11H-indolo[3,2-c]isoquinoline | 239-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 11H-indolo[3,2-c]isoquinoline
• CAS: 239-22-5
• 化学式: C₁₅H₁₀N₂
• 分子量: 218.258
• InChiKey: ZAEKWPWLIFDFEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11H-indolo[3,2-c]isoquinoline 、 碘甲烷 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 6-methyl-11H-indolo[3,2-c]isoquinoline hydroiodide
  参考文献：
  名称：

  6-甲基-6 H-吲哚并[3,2- c ]异喹啉和6-甲基-6 H-吲哚并[2,3- c ]异喹啉的合成：隐谷碱系列的两种新的非天然异喹啉异构体

  摘要：

  11 H-吲哚并[3,2- c ]异喹啉通过选择性的布赫瓦尔德-哈特维格反应，然后经钯催化的涉及C（sp 2）的分子内直接芳基化反应，从4-溴异喹啉和2-溴苯胺开始分两步合成。H激活。7 H-吲哚并[2,3- c ]异喹啉的合成是通过Suzuki反应与从4-溴异喹啉和{2-[（2,2-二甲基丙酰基）氨基]苯基开始的分子内氮插入反应的结合而实现的}硼酸。四环骨架的选择性甲基化产生标题化合物6-甲基-6 H-吲哚并[3,2- c ]异喹啉和6-甲基-6 H-吲哚并[2,3-c ]异喹啉，以前在文献中从未描述过。

  DOI：

  10.1016/j.tet.2008.08.116
• 作为产物：
  描述：

  3-amino-2-phenylindole 在 硫酸 作用下， 以 乙醇 为溶剂， 生成 11H-indolo[3,2-c]isoquinoline
  参考文献：
  名称：

  Hiremath, S. P.; Biradar, J. S.; Purohit, M. G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 3, p. 249 - 251

  摘要：

  DOI：

文献信息

• Two Annulated Azaheterocyclic Cores Readily Available from a Single Tetrahydroisoquinolonic Castagnoli–Cushman Precursor
  作者：Elizaveta Karchuganova、Olga Bakulina、Dmitry Dar’in、Mikhail Krasavin

  DOI：10.3390/molecules25092049

  日期：——

  A novel approach to indolo[3,2-c]isoquinoline and dibenzo[c,h][1,6]naphthyridine tetracyclic systems was discovered based on switchable reduction of 2-methoxy-3-(2-nitrophenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid prepared via Castagnoli–Cushman reaction. Reduction with ammonium formate resulted in the expected selective transformation of the nitro group (thus providing access to

  基于 2-甲氧基-3-(2-硝基苯基)-1-氧代的可切换还原，发现了一种用于吲哚[3,2-c]异喹啉和二苯并[c,h][1,6]萘啶四环系统的新方法-1,2,3,4-四氢异喹啉-4-羧酸通过 Castagnoli-Cushman 反应制备。用甲酸铵还原导致硝基的预期选择性转化（从而通过环化和脱氢获得取代的二苯并[c,h][1,6]萘啶）。然而，尝试用硫化钠还原引发了以前未知的反应级联反应，包括双重还原、环化和脱羧，导致在一个合成步骤中形成吲哚 [3,2-c] 异喹啉多杂环。
• Molecular yardsticks. Rigid probes to define the spatial dimensions of the benzodiazepine receptor binding site
  作者：Michael J. Martin、Mark L. Trudell、Hernando Diaz Arauzo、Michael S. Allen、Anthony J. LaLoggia、Li Deng、Christopher A. Schultz、Yun Chou Tan、Yingzhi Bi

  DOI：10.1021/jm00100a017

  日期：1992.10

  A series of rigid planar azadiindoles (8a, 8b, and 8d), benzannelated pyridodiindoles (11a, 11b, and 11d), and indolopyridoimidazoles (11c, 20, and 24) were synthesized from 4-oxo-1,2,3,4-tetrahydro-beta-carboline 5 via the Fischer indole cyclization with the appropriate arylhydrazines. These analogues were employed as probes ("molecular yardsticks") to define the spatial dimensions of the lipophilic regions of the benzodiazepine receptor (BzR) binding cleft. Benzannelated indoles 11a-d and indolopyridoimidazoles 20 and 24 were important in establishing an area of negative interaction (S1, see Figure 6, part b) in the binding cleft common to the interactions of both inverse agonists and agonists. Data from this chemical and computer-assisted analysis of the pharmacophore (see Figure 6) indicates that inverse agonists and agonists bind to the same binding region, but the pharmacophoric descriptors required for the two activities are different, in keeping with previous studies with these planar ligands. However, the hydrogen bond donating site H-1 and the lipophilic region L1 in the receptor binding site are common interactions experienced by both series of ligands. The low affinities of both indolo[3,2-c]carbazole (3a) and indolo[3,2-b]isoquinoline (3b) for the BzR are consonant with the requirements of a hydrogen bond acceptor interaction at donor site H-1 and a hydrogen bond donor interaction at acceptor site A2 for potent inverse agonist activity in the beta-carboline series. The hydrochloride salts of 1-aza- 8a (IC50 10.6 nM), 2-aza- 8b (IC50 51.5 nM), and 4-azadiindole 8d (IC50 11.2 nM) were found to be much more soluble in water than the corresponding salt of the parent diindole 2. Moreover, aza analogues 8a and 8b were shown to be partial inverse agonists with proconvulsant potencies comparable to that of the parent diindole 2.
• Straightforward synthesis of 11H-indolo[3,2-c]isoquinoline and benzofuro[3,2-c]isoquinoline by ring transformation
  作者：Mariann Béres、Géza Timári、György Hajós

  DOI：10.1016/s0040-4039(02)01244-3

  日期：2002.8

  An efficient method was established for the synthesis of 11H-indolo[3,2-c]isoquinoline and benzofuro[3,2-c]isoquinoline using thermal ring transformation of a benzisoxazolo[2,3-a]isoquinoline salt. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Hiremath, S. P.; Biradar, J. S.; Purohit, M. G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 3, p. 249 - 251
  作者：Hiremath, S. P.、Biradar, J. S.、Purohit, M. G.

  DOI：——

  日期：——
• Synthesis of 6-methyl-6H-indolo[3,2-c]isoquinoline and 6-methyl-6H-indolo[2,3-c]isoquinoline: two new unnatural isoquinoline isomers of the cryptolepine series
  作者：Gitte Van Baelen、Caroline Meyers、Guy L.F. Lemière、Steven Hostyn、Roger Dommisse、Louis Maes、Koen Augustyns、Achiel Haemers、Luc Pieters、Bert U.W. Maes

  DOI：10.1016/j.tet.2008.08.116

  日期：2008.12

  11H-indolo[3,2-c]isoquinoline has been synthesized in two steps starting from 4-bromoisoquinoline and 2-bromoaniline via a selective Buchwald–Hartwig reaction followed by a Pd-catalyzed intramolecular direct arylation involving C(sp2)–H activation. The synthesis of 7H-indolo[2,3-c]isoquinoline was achieved by a combination of a Suzuki reaction with an intramolecular nitrene insertion reaction starting from

  11 H-吲哚并[3,2- c ]异喹啉通过选择性的布赫瓦尔德-哈特维格反应，然后经钯催化的涉及C（sp 2）的分子内直接芳基化反应，从4-溴异喹啉和2-溴苯胺开始分两步合成。H激活。7 H-吲哚并[2,3- c ]异喹啉的合成是通过Suzuki反应与从4-溴异喹啉和2-[（2,2-二甲基丙酰基）氨基]苯基开始的分子内氮插入反应的结合而实现的}硼酸。四环骨架的选择性甲基化产生标题化合物6-甲基-6 H-吲哚并[3,2- c ]异喹啉和6-甲基-6 H-吲哚并[2,3-c ]异喹啉，以前在文献中从未描述过。