11-(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: 11-(1H-indol-3-yl)-5H-benzo[b]carbazole
• 英文别名: 11-(3-indolyl)benzo[b]carbazole
• 化学式: C₂₄H₁₆N₂
• 分子量: 332.404
• InChiKey: BCYOUSYBTLGDBG-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

• 作为反应物：
  描述：

  乙酸酐 、 11-(1H-indol-3-yl)-5H-benzo[b]carbazole 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以5%的产率得到1-(11-(1H-indol-3-yl)-5H-benzo[b]carbazol-5-yl)ethan-1-one
  参考文献：
  名称：

  Antistaphylococcal evaluation of indole–naphthalene hybrid analogs

  摘要：

  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.

  DOI：

  10.2147/dddt.s184965
• 作为产物：
  描述：

  吲哚 、 邻苯二甲醛 在 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以58%的产率得到11-(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

• Mechanism-controlled regioselective synthesis of indolyl benzo[b]carbazoles
  作者：David StC. Black、Donald C. Craig、Mardi Santoso

  DOI：10.1016/s0040-4039(99)01268-x

  日期：1999.9

  Benzo[b]carbazoles can be synthesised readily and in good yields from the combination of 2,3-unsubstituted indoles and o-phthaldialdehyde in the presence of acid catalysts. Use of phosphoryl chloride in chloroform gives rapid reactions and yields 11-(3-indolyl)benzo[b]carbazoles, whereas the use of p-toluenesulfonic acid in methanol gives slow reactions and yields the isomeric 6-(3-indolyl)benzo[b]carbazoles

  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。
• 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
• [DE] DERIVATE VON INDOLEN UND CARBAZOLEN, VERFAHREN ZU IHRER HERSTELLUNG SOWIE DEREN VERWENDUNG ALS MRSA-SENSITIVE ANTIBIOTIKA<br/>[EN] DERIVATIVES OF INDOLES AND CARBAZOLES, METHOD FOR THE PRODUCTION THEREOF AND USE THEREOF AS MRSA-SENSITIVE ANTIBIOTICS<br/>[FR] DÉRIVÉS D'INDOLS ET DE CARBAZOL, PROCÉDÉ POUR LES PRÉPARER ET LEUR UTILISATION COMME ANTIBIOTIQUE ACTIFS SUR LE SARM
  申请人：MARTIN LUTHER UNIVERSITÄT HALLE WITTENBERG

  公开号：WO2014139512A1

  公开（公告）日：2014-09-18

  Die erfindungsgemäß entwickelten 1,3-Bis(indol-3-yl)-tetrahydrocyclopenta[b]indole, 1,4-Bis(indol-3-yl)-tetrahydrocarbazole, 6,10-Bis(indol-3-yl)-hexahdrocyclohepta[b]indole, 6,11-Bis(indol-3-yl)-hexahydrocycloocta[b]indole und 11-(lndol-3-yl)-benzo[b]carbazole der allgemeinen Formeln (I) und (II) wirken selektiv hemmend auf das Wachstum von S. aureus und dem Methicillin-resistenten S. aureus (MRSA) im unteren micromolaren Konzentrationsbereich bei einem Screening an weiteren grampositiven und gramnegativen Bakterien und Pilzen. Die Darstellung der Verbindungen aus Dialdehyden und Indolen bei Raumtemperatur in Eisessig stellt ein schonendes Verfahren dar, in dem die neuen Strukturen in teilweise sehr guten Ausbeuten zugänglich sind.
• Antistaphylococcal evaluation of indole&amp;ndash;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.
• 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。