(S)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid | 130981-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: (S)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid
• 英文别名: (2S)-2-methyl-5-sulfamoyl-2,3-dihydro-1-benzofuran-7-carboxylic acid
• CAS: 130981-36-1
• 化学式: C₁₀H₁₁NO₅S
• 分子量: 257.267
• InChiKey: NPGSZKOIGNXFMG-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  106.69
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.5h， 生成 (2R,2S)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide
  参考文献：
  名称：

  Antidopaminergic effects of the stereoisomers of N-[(1-alkyl-2-pyrrolidinyl)methyl]-5-sulfamoylbenzamides and -2,3-dihydro-benzofuran-7-carboxamides

  摘要：

  The stereoisomers of some N-[(1-alkyl-2-pyrrolidinyl)methyl]5-sulfamoylbenzamides (3-8) and -2,3-dihydrobenzofuran-7-carboxamides (9-18) were prepared to compare their dopamine D2 receptor binding affinities (in vitro) and inhibitory effects on apomorphine-induced hyperactivity (in vivo). In the 1-ethyl substituted compounds of the two series, the stereoisomers with S absolute configuration at the 2-position of the pyrrolidine moiety (S enantiomer 3 and 2S diastereomers 9 and 10) were more potent in both of the above activities than those with R absolute configuration (R enantiomer 4 and 2R diastereomers 11 and 12, respectively), whereas the R enantiomer (8) was more potent than the S enantiomer (7) in the 1-n-hexyl-substituted-benzamides and the 2R diastereomers (15, 16, and 18) were more potent than the 2S diastereomers (13, 14, and 17) in the 1-n-butyl- and 1-n-hexyl-2,3-dihydrobenzofuran-7-carboxamies. It was found that the stereospecificity of the compound activities altered from the S configuration to the R configuration as the 1-alkyl side chain became longer in the two series. How these stereoisomers meet the configurational requirements to interact with the dopamine D2 receptors is also discussed.

  DOI：

  10.1021/jm00105a041
• 作为产物：
  描述：

  2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid 生成 (S)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid
  参考文献：
  名称：

  Antidopaminergic effects of the stereoisomers of N-[(1-alkyl-2-pyrrolidinyl)methyl]-5-sulfamoylbenzamides and -2,3-dihydro-benzofuran-7-carboxamides

  摘要：

  The stereoisomers of some N-[(1-alkyl-2-pyrrolidinyl)methyl]5-sulfamoylbenzamides (3-8) and -2,3-dihydrobenzofuran-7-carboxamides (9-18) were prepared to compare their dopamine D2 receptor binding affinities (in vitro) and inhibitory effects on apomorphine-induced hyperactivity (in vivo). In the 1-ethyl substituted compounds of the two series, the stereoisomers with S absolute configuration at the 2-position of the pyrrolidine moiety (S enantiomer 3 and 2S diastereomers 9 and 10) were more potent in both of the above activities than those with R absolute configuration (R enantiomer 4 and 2R diastereomers 11 and 12, respectively), whereas the R enantiomer (8) was more potent than the S enantiomer (7) in the 1-n-hexyl-substituted-benzamides and the 2R diastereomers (15, 16, and 18) were more potent than the 2S diastereomers (13, 14, and 17) in the 1-n-butyl- and 1-n-hexyl-2,3-dihydrobenzofuran-7-carboxamies. It was found that the stereospecificity of the compound activities altered from the S configuration to the R configuration as the 1-alkyl side chain became longer in the two series. How these stereoisomers meet the configurational requirements to interact with the dopamine D2 receptors is also discussed.

  DOI：

  10.1021/jm00105a041

文献信息

• MURAKAMI, SHU;MARUBAYASHI, NOBUHIRO;FUKUDA, TAKEMI;TAKEHARA, SHUZO;TAHARA+, J. MED. CHEM., 34,(1991) N, C. 261-267
  作者：MURAKAMI, SHU、MARUBAYASHI, NOBUHIRO、FUKUDA, TAKEMI、TAKEHARA, SHUZO、TAHARA+

  DOI：——

  日期：——