amino-3 bromo-6 dimethyl-1,4 9H-carbazole | 118484-85-8

• 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: amino-3 bromo-6 dimethyl-1,4 9H-carbazole
• 英文别名: 3-amino-6-bromo-1,4-dimethyl-9H-carbazole；9H-Carbazol-3-amine, 6-bromo-1,4-dimethyl-；6-bromo-1,4-dimethyl-9H-carbazol-3-amine
• CAS: 118484-85-8
• 化学式: C₁₄H₁₃BrN₂
• 分子量: 289.175
• InChiKey: DWQPWOASYIXCFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 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：

  amino-3 bromo-6 dimethyl-1,4 9H-carbazole 在 三乙胺 作用下， 以 甲苯 、 苯 为溶剂， 反应 2.0h， 生成 3-(6-bromo-1,4-dimethyl-9H-carbazol-3-yl)-1,1-bis(2-chloroethyl)urea
  参考文献：
  名称：

  Etude de la cytotoxicité in vitro de dérivés du carbazole II. Nitro et amino halogéno-6 diméthyl-1,4 9H-carbazoles

  摘要：

  DOI：

  10.1016/0223-5234(89)90028-7
• 作为产物：
  描述：

  6-bromo-1,4-dimethyl-9H-carbazole 在 硝酸 作用下， 以 乙酸酐 为溶剂， 生成 amino-3 bromo-6 dimethyl-1,4 9H-carbazole
  参考文献：
  名称：

  由二甲基咔唑衍生的新的三甲氧基苯甲酰胺和三甲氧基苯基脲作为细胞毒剂。第一部分

  摘要：

  据报道，从它们相应的吲哚衍生物开始，方便地合成了含有3,4,5-三甲氧基苯甲酰胺基-脲基或N-（3,4,5-三甲氧基苯基）脲基的新型功能化的1,4-二甲基咔唑衍生物。准备了三种衍生物（， ， 和 ）对白血病细胞系HL60具有活性。两个都 和 对KB细胞系显示出有效的抗增殖活性，可能与微管蛋白聚合的抑制有关。

  DOI：

  10.1002/jhet.1951

文献信息

• NEW CARBAZOLE DERIVATIVES SENSITIZING CELLS TO ANTI-CANCER AGENTS
  申请人：Centre National de la Recherche Scientifique

  公开号：EP3804812A1

  公开（公告）日：2021-04-14

  The invention concerns a compound of formula (I) wherein R, R1 and R2 are independently selected form the group consisting of: - a hydrogen atom, - a halogen atom, - an alkyl group, linear, cyclic or branched, saturated or unsaturated, possibly substituted, comprising from 1 to 10 carbon atoms, - an acyl group comprising from 1 to 10 carbon atoms, - a carboxyl group, - an amido group comprising from 1 to 10 carbon atoms, and - an imino group, possibly substituted by an alkyl group, linear, cyclic or branched, saturated or unsaturated, and wherein R3, R4, R5 and R6 are independently selected form the group consisting of: - a hydrogen atom, - a halogen atom, - a hydroxyl group, - an alkyl group, linear, cyclic or branched, saturated or unsaturated, possibly substituted, comprising from 1 to 10 carbon atoms, - an alkoxy group comprising from 1 to 10 carbon atoms, - an acyl group comprising from 1 to 10 carbon atoms, - a carboxyl group, and - a cyano group.

  这项发明涉及一种化合物，其化学式为（I），其中R、R1和R2分别独立地选自以下组成的群体：- 氢原子，- 卤素原子，- 烷基基团，线性、环状或支链，饱和或不饱和，可能被取代，含有1至10个碳原子，- 包含1至10个碳原子的酰基基团，- 羧基，- 包含1至10个碳原子的酰胺基团，和- 亚胺基团，可能被烷基基团取代，线性、环状或支链，饱和或不饱和，其中R3、R4、R5和R6独立地选自以下组成的群体：- 氢原子，- 卤素原子，- 羟基基团，- 烷基基团，线性、环状或支链，饱和或不饱和，可能被取代，含有1至10个碳原子，- 包含1至10个碳原子的烷氧基团，- 包含1至10个碳原子的酰基基团，- 羧基，和- 氰基。
• 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。
• In vitro cytotoxicity of carbazole derivatives. V. 9-Halogeno-substituted 5,11-dimethyl-6H-pyrido[3,2-b]carbazoles
  作者：V Moinet-Hedin、T Tabka、F Sichel、P Gauduchon、JY Le Talaër、C Saturnino、B Letois、JC Lancelot、M Robba

  DOI：10.1016/s0223-5234(97)87537-x

  日期：1997.1

  Thirty-seven new 5,11-dimethyl-6H-pyrido[3,2-b]carbazole derivatives have been synthesized. These compounds are structurally related to the 5,11-dimethyl-6H-pyrido[4,3-b]carbazole antitumor drug ellipticine. They bear either a fluorine, a bromine or a chlorine atom on position 9, and are variously substituted on the pyridine ring. Twenty-nine of these compounds (78%) were found active when tested in vitro for their cytotoxic activity in a clonogenic assay using murine leukemia L1210 cell line. Structure-activity relationships are described in detail.
• A rapid and versatile synthesis of novel pyrimido[5,4-b]carbazoles
  作者：Anna Caruso、Jean-Charles Lancelot、Hussein El-Kashef、Maria Stefania Sinicropi、Rémi Legay、Aurélien Lesnard、Sylvain Rault

  DOI：10.1016/j.tet.2009.10.025

  日期：2009.12

  A one-pot synthesis of 2-dialkylamino-5,11-dimethyl-6H-pyrimido[5,4-b]carbazol-4(3H)-ones, as new ellipticine analogs, starting from aminocarbazole derivatives is reported. This method allowed us to prepare a library of potentially useful compounds in the pharmaceutical field. (C) 2009 Elsevier Ltd. All rights reserved.
• TABKA, THABET;LETOIS, BERTRAND;LANCELOT, JEAN-CHARLES;GAUDUCHON, PASCAL;H+, EUR. J. MED. CHEM., 24,(1989) N, C. 605-610
  作者：TABKA, THABET、LETOIS, BERTRAND、LANCELOT, JEAN-CHARLES、GAUDUCHON, PASCAL、H+

  DOI：——

  日期：——