N-(4-chloro-2-iodophenyl)benzenesulfonamide | 927963-49-3

• 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-chloro-2-iodophenyl)benzenesulfonamide
• CAS: 927963-49-3
• 化学式: C₁₂H₉ClINO₂S
• 分子量: 393.632
• InChiKey: YKCFDBMPJNSZEY-UHFFFAOYSA-N

物化性质

• 沸点：
  456.6±55.0 °C(Predicted)
• 密度：
  1.851±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-chloro-2-iodophenyl)benzenesulfonamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 lithium hydroxide monohydrate 、 二乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 2-[[1-(benzenesulfonyl)-5-chloroindol-2-yl]methoxy]acetic acid
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of a Novel Series of Indole Sulfonamide Peroxisome Proliferator Activated Receptor (PPAR) α/γ/δ Triple Activators: Discovery of Lanifibranor, a New Antifibrotic Clinical Candidate

  摘要：

  Here, we describe the identification and synthesis of novel indole sulfonamide derivatives that activate the three peroxisome proliferator activated receptor (PPAR) isoforms. Starting with a PPAR alpha activator, compound 4, identified during a high throughput screening (HTS) of our proprietary screening library, a systematic optimization led to the discovery of lanifibranor (IVA337) 5, a moderately potent and well balanced pan PPAR agonist with an excellent safety profile. In vitro and in vivo, compound 5 demonstrated strong activity in models that are relevant to nonalcoholic steatohepatitis (NASH) pathophysiology suggesting therapeutic potential for NASH patients.

  DOI：

  10.1021/acs.jmedchem.7b01285
• 作为产物：
  描述：

  2-碘-4-氯苯胺 、 苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到N-(4-chloro-2-iodophenyl)benzenesulfonamide
  参考文献：
  名称：

  溴二氟乙酸乙酯合成烷基的三重模式：N或O-二氟甲基化，N-乙基化和S-（乙氧羰基）二氟甲基化

  摘要：

  在这份报告中，我们探索了溴二氟乙酸乙酯的化学反应的三重模式。通常，溴二氟乙酸已被用作软亲核试剂的二氟甲基化的二氟卡宾前体。在这里，我们已经公开了溴二氟乙酸乙酯的亲核性和碱依赖性发散化学反应性。它提供了氢氧化锂和碳酸铯，分别促进了甲苯磺酰基保护的苯胺和缺电子的酚的二氟甲基化作用。有趣的是，将碱从氢氧化锂转变为4- N，N-二甲基氨基吡啶（DMAP）甲苯磺酰基保护的苯胺，得到了相应的N-乙基化产物。而高度亲核的苯硫酚提供了相应的S羰基乙氧基二氟甲基化产物在酯水解之前通过快速的S N 2攻击溴原子而形成。这种机制差异是通过几个控制实验确定的。结果表明，二氟甲基化反应是通过串联原位酯水解/脱羧-脱溴化二氟卡宾的形成并随后被软亲核试剂-NHTs或电子缺陷型酚-OH基团捕获而进行的。在DMAP的存在下，酯的水解受到干扰，相反，在乙基部分的亲核攻击提供了N-乙基化产物。因此，除了开发实用的碱促氮素胺和电

  DOI：

  10.1002/adsc.201800824

文献信息

• Indole Compounds, Method of Preparing Them and Uses Thereof
  申请人：BINET Jean

  公开号：US20080153816A1

  公开（公告）日：2008-06-26

  Indole compounds corresponding to the formula (I): as defined in the claims, pharmaceutically acceptable addition salts of such compounds, pharmaceutical compositions containing such compounds, the process for their preparation, and their use as pharmacologically active substances, especially in the treatment of hypertriglyceridemia, hyperlipidemia, hypercholesterolemia, diabetes, endothelial dysfunction, cardiovascular disease, inflammatory disease and neurodegeneration.

  与公式（I）相对应的吲哚化合物，如权利要求中所定义的，这些化合物的药学上可接受的加盐物，含有这些化合物的药物组合物，其制备方法，以及它们作为药理活性物质的用途，特别是在治疗高三酰甘油血症、高脂血症、高胆固醇血症、糖尿病、内皮功能障碍、心血管疾病、炎症性疾病和神经退行性疾病方面。
• Propargylamine (secondary) as a building block in indole synthesis involving ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method: Unexpected formation of (pyrazole)imine derivatives
  作者：Gangireddy Sujeevan Reddy、Suresh Babu Nallapati、P.S.V.K. Sri Saranya、B. Sridhar、Varadaraj Bhat Giliyaru、Raghu Chandrashekhar Hariharapura、G. Gautham Shenoy、Manojit Pal

  DOI：10.1016/j.tetlet.2018.11.037

  日期：2018.12

  Propargylamine (secondary) has been explored as a building block in synthesizing indoles via an ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method. Indoles containing a pyrazole moiety at C-2 attached via the –CH2NH– linker (designed as potential anti-tubercular agents) were synthesized first and then generality/scope of the methodology was expanded by synthesizing other indoles. Unexpected

  丙炔胺（中学）已被探索为通过超声辅助Pd / Cu催化的偶联环化方法合成吲哚的基础。首先合成了通过–CH 2 NH–接头（设计为潜在的抗结核药物）在C-2处含有吡唑部分的吲哚，然后通过合成其他吲哚扩大了方法的通用性/范围。在第一种情况下，亚胺副产物的意外形成有助于通过铜催化的超声辅助前体胺的需氧氧化来合成相关的（吡唑）亚胺。
• Indole compounds, method of preparing them and uses thereof
  申请人：Laboratories Fournier S.A.

  公开号：US07795297B2

  公开（公告）日：2010-09-14

  Indole compounds corresponding to the formula (I): as defined in the claims, pharmaceutically acceptable addition salts of such compounds, pharmaceutical compositions containing such compounds, the process for their preparation, and their use as pharmacologically active substances, especially in the treatment of hypertriglyceridemia, hyperlipidemia, hypercholesterolemia, diabetes, endothelial dysfunction, cardiovascular disease, inflammatory disease and neurodegeneration.

  本发明涉及公式（I）所定义的吲哚化合物，这些化合物的药学上可接受的加盐体、含有这些化合物的制药组合物、它们的制备过程，以及它们作为药理活性物质的用途，特别是在高甘油三酯血症、高脂血症、高胆固醇血症、糖尿病、内皮功能障碍、心血管疾病、炎症性疾病和神经退行性疾病的治疗中的应用。
• Method of treating conditions involving PPAR-receptors with indole compounds
  申请人：Binet Jean

  公开号：US08436040B2

  公开（公告）日：2013-05-07

  Indole compounds corresponding to the formula (I): as defined in the claims, pharmaceutically acceptable addition salts of such compounds, pharmaceutical compositions containing such compounds, the process for their preparation, and their use as pharmacologically active substances, especially in the treatment of hypertriglyceridemia, hyperlipidemia, hypercholesterolemia, diabetes, endothelial dysfunction, cardiovascular disease, inflammatory disease and neurodegeneration.

  本发明涉及式（I）所定义的吲哚化合物，这些化合物的药学上可接受的加盐物，含有这些化合物的制药组合物，其制备过程以及它们作为药理活性物质的用途，特别是在高甘油三酯血症、高脂血症、高胆固醇血症、糖尿病、内皮功能障碍、心血管疾病、炎症性疾病和神经退行性疾病的治疗中。
• Method of Treating Conditions Involving PPAR-Receptors with Indole Compounds
  申请人：BINET Jean

  公开号：US20100286137A1

  公开（公告）日：2010-11-11

  Indole compounds corresponding to the formula (I): as defined in the claims, pharmaceutically acceptable addition salts of such compounds, pharmaceutical compositions containing such compounds, the process for their preparation, and their use as pharmacologically active substances, especially in the treatment of hypertriglyceridemia, hyperlipidemia, hypercholesterolemia, diabetes, endothelial dysfunction, cardiovascular disease, inflammatory disease and neurodegeneration.

  本发明涉及化合物的吲哚类似物(I)的配方，这些化合物的药学上可接受的加盐物，含有这些化合物的制药组合物，其制备过程，以及作为药理活性物质的用途，特别是在高甘油三酯血症，高脂血症，高胆固醇血症，糖尿病，内皮功能障碍，心血管疾病，炎症性疾病和神经退行性疾病的治疗中。