6-(1H-indol-3-yl)-5H-benzo[b]carbazole

• 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-(1H-indol-3-yl)-5H-benzo[b]carbazole
• 英文别名: 6-(1H-indol-3-yl)benzo[b]carbazole；6-(3-indolyl)benzo[b]carbazole
• 化学式: C₂₄H₁₆N₂
• 分子量: 332.404
• InChiKey: DCTFRDFVCTYXAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  吲哚 、 邻苯二甲醛 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以79%的产率得到6-(1H-indol-3-yl)-5H-benzo[b]carbazole
  参考文献：
  名称：

  机理控制的区域选择性合成吲哚基苯并[ b ]咔唑

  摘要：

  在酸催化剂的存在下，由2，3-未取代的吲哚和邻苯二甲醛的组合可以容易地并且以高收率合成苯并[ b ]咔唑。在氯仿中使用磷酰氯可快速反应，生成11-（3-吲哚基）苯并[ b ]咔唑，而在甲醇中使用对甲苯磺酸，则反应缓慢，并生成异构体6-（3-吲哚基）苯并[ b ]咔唑。

  DOI：

  10.1016/s0040-4039(99)01268-x

文献信息

• Novel Effective Small-Molecule Antibacterials against Enterococcus Strains
  作者：Kerolos Ashraf、Kaveh Yasrebi、Tobias Hertlein、Knut Ohlsen、Michael Lalk、Andreas Hilgeroth

  DOI：10.3390/molecules22122193

  日期：——

  Enterococcus species cause increasing numbers of infections in hospitals. They contribute to the increasing mortality rates, mostly in patients with comorbidities, who suffer from severe diseases. Enterococcus resistances against most antibiotics have been described, including novel antibiotics. Therefore, there is an ongoing demand for novel types of antibiotics that may overcome bacterial resistances. We discovered a novel class of antibiotics resulting from a simple one-pot reaction of indole and o-phthaldialdehyde. Differently substituted indolyl benzocarbazoles were yielded. Both the indole substitution and the positioning at the molecular scaffold influence the antibacterial activity towards the various strains of Enterococcus species with the highest relevance to nosocomial infections. Structure-activity relationships are discussed, and the first lead compounds were identified as also being effective in the case of a vancomycin resistance.

  肠球菌引起的医院感染越来越多。肠球菌导致死亡率上升，其中大部分是患有严重疾病的合并症患者。肠球菌对大多数抗生素都有耐药性，包括新型抗生素。因此，人们一直需要能克服细菌耐药性的新型抗生素。我们发现了一种新型抗生素，它是由吲哚和邻苯甲醛通过简单的一锅反应生成的。我们得到了不同取代的吲哚基苯并咔唑。吲哚的取代和分子支架上的位置都会影响其对各种肠球菌菌株的抗菌活性，而这些菌株与医院内感染的关系最为密切。对结构-活性关系进行了讨论，并确定了第一种先导化合物在万古霉素耐药的情况下也有效。
• Fe-catalyzed cycloaddition of indoles and o-phthalaldehyde for the synthesis of benzo[b]carbazoles with TMSCl- or acid-responsive properties
  作者：Jin-Feng Zou、Hu Wang、Li Li、Zheng Xu、Ke-Fang Yang、Li-Wen Xu

  DOI：10.1039/c4ra08012b

  日期：——

  one-pot iron-catalyzed cycloaddition of indole and o-phthalaldehyde afforded indolyl benzo[b]carbazoles via sequential carbon–carbon bond-forming addition, cyclization involving intramolecular alkylation and aromatization forming a benzene ring. In addition, the fluorescence properties of such indolyl benzo[b]carbazoles were investigated, in which significant changes in fluorescent intensity were observed

  一锅铁催化的吲哚和邻苯二甲醛环加成反应通过顺序形成碳-碳键的加成，涉及分子内烷基化的环化和芳构化形成苯环，得到吲哚基苯并[ b ]咔唑。另外，研究了这种吲哚基苯并[ b ]咔唑的荧光性质，其中在添加三甲基氯硅烷（TMSCl）或三氟乙酸（TFA）时观察到荧光强度的显着变化。
• Antistaphylococcal evaluation of indole–naphthalene hybrid analogs
  作者：Kerolos Ashraf、Kaveh Yasrebi、Emmanuel Tola Adeniyi、Tobias Hertlein、Knut Ohlsen、Michael Lalk、Frank Erdmann、Andreas Hilgeroth

  DOI：10.2147/dddt.s184965

  日期：——

  Resistance developments against established antibiotics are an emerging problem for antibacterial therapies. Infections with Staphylococcus aureus and methicillin-resistant S. aureus (MRSA) have become more difficult to treat with standard antibiotics that often fail, especially against MRSA. In consequence, novel antibiotics are urgently needed. Antibiotics from natural sources own complicated structures that cause difficulties for a chemical synthetic production. We developed novel small-molecule antibacterials that are easily accessible in a simple one-pot synthesis. The central indolonaphthalene core is substituted with indole residues at various positions. Both the varied indole substitutions and their positions at the molecular scaffold influence the determined antibacterial activity against the evaluated Staphylococcus strains. Best activities have been found for 5-chloro, -cyano, and -hydroxyl indole substitutions. Therefore, first promising lead compounds could be identified that are nontoxic in human HEK and SH-SY5Y cells and exceed the activity of used standard antibiotics, especially against MRSA.
• Succinimide-N-sulfonic acid catalyzed synthesis of bis(indolyl)methane and coumarin derivatives under mild conditions
  作者：Farhad Shirini、Nader Ghaffari Khaligh

  DOI：10.1016/s1872-2067(12)60669-x

  日期：2013.10

  A mild and simple procedure is described for the synthesis of bis(indolyl)methane and coumarin derivatives using succinimide-N-sulfonic acid as an efficient, cheap, and reusable catalyst under mild conditions. (C) 2013, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.
• DERIVATE VON INDOLEN UND CARBAZOLEN, VERFAHREN ZU IHRER HERSTELLUNG SOWIE DEREN VERWENDUNG ALS MRSA-SENSITIVE ANTIBIOTIKA
  申请人：Martin-Luther-Universität Halle-Wittenberg

  公开号：EP2968271A1

  公开（公告）日：2016-01-20