6-甲氧基-1-(苯基磺酰基)-1H-吲哚 | 56995-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 6-甲氧基-1-(苯基磺酰基)-1H-吲哚
• 英文名称: 1-(benzenesulfonyl)-6-methoxy-indole
• 英文别名: 6-methoxy-1-(phenylsulfonyl)-1H-indole；1-(benzenesulfonyl)-6-methoxyindole
• CAS: 56995-13-2
• 化学式: C₁₅H₁₃NO₃S
• 分子量: 287.339
• InChiKey: FYGDGGRRRGDZGP-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  483.9±37.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)
• 溶解度：
  2.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-甲氧基-1-(苯基磺酰基)-1H-吲哚 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以63%的产率得到6-hydroxy-1-(phenylsulfonyl)indole
  参考文献：
  名称：

  [EN] (AZA)INDOLE-, BENZOTHIOPHENE-, AND BENZOFURAN-3-SULFONAMIDES
  [FR] (AZA)INDOLE, BENZOTHIOPHÈNE ET BENZOFURAN-3-SULFONAMIDES

  摘要：

  揭示了具有GPR17调节特性的磺胺类化合物，可用于治疗或预防各种中枢神经系统和其他疾病，特别是用于预防和治疗髓鞘疾病或紊乱。

  公开号：

  WO2018122232A1
• 作为产物：
  描述：

  间氨基苯甲醚 在 吡啶 、 三氟化硼乙醚 、 碳酸氢钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 6-甲氧基-1-(苯基磺酰基)-1H-吲哚
  参考文献：
  名称：

  Synthesis and biological evaluation of new 3-(6-hydroxyindol-2-yl)-5-(Phenyl) pyridine or pyrazine V-Shaped molecules as kinase inhibitors and cytotoxic agents

  摘要：

  We here report the synthesis and biological evaluation of new 3-[(2-indolyl)]-5-phenyl-3,5-pyridine, 3-[(2-indolyl)]-5-phenyl-2,4-pyridine and 3-[(2-indolyl)]-5-phenyl-2,6-pyrazine derivatives designed as potential CDK inhibitors. Indoles and phenyls were used to generate several substitutions of the pyridine and pyrazine rings. The synthesis included Stille or Suzuki type reactions, which were carried out on the 3,5-dibromopyridine, 2,4-dichloropyridine and 2,6-dichloro-1-4-pyrazine moieties. Cell effects of the V-shaped family were in the micromolar range. Kinase assays were conducted and showed that compound 11 inhibited CDK5 with an inhibitory concentration of 160 nM with a moderate selectivity over GSK3 compared to the reference C which exhibited a slightly lower activity on CDK5 (1.5 mu M). Compound 11 was also found to be the most potent compound in the series and was identified as a new lead for DYRK1A inhibitor discovery (IC50 = 60 nM). Docking studies were carried out in order to investigate the inhibition of DYRK1A. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.048

文献信息

• [EN] IMIDAZO-PYRIDINE COMPOUNDS AS PAD INHIBITORS<br/>[FR] COMPOSÉS IMIDAZO-PYRIDINE À UTILISER EN TANT QU'INHIBITEURS DE PAD
  申请人：JUBILANT BIOSYS LTD

  公开号：WO2019077631A1

  公开（公告）日：2019-04-25

  Heterocyclic compounds of Formula (I), (II), and (III) are described herein along with their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof. The compounds described herein, their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosis, cutaneous lupus erythematosis, ulcerative colitis, cancer, cystic fibrosis, asthma, multiple sclerosis and psoriasis. The process of preparation of the compounds of Formula (I), (II), and (III), their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof, along with a pharmaceutical composition comprising a compound of Formula (I), Formula (II), Formula (III), or a pharmaceutically acceptable salt thereof have also been described.

  公式（I）、（II）和（III）的杂环化合物以及它们的多晶形态、立体异构体、前药、溶剂合物、共晶体、中间体、药学上可接受的盐和代谢物在本文中被描述。本文描述的化合物、它们的多晶形态、立体异构体、前药、溶剂合物、共晶体、中间体、药学上可接受的盐和代谢物是PAD4抑制剂，可能在治疗各种疾病中有用，例如类风湿关节炎、血管炎、系统性红斑狼疮、皮肤红斑狼疮、溃疡性结肠炎、癌症、囊性纤维化、哮喘、多发性硬化和牛皮癣。还描述了制备公式（I）、（II）和（III）的化合物、它们的多晶形态、立体异构体、前药、溶剂合物、共晶体、中间体、药学上可接受的盐和代谢物的过程，以及包含公式（I）、公式（II）、公式（III）的化合物或其药学上可接受的盐的药物组合物。
• Syntheses of 6-Substituted Truncated Yuehchukene Analogues.
  作者：Kin-Fai Cheng、Man-Ki Cheung、Yun Cheung Kong

  DOI：10.1071/c96113

  日期：——

  Facile syntheses of 2-t-butyl-3-(indol-3′-yl)-1,2,3,4-tetrahydrocyclopent[b]indol-6-ol (3), and its 6-methoxy (4) and 6-acetyloxy (5) derivatives are described.

  简单合成 2-t-butyl-3-(indol-3′-yl)-1,2,3,4-tetrahydrocyclopent[b]indol-6-ol (3) 及其 6-甲氧基 (4) 和 6-乙酰氧基 (5) 衍生物。
• Synthesis and biological evaluation of isomeric methoxy substitutions on anti-cancer indolyl-pyridinyl-propenones: Effects on potency and mode of activity
  作者：Christopher J. Trabbic、Sage M. George、Evan M. Alexander、Shengnan Du、Jennifer M. Offenbacher、Emily J. Crissman、Jean H. Overmeyer、William A. Maltese、Paul W. Erhardt

  DOI：10.1016/j.ejmech.2016.06.016

  日期：2016.10

  isomeric methoxy substitutions on the indole ring. Additionally, analogues containing a trimethoxyphenyl group in place of the pyridinyl moiety were evaluated for anticancer activity. The results demonstrate that the location of the methoxy group can alter both the potency and the mechanism of cell death. Remarkably, changing the methoxy from the 5-position to the 6-position switched the biological activity

  某些吲哚基-吡啶基-丙烯酮类似物杀死已经对常规治疗药物产生抗性的胶质母细胞瘤细胞。这些类似物中的一些诱导了一种新形式的非凋亡性细胞死亡，称为变态，而其他类似物则主要引起微管破坏。当存在一个简单的甲氧基时，对5-吲哚取代的容易获得对这两种类型的机理都至关重要。现在，我们报告吲哚环上异构甲氧基取代的合成和生物学效应。另外，评估了含有三甲氧基苯基代替吡啶基部分的类似物的抗癌活性。结果表明，甲氧基的位置可以改变效力和细胞死亡的机制。值得注意的是 将甲氧基从5位更改为6位可将生物学活性从诱导变色转变为破坏微管。后者可以代表具有潜在治疗用途的新型有丝分裂抑制剂的原型。
• [EN] PYRIDINYL AND PYRAZINYL-(AZA)INDOLSULFONAMIDES<br/>[FR] PYRIDINYLE ET PYRAZINYL-(AZA)INDOLSULFONAMIDES
  申请人：UCB PHARMA GMBH

  公开号：WO2019243303A1

  公开（公告）日：2019-12-26

  The present invention relates to pyridinyl and pyrazinyl-(aza)indolsulfonamides having GPR17 modulator activity. The compounds have utility in the treatment of a variety of GPR17-associated disorders.

  本发明涉及具有GPR17调节剂活性的吡啶基和吡嗪基-(氮杂)吲哚磺酰胺。这些化合物在治疗各种与GPR17相关的疾病中具有用途。
• Chiral Thioureas Promote Enantioselective Pictet–Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction
  作者：Rebekka S. Klausen、C. Rose Kennedy、Alan M. Hyde、Eric N. Jacobsen

  DOI：10.1021/jacs.7b06811

  日期：2017.9.6

  mechanism of benzoic acid/thiourea co-catalysis in the asymmetric Pictet–Spengler reaction is reported. Kinetic, computational, and structure–activity relationship studies provide evidence that rearomatization via deprotonation of the pentahydro-β-carbolinium ion intermediate by a chiral thiourea·carboxylate complex is both rate- and enantioselectivity-determining. The thiourea catalyst induces rate acceleration

  报告了不对称Pictet-Spengler反应中苯甲酸/硫脲共催化机理的研究。动力学，计算和结构与活性之间的关系研究提供了证据，表明手性硫脲·羧酸盐配合物通过五氢-β-咔啉离子中间体的去质子化而进行的重质化是速率和对映体选择性的决定因素。硫脲催化剂通过稳定导致并包括最终选择性确定步骤的每个中间体和过渡态，在单独由苯甲酸介导的本底反应中诱导速率加速。用密度泛函理论预测的去质子过渡结构的畸变-相互作用分析表明，由多个氢键组成的支架内的π-π和CH-··π微分相互作用决定了立体选择性。预期本文所述的速率加速和对映体控制的原理对涉及高能中间体去质子化的选择性转化的设计具有一般意义。