1,4-dimethyl 6-nitro 9H-carbazole | 133591-38-5

• 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: 1,4-dimethyl 6-nitro 9H-carbazole
• 英文别名: 1,4-Dimethyl-6-nitro-9H-carbazole
• CAS: 133591-38-5
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: OEENCKLKSYVWPU-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C
• 沸点：
  464.4±40.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 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：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-dimethyl 6-nitro 9H-carbazole 在 palladium on activated charcoal 氢气 、 硝酸 、 乙酸酐 作用下， 以 乙醇 为溶剂， 25.0~80.0 ℃ 、7.84 MPa 条件下， 反应 6.0h， 生成 3,6-diamino-1,4-dimethyl-9H-carbazole
  参考文献：
  名称：

  Étude de la cytotoxicitéin vitro de dérivés du carbazole III. 3-Amino et 3-nitro-1,4-diméthyl-9H-carbazoles diversement substitués en position 6

  摘要：

  In vitro cytotoxicity study of carbazole III 3-amino and 3-nitro-1,4-dimethyl-9H-carbazoles derivatives, diversely substituted in 6. The synthesis of a series of nitro and amino-1,4-dimethyl-9H-carbazoles is described. Their cytotoxic activities, as assayed in vitro using clonogenic cell culture of murine leukemia L1210, vary greatly with the nature and position of substituents. The most cytotoxic derivatives, 3-amino-6-hydroxy 1,4-dimethyl-9H-carbazole, displays an activity similar to that of N2-methyl-9-hydroxy ellipticinium acetate (NMHE). These results, together with those previously published by us, allow a detailed analysis of structure-activity relationships in the 9H-carbazole and 1,4-dimethyl-9H-carbazole series. For the 3-amino-1,4-dimethyl 9H-carbazole derivatives, a mechanism of action similar to that of ellipticine derivatives is proposed.

  DOI：

  10.1016/0223-5234(90)90197-b
• 作为产物：
  描述：

  2,5-己二醇 、 5-硝基吲哚 在 montmorillonite K-10 作用下， 反应 1.0h， 以75%的产率得到1,4-dimethyl 6-nitro 9H-carbazole
  参考文献：
  名称：

  Microwave-Assisted Solid-Acid-Catalyzed Friedel-Crafts Alkylation and Electrophilic Annulation of Indoles Using Alcohols as Alkylating Agents

  摘要：

  醇类被认为是环境友好的烷基化试剂，因为它们反应的唯一副产物是水。本文报道了利用微波辅助的Friedel-Crafts烷基化和亲电环化反应，使用醇作为烷基化试剂对吲哚进行修饰。使用叔丁醇对吲哚进行烷基化反应，得到3-取代的叔丁基吲哚。通过使用己二醇-2,5作为反应剂，可实现吲哚的亲电环化/芳构化级联反应，生成取代的咔唑。该反应由强固体酸催化剂蒙脱石K-10催化。产物获得了良好的产率和高度选择性。

  DOI：

  10.1055/s-0029-1217052

文献信息

• Lancelot, Jean-Charles; Letois, Bertrand; Rault, Sylvain, Gazzetta Chimica Italiana, 1991, vol. 121, # 6, p. 301 - 307
  作者：Lancelot, Jean-Charles、Letois, Bertrand、Rault, Sylvain、Dung, Nguyen Huy、Saturnino, Carmela、Robba, Max

  DOI：——

  日期：——
• [EN] USE OF CARBAZOLE-PHENONE DERIVATIVES FOR TREATING CANCER<br/>[FR] UTILISATION DE DÉRIVÉS DE CARBAZOLOPHÉNONE POUR LE TRAITEMENT DU CANCER
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2013121385A1

  公开（公告）日：2013-08-22

  La présente invention concerne des dérivés de carbazolophénone de formule (I) : (I) et leur mise en oeuvre comme médicaments, et notamment pour prévenir et/ou traiter le cancer.
• Étude de la cytotoxicitéin vitro de dérivés du carbazole III. 3-Amino et 3-nitro-1,4-diméthyl-9H-carbazoles diversement substitués en position 6
  作者：B Letois、JC Lancelot、S Rault、M Robba、T Tabka、P Gauduchon、E Bertreux、JY Le Talaer

  DOI：10.1016/0223-5234(90)90197-b

  日期：1990.11

  In vitro cytotoxicity study of carbazole III 3-amino and 3-nitro-1,4-dimethyl-9H-carbazoles derivatives, diversely substituted in 6. The synthesis of a series of nitro and amino-1,4-dimethyl-9H-carbazoles is described. Their cytotoxic activities, as assayed in vitro using clonogenic cell culture of murine leukemia L1210, vary greatly with the nature and position of substituents. The most cytotoxic derivatives, 3-amino-6-hydroxy 1,4-dimethyl-9H-carbazole, displays an activity similar to that of N2-methyl-9-hydroxy ellipticinium acetate (NMHE). These results, together with those previously published by us, allow a detailed analysis of structure-activity relationships in the 9H-carbazole and 1,4-dimethyl-9H-carbazole series. For the 3-amino-1,4-dimethyl 9H-carbazole derivatives, a mechanism of action similar to that of ellipticine derivatives is proposed.
• Microwave-Assisted Solid-Acid-Catalyzed Friedel-Crafts Alkylation and Electrophilic Annulation of Indoles Using Alcohols as Alkylating Agents
  作者：Béla Török、Aditya Kulkarni、Phong Quang

  DOI：10.1055/s-0029-1217052

  日期：2009.12

  Alcohols are considered environmentally benign alkylating agents since the only by-product generated in their reactions is water. Herein, we report a microwave-assisted Friedel-Crafts alkylation and electrophilic annulation of indoles using alcohols as alkylating agents. Alkylation of indoles using tert-butyl alcohol gives 3-substituted tert-butylindoles. A domino electrophilic annulation/aromatization­ of indoles using hexane-2,5-diol results in the formation of substituted carbazoles. The reaction is catalyzed by a strong, solid-acid catalyst montmorillonite K-10. The products were obtained in good yields and high selectivities.

  醇类被认为是环境友好的烷基化试剂，因为它们反应的唯一副产物是水。本文报道了利用微波辅助的Friedel-Crafts烷基化和亲电环化反应，使用醇作为烷基化试剂对吲哚进行修饰。使用叔丁醇对吲哚进行烷基化反应，得到3-取代的叔丁基吲哚。通过使用己二醇-2,5作为反应剂，可实现吲哚的亲电环化/芳构化级联反应，生成取代的咔唑。该反应由强固体酸催化剂蒙脱石K-10催化。产物获得了良好的产率和高度选择性。