2,8-diphenyl-1,2,3,8-tetrahydroindolo[2,3-b]carbazole | 27152-07-4

• 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: 2,8-diphenyl-1,2,3,8-tetrahydroindolo[2,3-b]carbazole
• 英文别名: 2,8-Diphenyl-1,2,3,8-tetrahydro-cyclohexa<1,2-b:5,4-b'>diindol；6,12-diphenyl-5,6,7,12-tetrahydro-indolo[2,3-b]carbazole；6,12-Diphenyl-5,6,7,12-tetrahydro-indolo[2,3-b]carbazol；6,12-diphenyl-5,6,7,12-tetrahydroindolo[2,3-b]carbazole
• CAS: 27152-07-4
• 化学式: C₃₀H₂₂N₂
• 分子量: 410.518
• InChiKey: XIROMUDTXRCSMD-UHFFFAOYSA-N

物化性质

• 沸点：
  638.7±50.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  32.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  31.58
• 氢给体数：
  2.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 2,8-diphenyl-1,2,3,8-tetrahydroindolo[2,3-b]carbazole
  参考文献：
  名称：

  Passerini; Albani, Gazzetta Chimica Italiana, 1935, vol. 65, p. 933,937

  摘要：

  DOI：

文献信息

• Novel Synthesis of 6,12-dihydroindolo[3,2-<i>b</i>]carbazoles catalysed by <i>p</i>-toluenesulfonic acid
  作者：Can Jin、Bo Zhang、Chuanming Yu、Weike Su

  DOI：10.3184/030823409x424858

  日期：2009.3

  An efficient and straightforward procedure for the synthesis of 6,12-dihydroindolo[3,2-b]carbazoles has been achieved through the one-pot reaction of indole with aromatic aldehydes in the presence of p-toluenesulfonic acid (pTSA) as the catalyst.

  在对甲苯磺酸 (pTSA) 作为催化剂存在下，吲哚与芳香醛的一锅反应实现了合成 6,12-二氢吲哚并[3,2-b]咔唑的一种高效且直接的方法.
• Synthesis, cytostatic evaluation and structure activity relationships of novel bis-indolylmethanes and their corresponding tetrahydroindolocarbazoles
  作者：Mardia T. El Sayed、Khadiga M. Ahmed、Kazem Mahmoud、Andreas Hilgeroth

  DOI：10.1016/j.ejmech.2014.12.008

  日期：2015.1

  BIMs (bis-indolylmethanes) (1(a-n)) were synthesized using glacial acetic acid as a protic acid for promotion of the condensation reaction of indoles with aldehydes in high yields (86-98 %). Corresponding tetrahydroindolo[2,3-b]carbazoles (2(a-m)) were synthesized via condensation of BIMs with aldehydes. Ten synthesized compounds have been submitted to the national cancer institute in the USA where all the submitted samples have been selected for one dose screening. As a result of the one dose screening of BIMs (1(e,f,h,i,n)) and of the indolocarbazoles (2(e,f,h,i,j)) the average highest cytostatic effects was recorded here for the BIM 1(h) and the indolocarbazole (2e) that showed the lowest mean values of "47.39%" and of "21.63%" respectively. Both compounds (1(h) and 2(e)) were further tested in five dose screening with the tested substance (1(h)) being significantly more sensitive for several cancers cell line as corresponding to their GI(50) values. Furthermore, the basically substituted derivative 2(e) showed the highest antipoliferative activity in a nanomolar scale towards the three selected cancers cell lines Non small lung cell NCI-H460 with GI(50) "616 nM", Ovarian Cancer cell line OVCAR-4 with GI(50) "562 nM" and Breast Cancer cell line MCF7 with GI(50) "930 nM". (C) 2014 Elsevier Masson SAS. All rights reserved.
• Passerini; Bonciani, Gazzetta Chimica Italiana, 1933, vol. 63, p. 142
  作者：Passerini、Bonciani

  DOI：——

  日期：——
• v Dobeneck; Prietzel, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1955, vol. 299, p. 214,224
  作者：v Dobeneck、Prietzel

  DOI：——

  日期：——