2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid | 96696-20-7

• 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: 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid
• 英文别名: 2-methyl-5-sulfamoyl-2,3-dihydro-1-benzofuran-7-carboxylic acid
• CAS: 96696-20-7
• 化学式: C₁₀H₁₁NO₅S
• 分子量: 257.267
• InChiKey: NPGSZKOIGNXFMG-UHFFFAOYSA-N

物化性质

• 沸点：
  519.6±60.0 °C(Predicted)
• 密度：
  1.504±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  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
  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-甲基-2,3-二氢苯并呋喃-7-羧酸 在 氯磺酸 、 ammonium hydroxide 作用下， 生成 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid
  参考文献：
  名称：

  潜在的抗精神病药，N-[（（2-吡咯烷基）甲基] -2,3-二氢苯并呋喃-7-羧酰胺衍生物。

  摘要：

  合成了一系列具有稳定分子内氢键的2,3-二氢苯并呋喃-7-羧酰胺，并在药理学模型中评估了其抗精神病活性。其中，N-[（（1-丁基-2-吡咯烷基）甲基] -2-甲基-5-氨磺酰基-2，3-二氢苯并呋喃-7-羧酰胺（15）显示出与sulpiride（1 ）和比1更高的亲脂性。化合物15对阿扑吗啡诱导的小鼠过度活动（ED50 = 30 mg / kg，口服）的拮抗活性比对甲基苯丙胺致死力的增强作用强11倍，而对15如阿斯吗啡对大鼠的刻板印象抑制作用弱（ED50大于500 mg / kg，口服）为1。另一方面，N-[（1-乙基-2-吡咯烷基）甲基] -2-甲基- 5-甲硫基-2，3-二氢苯并呋喃-7-羧酰胺（30）在对阿扑吗啡诱导的小鼠过度活动的拮抗活性方面表现出与氟哌啶醇相当的经典抗精神病药（ED50 = 0.65 mg / kg，口服）。还讨论了结构-活性关系。

  DOI：

  10.1248/cpb.38.1609

文献信息

• Benzofuran- and benzopyran-carboxamide derivatives
  申请人：Yoshitomi Pharmaceutical Industries Ltd.

  公开号：US04617314A1

  公开（公告）日：1986-10-14

  Benzofuran- and benzopyran-carboxamide derivatives of the formula: ##STR1## wherein l is 1 or 2; X is hydrogen atom, amino group or halogen atom; Y is --S(O).sub.m --R.sup.3 wherein R.sup.3 is lower alkyl group and m is 0, 1 or 2, or ##STR2## wherein R.sup.4 and R.sup.5 are the same or different and are each hydrogen atom or lower alkyl group; R.sup.1 is hydrogen atom, lower alkyl group, arylthiomethyl group, halogenomethyl group or ##STR3## wherein R.sup.6 and R.sup.7 are the same or different and are each hydrogen atom or lower alkyl group or R.sup.6 and R.sup.7 together with the adjacent nitrogen atom form a hetrocycle; R.sup.2 is hydrogen atom or lower alkyl group; and Z is ##STR4## wherein p is 2 or 3, R.sup.8 and R.sup.9 are the same or different and are each lower alkyl group or R.sup.8 and R.sup.9 together with the adjacent nitrogen atom form a heterocycle, or ##STR5## wherein q is 0 or 1, n is 1 or 2, R.sup.10 is lower alkyl group, lower alkenyl group, lower alkinyl group, aralkyl group or cycloalkyl group and R.sup.11 is hydrogen atom or lower alkyl group, their physiologically acceptable salts or their optical isomers, and a method of preparing same. These compounds are useful as psychotropic and antipsychotic agents.

  苯并呋喃和苯并吡喃-羧酰胺衍生物的化学式如下：##STR1## 其中l为1或2；X为氢原子、氨基或卤原子；Y为--S(O).sub.m --R.sup.3，其中R.sup.3为低碳基且m为0、1或2，或##STR2## 其中R.sup.4和R.sup.5相同或不同，均为氢原子或低碳基；R.sup.1为氢原子、低碳基、芳基硫甲基、卤甲基或##STR3## 其中R.sup.6和R.sup.7相同或不同，均为氢原子或低碳基，或R.sup.6和R.sup.7与相邻的氮原子一起形成杂环；R.sup.2为氢原子或低碳基；Z为##STR4## 其中p为2或3，R.sup.8和R.sup.9相同或不同，均为低碳基或R.sup.8和R.sup.9与相邻的氮原子一起形成杂环，或##STR5## 其中q为0或1，n为1或2，R.sup.10为低碳基、低烯基、低炔基、芳基烷基或环烷基，R.sup.11为氢原子或低碳基，它们的生理上可接受的盐或其光学异构体，以及其制备方法。这些化合物可用作精神药和抗精神病药。
• TAHARA, TETSUYA;HAYANO, KIYOHARU;MURAKAMI, SHU;FUKUDA, TAKEMI;SETOGUCHI, +, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1609-1615
  作者：TAHARA, TETSUYA、HAYANO, KIYOHARU、MURAKAMI, SHU、FUKUDA, TAKEMI、SETOGUCHI, +

  DOI：——

  日期：——
• 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：——
• ——
  作者：TAHARA TETSUYA、 HAYANA KIYOHARU、 SETOGUCHI MICHIHIDE、 FUKUDA TAKEMI

  DOI：——

  日期：——
• US4617314A
  申请人：——

  公开号：US4617314A

  公开（公告）日：1986-10-14