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| Enantiospecific Synthesis of All Four Stereoisomers of Novel Bicyclic Arylacetamides as κ—Opioid Agonists | |
| 引用本文： | 龙亚秋 牟奇勇 仇达萍 吴瑞琴. Enantiospecific Synthesis of All Four Stereoisomers of Novel Bicyclic Arylacetamides as κ—Opioid Agonists[J]. 中国化学, 2002, 20(10): 1073-1079. DOI: 10.1002/cjoc.20020201028 |
| 作者姓名： | 龙亚秋 牟奇勇 仇达萍 吴瑞琴 |
| 作者单位： | ShanghaiInstituteofMateriaMedica,xhanghaiInstitutesforBiologicalSciences,ChineseAcademyofSciences,Shanghai200031,china |
| 基金项目： | ProjectsupportedbyChineseAcademyofSciencesandtheMinistryofPersonnelofChina . |
| 摘 要： | Conformationally constrained bicyclic derivatives of the potent and selective κ-opioid receptor agonist 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1-Phenyl-2-(1-Pyrrolidinyl)-ethyl]acetamide(3,ICI-199,441)were designed to explore the effect of the conformational restriction and stereochemistry of the pharmacophoric ethylenediamine incorporated into the pyrrolidine on the affinity and κ-selectivity.A facile enantiosipecitfic synthetic route was extablished to afford all four stereoisomers starting from readily available amino acids through mild cyclization and amide formation. |
| 关 键 词： | 对称合成 立体异构体 二芳基乙酰胺 结构 |
Enantiospecific Synthesis of All Four Stereoisomers of Novel Bicyclic Arylacetamides as k ‐Opioid Agonists |
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| LONG,Ya-Qiu MOU,Qi-Yong QIU,Da-Ping WU,Rui-Qin. Enantiospecific Synthesis of All Four Stereoisomers of Novel Bicyclic Arylacetamides as k ‐Opioid Agonists[J]. Chinese Journal of Chemistry, 2002, 20(10): 1073-1079. DOI: 10.1002/cjoc.20020201028 | |
| Authors: | LONG Ya-Qiu MOU Qi-Yong QIU Da-Ping WU Rui-Qin |
| Affiliation: | LONG,Ya-Qiu MOU,Qi-Yong QIU,Da-Ping WU,Rui-QinShanghai Institute of Materia Medica,Shanghai Institutes for Biological Sciences,Chinese Academy of Sciences,Shanghai 200031,China |
| Abstract: | Conformationally constrained bicyclic derivatives of the potent and selective K‐opioid receptor agonist 2‐(3,4‐dichlorophenyl)‐N‐methyl‐N‐[(1S)‐1‐phenyl‐2‐(1‐pyrrolidinyl)‐ethlyl] acetamide (3, ICI‐199, 441) were designed to explore the effect of the conformational restriction and stereochemistry of the pharmacophoric ethylenediamine incorporated into the pyrrolidine on the affinity and K‐selectivity. A facile enantiospecific synthetic route was established to afford all four stereoisomers starting from readily available amino adds through mild cyclization and amide formation. |
| Keywords: | opioid receptor agonist bicyclic arylacetamide conformational restriction enantiospecific synthesis |
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