dimethyl-1,4 (diethoxy-2,2 ethylaminomethyl)-3 methoxy-6 carbazole | 103771-52-4

• 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: dimethyl-1,4 (diethoxy-2,2 ethylaminomethyl)-3 methoxy-6 carbazole
• 英文别名: 3-(2,2-diethoxyethylaminomethyl)-6-methoxy-1,4-dimethylcarbazole；(2,2-diethoxyethyl)[(6-methoxy-1,4-dimethyl-9H-carbazol-3-yl)methyl]amine；2,2-diethoxy-N-((6-methoxy-1,4-dimethyl-9H-carbazol-3-yl)methyl)ethanamine；2,2-diethoxy-N-[(6-methoxy-1,4-dimethyl-9H-carbazol-3-yl)methyl]ethanamine
• CAS: 103771-52-4
• 化学式: C₂₂H₃₀N₂O₃
• 分子量: 370.492
• InChiKey: AGWYGHJOHIVGBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.51
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl-1,4 (diethoxy-2,2 ethylaminomethyl)-3 methoxy-6 carbazole 在 sodium hydride 、 sodium carbonate 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 9-甲氧基-5,6,11-三甲基-6H-吡啶并[4,3-b]咔唑
  参考文献：
  名称：

  Ellipticines and 9-acridinylamines as inhibitors of d-alanine:d-alanine ligase

  摘要：

  D-Alanine:D-alanine ligase (Ddl), an intracellular bacterial enzyme essential for cell wall biosynthesis, is an attractive target for development of novel antimicrobial drugs. This study focused on an extensive evaluation of two families of Ddl inhibitors encountered in our previous research. New members of both families were obtained through similarity search and synthesis. Ellipticines and 9-acridinylamines were both found to possess inhibitory activity against Ddl from Escherichia coli and antimicrobial activity against E. coli and Staphylococcus aureus. Ellipticines with a quaternary methylpyridinium moiety were the most potent among all studied compounds, with MIC values as low as 2 mg/L in strains with intact efflux mechanisms. Antimicrobial activity of the studied compounds was connected to membrane damage, making their development as antibacterial drug candidates unlikely unless analogues devoid of this nonspecific effect can be discovered. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.020
• 作为产物：
  描述：

  dimethyl-1,4 (diethoxy-2,2 ethyliminomethyl)-3 methoxy-6 carbazole 在 sodium tetrahydroborate 、 乙醇 作用下， 反应 1.0h， 生成 dimethyl-1,4 (diethoxy-2,2 ethylaminomethyl)-3 methoxy-6 carbazole
  参考文献：
  名称：

  一种制备玫瑰树碱或取代玫瑰树碱的方法

  摘要：

  本发明涉及制备玫瑰树碱的合成工艺。采用六步反应经三步结晶分离得到玫瑰树碱，目标产物总收率高，且中间产物和目标产物无需柱层析分离，特别适合于放大量制备。

  公开号：

  CN111100123B

文献信息

• An efficient modification of ellipticine synthesis and preparation of 13-hydroxyellipticine
  作者：Martin Dračínský、Jan Sejbal、Barbora Rygerová、Marie Stiborová

  DOI：10.1016/j.tetlet.2007.07.160

  日期：2007.9

  A simple modification of a previously published ellipticine synthesis is reported, which decreases the reaction time and increases the yield and purity of the product. Benzylic oxidations of 1,4-dimethylcarbazole and ellipticine derivatives were studied and 13-hydroxyellipticine was prepared.

  据报道，对先前公开的玫瑰树碱合成进行了简单的修改，其减少了反应时间并提高了产物的收率和纯度。研究了1，4-二甲基咔唑和玫瑰树碱衍生物的苯甲酰氧化反应，制备了13-羟基玫瑰树碱。
• 一种NSC69187及其衍生物的合成方法与应用
  申请人：南方医科大学

  公开号：CN115650973A

  公开（公告）日：2023-01-31

  本发明公开了一种NSC69187及其衍生物的合成方法与应用，具体的说，发明所制备的NSC69187衍生物CX24能够特异性抑制TLR3，且具有良好的体内外抗炎活性；在体内动脉粥样硬化模型中，可以抑制斑块形成、提高斑块稳定性以及减少病变部位炎症浸润，表现出良好的抗动脉粥样硬化作用，为临床动脉粥样硬化治疗提供新的分子选择和理论依据。
• Martin-Onraet; Gansser; Plat, Farmaco, Edizione Scientifica, 1985, vol. 40, # 10, p. 745 - 754
  作者：Martin-Onraet、Gansser、Plat、et al.

  DOI：——

  日期：——
• Discovery of an ellipticine derivative as TLR3 inhibitor against influenza A virus and SARS-CoV-2
  作者：Yue Pan、Qiuyue Fu、Yinyan Li、Jie Yang、Kui Cheng

  DOI：10.1016/j.bmcl.2024.129672

  日期：2024.3