4-bromo-N-[2-(1-methyl-1H-indol-3-yl)ethyl]benzenesulfonamide | 1622137-55-6

• 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: 4-bromo-N-[2-(1-methyl-1H-indol-3-yl)ethyl]benzenesulfonamide
• 英文别名: 4-bromo-N-[2-(1-methylindol-3-yl)ethyl]benzenesulfonamide
• CAS: 1622137-55-6
• 化学式: C₁₇H₁₇BrN₂O₂S
• 分子量: 393.304
• InChiKey: HSVZVJUHFLTDPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  59.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-N-[2-(1-methyl-1H-indol-3-yl)ethyl]benzenesulfonamide 在 N-甲基吗啉 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.83h， 生成
  参考文献：
  名称：

  Indole-3-ethylsulfamoylphenylacrylamides: Potent histone deacetylase inhibitors with anti-inflammatory activity

  摘要：

  A series of 2-methyl-1H-indol-3-ethylsulfamoylphenylacrylamides based on LBH589-PXD101 core have been synthesized and evaluated for their histone deacetylase (HDAC) inhibitory and anti-inflammatory activity. In vitro, compounds 9-12 show 2.6-fold better HDAC inhibition and 3-fold better IL-6 suppression compared to LBH589.HCl (1.HCl). Furthermore, these compounds did not show apparent cell viability suppression on macrophages while in contrast, treatment with 1.HCl resulted in significant reduction in cell viability as demonstrated by an MTT assay. Repressed expression of iNOS, COX-2 and reduced phosphorylation of p65 revealed the inhibitory effect of these analogues on inflammatory mediator release which is related to inhibited NF-kappa B signals. (N-Hydroxy-3-{3-[2-(2-methyl-1H-indol-3-yl)-ethylsulfamoyl]-phenyl}-acrylamide) (9), exhibited ability superior to that of 1.HCl, was able to reduce carrageenan-induced acute inflammation in an animal model. Compounds 9-12 have potential anti-inflammatory activity and compound 9 can serve as lead compound for further development. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.020
• 作为产物：
  描述：

  色胺 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 4-bromo-N-[2-(1-methyl-1H-indol-3-yl)ethyl]benzenesulfonamide
  参考文献：
  名称：

  铜(I)催化吲哚基酰胺氧化/脱芳构化：有价值的吲哚啉支架的发散性和区域选择性合成

  摘要：

  描述了一种非常方便的铜（I）催化氧化引发的吲哚基炔酰胺环丙烷化反应，用于快速构建吲哚稠合环丙烷-内酰胺，据我们所知，这代表了第一个非贵金属催化的吲哚基通过原位生成的α-氧代铜卡宾进行炔酰胺氧化/脱芳构化。与腙和重氮相比，使用炔烃作为卡宾前体可以使环丙烷化在安全且方便的途径下发生。此外，这种转化可以导致五环螺吲哚啉的不同合成，涉及通过改造底物结构来逆转 ynamide 区域选择性。

  DOI：

  10.1021/acs.orglett.4c00719

文献信息

• Diels‐Alder Cycloaddition of Azepino[4,5‐ <i>b</i> ]indoles Towards Hydrocarbazole Derivatives and Related Heterocycles
  作者：Fukai Xie、Xiang Li、Liangyu Xu、Jun Ma、Lei Sun、Bo Zhang、Bin Lin、Maosheng Cheng、Yongxiang Liu

  DOI：10.1002/adsc.202101401

  日期：2022.2.15

  from azepino[4,5-b]indoles and commercially available dienophiles. The method provided a range of hydrocarbazoles in 63–99% yields. The practicality of this transformation was demonstrated by a scale-up experiment and various transformations to several hydrocarbazole derivatives and the tetracyclic indoline scaffold. Moreover, hetero-Diels-Alder cycloadditions of azepino[4,5-b]indoles were explored with

  通过 Brønsted 酸引发的 Diels-Alder 环加成/retro-aza-Michael 加成级联过程，从 azepino[4,5- b ] 吲哚和市售的双烯体中开发了一种在 C4a 位置具有全碳四元中心的烃咔唑的方法。该方法以 63-99% 的收率提供了一系列烃类。这种转化的实用性通过放大实验和对几种烃类衍生物和四环二氢吲哚支架的各种转化得到证明。此外，用 4-phenyl-3 H -1,2,4-triazole-3,5(4 H )-dione (PTAD) 和 82探索了 azepino[4,5- b ] 吲哚的杂 Diels-Alder 环加成反应。获得了 –99% 的收率。
• Copper-Catalyzed Cyclization/Dimerization of Tryptamines with O₂/Air as the Sole Oxidant: Direct Access to Complex Bispyrrolidino[2,3-<i>b</i>]indoline
  作者：Zhi-Yao Li、Wei Wang、Jun-Rong Song、Rui-An Wang、Jun Shi、Qin Chi、Yan Li、Hai Ren、Wei-Dong Pan

  DOI：10.1021/acs.joc.1c02277

  日期：2021.12.3

  The first transition metal catalytic one-step synthesis of the 3a, 3a′-bispyrrolidino [2,3-b] indoline scaffold via tandem cyclization/dimerization of tryptamines has been realized with the environmentally friendly O2/air as the sole oxidant. Different from the traditional direct oxidation of indole “N-H” group by excess amount of metal salts, a copper-catalyzed oxidative cyclization reaction is developed

  以环境友好的O 2 /空气为唯一氧化剂，通过色胺的串联环化/二聚化实现了第一个过渡金属催化一步合成3a，3a'-双吡咯烷[2,3- b ]二氢吲哚支架。与传统的通过过量金属盐直接氧化吲哚“NH”基团不同，当前策略中开发了一种铜催化的氧化环化反应形成自由基吡咯烷二氢吲哚中间体。这种方法的稳健性和实用性通过天然产物 (±)-叶黄素和中间体-叶黄素的分步经济、不同的全合成得到证明。
• 一种3a,3a’-双吡咯[2,3-b]吲哚啉类化合物的制备方法
  申请人：贵州省中国科学院天然产物化学重点实验室（贵州医科大学天然产物化学重点实验室）

  公开号：CN114456196A

  公开（公告）日：2022-05-10

  本发明提供了一种3a,3a'‑双吡咯[2,3‑b]吲哚啉类化合物的制备方法，属于药物及药物中间体合成技术领域。本发明在空气条件下，在铜盐催化剂作用下通过一步合成反应，进行自由基串联反应，得到3a,3a'‑双吡咯[2,3‑b]吲哚啉类化合物，从原料到产物没有多余原子的浪费和丢失，反应效率高且反应收率高。本发明在空气条件下反应，无需额外添加氧化剂，且所用铜盐催化剂廉价，催化剂用量少，反应原子经济性高，无任何副产物，适用取代基范围广，具有合成步骤短，操作简单，放大量实验结果稳定，有望实现工业化应用前景。
• Indole-3-ethylsulfamoylphenylacrylamides: Potent histone deacetylase inhibitors with anti-inflammatory activity
  作者：Samir Mehndiratta、Yi-Ling Hsieh、Yi-Min Liu、Amber Weiching Wang、Hsueh-Yun Lee、Lung-Yu Liang、Sunil Kumar、Che-Ming Teng、Chia-Ron Yang、Jing-Ping Liou

  DOI：10.1016/j.ejmech.2014.08.020

  日期：2014.10

  A series of 2-methyl-1H-indol-3-ethylsulfamoylphenylacrylamides based on LBH589-PXD101 core have been synthesized and evaluated for their histone deacetylase (HDAC) inhibitory and anti-inflammatory activity. In vitro, compounds 9-12 show 2.6-fold better HDAC inhibition and 3-fold better IL-6 suppression compared to LBH589.HCl (1.HCl). Furthermore, these compounds did not show apparent cell viability suppression on macrophages while in contrast, treatment with 1.HCl resulted in significant reduction in cell viability as demonstrated by an MTT assay. Repressed expression of iNOS, COX-2 and reduced phosphorylation of p65 revealed the inhibitory effect of these analogues on inflammatory mediator release which is related to inhibited NF-kappa B signals. (N-Hydroxy-3-3-[2-(2-methyl-1H-indol-3-yl)-ethylsulfamoyl]-phenyl}-acrylamide) (9), exhibited ability superior to that of 1.HCl, was able to reduce carrageenan-induced acute inflammation in an animal model. Compounds 9-12 have potential anti-inflammatory activity and compound 9 can serve as lead compound for further development. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Copper(I)-Catalyzed Indolyl Ynamide Oxidation/Dearomatization: Divergent and Regioselective Synthesis of Valuable Indoline Scaffolds
  作者：Guang-Xin Ru、Qing Liu、Kua-Fei Wei、Xiu-Hong Zhu、Xiao-Lei Jiang、Li-Xia Xie、Hui Su、Dong-Can Lv、Xinfeng Xie、Wen-Bo Shen

  DOI：10.1021/acs.orglett.4c00719

  日期：——

  A highly convenient copper(I)-catalyzed oxidation-initiated cyclopropanation of indolyl ynamide for the rapid construction of indole-fused cyclopropane-lactams is described, which represents, to the best of our knowledge, the first non-noble-metal-catalyzed indolyl ynamide oxidation/dearomatization by the in situ generated α-oxo copper carbenes. Compared to hydrazone and diazo, the use of alkynes as

  描述了一种非常方便的铜（I）催化氧化引发的吲哚基炔酰胺环丙烷化反应，用于快速构建吲哚稠合环丙烷-内酰胺，据我们所知，这代表了第一个非贵金属催化的吲哚基通过原位生成的α-氧代铜卡宾进行炔酰胺氧化/脱芳构化。与腙和重氮相比，使用炔烃作为卡宾前体可以使环丙烷化在安全且方便的途径下发生。此外，这种转化可以导致五环螺吲哚啉的不同合成，涉及通过改造底物结构来逆转 ynamide 区域选择性。