1021/jm030398k

  日期：2004.3.1

  s and 2-fluoro-2-phenylcyclopropylalkylamines, as well as 2-fluoro-1-phenylcyclopropylamines and 2-fluoro-1-phenylcyclopropylmethylamines, were synthesized in order to study the effects of fluorine substitution on monoamine oxidase inhibition. Inhibitory activity was assayed using commercially available microbial tyramine oxidase. Characterization of tyramine oxidase, carried out prior to the inhibition

  为了研究效果，合成了两个非对映体纯的苯基环丙胺类似物2-氟-2-苯基环丙胺和2-氟-2-苯基环丙基烷基胺，以及2-氟-1-苯基环丙胺和2-氟-1-苯基环丙基甲胺。取代对单胺氧化酶抑制的影响 使用可商购的微生物酪胺氧化酶测定抑制活性。在抑制实验之前进行酪胺氧化酶的表征，证实了较早的建议，即该酶是对氨基脲敏感的含铜单胺氧化酶。最有效的竞争性抑制剂是反式-2-氟-2-苯基环丙胺，其IC（50）值比非氟化化合物tranylcypromine低10倍。发现2-氟-1-苯基环丙基甲基胺是酪胺氧化酶的弱非竞争性抑制剂。直接与环丙烷环键合的游离氨基和与氨基成顺式关系的氟原子的存在是增加酪氨酸氧化酶抑制作用的结构特征。
• 5-HT2C Receptor Agonists as Anorectic Agents
  申请人：Kozikowski Alan

  公开号：US20090203750A1

  公开（公告）日：2009-08-13

  This invention relates to compounds which modulate receptors of the 5-HT2 family of receptors, and particularly to compounds which modulate 5-HT2C receptors. Compounds of the invention include agonists and selective agonists for the 5-HT2C receptor Compounds of the invention include selective agonists for the 5-HT2C receptor which exhibit significantly less or no agonist activity on the 5-HT2A receptor and/or the 5-HT2B receptor. Compounds of this invention are those of Formula I and pharmaceutically acceptable salts, esters and solvates (including hydrates) wherein variables are defined in the specification hereof.

  本发明涉及调节5-HT2家族受体的化合物，特别是调节5-HT2C受体的化合物。本发明的化合物包括5-HT2C受体的激动剂和选择性激动剂。本发明的化合物包括5-HT2C受体的选择性激动剂，其在5-HT2A受体和/或5-HT2B受体上表现出显著较少或无激动剂活性。本发明的化合物包括式I和药学上可接受的盐、酯和溶剂（包括水合物），其中变量在本规范中定义。
• Conformational analogs of antihypertensive agents related to guanethidine
  作者：R. F. Borne、M. L. Forrester、I. W. Waters

  DOI：10.1021/jm00216a007

  日期：1977.6

  In an effort to clarify the conformational requirements, if any, of agents producing adrenergic neuronal blockade through mechanisms similar to guanethidine, the synthesis and pharmacological evaluation of 15 analogues of cinnamylguanidine are described. These analogues represent derivatives in which the distance between the center of the ring system and the guanidinium nitrogen atom varies from 3.9 to 6.2 A. While conformational relationships could not be defined in this study, three analogues (3, 4, and 5) were apparently more potent than guanethidine in the in vitro assay employed.
• [EN] 5-HT2C RECEPTOR AGONISTS AS ANORECTIC AGENTS<br/>[FR] AGONISTES DE RECEPTEUR 5-HT2C UTILISES EN TANT QU'AGENTS ANOREXIGENES
  申请人：UNIV ILLINOIS CHICAGO

  公开号：WO2007025144A1

  公开（公告）日：2007-03-01

  [EN] This invention relates to compounds which modulate receptors of the 5-HT2 family of receptors, and particularly to compounds which modulate 5-HT2C receptors. Compounds of the invention include agonists and selective agonists for the 5-HT2C receptor. Compounds of the invention include selective agonists for the 5-HT2C receptor which exhibit significantly less or no agonist activity on the 5-HT2A receptor and/or the 5-HT2B receptor. Compounds of this invention are those of Formula I and pharmaceutically acceptable salts, esters and solvates (including hydrates) wherein variables are defined in the specification hereof.
  [FR] L'invention concerne des composés qui modulent des récepteurs de la famille des récepteurs 5-HT2, et plus particulièrement des composés qui modulent des récepteurs 5-HT2C. Les composés de l'invention consistent en des agonistes et des agonistes sélectifs pour le récepteur 5-HT2C. Ces composés consistent en des agonistes sélectifs pour le récepteur 5-HT2C qui présentent une activité non agoniste ou une activité agoniste sensiblement faible sur le récepteur 5-HT2A et/ou le récepteur 5-HT2B. Les composés de l'invention sont ceux présentés dans la formule (I) et des sels, des esters et des solvates (y compris des hydrates) acceptables sur le plan pharmaceutique dans lesquels des variables sont telles que définies dans la description.
• Dupin,C.; Fraisse-Jullien,R., Bulletin de la Societe Chimique de France, 1964, p. 1993 - 2000
  作者：Dupin,C.、Fraisse-Jullien,R.

  DOI：——

  日期：——