1-Methyl-1H-indole-2-carboxylic acid adamantan-1-ylamide

• 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: 1-Methyl-1H-indole-2-carboxylic acid adamantan-1-ylamide
• 英文别名: N-(1-adamantyl)-1-methylindole-2-carboxamide
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: LQLVGOWOCVCVEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Methyl-1H-indole-2-carboxylic acid adamantan-1-ylamide 、 对苯醌 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver(I) acetate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以94%的产率得到N-(adamantan-1-yl)-3-(3,6-dioxocyclohexa-1,4-dien-1-yl)-1-methyl-1H-indole-2-carboxamide
  参考文献：
  名称：

  Rh(iii)-catalyzed direct C–H/C–H cross-coupling of quinones with arenes assisted by a directing group: identification of carbazole quinones as GSKβ inhibitors

  摘要：

  铑催化的直接交叉偶联反应可将各种(杂)芳烃与醌进行偶联。该方案适用于广泛的底物和多种取向基团。

  DOI：

  10.1039/c4ob02624a
• 作为产物：
  描述：

  1-甲基吲哚-2-甲酸 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-Methyl-1H-indole-2-carboxylic acid adamantan-1-ylamide
  参考文献：
  名称：

  Indoles and pyridazino[4,5-b]indoles as nonnucleoside analog inhibitors of HIV-1 reverse transcriptase

  摘要：

  The synthesis and the study of the activity of new indol-2-carboxamides and pyridazino[4,5-b]indoles as inhibitors of HIV-1 reverse transcriptase (RT) are presented. The activity of the compounds synthesized as inhibitors of different types of HIV-1 RT (wild type enzyme and mutant forms P236L, Y181C and P236L/Y181C) was evaluated. The activity of the most active compounds was investigated in the syncytia reduction in vitro assay, in HIV-1(IIIB)-infected HT4lacZ-1 cells. Their potential cytotoxicity was determined in parallel. Two lead compounds, N-[1-[2-(3-isopropylamino)pyridyl]piperazin]-5,6-methylenedioxy indol-2-carboxamide 7q and N-[1-[2-(3-ethylamino)pyridyl]piperazin] 7s have been identified.

  DOI：

  10.1016/0223-5234(96)88316-4

文献信息

• Rh(<scp>iii</scp>)-catalyzed direct C–H/C–H cross-coupling of quinones with arenes assisted by a directing group: identification of carbazole quinones as GSKβ inhibitors
  作者：Youngtaek Moon、Yujeong Jeong、Daehyuk Kook、Sungwoo Hong

  DOI：10.1039/c4ob02624a

  日期：——

  Rh-catalyzed direct cross-coupling of various (hetero)arenes with quinones is developed. This protocol is effective for a broad range of substrates and a wide range of directing groups.

  铑催化的直接交叉偶联反应可将各种(杂)芳烃与醌进行偶联。该方案适用于广泛的底物和多种取向基团。
• Indoles and pyridazino[4,5-b]indoles as nonnucleoside analog inhibitors of HIV-1 reverse transcriptase
  作者：M Font、A Monge、A Cuartero、A Elorriaga、J.J. Martínez-Irujo、E Alberdi、E Santiago、I Prieto、J.J. Lasarte、P Sarobe、F Borrás

  DOI：10.1016/0223-5234(96)88316-4

  日期：1995.1

  The synthesis and the study of the activity of new indol-2-carboxamides and pyridazino[4,5-b]indoles as inhibitors of HIV-1 reverse transcriptase (RT) are presented. The activity of the compounds synthesized as inhibitors of different types of HIV-1 RT (wild type enzyme and mutant forms P236L, Y181C and P236L/Y181C) was evaluated. The activity of the most active compounds was investigated in the syncytia reduction in vitro assay, in HIV-1(IIIB)-infected HT4lacZ-1 cells. Their potential cytotoxicity was determined in parallel. Two lead compounds, N-[1-[2-(3-isopropylamino)pyridyl]piperazin]-5,6-methylenedioxy indol-2-carboxamide 7q and N-[1-[2-(3-ethylamino)pyridyl]piperazin] 7s have been identified.