N-(p-tolyl)-1H-indole-3-carboxamide | 26977-46-8

• 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-(p-tolyl)-1H-indole-3-carboxamide
• 英文别名: N-(4-methylphenyl)-1H-indole-3-carboxamide
• CAS: 26977-46-8
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: MIJAAWLSPYITAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吲哚-3-乙醛酰氯 在 乙酸乙酯 、 1,1,2,2-四氯乙烷 作用下， 生成 N-(p-tolyl)-1H-indole-3-carboxamide
  参考文献：
  名称：

  Notes - Decarbonylation of 3-Indoleglyoxalyl Chloride

  摘要：

  DOI：

  10.1021/jo01096a606

文献信息

• Synthesis of Some Analogs of Indole Phytoalexins Brassinin and Methoxybrassenin B and Their Positional Isomers
  作者：Peter Kutschy、Milan Dzurilla、Mitsuo Takasugi、Adriana Sabová

  DOI：10.1135/cccc19990348

  日期：——

  Treatment of indole-3-carboxylic acid with phosphorus trichloride and subsequent reaction of the obtained acid chloride with potassium thiocyanate afforded indol-3-ylcarbonyl isothiocyanate (13). Its treatment with sodium hydrogensulfide in the presence of methyl iodide lead to the corresponding methyl dithiocarbamate, an oxo derivative of brassinin (oxobrassinin, 14), which by methylation with methyl iodide afforded brassenin B (8). Corresponding 2-isomers, 21 and 23, were obtained by an analogous sequence, starting from indole-2-carboxylic acid. During the preparation of isooxobrassinin (21), which appeared to be unstable in the basic reaction medium, also an imidazo[3,4-a]indole derivative 22 has been isolated as an unexpected side product. Related oxobrassinin analogs and their 2-isomers were prepared by treatment of indol-3- and indol-2-ylcarbonyl isothiocyanate with methanol and amines. In the case of isothiocyanate 13, besides the expected products of nucleophilic addition to NCS group (monothiocarbamate 25a and thiourea derivatives 25b-25g), also the substitution products were obtained. Their formation could be explained by partial decomposition of the starting isothiocyanate to an unstable ketene, which reacts with methanol and amines to afford the corresponding methyl carboxylate 26a and carboxamides 26b-26g. Antifungal activity of the prepared compounds has been examined, using the fungus Bipolaris leersiae. All of the compounds exhibited lower activity than phytoalexin brassinin.

  将吲哚-3-羧酸与三氯化磷反应，然后将得到的酸氯化物与硫氰酸钾反应，得到吲哚-3-基羰基异硫氰酸酯（13）。在甲基碘存在下，用氢亚硫酸钠处理它，得到相应的甲基二硫代氨基甲酸酯，即油菜硫代氨基甲酸酯（氧代油菜硫代氨基甲酸，14），通过用甲基碘进行甲基化，得到油菜硫代氨基甲酸B（8）。类似的序列从吲哚-2-羧酸开始，得到相应的2-异构体21和23。在制备异氧代油菜硫代氨基甲酸（21）的过程中，它在碱性反应介质中似乎不稳定，还分离出一种意外的副产物咪唑并[3,4-a]吲哚衍生物22。通过用甲醇和胺处理吲哚-3-和吲哚-2-基羰基异硫氰酸酯，制备了相关的氧代油菜硫代氨基甲酸酯及其2-异构体。在异硫氰酸酯13的情况下，除了预期的亲核加成产物（单硫代氨基甲酸酯25a和硫脲衍生物25b-25g）外，还得到了取代产物。它们的形成可以通过起始异硫氰酸酯部分分解为不稳定的酮烯，后者与甲醇和胺反应，形成相应的甲基羧酸酯26a和羧酰胺26b-26g。使用真菌Bipolaris leersiae检测了所制备化合物的抗真菌活性。所有化合物的活性均低于植物抗生素油菜硫代氨基甲酸。
• 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。
• 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。
• [EN] CELL ADHESION INHIBITORS<br/>[FR] INHIBITEURS DE L'ADHERENCE CELLULAIRE
  申请人：BIOGEN, INC.

  公开号：WO1996022966A1

  公开（公告）日：1996-08-01

  (EN) The present invention relates to novel compounds that are useful for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. This invention also relates to pharmaceutical formulations comprising these compounds and methods of using them for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. The compounds and pharmaceutical compositions of this invention can be used as therapeutic or prophylactic agents. They are particularly well-suited for treatment of many inflammatory and autoimmune diseases.(FR) L'invention concerne de nouveaux composés utiles pour inhiber et prévenir l'adhérence cellulaire, ainsi que les pathologies provoquées par l'adhérence cellulaire. Elle concerne également des compositions pharmaceutiques contenant ces composés, ainsi que des procédés permettant de les utiliser pour inhiber et prévenir l'adhérence cellulaire et les pathologies provoquées par l'adhérence cellulaire. On peut utiliser ces composés et ces compositions pharmaceutiques en tant qu'agents thérapeutiques et prophylactiques. Ils sont particulièrement appropriés pour le traitement de nombreuses maladies inflammatoires et auto-immunes.

  本发明涉及新型化合物，可用于抑制和预防细胞黏附和细胞黏附介导的病理过程。本发明还涉及包含这些化合物的制药配方和使用它们抑制和预防细胞黏附和细胞黏附介导的病理过程的方法。本发明的化合物和制药组合物可用作治疗或预防剂。它们特别适用于治疗许多炎症和自身免疫性疾病。
• Cell adhesion inhibitors
  申请人：——

  公开号：US20030018016A1

  公开（公告）日：2003-01-23

  The present invention relates to novel compounds that are useful for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. This invention also relates to pharmaceutical formulations comprising these compounds and methods of using them for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. The compounds and pharmaceutical compositions of this invention can be used as therapeutic or prophylactic agents. They are particularly well-suited for treatment of many inflammatory and autoimmune diseases.

  本发明涉及新型化合物，其对细胞粘附和细胞粘附介导的病理过程的抑制和预防具有用处。本发明还涉及包含这些化合物的制药配方和使用它们抑制和预防细胞粘附和细胞粘附介导的病理过程的方法。本发明的化合物和制药组合物可用作治疗或预防剂。它们特别适用于治疗许多炎症和自身免疫性疾病。