6,12-di(benzo[d][1,3]dioxol-5-yl)-5,6,11,12-tetrahydroindolo[3,2-b]carbazole | 1190695-69-2

• 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: 6,12-di(benzo[d][1,3]dioxol-5-yl)-5,6,11,12-tetrahydroindolo[3,2-b]carbazole
• 英文别名: 6,12-di(benzo[d][1,3]dioxol-5-yl)-6,12-dihydroindolo[3,2-b]carbazole；6,12-Bis(1,3-benzodioxol-5-yl)-5,6,11,12-tetrahydroindolo[3,2-b]carbazole
• CAS: 1190695-69-2
• 化学式: C₃₂H₂₂N₂O₄
• 分子量: 498.538
• InChiKey: CCGWPUHYKJCGPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  38.0
• 可旋转键数：
  2.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.5
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6,12-di(benzo[d][1,3]dioxol-5-yl)-5,6,11,12-tetrahydroindolo[3,2-b]carbazole 在 potassium hydroxide 作用下， 以 邻二甲苯 、 水 、 二甲基亚砜 为溶剂， 反应 11.0h， 生成 6,12-Bis(1,3-benzodioxol-5-yl)-5,11-bis(prop-2-ynyl)indolo[3,2-b]carbazole
  参考文献：
  名称：

  TW2022/31640

  摘要：

  公开号：
• 作为产物：
  描述：

  吲哚 、 胡椒醛 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以92%的产率得到6,12-di(benzo[d][1,3]dioxol-5-yl)-5,6,11,12-tetrahydroindolo[3,2-b]carbazole
  参考文献：
  名称：

  对甲苯磺酸催化合成6,12-二氢吲哚并[3,2- b ]咔唑

  摘要：

  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.

  DOI：

  10.3184/030823409x424858

文献信息

• Tetrahydroindolocarbazoles (THICZs) as new class of urokinase (uPA) inhibitors: Synthesis, anticancer evaluation, DNA-damage determination, and molecular modelling study
  作者：Marwa A.M.Sh. El-Sharief、Mohamed H. El-Naggar、Entesar M. Ahmed、Shahenda M. El-Messery、Abeer E. Mahmoud、Mamdouh M. Ali、Lamiaa M. Salem、Karima F. Mahrous、Mardia T. El Sayed

  DOI：10.1016/j.bioorg.2018.06.033

  日期：2018.10

  Tetrahydroindolocarbazoles (THICZs) with versatile substituents, have been designed, synthesized, structure characterized, then investigated for their in-vitro anticancer screening, urokinase inhibition (uPA) evaluated, DNA-damage determination was further explored. Compounds 5, 8, 10 and 17 displayed the most promising antitumor activities against the breast cancer cell line as compared to the standard drug, doxorubicin with IC50 = 5.24 +/- 0.37, 4.00 +/- 0.52, 7.20 +/- 0.90 and 9.60 +/- 1.10 mu g/ml (versus 3.30 +/- 0.48 mu g/ml for doxorubicin). Compounds 5, 8, 10 and 17 represents the most significant uPA inhibitors of our study with IC50 of 3.80, 2.70. 4.75, 10.80 (ng/ml) respectively. The expression levels of CDKN2A gene were decreased in 8, 10 and 17 cell lines as compared to those in positive control samples. Cell lines treated with 5, 8, 10 and 17 clearly observed a high score of damaged DNA cells. A deeper examination revealed that our hetroaromatics showed an extensive hydrogen bonding interactions that is required in the S pocket which is important for activity Arg 217, Gly 219, Gly 216, Lys 143 and Ser 190. So we present THICZs as promising uPA inhibitors expected as significant promise for further development as anti-invasiveness drugs.