1-(3-methoxyphenyl)-N-methyl-2-pyrrolidin-1-ylethanamine | 125190-67-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3-methoxyphenyl)-N-methyl-2-pyrrolidin-1-ylethanamine
• CAS: 125190-67-2
• 化学式: C₁₄H₂₂N₂O
• mdl: MFCD16225538
• 分子量: 234.341
• InChiKey: WORZNXJOGLSUKU-UHFFFAOYSA-N

物化性质

• 沸点：
  337.1±32.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-methoxyphenyl)-N-methyl-2-pyrrolidin-1-ylethanamine 在 三溴化硼 、 potassium carbonate 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [3-(1-{Methyl-[2-(4-trifluoromethyl-phenyl)-acetyl]-amino}-2-pyrrolidin-1-yl-ethyl)-phenoxy]-acetic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and evaluation of novel peripherally restricted κ-opioid receptor agonists

  摘要：

  A series of 3-substituted analogs (3) of the parent K agonist, 1, were prepared to limit access to the central nervous system. With the exception of compound 3j, all other compounds bound to the human K opioid receptor with high affinity (K-i = 0.31-9.5 nM) and were selective for K over mu and 6 opioid receptors. Compounds 3c, d, and 3g-i produced potent antinociceptive activity in the rat formalin assay (i.paw) and the mouse acetic acid-induced writhing assay (s.c.), with weak activity in the mouse platform sedation test. The peripheral restriction indices of 3e, d, 3g, and X were improved 2- to 7-fold compared to the parent compound 1, and these compounds were approximately 2- to 5-fold more potent than the peripheral K agonist ICI 204448. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.018
• 作为产物：
  描述：

  氨基-(3-甲氧基-苯基)-乙酸 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 1-(3-methoxyphenyl)-N-methyl-2-pyrrolidin-1-ylethanamine
  参考文献：
  名称：

  Synthesis and evaluation of novel peripherally restricted κ-opioid receptor agonists

  摘要：

  A series of 3-substituted analogs (3) of the parent K agonist, 1, were prepared to limit access to the central nervous system. With the exception of compound 3j, all other compounds bound to the human K opioid receptor with high affinity (K-i = 0.31-9.5 nM) and were selective for K over mu and 6 opioid receptors. Compounds 3c, d, and 3g-i produced potent antinociceptive activity in the rat formalin assay (i.paw) and the mouse acetic acid-induced writhing assay (s.c.), with weak activity in the mouse platform sedation test. The peripheral restriction indices of 3e, d, 3g, and X were improved 2- to 7-fold compared to the parent compound 1, and these compounds were approximately 2- to 5-fold more potent than the peripheral K agonist ICI 204448. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.018

文献信息

• Structure activity studies related to 2-(3,4-dichlorophenyl)-N-methyl-N-[2-(1-pyrrolidinyl)-1-substituted-ethyl]acetamides: a novel series of potent and selective .kappa.-opioid agonists
  作者：Jeffrey J. Barlow、Thomas P. Blackburn、Gerard F. Costello、Roger James、David J. Le Count、Brian G. Main、Robert J. Pearce、Keith Russell、John S. Shaw

  DOI：10.1021/jm00115a001

  日期：1991.11

  optimum was found to be exemplified by 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1-(1-methylethyl)-2- (1-pyrrolidinyl)ethyl]acetamide (13). Subsequently, racemic or chiral amino acids were used to introduce other alkyl and aryl substituents at C1 of the ethyl linking moiety. A series of potent compounds, bearing substituted-aryl groups at C1, were discovered, typified by 2-(3,4-dichloro-phenyl)-N-methyl-N-[(1R

  本文描述了一系列N- [2-（1-吡咯烷基）乙基]乙酰胺及其相关类似物的合成，以及它们作为阿片样物质的生物学评价，这些酰胺在邻近酰胺氮（C1）的碳上被取代。激动剂。在研究的第一部分中，研究了当C1处的取代基为1-甲基乙基时，N-酰基，N-烷基和氨基官能团的变异体，并以2-（3,4-二氯苯基）为例进行了研究。 ）-N-甲基-N-[（1S）-1-（1-甲基乙基）-2-（1-吡咯烷基）乙基]乙酰胺（13）。随后，使用外消旋或手性氨基酸在乙基连接部分的C1处引入其他烷基和芳基取代基。发现了一系列在C1上带有取代芳基的有效化合物，其典型值为2-（3,4-二氯-苯基）-N-甲基-N-[（1R，
• Kappa agonist compounds, pharmaceutical formulations and method of prevention and treatment of pruritus therewith
  申请人：——

  公开号：US20020013296A1

  公开（公告）日：2002-01-31

  Method for the prevention or treatment of pruritus with anti-pruritic compounds is provided. The compounds of formulae I, II, IIA, III, IIIA, IV and IVA have the structure: 1 wherein R 1 , R 2 , R 3 , R 4 ; and X, X 4 , X 5 , X 7 , X 9 ; Y, Z and n are as described in the specification.

  本发明提供了使用抗瘙痒化合物预防或治疗瘙痒的方法。公式I、II、IIA、III、IIIA、IV和IVA的化合物具有以下结构：其中R1、R2、R3、R4；和X、X4、X5、X7、X9；Y、Z和n如规范中所述。
• [EN] PYRAZOLE COMPOUND USED AS RHO KINASE INHIBITOR<br/>[FR] COMPOSÉ DE PYRAZOLE TENANT LIEU D'INHIBITEUR DE LA RHO-KINASE<br/>[ZH] 作为RHO激酶抑制剂的吡唑类化合物
  申请人：MEDSHINE DISCOVERY INC

  公开号：WO2019201296A1

  公开（公告）日：2019-10-24

  本发明公开了一类作为RHO激酶抑制剂的吡唑类化合物，其药物组合物以及它们在制备RHO抑制剂药物中的应用；具体公开了式(I-1)所示化合物、其药学上可接受的盐或其异构体。
• Synthesis and evaluation of novel peripherally restricted κ-opioid receptor agonists
  作者：Virendra Kumar、Deqi Guo、Joel A. Cassel、Jeffrey D. Daubert、Robert N. DeHaven、Diane L. DeHaven-Hudkins、Erin K. Gauntner、Susan L. Gottshall、Susan L. Greiner、Michael Koblish、Patrick J. Little、Erik Mansson、Alan L. Maycock

  DOI：10.1016/j.bmcl.2004.12.018

  日期：2005.2

  A series of 3-substituted analogs (3) of the parent K agonist, 1, were prepared to limit access to the central nervous system. With the exception of compound 3j, all other compounds bound to the human K opioid receptor with high affinity (K-i = 0.31-9.5 nM) and were selective for K over mu and 6 opioid receptors. Compounds 3c, d, and 3g-i produced potent antinociceptive activity in the rat formalin assay (i.paw) and the mouse acetic acid-induced writhing assay (s.c.), with weak activity in the mouse platform sedation test. The peripheral restriction indices of 3e, d, 3g, and X were improved 2- to 7-fold compared to the parent compound 1, and these compounds were approximately 2- to 5-fold more potent than the peripheral K agonist ICI 204448. (C) 2004 Elsevier Ltd. All rights reserved.