2,4,5,6-tetrahydro-1H-pyrazino[3,2,1-jk]carbazole | 56903-46-9

• 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: 2,4,5,6-tetrahydro-1H-pyrazino[3,2,1-jk]carbazole
• 英文别名: 1,4-Diazatetracyclo[7.6.1.05,16.010,15]hexadeca-4,9(16),10,12,14-pentaene
• CAS: 56903-46-9
• 化学式: C₁₄H₁₄N₂
• 分子量: 210.279
• InChiKey: XRMAMWMDSAVLAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4,5,6-tetrahydro-1H-pyrazino[3,2,1-jk]carbazole 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到2,3,3a,4,5,6-六氢-1H-吡嗪并[3,2,1-JK]咔唑
  参考文献：
  名称：

  NB 06: From a simple lysosomotropic aSMase inhibitor to tools for elucidating the role of lysosomes in signaling apoptosis and LPS-induced inflammation

  摘要：

  Ceramide generation is involved in signal transduction of cellular stress response, in particular during stress-induced apoptosis in response to stimuli such as minimally modified Low-density lipoproteins, TNFalpha and exogenous C-6-ceramide. In this paper we describe 48 diverse synthetic products and evaluate their lysosomotropic and acid sphingomyelinase inhibiting activities in macrophages. A stimuli induced increase of C-16-ceramide in macrophages can be almost completely suppressed by representative compound NB 06 providing an effective protection of macrophages against apoptosis. Compounds like NB 06 thus offer highly interesting fields of application besides prevention of apoptosis of macrophages in atherosclerotic plaques in vessel walls. Most importantly, they can be used for blocking pH dependent lysosomal processes and enzymes in general as well as for analyzing lysosomal dependent cellular signaling. Modulation of gene expression of several prominent inflammatory messengers IL1B, IL6, IL23A, CCL4 and CCL20 further indicate potentially beneficial effects in the field of (systemic) infections involving bacterial endotoxins like LPS or infections with influenza A virus. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.09.021
• 作为产物：
  描述：

  1,2,3,4-四氢咔唑 在 五氧化二碘 、 五氯化磷 、 potassium carbonate 、 calcium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 20.5h， 生成 2,4,5,6-tetrahydro-1H-pyrazino[3,2,1-jk]carbazole
  参考文献：
  名称：

  NB 06: From a simple lysosomotropic aSMase inhibitor to tools for elucidating the role of lysosomes in signaling apoptosis and LPS-induced inflammation

  摘要：

  Ceramide generation is involved in signal transduction of cellular stress response, in particular during stress-induced apoptosis in response to stimuli such as minimally modified Low-density lipoproteins, TNFalpha and exogenous C-6-ceramide. In this paper we describe 48 diverse synthetic products and evaluate their lysosomotropic and acid sphingomyelinase inhibiting activities in macrophages. A stimuli induced increase of C-16-ceramide in macrophages can be almost completely suppressed by representative compound NB 06 providing an effective protection of macrophages against apoptosis. Compounds like NB 06 thus offer highly interesting fields of application besides prevention of apoptosis of macrophages in atherosclerotic plaques in vessel walls. Most importantly, they can be used for blocking pH dependent lysosomal processes and enzymes in general as well as for analyzing lysosomal dependent cellular signaling. Modulation of gene expression of several prominent inflammatory messengers IL1B, IL6, IL23A, CCL4 and CCL20 further indicate potentially beneficial effects in the field of (systemic) infections involving bacterial endotoxins like LPS or infections with influenza A virus. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.09.021

文献信息

• Pyrazino-carbazole, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Mittel
  申请人：CASSELLA Aktiengesellschaft

  公开号：EP0028270A1

  公开（公告）日：1981-05-13

  In 8-Stellung substituierte 2,4,5,6-Tetrahydro-1H-pyrazino (3,2,1-jk] carbazole der Formel I wobei R für eine Alkyl-oder Alkoxygruppe mit 1-4 Kohlenstoffatomen oder ein Fluor-, Chlor-oderBromatom steht, werden dadurch hergestellt, daß ein 6,9-disubstituiertes 1,2,3,4-Tetrahydrocarbazol-1-on der Formel II wobei X ein Brom-, Chlor- oder Jodatom oder den Rest der Formel-O-SO2-R' und R' einen Alkylrest mit 1-3 Kohlenstoffatomen, Phenyl oder Tolyl bedeutet, mit Ammoniak unter Ringschluß umgesetzt wird. Die Verbindungen der Formel besitzen eine stark ausgeprägte psychotrope, insbesondere antidepressive Wirkung und sind außerdem Zwischenprodukte für die Herstellung anderer pharmakologisch aktiver Verbindungen.

  2,4,5,6-Tetrahydro-1H-pyrazino (3,2,1-jk] carbazoles substituted in the 8-position of the formula I 其中 R 是具有 1-4 个碳原子的烷基或烷氧基或氟、氯或溴原子，通过与式 II 中的 6，9-二取代的 1，2，3，4-四氢咔唑-1-酮反应制备而成 其中 X 是溴原子、氯原子或碘原子，或式 O-SO2-R'的自由基，R'是具有 1-3 个碳原子的烷基、苯基或甲苯基。式中化合物具有明显的精神作用，特别是抗抑郁作用，也是生产其他药理活性化合物的中间体。
• GATTA F.; CHIAVARELLI S., FARMACO, ED. SCI. <FRPS-AX>, 1975, 30, NO 8, 631-641
  作者：GATTA F.、 CHIAVARELLI S.

  DOI：——

  日期：——
• Verfahren zur Herstellung gegebenenfalls substituierter 1,2,3,4-Tetrahydro-9-cyanmethyl-carbazol-1-onen
  申请人：CASSELLA Aktiengesellschaft

  公开号：EP0095067B1

  公开（公告）日：1986-11-12
• US4258043A
  申请人：——

  公开号：US4258043A

  公开（公告）日：1981-03-24
• US4271073A
  申请人：——

  公开号：US4271073A

  公开（公告）日：1981-06-02