7-甲氧基-4,9-二氢-3H-吡啶并[3,4-b]吲哚 | 31652-37-6

• 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
• 中文名称: 7-甲氧基-4,9-二氢-3H-吡啶并[3,4-b]吲哚
• 英文名称: 7-methoxy-3,4-dihydro-β-carboline
• 英文别名: 7-methoxy-4,9-dihydro-3H-pyrido[3,4-b]indole；Harmalin；7-Methoxy-3,4-dihydro-β-carbolin；CGS 19281A；7-methoxy-4,9-dihydro-3H-β-carboline；4,9-Dihydro-7-methoxy-3H-pyrido(3,4b)indole
• CAS: 31652-37-6
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: VTEZDUSEJVSZGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  7-甲氧基-4,9-二氢-3H-吡啶并[3,4-b]吲哚 在 （2S）-2-[[[[[[（（1R，2R）-2-氨基环己基]氨基]硫代甲基]氨基]-N-（二苯甲基）-N，3,3-三甲基丁酰胺 、 caesium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 72.0h， 生成 (4R,12bS)-10-methoxy-4-propyl-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one
  参考文献：
  名称：

  Enantioselective Formal Aza-Diels–Alder Reactions of Enones with Cyclic Imines Catalyzed by Primary Aminothioureas

  摘要：

  A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.

  DOI：

  10.1021/ja310718f
• 作为产物：
  描述：

  2-氧代哌啶-3-羧酸 在 吲哚 、 lithium aluminium tetrahydride 、 苯亚硒酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 7-甲氧基-4,9-二氢-3H-吡啶并[3,4-b]吲哚
  参考文献：
  名称：

  Pouilhes, Annie; Langlois, Yves, Heterocycles, 1985, vol. 23, # 4, p. 935 - 938

  摘要：

  DOI：

文献信息

• Discovery of Evodiamine Derivatives as Highly Selective PDE5 Inhibitors Targeting a Unique Allosteric Pocket
  作者：Tianhua Zhang、Zengwei Lai、Suying Yuan、Yi-You Huang、Guoqiang Dong、Chunquan Sheng、Hengming Ke、Hai-Bin Luo

  DOI：10.1021/acs.jmedchem.0c00983

  日期：2020.9.10

  Clinical use of phosphodiesterase-5 (PDE5) inhibitors is limited by several side effects due to weak isoform selectivity. Herein, a unique allosteric pocket of PDE5 is identified by molecular modeling and structural biology, which enables the discovery of highly selective PDE5 inhibitors from natural product evodiamine (EVO). The crystal structure of PDE5 with bound EVO derivative (S)-7e revealed that

  由于弱的同工型选择性，磷酸二酯酶5（PDE5）抑制剂的临床应用受到多种副作用的限制。本文中，通过分子建模和结构生物学鉴定了PDE5的独特变构口袋，这使得能够从天然产物evodiamine（EVO）中发现高选择性PDE5抑制剂。PDE5的与结合EVO衍生物的晶体结构（小号）-7e揭示的结合（小号）-7e新颖的变构口袋诱导了H环的显着构象变化，其Cα原子最大移动了24Å。这种运动直接阻止了底物/抑制剂与PDE5活性位点的结合，这与所有传统PDE5抑制剂（如昔多芬，他达拉非和伐地那非）不同。这些衍生物显示出超过PDE6C和PDE11A 570倍的选择性，并在体内有效治疗肺动脉高压方面达到了有效的功效。
• POUILHES, A.;LANGLOIS, Y., HETEROCYCLES, 1985, 23, N 4, 935-938
  作者：POUILHES, A.、LANGLOIS, Y.

  DOI：——

  日期：——
• IDO INHIBITORS
  申请人：Newlink Genetics

  公开号：EP2227233A2

  公开（公告）日：2010-09-15
• [EN] IDO INHIBITORS<br/>[FR] INHIBITEURS DE L'IDO
  申请人：NEWLINK GENETICS

  公开号：WO2009073620A2

  公开（公告）日：2009-06-11

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.