2-(1H-吲哚-3-磺酰基)-乙胺 | 61021-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 2-(1H-吲哚-3-磺酰基)-乙胺
• 英文名称: 3-<(2-aminoethyl)thio>indole
• 英文别名: 2-indol-3-ylsulfanyl-ethylamine；3-(2-aminoethylthio)indole；2-(1H-Indol-3-ylsulfanyl)-ethylamine；2-(1H-indol-3-ylsulfanyl)ethanamine
• CAS: 61021-52-1
• 化学式: C₁₀H₁₂N₂S
• mdl: MFCD00297155
• 分子量: 192.285
• InChiKey: RZCPVVSHZUUUCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(1H-吲哚-3-磺酰基)-乙胺 、 Dimethyl-[α-(ethoxy)-ethyliden]-ammonium-Ion 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 N'-<2-(indol-3-ylthio)ethyl>-N,N-dimethylethanimidamide
  参考文献：
  名称：

  Cardiac-slowing amidines containing the 3-thioindole group. Potential antianginal agents

  摘要：

  A series of 3-thioindolamidines (and 3-indolamidines) related to mixidine (1) was studied for cardiac-slowing properties, following the discovery of activity for prototype thioindole 2. Structure-activity relationships were explored, leading to many potent antitachycardiac agents (6-9, 12, 13, 15-17, 20, 23, 24, 30, 34, 35, 45, and 47-49). Relative to 2, cardiac-slowing activity is enhanced by substitution of the indole nitrogen with small (C1-C3) saturated alkyl groups (6-9), unsaturated alkyl groups (12, 13, and 15-17), or a methoxyethyl group (20); replacement of the N-methyl group with alkyl (23) or phenyl groups (24); and extension of the ethylene bridge by two methylene units (34). Dethio (i.e., 3-indole) analogues of 2 with alkyl substitution on the indole nitrogen (47-49) have greater activity as well. Several potent compounds were also found to have minimal myocardial depression (6-9, 13, 45, and 47). Secondary pharmacological testing is reported for thioindoles 2, 6, 7, 9, and 28.

  DOI：

  10.1021/jm00356a021
• 作为产物：
  描述：

  sodium 3-indolylthiolate 在 sodium hydroxide 、 三氟化硼四氢呋喃络合物 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 反应 20.0h， 生成 2-(1H-吲哚-3-磺酰基)-乙胺
  参考文献：
  名称：

  Cardiac-slowing amidines containing the 3-thioindole group. Potential antianginal agents

  摘要：

  A series of 3-thioindolamidines (and 3-indolamidines) related to mixidine (1) was studied for cardiac-slowing properties, following the discovery of activity for prototype thioindole 2. Structure-activity relationships were explored, leading to many potent antitachycardiac agents (6-9, 12, 13, 15-17, 20, 23, 24, 30, 34, 35, 45, and 47-49). Relative to 2, cardiac-slowing activity is enhanced by substitution of the indole nitrogen with small (C1-C3) saturated alkyl groups (6-9), unsaturated alkyl groups (12, 13, and 15-17), or a methoxyethyl group (20); replacement of the N-methyl group with alkyl (23) or phenyl groups (24); and extension of the ethylene bridge by two methylene units (34). Dethio (i.e., 3-indole) analogues of 2 with alkyl substitution on the indole nitrogen (47-49) have greater activity as well. Several potent compounds were also found to have minimal myocardial depression (6-9, 13, 45, and 47). Secondary pharmacological testing is reported for thioindoles 2, 6, 7, 9, and 28.

  DOI：

  10.1021/jm00356a021

文献信息

• Methods for the treatment of ventricular dysrhythmia and prevention of
  申请人：McNeilab, Inc.

  公开号：US04584302A1

  公开（公告）日：1986-04-22

  Various indole and benzothiophene compounds having a pendant pyrrolidinylidene amino or piperidinylideneamino group are useful in the prevention of ventricular fibrillation, e.g., in humans. The invention comprises methods for the treatment of ventricular dysrhythymia or the prevention of ventricular fibrillation.

  具有附着的吡咯啉基氨基或哌啶基氨基团的各种吲哚和苯并噻吩化合物对于预防心室颤动，例如在人类中是有用的。该发明涉及用于治疗心室心律失常或预防心室颤动的方法。
• Substituted indoles
  申请人：McNeil Laboratories, Incorporated

  公开号：US04059583A1

  公开（公告）日：1977-11-22

  Substituted thioindoles and their sulfoxide and sulfone derivatives, useful as cardiac rate lowering agents and for other pharmacological properties, and precursors therefor.

  替代硫代吲哚及其亚砜和砜氧化物衍生物，可用作心脏降速剂和具有其他药理特性，以及它们的前体。
• ZELESKO, M. J.;MCCOMSEY, D. F.;HAGEMAN, W. E.;NORTEY, S. O.;BAKER, C. A.;+, J. MED. CHEM., 1983, 26, N 2, 230-237
  作者：ZELESKO, M. J.、MCCOMSEY, D. F.、HAGEMAN, W. E.、NORTEY, S. O.、BAKER, C. A.、+

  DOI：——

  日期：——
• ——
  作者：HAGEMAN W. E.、 ZELESKO M. J.

  DOI：——

  日期：——
• INDOLE DERIVATIVES, THEIR PREPARATION AND USE
  申请人：NOVO NORDISK A/S

  公开号：EP0495826A1

  公开（公告）日：1992-07-29