Cyclopropanecarboxylic acid ((R)-1-methyl-2-phenyl-ethyl)-amide | 132017-81-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Cyclopropanecarboxylic acid ((R)-1-methyl-2-phenyl-ethyl)-amide
• 英文别名: N-[(2R)-1-phenylpropan-2-yl]cyclopropanecarboxamide
• CAS: 132017-81-3
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: FUOFVLFEHJAGIE-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Cyclopropanecarboxylic acid ((R)-1-methyl-2-phenyl-ethyl)-amide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 Cyclopropylmethyl-((R)-1-methyl-2-phenyl-ethyl)-amine
  参考文献：
  名称：

  Identification and exploitation of the .sigma.-opiate pharmacophore

  摘要：

  Certain benzomorphan ''sigma-opiates'' such as N-allylnormetazocine (NANM) bind at sigma receptors with modest affinity and with little selectivity (i.e., they also bind at phencyclidine or PCP sites). In order to identify the primary pharmacophore of the benzomorphans, we prepared several amine-substituted derivatives of 1-phenyl-2-aminopropane. Several simple alkyl-substituted analogues were shown to bind at sigma sites with affinities comparable to that of NANM itself; among these was the N-benzyl derivative 9 (K(i) = 117 nM). Lengthening the spacer between the terminal amine and the phenyl group from one to five methylene units resulted in a significant increase in affinity (e.g. 15, K(i) = 6.3 nM). In addition, unlike the benzomorphans, these phenalkylamines do not bind at PCP sites. The results of the present study reveal that (a) the 1-phenyl-2-aminopropane nucleus of the benzomorphans is sufficient for binding at sigma sites provided that the terminal amine is not a primary amine and that (b) introduction of (phenylalkyl)amine substituents affords compounds that represent a new class of high-affinity sigma-selective agents.

  DOI：

  10.1021/jm00107a033
• 作为产物：
  描述：

  左苯丙胺 、 环丙基甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Cyclopropanecarboxylic acid ((R)-1-methyl-2-phenyl-ethyl)-amide
  参考文献：
  名称：

  Identification and exploitation of the .sigma.-opiate pharmacophore

  摘要：

  Certain benzomorphan ''sigma-opiates'' such as N-allylnormetazocine (NANM) bind at sigma receptors with modest affinity and with little selectivity (i.e., they also bind at phencyclidine or PCP sites). In order to identify the primary pharmacophore of the benzomorphans, we prepared several amine-substituted derivatives of 1-phenyl-2-aminopropane. Several simple alkyl-substituted analogues were shown to bind at sigma sites with affinities comparable to that of NANM itself; among these was the N-benzyl derivative 9 (K(i) = 117 nM). Lengthening the spacer between the terminal amine and the phenyl group from one to five methylene units resulted in a significant increase in affinity (e.g. 15, K(i) = 6.3 nM). In addition, unlike the benzomorphans, these phenalkylamines do not bind at PCP sites. The results of the present study reveal that (a) the 1-phenyl-2-aminopropane nucleus of the benzomorphans is sufficient for binding at sigma sites provided that the terminal amine is not a primary amine and that (b) introduction of (phenylalkyl)amine substituents affords compounds that represent a new class of high-affinity sigma-selective agents.

  DOI：

  10.1021/jm00107a033

文献信息

• Substituted-1-Phthalazinamines As Vr- 1 Antagonists
  申请人：Chakravarty Pasun K.

  公开号：US20090048227A1

  公开（公告）日：2009-02-19

  Substituted piperidine compounds represented by Formula I, or pharmaceutically acceptable salts thereof. Pharmaceutical compositions comprise an effective amount of the instant compounds, either alone, or in combination with one or more other therapeutically active compounds, and a pharmaceutically acceptable carrier. Methods of treating conditions associated with, or caused by, sodium channel activity, including, for example, acute pain, chronic pain, visceral pain, inflammatory pain, neuropathic pain, urinary incontinence, itchiness, allergic dermatitis, epilepsy, irritable bowel syndrome, depression, anxiety, multiple sclerosis, and bipolar disorder, comprise administering an effective amount of the present compounds, either alone, or in combination with one or more other therapeutically active compounds.

  以式I表示的取代哌啶化合物，或其药学上可接受的盐。制药组合物包括即时化合物的有效量，可以单独使用，或与一个或多个其他治疗活性化合物结合，并与药学上可接受的载体一起使用。治疗与钠通道活性相关或由其引起的病症的方法，包括例如急性疼痛、慢性疼痛、脏器疼痛、炎症性疼痛、神经病性疼痛、尿失禁、瘙痒、过敏性皮炎、癫痫、肠易激综合症、抑郁症、焦虑症、多发性硬化症和双相障碍，包括单独使用即时化合物的有效量或与一个或多个其他治疗活性化合物结合使用。
• [EN] SUBSTITUTED PIPERIDINES AS CALCIUM CHANNEL BLOCKERS<br/>[FR] PIPÉRIDINES SUBSTITUÉES EN TANT QUE BLOQUEURS DES CANAUX CALCIQUES
  申请人：MERCK & CO INC

  公开号：WO2007075524A2

  公开（公告）日：2007-07-05

  [EN] Substituted piperidine compounds represented by Formula I, or pharmaceutically acceptable salts thereof. Pharmaceutical compositions comprise an effective amount of the instant compounds, either alone, or in combination with one or more other therapeutically active compounds, and a pharmaceutically acceptable carrier. Methods of treating conditions associated with, or caused by, sodium channel activity, including, for example, acute pain, chronic pain, visceral pain, inflammatory pain, neuropathic pain, urinary incontinence, itchiness, allergic dermatitis, epilepsy, irritable bowel syndrome, depression, anxiety, multiple sclerosis, and bipolar disorder, comprise administering an effective amount of the present compounds, either alone, or in combination with one or more other therapeutically active compounds.
  [FR] Composés de la pipéridine substitués représentés par la formule I ou sels acceptables du point de vue pharmaceutique de ceux-ci. Les compositions pharmaceutiques selon l'invention comprennent une quantité efficace des présents composés, soit seuls, soit en association avec un ou plusieurs autres composés actifs du point de vue thérapeutique, et un véhicule acceptable du point de vue pharmaceutique. L'invention concerne également des procédés de traitement de maladies associées à l'activité des canaux ioniques, ou provoquées par celle-ci, dont, par exemple, la douleur aiguë, la douleur chronique, la douleur viscérale, la douleur inflammatoire, la douleur neuropathique, l'incontinence urinaire, les démangeaisons, la dermatite allergique, l'épilepsie, le syndrome du côlon irritable, la dépression, l'anxiété, la sclérose en plaques et les troubles bipolaires, qui consistent à administrer une quantité efficace des présents composés, soit seuls, soit en association avec un ou plusieurs autres composés actifs du point de vue thérapeutique.
• Identification and exploitation of the .sigma.-opiate pharmacophore
  作者：Richard A. Glennon、J. Doyle Smith、Abd M. Ismaiel、Mahmoud El-Ashmawy、George Battaglia、James B. Fischer

  DOI：10.1021/jm00107a033

  日期：1991.3

  Certain benzomorphan ''sigma-opiates'' such as N-allylnormetazocine (NANM) bind at sigma receptors with modest affinity and with little selectivity (i.e., they also bind at phencyclidine or PCP sites). In order to identify the primary pharmacophore of the benzomorphans, we prepared several amine-substituted derivatives of 1-phenyl-2-aminopropane. Several simple alkyl-substituted analogues were shown to bind at sigma sites with affinities comparable to that of NANM itself; among these was the N-benzyl derivative 9 (K(i) = 117 nM). Lengthening the spacer between the terminal amine and the phenyl group from one to five methylene units resulted in a significant increase in affinity (e.g. 15, K(i) = 6.3 nM). In addition, unlike the benzomorphans, these phenalkylamines do not bind at PCP sites. The results of the present study reveal that (a) the 1-phenyl-2-aminopropane nucleus of the benzomorphans is sufficient for binding at sigma sites provided that the terminal amine is not a primary amine and that (b) introduction of (phenylalkyl)amine substituents affords compounds that represent a new class of high-affinity sigma-selective agents.