4-amino-1,3,4,5-tetrahydro-1-(p-tolylsulphonyl)benzindol-5-one hydrochloride | 40380-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-amino-1,3,4,5-tetrahydro-1-(p-tolylsulphonyl)benzindol-5-one hydrochloride
• 英文别名: 4-amino-3,4-dihydro-1-(p-tolylsulfonyl)benzindol-5(1H)-one hydrochloride；(+/-)-4-amino-3,4-dihydro-1-[(methylphenyl)sulfonyl]benz[cd]indol-5(1H)-one hydrochloride；4-Amino-1-(4-methylphenyl)sulfonyl-3,4-dihydrobenzo[cd]indol-5-one;hydrochloride
• CAS: 40380-71-0
• 化学式: C₁₈H₁₆N₂O₃S*ClH
• 分子量: 376.864
• InChiKey: OEDDVBUJRQCNGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-1,3,4,5-tetrahydro-1-(p-tolylsulphonyl)benzindol-5-one hydrochloride 在 palladium on activated charcoal sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氢气 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 6-乙基-9-氧杂麦角灵
  参考文献：
  名称：

  （7R）-7H-吲哚并[3,4-gh] [1,4]苯并恶嗪的合成，一种新型的具有多巴胺激动剂活性的D-杂麦角灵。

  摘要：

  介绍了9-氧杂麦角环系统几个成员的合成。制备了4,6,6a，8,9,10a-六氢-7-乙基-7H-吲哚并[3,4-gh] [1,4]苯并恶嗪的C / D顺式和C / D反式异构体，并将C / D反式异构体拆分为其旋光异构体。对[3H]阿扑吗啡结合位点具有最高亲和力的对映体（-）-反式-6-乙基-9-氧杂麦角碱[（-）-6b]具有与天然麦角灵相同的绝对构型，即，6aR，10aR。体内和体外药理学评估表明，这些9-氧杂麦角碱具有有效的多巴胺激动剂特性。

  DOI：

  10.1021/jm00357a010

文献信息

• Amino substituted tetrahydrobenzindoles, a process for preparing and a pharmaceutical composition containing the same
  申请人：Merck & Co., Inc.

  公开号：EP0029581A2

  公开（公告）日：1981-06-03

  Aminosubstituted tetrahydrobenzindoles having the formula and pharmaceutically acceptable salts thereof wherein R is H, alkyl or aryl, R1 is H or halogen, R2 is H, alkyl or aralkyl and R3 is H, OH, halogen, C1-C3 alkyl or alkoxy and a process for preparing them are disclosed. Those compounds have antihypertensive activity.

  具有以下式子的氨基取代的四氢苯吲哚 及其药学上可接受的盐类，其中 R 是 H、烷基或芳基、 R1 是 H 或卤素 R2 是 H、烷基或芳烷基，以及 R3 是 H、OH、卤素、C1-C3 烷基或烷氧基 公开了这些化合物及其制备方法。这些化合物具有抗高血压活性。
• <i>N</i>-Arylsulfonylindole Derivatives as Serotonin 5-HT₆ Receptor Ligands
  作者：Michael G. N. Russell、Robert J. Baker、Laura Barden、Margaret S. Beer、Linda Bristow、Howard B. Broughton、Michael Knowles、George McAllister、Smita Patel、José L. Castro

  DOI：10.1021/jm010943m

  日期：2001.11.1

  A series of N-1-arylsulfonyltryptamines were found to be potent ligands of the human serotonin 5-HT6 receptor with the 5-methoxy-1-benzenesulfonyl analogue (19) having the highest affinity. Additionally, it was discovered that a group such as 3-(3-methoxybenzyl)-1,2,4-oxadiazol-5-yI in the 2-position of the indole ring (43) can replace the arylsulfonyl substituent in the 1-position with no loss of affinity. This suggested that the binding conformation of the aminoethyl side chain at this receptor was toward the 4-position of the indole ring and was supported by the fact that the 4-(aminoethyl)indoles (45) also displayed high affinity, as did the conformationally rigid 1,3,4,5-tetrahydrobenz[c,d]indole (49). Molecular modeling showed that 19, 43, and 45 all had low-energy conformers that overlaid well onto 49. Both 19 and 49 had good selectivity over other serotonin receptors tested, with 49 also showing excellent selectivity over all dopamine receptors. In a functional adenylate cyclase stimulation assay, 19 and 49 had no agonist activity, whereas 45 behaved as a partial agonist. Finally, it was shown that 19 had good activity in the 5-HT2A centrally mediated mescaline-induced head twitch assay, which implies that it is brain-penetrant.
• Bowman, Ralph E., Journal of the Chemical Society. Perkin transactions I, 1982, # 8, p. 1897 - 1904
  作者：Bowman, Ralph E.

  DOI：——

  日期：——
• BALDWIN, J. J.;JONES, J. H.;LUNDELL, G. F.
  作者：BALDWIN, J. J.、JONES, J. H.、LUNDELL, G. F.

  DOI：——

  日期：——
• US4282240A
  申请人：——

  公开号：US4282240A

  公开（公告）日：1981-08-04