5-(氨基磺酰基)-N-(2,5-二氯戊基)-2-甲氧基苯甲酰胺 | 67833-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(氨基磺酰基)-N-(2,5-二氯戊基)-2-甲氧基苯甲酰胺
• 英文名称: N-(2,5-dichloropentyl)-2-methoxy-5-sulfamoylbenzamide
• 英文别名: 5-(aminosulfonyl)-N-(2,5-dichloropentyl)-2-methoxybenzamide；N-(2,5-dichloropentyl)-2-methoxy-5-sulphamoyl-benzamide；5-(Aminosulphonyl)-N-(2,5-dichloropentyl)-2-methoxybenzamide
• CAS: 67833-50-5
• 化学式: C₁₃H₁₈Cl₂N₂O₄S
• 分子量: 369.269
• InChiKey: QTWZISKLRIHFNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(氨基磺酰基)-N-(2,5-二氯戊基)-2-甲氧基苯甲酰胺 在 sodium sulfide 作用下， 以 甲醇 为溶剂， 反应 141.0h， 生成 2-<(2-methoxy-5-sulfamoylbenzamido)methyl>-1-ethyltetrahydrothiophenium iodide
  参考文献：
  名称：

  Synthesis and D2 dopaminergic activity of pyrrolidinium, tetrahydrothiophenium, and tetrahydrothiophene analogs of sulpiride

  摘要：

  All of the existing dopamine receptor models recognize the amine nitrogen of agonist and antagonist drugs as playing a crucial role in receptor interactions. However, there has been some controversy as to which molecular form of the amine, charged or uncharged, is most important in these interactions. We have synthesized and examined the biological activity of permanently charged and permanently uncharged analogues of the dopaminergic antagonist, sulpiride. Sulpiride and the permanently charged pyrrolidinium (6,7) and tetrahydrothiophenium (9) analogues were able to antagonize the inhibitory effect of apomorphine on the K+-induced release of [3H]acetylcholine from striatal slices. In contrast, the permanently uncharged tetrahydrothiophene analogue 8 was inactive at concentrations up to 100 microM. Additionally, both sulpiride and the tetrahydrothiophenium analogue were able to displace [3H]spiperone from D2 binding sites, while the tetrahydrothiophene analogue was unable to produce any significant displacement. These results are consistent with our previous observations on permanently charged chlorpromazine analogues and provide further evidence that dopaminergic antagonists bind in their charged molecular forms to anionic sites on the D2 receptor.

  DOI：

  10.1021/jm00124a024
• 作为产物：
  描述：

  邻甲氧基苯甲酸 在 chlorosulphuric acid 、 氨 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.17h， 生成 5-(氨基磺酰基)-N-(2,5-二氯戊基)-2-甲氧基苯甲酰胺
  参考文献：
  名称：

  Synthesis and D2 dopaminergic activity of pyrrolidinium, tetrahydrothiophenium, and tetrahydrothiophene analogs of sulpiride

  摘要：

  All of the existing dopamine receptor models recognize the amine nitrogen of agonist and antagonist drugs as playing a crucial role in receptor interactions. However, there has been some controversy as to which molecular form of the amine, charged or uncharged, is most important in these interactions. We have synthesized and examined the biological activity of permanently charged and permanently uncharged analogues of the dopaminergic antagonist, sulpiride. Sulpiride and the permanently charged pyrrolidinium (6,7) and tetrahydrothiophenium (9) analogues were able to antagonize the inhibitory effect of apomorphine on the K+-induced release of [3H]acetylcholine from striatal slices. In contrast, the permanently uncharged tetrahydrothiophene analogue 8 was inactive at concentrations up to 100 microM. Additionally, both sulpiride and the tetrahydrothiophenium analogue were able to displace [3H]spiperone from D2 binding sites, while the tetrahydrothiophene analogue was unable to produce any significant displacement. These results are consistent with our previous observations on permanently charged chlorpromazine analogues and provide further evidence that dopaminergic antagonists bind in their charged molecular forms to anionic sites on the D2 receptor.

  DOI：

  10.1021/jm00124a024

文献信息

• New substituted heterocyclic benzamides, methods of preparing them and
  申请人：Societe d'Etudes Scientifiques et Industrielle de l'Ile de France

  公开号：US04673686A1

  公开（公告）日：1987-06-16

  There are provided new substituted heterocyclic benzamides and derivatives hereof which provide modifications on the central nervous system.

  这里提供了新的替代杂环苯甲酰胺及其衍生物，这些化合物对中枢神经系统产生改变。
• HARROLD, M. W.;WALLACE, R. A.;FARROOQUI, T.;WALLACE, L. J.;URETSKY, N.;MI+, J. MED. CHEM., 32,(1989) N, C. 874-880
  作者：HARROLD, M. W.、WALLACE, R. A.、FARROOQUI, T.、WALLACE, L. J.、URETSKY, N.、MI+

  DOI：——

  日期：——
• US4673686A
  申请人：——

  公开号：US4673686A

  公开（公告）日：1987-06-16
• Synthesis and D2 dopaminergic activity of pyrrolidinium, tetrahydrothiophenium, and tetrahydrothiophene analogs of sulpiride
  作者：Marc W. Harrold、Raye Ann Wallace、Tahira Farooqui、Lane J. Wallace、Norman Uretsky、Duane D. Miller

  DOI：10.1021/jm00124a024

  日期：1989.4

  All of the existing dopamine receptor models recognize the amine nitrogen of agonist and antagonist drugs as playing a crucial role in receptor interactions. However, there has been some controversy as to which molecular form of the amine, charged or uncharged, is most important in these interactions. We have synthesized and examined the biological activity of permanently charged and permanently uncharged analogues of the dopaminergic antagonist, sulpiride. Sulpiride and the permanently charged pyrrolidinium (6,7) and tetrahydrothiophenium (9) analogues were able to antagonize the inhibitory effect of apomorphine on the K+-induced release of [3H]acetylcholine from striatal slices. In contrast, the permanently uncharged tetrahydrothiophene analogue 8 was inactive at concentrations up to 100 microM. Additionally, both sulpiride and the tetrahydrothiophenium analogue were able to displace [3H]spiperone from D2 binding sites, while the tetrahydrothiophene analogue was unable to produce any significant displacement. These results are consistent with our previous observations on permanently charged chlorpromazine analogues and provide further evidence that dopaminergic antagonists bind in their charged molecular forms to anionic sites on the D2 receptor.