5-methoxy-3-cyanomethylthioindole | 61021-31-6

• 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: 5-methoxy-3-cyanomethylthioindole
• 英文别名: 2-[(5-methoxy-1H-indol-3-yl)sulfanyl]acetonitrile
• CAS: 61021-31-6
• 化学式: C₁₁H₁₀N₂OS
• 分子量: 218.279
• InChiKey: QZXRJMUWJXHLQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-3-cyanomethylthioindole 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 2-[(5-methoxy-1H-indol-3-yl)sulfanyl]ethanamine
  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：

  5-甲氧基吲哚 在 sodium hydroxide 、 碘 、 硫脲 、 potassium iodide 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 4.5h， 生成 5-methoxy-3-cyanomethylthioindole
  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
• 作为试剂：
  描述：

  5-甲氧基吲哚 、 吲哚-1-甲腈 在 I2 、 BH₃ 、 Ki 、 硫脲 作用下， 以 四氢呋喃 、 盐酸 、 甲醇 、 sodium hydroxide 、 5-methoxy-3-cyanomethylthioindole 、 乙醚 、 水 为溶剂， 生成 5-methoxy-3-aminoethylthio indole
  参考文献：
  名称：

  Methods for the treatment of ventricular dysrhythmia and prevention of

  摘要：

  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。

  公开号：

  US04584302A1

文献信息

• Chiral Phosphoric Acid‐Catalyzed Chemo‐ and Enantioselective N‐Alkylation of Indoles with Imines
  作者：Shuyuan Yang、Linger Li、Junling Zhao

  DOI：10.1002/adsc.202201077

  日期：2022.12.8

  A chemo- and enantioselective protocol for the N-alkylation of indoles with imines was developed. This process was catalyzed by a BINOL-derived phosphoric acid catalyst to give the corresponding acyclic aminals of indoles in 46–99% yields with 70–98% ee. The application of this method for the “late-stage” functionalization of a bioactive compound was performed with high efficency. The products showed

  开发了用亚胺对吲哚进行 N-烷基化的化学和对映选择性方案。该过程由 BINOL 衍生的磷酸催化剂催化，以 46-99% 的产率和 70-98% ee 得到相应的吲哚无环缩醛胺。该方法用于生物活性化合物“后期”功能化的应用效率很高。产品表现出良好的稳定性，并可以进行许多进一步的转化。
• HAGEMAN, WILLIAM E.;ZELESKO, MICHAEL J.
  作者：HAGEMAN, WILLIAM E.、ZELESKO, MICHAEL J.

  DOI：——

  日期：——
• US4584302A
  申请人：——

  公开号：US4584302A

  公开（公告）日：1986-04-22
• US4725604A
  申请人：——

  公开号：US4725604A

  公开（公告）日：1988-02-16
• 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.