2-(3,4-dichlorophenyl)-N-methyl-N-[(1R,2R)-2-pyrrolidin-1-ylcyclohexyl]acetamide | 67198-13-4

• 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: 2-(3,4-dichlorophenyl)-N-methyl-N-[(1R,2R)-2-pyrrolidin-1-ylcyclohexyl]acetamide
• 英文别名: (+)-U 50488；trans-(+/-)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)-cyclohexyl]-benzeneacetamide；(-)-(trans)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide；trans-(+/-)-3,4-dichloro-N-methyl-N-(2-[1-pirrolidinyl]cyclohexyl)benzeneacetamide；trans-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-benzeneacetamide；(+)-(trans)-(1R,2R)-U50,488
• CAS: 67198-13-4
• 化学式: C₁₉H₂₆Cl₂N₂O
• 分子量: 369.334
• InChiKey: VQLPLYSROCPWFF-QZTJIDSGSA-N

物化性质

• 熔点：
  204-208℃

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3,4-dichlorophenyl)-N-methyl-N-[(1R,2R)-2-pyrrolidin-1-ylcyclohexyl]acetamide 在 aluminium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 (1R,2R)-(-)-trans-N-<2-(3,4-dichlorophenyl)ethyl>-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine
  参考文献：
  名称：

  Synthesis and receptor binding of enantiomeric N-substituted cis-N-[2-(3,4-dichlorophenyl)ethyl]-2-(1-pyrrolidinyl)cyclohexylamines as high-affinity .sigma. receptor ligands

  摘要：

  N-Alkyl-substituted derivatives of (+)- and (-)-cis-N-[2-(3,4-dichlorophenyl)ethyl]-2-(1-pyrrolidinyl)cyclohexylamine have been synthesized in nine steps in a stereospecific manner starting from cyclohexene oxide. The key step in the reaction sequence involved catalytic hydrogenation of oxime 8 in the presence of PtO2 and AcOH to give the cis diamine (+/-)-7. Most of the compounds in this series exhibited very high affinity at sigma-receptors when tested against [H-3]-(+)-3-PPP, and in general it was observed that the 1R,2S enantiomers bound more potently to sigma-receptors than their corresponding 1S,2R enantiomers. The most potent sigma-ligand found in this class was the unsubstituted derivative (1R,2S)-(-)-4, which exhibited an affinity constant of 0.49 nM. This compound was also found to be very selective for sigma-receptors. It exhibited little or no affinity for kappa-opioid, PCP, and dopamine-D2 receptors. It was also demonstrated that the cis configuration as opposed to the trans configuration of (+)- and (-)-5 was necessary for a higher sigma-receptor affinity.

  DOI：

  10.1021/jm00114a015
• 作为产物：
  描述：

  3,4-二氯苯乙酸 生成 2-(3,4-dichlorophenyl)-N-methyl-N-[(1R,2R)-2-pyrrolidin-1-ylcyclohexyl]acetamide
  参考文献：
  名称：

  MCCALL, J. M.;LAHTI, R. A.

  摘要：

  DOI：

文献信息

• [EN] NOVEL OPIATE COMPOUNDS, METHODS OF MAKING AND METHODS OF USE<br/>[FR] NOUVEAUX COMPOSES OPIACES ET LEURS PROCEDES DE PREPARATION ET D'UTILISATION
  申请人：RESEARCH TRIANGLE INSTITUTE

  公开号：WO1999045925A1

  公开（公告）日：1999-09-16

  (EN) The present invention relates to a class of nitrogen-containing heterocyclic compounds which bind to opioid receptors. The inventive compounds can be used to treat a variety of disease states which involve the opioid receptors.(FR) L'invention porte sur une classe de composés hétérocycliques azotés se fixant au récepteurs opioïdes et pouvant servir à traiter différentes maladies impliquant lesdits récepteurs.

  (中) 本发明涉及一类与阿片受体结合的含氮杂环化合物。这些创新化合物可用于治疗涉及阿片受体的各种疾病状态。(法) 本发明涉及一类与阿片受体结合的含氮杂环化合物，可用于治疗涉及阿片受体的各种疾病状态。
• [EN] AMINOCYCLOHEXYLAMIDES FOR ANTIARRHYTHMIC AND ANAESTHETIC USES
  申请人：THE UNIVERSITY OF BRITISH COLUMBIA

  公开号：WO1993019056A1

  公开（公告）日：1993-09-30

  (EN) This invention provides aminocyclohexylamides for use within methods of blocking sodium channels in cardiac or neuronal tissue and for use in the manufacture of medicaments to block sodium channels in cardiac or neuronal tissue. This invention also provides commercial kits comprising a pharmaceutical composition containing aminocyclohexylamides and, instructions for the use of the pharmaceutical composition for arrhythmia or for the inducement of local anaesthesia.(FR) L'invention se rapporte à des aminocyclohexylamides devant être utilisés avec des procédés de blocage de canaux de sodium dans des tissus cardiaques ou neuronaux, et devant être utilisés pour la production de médicaments bloquant les canaux de sodium dans des tissus cardiaques ou neuronaux. L'invention se rapporte également à des kits pouvant être utilisés dans le commerce, et comprenant une composition pharmaceutique contenant ces aminocyclohexylamides ainsi que des instructions permettant d'utiliser la composition pharmaceutique pour traiter l'arythmie ou pour produire une anesthésie locale.

  该发明提供了氨基环己基酰胺，用于阻断心脏或神经组织中的钠通道的方法，并用于制造阻断心脏或神经组织中的钠通道的药物。该发明还提供商业套件，包括含有氨基环己基酰胺的药物组合物和用于心律失常或诱导局部麻醉的使用说明。
• Aralkyl diaxabicycloalkane derivatives for CNS disorders
  申请人：——

  公开号：US20020045624A1

  公开（公告）日：2002-04-18

  Certain aralkl diazabicycloalkyl compounds are described for treatment of CNS disorders such as cerebral ischemia, psychoses and convulsions. Compounds of particular interest are of the formula: 1 wherein each of R 1 , R 4 , R 5 , R 6 and R 7 is independently selected from hydrido, lower alkyl, benzyl, and haloloweralkyl; wherein each of R 2 , R 3 and R 8 through R 11 is independently selected from hydrido, hydroxy, loweralkyl, benzyl, phenols, benzyloxy and haloloweralkyl; wherein n is an integer of from four to six; wherein m is an integer of from two to four; wherein A is selected from phenyl, naphthyl, benzothienyl, benzofuranyl and thienyl; wherein any of the foregoing A groups can be further substituted with one or more substituents independently selected from hydrido, hydroxy, loweralkyl, loweralkoxy, halo, haloloweralkyl, amino, monoloweralkylamino and diloweralkylamino; or a pharmaceutically acceptable salt thereof.

  本文描述了某些阿拉克尔二氮杂双环烷化合物，用于治疗中枢神经系统疾病，如脑缺血、精神病和抽搐。特别感兴趣的化合物的公式为：1其中R1、R4、R5、R6和R7中的每一个独立选择自氢、低级烷基、苯甲基和卤代低级烷基；其中R2、R3和R8至R11中的每一个独立选择自氢、羟基、低级烷基、苯甲基、酚、苯氧基和卤代低级烷基；其中n为4至6的整数；其中m为2至4的整数；其中A选择自苯基、萘基、苯并噻吩基、苯并呋喃基和噻吩基；其中任何上述A基团都可以进一步用一个或多个取代基独立选择自氢、羟基、低级烷基、低级烷氧基、卤素、卤代低级烷基、氨基、单低级烷基氨基和双低级烷基氨基取代；或其药学上可接受的盐。
• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• 2-Aminocycloalkenyl carboxamides and their tritiated 2-aminocycloalkyl carboxamide derivatives
  申请人：THE UPJOHN COMPANY

  公开号：EP0129991A1

  公开（公告）日：1985-01-02

  2-Aminocycloalkenyl benzamides and phenylacet- amides, e.g. 3,4-dichloro-N-methyl-N-[6-(1- pyrrolidinyl) -3-cyclohexenyl]benzeneacetamide, and their salts, are of potential value as analgesics. The corresponding tritiated, saturated compounds are also new, and of utility as radio-labelled compounds for pharmacological and metabolic studies in animals.

  2-Aminocycloalkenyl benzamides and phenylacet- amides, e.g. 3,4-dichloro-N-methyl-N-[6-(1- pyrrolidinyl) -3-cyclohexenyl]benzeneacetamide, and their salts, are of potential value as analgesics.相应的三价饱和化合物也是一种新化合物，可作为放射性标记化合物用于动物药理和代谢研究。