8-methoxy-5H-pyrido[3,2-b]indole | 162254-04-8

• 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: 8-methoxy-5H-pyrido[3,2-b]indole
• CAS: 162254-04-8
• 化学式: C₁₂H₁₀N₂O
• 分子量: 198.224
• InChiKey: TVUHNFXQQPLNPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-methoxy-5H-pyrido[3,2-b]indole 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 5,7-dibromo-6-methoxy-δ-carboline
  参考文献：
  名称：

  Structure-activity relationship of bromoeudistomin D, a powerful Ca2+ releaser in skeletal muscle sarcoplasmic reticulum

  摘要：

  Bromoeudistomin D and 9-methyl-7-bromoeudistomin D which have a beta-carboline skeleton are powerful Ca2+ releasers from skeletal muscle sarcoplasmic reticulum exhibiting caffeine-like properties. We examined the effects of bromoeudistomin D analogues on Ca(2+)-induced Ca2+ release from skeletal muscle sarcoplasmic reticulum. Among bromoeudistomin D analogues, the Ca(2+)-releasing activities of carboline derivatives were higher than those of carbazole derivatives, suggesting that a carboline skeleton is significantly important for the manifestation of Ca(2+)-releasing activity and Ca2+ sensitivity of Ca(2+)-induced Ca2+ release. On the contrary, the analogues which have a carbazole skeleton and bromine at C-6 inhibit both Ca(2+)- and caffeine-induced Ca2+ release. 9-Methyl-substitution of the analogue elevated its Ca(2+)-releasing activity. Moreover, there is a close correlation between the enhancement of [3H]ryanodine binding to sarcoplasmic reticulum by the analogues and the activation of Ca2+ release by them. Bromoudistomin D analogues may provide valuable information about the structure-function relationship of the ryanodine receptor/Ca2+ release channels in skeletal muscle sarcoplasmic reticulum.

  DOI：

  10.1016/0922-4106(95)90040-3
• 作为产物：
  描述：

  N-(4-甲氧基苯基)-3-吡啶胺 在 palladium diacetate 、 三氟乙酸 、 氨 作用下， 以 水 为溶剂， 反应 6.0h， 以36%的产率得到8-methoxy-5H-pyrido[3,2-b]indole
  参考文献：
  名称：

  δ-Carbolines and their ring-opened analogs: Synthesis and evaluation against fungal and bacterial opportunistic pathogens

  摘要：

  Previous studies have indicated that the delta-carboline (2) ring system derived from the natural product cryptolepine (1) may represent a pharmacophore for anti-infective activity. This paper describes the design and synthesis of a small library of substituted delta-carbolines and the evaluation of the anti-fungal and anti-bacterial activities. An evaluation of the anti-bacterial activity of a previously reported library of ring-opened analogs was also conducted to provide an opportunity to test the hypothesis that both group of compounds may have the same biological target. Results indicate that against a selected group of fungal pathogens, substituted delta-carbolinium analogs displayed higher potency and several fold lower cytotoxicity than cryptolepine the parent natural product. Both the delta-carbolinium compounds and their ring-opened analogs, exhibited equally high anti-bacterial activity against the selected pathogens and especially against the gram positive bacteria evaluated. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.03.021

文献信息

• Pd-catalyzed intramolecular direct arylations at high temperature
  作者：Philippe Franck、Steven Hostyn、Beáta Dajka-Halász、Ágnes Polonka-Bálint、Katrien Monsieurs、Peter Mátyus、Bert U.W. Maes

  DOI：10.1016/j.tet.2008.01.060

  日期：2008.6

  azaheteroaromatic C–Cl bonds and C(sp2)–H activation have been investigated at high reaction temperatures (180–200 °C). This allowed the fast (10–30 min) synthesis of a variety of azaheteroaromatic ring systems (dibenzo[f,h]phthalazine, dibenzo[f,h]cinnoline, benzofuro[2,3-d]pyridazine, 5H-pyridazino[4,5-b]indole, 7H-indolo[2,3-c]quinoline and 5H-δ-carboline) in moderate to good yields.

  在高反应温度（180-200°C）下，已研究了钯催化的环加氢卤化反应，涉及芳族C-Br或活化的氮杂杂芳族C-Cl键的氧化加成和C（sp 2）-H活化。这使得各种azaheteroaromatic环系统（二苯并[的快速（10-30分钟）的合成˚F，ħ ]酞嗪，二苯并[ ˚F，ħ ]噌啉，苯并呋喃并[2,3- d ]哒嗪，5 ħ -pyridazino [ 4,5- b ]吲哚，7 ħ吲哚并[2,3- c ^ ]喹啉和5- ħ -δ咔啉）在中度至良好的产率。
• 有机金属化合物和包括其的有机发光装置
  申请人：三星显示有限公司

  公开号：CN113831370A

  公开（公告）日：2021-12-24

  本发明涉及有机金属化合物和包括其的有机发光装置。有机发光装置包括：第一电极；面对第一电极的第二电极；以及在第一电极和第二电极之间的有机层，有机层包括发射层，其中有机发光装置包括由式1表示的有机金属化合物。当有机金属化合物用于有机发光装置时，有机发光装置在驱动电压、效率、颜色纯度和/或寿命方面可具有卓越的效果：式1
• Solvent-free synthesis of δ-carbolines/carbazoles from 3-nitro-2-phenylpyridines/2-nitrobiphenyl derivatives using DPPE as a reducing agent
  作者：Haixia Peng、Xuxing Chen、Yanhong Chen、Qian He、Yuyuan Xie、Chunhao Yang

  DOI：10.1016/j.tet.2011.06.027

  日期：2011.8

  A green and efficient preparation of functionalized delta-carbolines/carbazoles via reductive ring closure by 1,2-bis(dipenylphosphino)ethane under solvent-free conditions is described. The starting materials 3-nitro-2-phenylpyridines/2-nitrobiphenyl derivatives are readily prepared through Suzuki-Miyaura cross-coupling reaction from commercially available compounds. And the polar by-product ethane-1,2-diylbis(diphenylphosphine oxide) is easily removed from the relatively polar reaction mixture. Various substituted delta-carbolines/carbazoles are obtained in acceptable yields. It is particularly worth mentioning that substrates with electron-withdrawing groups (EWG) also give the desired products in good yield. (C) 2011 Elsevier Ltd. All rights reserved.
• ECTONUCLEOTIDE PYROPHOSPHATASE-PHOSPHODIESTERASE-1 INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：[en]LEGOCHEM BIOSCIENCES, INC.

  公开号：WO2023242631A1

  公开（公告）日：2023-12-21

  The present disclosure relates compounds for inhibiting ectonucleotide pyrophosphatase/phosphodiesterase-1 (ENPP-1), or a pharmaceutically acceptable salts thereof.
• Structure-activity relationship of bromoeudistomin D, a powerful Ca2+ releaser in skeletal muscle sarcoplasmic reticulum
  作者：Yukiko Takahashi、Ken-Ichi Furukawa、Masami Ishibashi、Daisuke Kozutsumi、Haruaki Ishiyama、Jun'ichi Kobayashi、Yasushi Ohizumi

  DOI：10.1016/0922-4106(95)90040-3

  日期：1995.2

  Bromoeudistomin D and 9-methyl-7-bromoeudistomin D which have a beta-carboline skeleton are powerful Ca2+ releasers from skeletal muscle sarcoplasmic reticulum exhibiting caffeine-like properties. We examined the effects of bromoeudistomin D analogues on Ca(2+)-induced Ca2+ release from skeletal muscle sarcoplasmic reticulum. Among bromoeudistomin D analogues, the Ca(2+)-releasing activities of carboline derivatives were higher than those of carbazole derivatives, suggesting that a carboline skeleton is significantly important for the manifestation of Ca(2+)-releasing activity and Ca2+ sensitivity of Ca(2+)-induced Ca2+ release. On the contrary, the analogues which have a carbazole skeleton and bromine at C-6 inhibit both Ca(2+)- and caffeine-induced Ca2+ release. 9-Methyl-substitution of the analogue elevated its Ca(2+)-releasing activity. Moreover, there is a close correlation between the enhancement of [3H]ryanodine binding to sarcoplasmic reticulum by the analogues and the activation of Ca2+ release by them. Bromoudistomin D analogues may provide valuable information about the structure-function relationship of the ryanodine receptor/Ca2+ release channels in skeletal muscle sarcoplasmic reticulum.