nostocarboline | 874351-71-0

• 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: nostocarboline
• 英文别名: nostocarboline iodide；Nostocarboline hydroiodide；6-chloro-2-methyl-9H-pyrido[3,4-b]indol-2-ium;iodide
• CAS: 874351-71-0
• 化学式: C₁₂H₁₀ClN₂*I
• 分子量: 344.582
• InChiKey: YSZAXPOWTBYIJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  19.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  nostocarboline 在 sodium hydroxide 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 0.17h， 以88%的产率得到6-Chlor-2-methyl-2H-pyrido<3.4-b>indol
  参考文献：
  名称：

  抗疟疾和抗结核诺斯卡布林和芥子油酮衍生物：合成，体内和体外生物学评估

  摘要：

  合成了九种二甲基咔啉衍生物，其中2-甲基被烷基，芳基和官能化残基取代； 10个对称的双阳离子二聚体（通过海洋生物碱eudistomin N和O的2位连接6-氯正壬烷）和十五种衍生物被合成。报告。这些化合物在体外评价对四名寄生虫（布氏锥虫罗得西亚STIB 900，克氏锥虫Tulahuen C2C4，杜氏利什曼原虫MHOM-ET-67 / L82无菌无鞭毛体，和恶性疟原虫K1株），针对结核分枝杆菌H37Rv的，耻垢分枝杆菌MC 2 155和谷氨酸棒杆菌ATCC13032，并确定了对L6大鼠成肌细胞的细胞毒性。Nostocarboline及其衍生物显示出对恶性疟原虫的有效且选择性的体外抑制作用，且细胞毒性较弱。二聚体显示的亚微摩尔的抑制杜氏利什曼原虫和布氏锥虫和纳摩尔的活性针对恶性疟原虫，尽管具有显着的细胞毒性。一个二聚体显示出针对结核分枝杆菌的MIC 99值为2.5μg/ ml。烷基化的芥末胺

  DOI：

  10.1016/j.bmc.2010.01.013
• 作为产物：
  描述：

  9H-吡啶[3,4-b]吲哚 在 sodium hypochlorite 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 5.33h， 生成 nostocarboline
  参考文献：
  名称：

  Potent Algicides Based on the Cyanobacterial Alkaloid Nostocarboline

  摘要：

  Nostocarboline and seven derivatives were prepared and displayed minimal inhibitory concentration (MIC) values >= 100 nM against the growth of Microcystis aeruginosa PCC 7806, Synechococcus PCC 6911, and Kirchneriella contorta SAG 11.81, probably via the inhibition of photosynthesis. The natural product hybrid nostocarboline/ciprofloxacin displayed additional antibacterial activity against several Gram-negative bacteria (MICs >= 0.7 mu M). Nostocarboline can thus be considered a potent, selective, readily available, natural algicide.

  DOI：

  10.1021/ol052968b

文献信息

• Heterocyclic compounds and their use as antifouling agents
  申请人：Eidgenössische Technische Hochschule Zürich

  公开号：EP1783128A1

  公开（公告）日：2007-05-09

  The present invention relates to a nostocarboline compound of the formula (I) and its use as a biocidal agent. In this formula R1, R3, R4 and R6 are selected from the group consisting of H, F, Cl, Br, I, a C1-C20 aliphatic residue, and a C1-C20 aliphatic residue comprising a carbocyclic or heterocyclic residue; R2 is selected from the group consisting of H and Cl; R5 is selected from the group consisting of H, a C1-C20 aliphatic residue, and a C1-C20 aliphatic residue comprising a carbocyclic or heterocyclic residue; R7 is selected from the group consisting of a C1-C20 aliphatic residue, a C1-C20 aliphatic residue comprising a carbocyclic or heterocyclic residue, and a linker bound to a bioactive factor; R8 is selected from the group consisting of H, a C1-C6 aliphatic carboxylic acid, ester, or amide, and a C3-C20 carbocyclic residue; and X- is a negatively charged ion.

  本发明涉及一种nostocarboline化合物，其化学式为(I)，以及其作为生物杀灭剂的用途。在该式中，R1、R3、R4和R6从H、F、Cl、Br、I、C1-C20脂肪残基和包含碳环或杂环残基的C1-C20脂肪残基组成的群体中选择；R2从H和Cl组成的群体中选择；R5从H、C1-C20脂肪残基和包含碳环或杂环残基的C1-C20脂肪残基组成的群体中选择；R7从C1-C20脂肪残基、包含碳环或杂环残基的C1-C20脂肪残基和与生物活性因子结合的连接物组成的群体中选择；R8从H、C1-C6脂肪羧酸、酯或酰胺和C3-C20碳环残基组成的群体中选择；X-为负离子。
• Potent and selective antiplasmodial activity of the cyanobacterial alkaloid nostocarboline and its dimers
  作者：Damien Barbaras、Marcel Kaiser、Reto Brun、Karl Gademann

  DOI：10.1016/j.bmcl.2008.06.049

  日期：2008.8

  The quaternary beta-carbolinium alkaloid nostocarboline from the cyanobacterium Nostoc 78-12A and 10 bis-cationic dimeric derivatives were evaluated against four protozoan parasites and low micromolar values against Trypanosoma brucei, submicromolar values against Leishmania donovani and low nanomolar values against Plasmodium falciparum K1 were determined. Selectivity against rat myoblasts (L6 cells) was found to be up to > 2500-fold. (c) 2008 Elsevier Ltd. All rights reserved.
• Nostocarboline:  Isolation and Synthesis of a New Cholinesterase Inhibitor from <i>Nostoc</i> 78-12A
  作者：Paul G. Becher、Julien Beuchat、Karl Gademann、Friedrich Jüttner

  DOI：10.1021/np050312l

  日期：2005.12.1

  A new quaternary beta-carboline alkaloid, nostocarboline (1), was isolated from the freshwater cyanobacterium Nostoc 78-12A, and its constitution was assigned by 2D-NMR methods. The structure was proven by its total synthesis starting from norharmane via chlorination at C-6 and methylation at N-2. Nostocarboline (1) was found to be a potent butyrylcholinesterase (BChE) inhibitor, with an IC50 of 13.2 mu M. The related 2-methylnorharmane, which is present in the human brain and might be relevant to Parkinson's disease (PD), was also determined to be a BChE inhibitor (11.2 mu M). These inhibitory concentrations are comparable to galanthamine, an approved drug for the treatment of Alzheimer's disease (AID). Nostocarboline (1) can thus be considered as a lead for the development of novel neurochemicals.