3-<(4-aminobutyl)thio>indole | 61021-93-0

• 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
• 英文名称: 3-<(4-aminobutyl)thio>indole
• 英文别名: 3-[(4-aminobutyl)thio]indole；4-[(1H-Indol-3-yl)sulfanyl]butan-1-amine；4-(1H-indol-3-ylsulfanyl)butan-1-amine
• CAS: 61021-93-0
• 化学式: C₁₂H₁₆N₂S
• 分子量: 220.338
• InChiKey: WEUSGRBRZNLKBY-UHFFFAOYSA-N

物化性质

• 沸点：
  413.7±25.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲基-2-(甲硫基)-4,5-二氢-1h-咪唑氢碘化物 、 3-<(4-aminobutyl)thio>indole 以 异丙醇 为溶剂， 反应 18.0h， 生成 N-[4-(1H-indol-3-ylsulfanyl)butyl]-1-methyl-4,5-dihydroimidazol-2-amine
  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：

  (indol-3-ylthio)butyronitrile 在 三氟化硼四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 3-<(4-aminobutyl)thio>indole
  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

• 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：——
• Cardiac-slowing amidines containing the 3-thioindole group. Potential antianginal agents
  作者：Michael J. Zelesko、David F. McComsey、William E. Hageman、Samuel O. Nortey、Carol A. Baker、Bruce E. Maryanoff

  DOI：10.1021/jm00356a021

  日期：1983.2

  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.