2,3,4,4a,9,13c-hexahydro-7-isopropyl-1,4a-dimethyl-9-(2-(piperazin-1-yl)ethyl)-1H-dibenzo[a,c]carbazole-1-carboxylic acid methyl ester | 1529761-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,3,4,4a,9,13c-hexahydro-7-isopropyl-1,4a-dimethyl-9-(2-(piperazin-1-yl)ethyl)-1H-dibenzo[a,c]carbazole-1-carboxylic acid methyl ester
• 英文别名: methyl (8S,12R,13S)-8,12-dimethyl-21-(2-piperazin-1-ylethyl)-4-propan-2-yl-21-azapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,5,15,17,19-heptaene-12-carboxylate
• CAS: 1529761-64-5
• 化学式: C₃₃H₄₃N₃O₂
• 分子量: 513.723
• InChiKey: GLPBNKPXUVMLGA-JORIVFIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dehydroabietic acid chloride 在 chromium(VI) oxide 、 盐酸 、 四丁基溴化铵 、 乙酸酐 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 、 sodium hydroxide 作用下， 以 水 、 乙腈 、 苯 为溶剂， 反应 29.0h， 生成 2,3,4,4a,9,13c-hexahydro-7-isopropyl-1,4a-dimethyl-9-(2-(piperazin-1-yl)ethyl)-1H-dibenzo[a,c]carbazole-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of novel N-substituted 1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid as potential antimicrobial agents

  摘要：

  A series of new N-substituted 1H-dibenzo[a,c]carbazole derivatives were synthesized from dehydroabietic acid, and their structures were characterized by IR, H-1 NMR and HRMS spectral data. All compounds were evaluated for their antibacterial and antifungal activities against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas fluorescens) and three fungi (Candida albicans, Candida tropicalis and Aspergillus niger) by serial dilution technique. Some of the synthesized compounds displayed pronounced antimicrobial activity against tested strains with low MIC values ranging from 0.9 to 15.6 mu g/ml. Among them, compounds 6j and 6r exhibited potent inhibitory activity comparable to reference drugs amikacin and ketoconazole. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.009

文献信息

• Synthesis and biological evaluation of novel <i>N</i>-(piperazin-1-yl)alkyl-1<i>H</i>-dibenzo[<i>a</i>,<i>c</i>]carbazole derivatives of dehydroabietic acid as potential MEK inhibitors
  作者：Hao Chen、Chao Qiao、Ting-Ting Miao、A-Liang Li、Wen-Yan Wang、Wen Gu

  DOI：10.1080/14756366.2019.1655407

  日期：2019.1.1

  In this paper, a series of novel 1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid bearing different N-(piperazin-1-yl)alkyl side chains were designed, synthesised and evaluated for their in vitro anticancer activities against three human hepatocarcinoma cell lines (SMMC-7721, HepG2 and Hep3B). Among them, compound 10g exhibited the most potent activity against three cancer cell lines with

  在本文中，设计，合成和评估一系列新型的脱氢松香酸的1H-二苯并[a，c]咔唑衍生物，它们带有不同的N-（哌嗪-1-基）烷基侧链，并在体外对三种人的抗癌活性进行了评估。肝癌细胞系（SMMC-7721，HepG2和Hep3B）。其中，化合物10g对三种癌细胞具有最强的活性，IC50值分别为1.39±0.13、0.51±0.09和0.73±0.08 µM。在激酶抑制试验中，化合物10g可以显着抑制MEK1激酶活性，IC50为0.11±0.02 µM，这已通过蛋白质印迹分析和分子对接研究得到证实。此外，化合物10g可能会升高细胞内ROS水平，降低线粒体膜电位，破坏细胞膜完整性，最终导致HepG2细胞的凋亡和凋亡。因此，化合物10g可能是有效的MEK抑制剂和有希望的抗癌药，值得进一步研究。
• Synthesis and biological evaluation of novel N-substituted 1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid as potential antimicrobial agents
  作者：Wen Gu、Chao Qiao、Shi-Fa Wang、Yun Hao、Ting-Ting Miao

  DOI：10.1016/j.bmcl.2013.11.009

  日期：2014.1

  A series of new N-substituted 1H-dibenzo[a,c]carbazole derivatives were synthesized from dehydroabietic acid, and their structures were characterized by IR, H-1 NMR and HRMS spectral data. All compounds were evaluated for their antibacterial and antifungal activities against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas fluorescens) and three fungi (Candida albicans, Candida tropicalis and Aspergillus niger) by serial dilution technique. Some of the synthesized compounds displayed pronounced antimicrobial activity against tested strains with low MIC values ranging from 0.9 to 15.6 mu g/ml. Among them, compounds 6j and 6r exhibited potent inhibitory activity comparable to reference drugs amikacin and ketoconazole. (C) 2013 Elsevier Ltd. All rights reserved.