3-amino-1,4-dimethyl-9H-carbazole | 111249-52-6

• 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
• 英文名称: 3-amino-1,4-dimethyl-9H-carbazole
• 英文别名: amino-3 dimethyl-1,4 carbazole；1,4-dimethyl-3-aminocarbazole；3-amino-1,4-dimethylcarbazole；1,4-dimethyl-9H-carbazol-3-amine
• CAS: 111249-52-6
• 化学式: C₁₄H₁₄N₂
• 分子量: 210.279
• InChiKey: KZQZOUXUEGIOQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-amino-1,4-dimethyl-9H-carbazole 在 溶剂黄146 作用下， 以 二苯醚 、 苯 为溶剂， 反应 3.33h， 生成 1,4-dihydro-5,11-dimethyl-4-oxo-2-propyl-6H-pyrido<3,2-b>carbazole
  参考文献：
  名称：

  In vitro cytotoxicity of carbazole derivatives IV. 5,11-Dimethyl-6H-pyrido[3,2-b]carbazoles substituted on the pyridine ring

  摘要：

  A series of 5,11-dimethyl-6H-pyrido[3,2-b]carbazoles, structurally related to the antitumor drug ellipticine, were synthesized from 3-amino-1,4-dimethyl-9H-carbazole. Among 17 derivatives, bearing various substituents on the pyridine ring, and preliminarily evaluated for cytotoxicity on L1210-cultured cells, 13 (76%) were found to be active. One of them, 5,11-dimethyl-4-ethoxy-6H-pyrido[3,2-b]carbazole, although non-substituted on C-9, displayed an activity similar to that of 9-hydroxy-N-2-methylellipticinium acetate. Structure-activity relationships have been described in detail.

  DOI：

  10.1016/0223-5234(93)90032-a
• 作为产物：
  描述：

  2,5-Dimethyl-4-nitrophenylhydrazine hydrochloride 在 盐酸 、 sodium acetate 、 镍 、 一水合肼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 xylene 为溶剂， 反应 5.67h， 生成 3-amino-1,4-dimethyl-9H-carbazole
  参考文献：
  名称：

  Alunni-Bistocchi, Giovanni; Orvietani, Pierluigi; Mauffret, Olivier, Journal of the Chemical Society. Perkin transactions I, 1992, # 21, p. 2935 - 2942

  摘要：

  DOI：

文献信息

• Synthesis of novel 2-cyanothiazolocarbazoles analogues of ellipticine
  作者：Hadjila Chabane、Christelle Lamazzi、Valérie Thiéry、Gérald Guillaumet、Thierry Besson

  DOI：10.1016/s0040-4039(02)00353-2

  日期：2002.4

  Novel linear thiazolocarbazoles, which are structurally very close to the natural alkaloid ellipticine, have been rapidly synthesised via imino-1,2,3-dithiazoles, themselves readily obtained by treatment of the appropriate 3-aminocarbazoles with 4,5-dichloro-1,2,3-dithiazolium chloride 1 (Appel salt).

  已经通过亚氨基1,2,3-二噻唑迅速合成了新型的线性噻唑并咔唑，其结构与天然生物碱玫瑰树碱非常接近，它们本身可以通过用4,5-二氯-1处理适当的3-氨基咔唑而容易地获得， 2,3-二噻唑鎓氯化物1（阿珀尔盐）。
• CAN-Catalyzed Regioselective Synthesis of Pyrido[2,3-c]carbazoles by the Povarov Reaction
  作者：Rajagopal Nagarajan、Mayavan Viji

  DOI：10.1055/s-0031-1289967

  日期：2012.1

  A simple route for the synthesis of 3-methyl-3H-pyrido[2,3-c]carbazoles via Povarov reaction of 3-aminocarbazoles, and ethyl vinyl ether is described. This transformation, catalyzed by cerium(IV) ammonium nitrate (CAN) under mild reaction conditions, provides the pyrido[2,3-c]carbazoles in good yields with high regioselectivity. Povarov reaction - annulations - heterocycles - Lewis acids­ - regioselectivity

  描述了一种通过3-氨基咔唑与乙基乙烯基醚的Povarov反应合成3-甲基-3 H-吡啶并[2,3- c ]咔唑的简单方法。在温和的反应条件下，硝酸铈（IV）铵（CAN）催化的这种转化以高收率和高区域选择性提供了吡啶并[2,3- c ]咔唑。 Povarov反应-环空-杂环-路易斯酸-区域选择性
• CuI/La(OTf)3 catalyzed, one-pot synthesis of isomeric ellipticine derivatives in ionic liquid
  作者：Vikram Gaddam、Subburethinam Ramesh、Rajagopal Nagarajan

  DOI：10.1016/j.tet.2010.03.095

  日期：2010.6

  An efficient method for one-pot synthesis of isomeric ellipticine derivatives through CuI/La(OTf)3 catalyzed sequential inter/intramolecular cyclization of substituted alkynes with imines followed by aromatization is reported in good to excellent yields.

  据报道，通过CuI / La（OTf）3催化亚炔基与亚胺的连续炔间/分子内环化继而芳构化的一锅法合成玫瑰树碱衍生物的有效方法，收率良好。
• Synthesis and evaluation of cytotoxic activities of new guanidines derived from carbazoles
  作者：Anna Caruso、Maria Stefania Sinicropi、Jean-Charles Lancelot、Hussein El-Kashef、Carmela Saturnino、Geneviève Aubert、Céline Ballandonne、Aurélien Lesnard、Thierry Cresteil、Patrick Dallemagne、Sylvain Rault

  DOI：10.1016/j.bmcl.2013.12.047

  日期：2014.1

  Several new alkylguanidines derived from carbazole have been synthesized in a simple one-pot reaction starting from 3-aminocarbazole derivatives. The aminocarbazoles were reacted with ethoxycarbonylisothiocyanate, to give thiourea intermediates, followed by the addition of an alkylamine and HgCl2 to give ethoxycarbonylguanidine intermediates. The reaction mixture was then heated at 160 °C to give the

  从3-氨基咔唑衍生物开始，在简单的一锅反应中合成了几种衍生自咔唑的新烷基胍。使氨基咔唑与乙氧基羰基异硫氰酸酯反应，得到硫脲中间体，然后加入烷基胺和HgCl 2，得到乙氧基羰基胍中间体。然后将反应混合物在160℃下加热，得到Ñ - （1,4-二甲基-9- ħ咔唑-3-基） - ñ '-alkylguanidines。 评估了所有合成胍对不同细胞系的细胞毒活性。
• EFFICIENT SYNTHESIS OF 6H-PYRIDO [3, 2-b] CARBAZOLE DERIVATIVES FROM 3-AMINO-1, 4-DIMETHYL CARBAZOLE
  作者：Jean-Charles Lancelot、Sylvain Rault、Max Robba、Nguyen Huy Dung

  DOI：10.1248/cpb.35.425

  日期：——

  The synthesis of 3-amino-1, 4-dimethylcarbazole is described and its reaction with β-ketoesters gives new 6H-pyrido [3, 2-b] carbazole derivatives.

  介绍了 3-氨基-1，4-二甲基咔唑的合成及其与 β-酮酯的反应，从而得到了新的 6H 吡啶并[3，2-b] 咔唑衍生物。