N-(4-chlorophenyl)-1H-indole-3-carboxamide | 26977-44-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-chlorophenyl)-1H-indole-3-carboxamide
• CAS: 26977-44-6
• 化学式: C₁₅H₁₁ClN₂O
• 分子量: 270.718
• InChiKey: GKHUQLGABBRKDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)-1H-indole-3-carboxamide 在 劳森试剂 、 溴 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 1.25h， 生成 2-(1H-indol-3-yl)-6-chloro-1,3-benzothiazole
  参考文献：
  名称：

  Synthesis of 4,6-Disubstituted-2-(1H-indol-3-yl)benzothiazoles

  摘要：

  描述了一种新的四步合成方法，用于合成取代的2-(1H-吲哚-3-基)苯并噻唑，使用N^3-苯基-1H-吲哚-3-羰硫胺作为关键中间体。通过红外光谱、^1H、^13C核磁共振和质谱方法确定了所得产物的结构。

  DOI：

  10.1135/cccc20040453
• 作为产物：
  描述：

  4-氯-N-羟基苯甲酰胺 在 potassium tert-butylate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 N-(4-chlorophenyl)-1H-indole-3-carboxamide
  参考文献：
  名称：

  1,4,2-Dioxazol-5-ones 作为异氰酸酯等价物：吲哚的化学选择性非金属催化羧酰胺化

  摘要：

  已知 1,4,2-Dioxazol-5-ones 在热条件下会发生脱羧反应，然后发生 Lossen 重排以产生异氰酸酯。本文描述的是通过吲哚原位捕获异氰酸酯，以良好至优异的产率得到吲哚-3-羧酰胺。

  DOI：

  10.1055/s-0041-1737338

文献信息

• Chemoselective Cu-catalyzed synthesis of diverse <i>N</i>-arylindole carboxamides, β-oxo amides and <i>N</i>-arylindole-3-carbonitriles using diaryliodonium salts
  作者：Manish Kumar Mehra、Monika Malik、Bintu Kumar、Dalip Kumar

  DOI：10.1039/d0ob02247k

  日期：——

  Chemoselective copper-catalyzed synthesis of diverse N-arylindole-3-carboxamides, β-oxo amides and N-arylindole-3-carbonitriles from readily accessible indole-3-carbonitriles, α-cyano ketones and diaryliodonium salts has been developed. Diverse N-arylindole-3-carboxamides and β-oxo amides were successfully achieved in high yields under copper-catalyzed neutral reaction conditions, and the addition

  已经开发了由易获得的吲哚-3-腈，α-氰基酮和二芳基碘鎓盐化学合成的铜催化的各种N-芳基吲哚-3-羧酰胺，β-氧代酰胺和N-芳基吲哚-3-腈的化学合成方法。在铜催化的中性反应条件下，成功地以高收率成功地获得了多种N-芳基吲哚-3-羧酰胺和β-氧代酰胺，加入有机碱（DIPEA）产生了完全不同的选择性模式，从而生产N-芳基吲哚- 3-腈。此外，通过吲哚喹诺酮和N -（（1 H-吲哚-3-基）甲基）苯胺并通过一步克级合成天然存在的头孢烯酮A类似物。
• Antimicrobial Evaluation, Molecular Docking and ADME Properties of Indole Amide Derivatives
  作者：Derya Doğanay、Sevval M. Özcan、Ahmet M. Şentürk、Süreyya Ölgen

  DOI：10.2174/1570180818666211006122758

  日期：2022.5

  Besides the viral infections, bacterial infections can cause serious and lifethreatening complications and drug resistance is an important problem to fight bacterial infections. Therefore, it is important to discover novel antimicrobial agents to fight such infections.

  Several indole containing antimicrobial drug development studies have been reported in literature that provided strong evidence for good antimicrobial activities against a variety of microorganisms. Taken into consideration from these findings, antimicrobial properties of previously synthesized 16 indole amide derivatives were evaluated by in vitro tests against 14 different microorganisms, and also molecular docking and in silico prediction studies were used to identify structure-activity relationship of compounds.

  Antimicrobial activity of compounds was determined by disc diffusion and tube dilution methods. Molecular docking of compounds was studied to determine the relationship between the structure of compounds with DNA gyrase interactions of microorganisms by using the version of Autodock vina 4.2.6. Mol inspiration and Swiss ADME prediction online software programs were also used to identify drug-like properties of compounds.

  The results showed that some compounds exhibited quite pronounced antibacterial and antifungal activities compared to reference drugs. These results were also supported by molecular docking studies and in silico ADME calculations presented that all tested compounds obey Lipinski’s Rule of Five and are metabolized by CYP450 enzymes.

  It can be concluded that these results can be taken as a reference in the development of new indole-based antimicrobial agents.

  背景：除了病毒感染外，细菌感染也会导致严重和危及生命的并发症，而药物耐药性是对抗细菌感染的一个重要问题。因此，发现新型抗微生物药物对抗这些感染非常重要。 目标：文献中报道了几项含有吲哚类抗微生物药物的开发研究，提供了强有力的证据表明这些药物对多种微生物具有良好的抗微生物活性。基于这些发现，通过体外测试评估了先前合成的16种吲哚酰胺衍生物的抗微生物性质，针对14种不同的微生物进行了分子对接和计算机预测研究，以确定化合物的结构-活性关系。 方法：通过盘扩散和管稀释法确定化合物的抗微生物活性。使用Autodock vina4.2.6版本对化合物进行分子对接研究，以确定化合物的结构与微生物DNA酶互作之间的关系。还使用Mol inspiration和Swiss ADME预测在线软件程序来确定化合物的药物样性质。 结果：结果表明，一些化合物与参考药物相比表现出相当显著的抗菌和抗真菌活性。这些结果也得到了分子对接研究的支持，并且计算机模拟ADME显示，所有测试化合物都遵守Lipinski的五项规则，并且被CYP450酶代谢。 结论：可以得出结论，这些结果可以作为开发新型基于吲哚的抗微生物药物的参考。
• TREATMENTS FOR ARTERIAL STIFFENING, HYPERTENSION AND ANTI-AGING
  申请人：The Board of Regents of the University of Oklahoma

  公开号：US20180338951A1

  公开（公告）日：2018-11-29

  Compositions and methods for the treatment and amelioration of arterial stiffness, hypertension, and/or arterial aging in a subject. In certain embodiments, the active agents of the compositions provide anti-aging treatments by causing arterial remodeling by decreasing collagen production and increasing elastin production in a subject. In certain embodiments, the active agents can be used to treat a subject having diabetes or a diabetes-related disease or condition, such as but not limited to, Type 1 diabetes mellitus (T1DM), Type 2 diabetes mellitus (T2DM), and hyperinsulenima (pre-diabetes). In certain embodiments, the active agents can be used to treat subjects having hypertension, aortic disease, cardiovascular disease, including heart failure (such as congestive heart failure), kidney disease, osteoporosis, Alzheimer's disease, infertility, and emphysema.
• 1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: Chemoselective Non-Metal-Catalyzed Carboxamidation of Indoles
  作者：Jigar Y. Soni、Anand Vala、Deepa Parmar、Rahul Rayani、Rakesh Kusurkar、Ramakrishna Guduru、Uttam Kaneriya、Uday Gondaliya、Nirali Parmar

  DOI：10.1055/s-0041-1737338

  日期：2022.4

  1,4,2-Dioxazol-5-ones are known to undergo decarboxylation under thermal conditions followed by Lossen’s rearrangement to give isocyanates. Described herein is the in situ trapping of the isocyanates by indoles to give indole-3-carboxamides in good to excellent yields.

  已知 1,4,2-Dioxazol-5-ones 在热条件下会发生脱羧反应，然后发生 Lossen 重排以产生异氰酸酯。本文描述的是通过吲哚原位捕获异氰酸酯，以良好至优异的产率得到吲哚-3-羧酰胺。
• Synthesis of 4,6-Disubstituted-2-(1H-indol-3-yl)benzothiazoles
  作者：Janka Záletová、Milan Dzurilla、Peter Kutschy、Pavel Pazdera、Vladimír Kováčik、Juraj Aldölfi、Slávka Bekešová

  DOI：10.1135/cccc20040453

  日期：——

  A new four-step synthesis of substituted 2-(1H-indol-3-yl)benzothiazoles is described, using N³-phenyl-1H-indole-3-carbothioamides as key intermediates. The structure of the obtained products was determined by IR, ¹H, ¹³C NMR and MS spectral methods.

  描述了一种新的四步合成方法，用于合成取代的2-(1H-吲哚-3-基)苯并噻唑，使用N^3-苯基-1H-吲哚-3-羰硫胺作为关键中间体。通过红外光谱、^1H、^13C核磁共振和质谱方法确定了所得产物的结构。