5-chloro-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde | 701203-80-7

• 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: 5-chloro-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde
• 英文别名: 5-chloro-(1-phenylsulfonyl)-indole-3-carboxaldehyde；1-benzenesulfonyl-5-chloro-1H-indole-3-carboxaldehyde；1-(Benzenesulfonyl)-5-chloroindole-3-carbaldehyde；1-(benzenesulfonyl)-5-chloroindole-3-carbaldehyde
• CAS: 701203-80-7
• 化学式: C₁₅H₁₀ClNO₃S
• 分子量: 319.768
• InChiKey: BHEOQSLAHNCZRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙二醇二甲醚 为溶剂， 生成 2,4-dichloro-5-(5-chloro-1H-indol-3-yl)oxazole
  参考文献：
  名称：

  新型链霉素的类似物的合成及其抗真菌活性

  摘要：

  链霉菌素是1988年从链霉菌属菌丝体的亲脂性提取物中首次分离出的新抗生素，是一种具有多种生物活性的吲哚天然产物。根据在我们实验室开发的合成嘧啶的方法，我们合成了一系列吲哚修饰的链霉素类似物，并测量了它们对七种植物病原真菌的活性。一些类似物在第一测定中显示良好的活性，和七个化合物10b的，10C，11E，13E，21，22C和22E（如图1所示）被确定为最有希望进行进一步研究的候选人。结构优化仍在进行中，目的是发现具有改进的抗真菌活性的合成类似物。

  DOI：

  10.1016/j.ejmech.2015.01.043
• 作为产物：
  描述：

  5-氯吲哚 在 sodium hydride 、 三氯氧磷 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 2.5h， 生成 5-chloro-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  First discovery of pimprinine derivatives and analogs as novel potential herbicidal, insecticidal and nematicidal agents

  摘要：

  DOI：

  10.1016/j.tet.2020.131835

文献信息

• [EN] N-ARYLSULFONYL-3-SUBSTITUTED INDOLES HAVING SEROTONIN RECEPTOR AFFINITY, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITION CONTAINING THEM<br/>[FR] INDOLES N-ARYLSULFONYL-3-SUBSTITUES PRESENTANT UNE AFFINITE POUR LE RECEPTEUR DE LA SEROTONINE, METHODE DE PREPARATION ET COMPOSITION PHARMACEUTIQUE CONTENANT CES INDOLES
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2004048330A1

  公开（公告）日：2004-06-10

  The present invention relates to novel N-arylsulfonyl-3-substituted indole compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their geometric forms, their N-oxides, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them. This invention particularly relates to novel N-arylsulfonyl-3-substituted indoles of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, and pharmaceutically acceptable compositions containing them. This invention also relates to the process for preparing compounds of the general formula (I), pharmaceutical compositions containing such compounds and the use of such compounds and compositions in medicine. This invention also relates to the novel intermediates involved therein and process of their preparation.

  本发明涉及新型的N-芳基亚磺酰基-3-取代吲哚化合物、其衍生物、类似物、互变异构体、立体异构体、几何异构体、N-氧化物、多晶型、药物可接受的盐、药物可接受的溶剂化物以及含有它们的药物可接受组合物。本发明特别涉及具有通用公式(I)的新型N-芳基亚磺酰基-3-取代吲哚、其衍生物、类似物、互变异构体、立体异构体、多晶型、药物可接受的盐、药物可接受的溶剂化物以及含有它们的药物可接受组合物。本发明还涉及制备通用公式(I)化合物的过程、含有此类化合物的药物组合物以及此类化合物和组合物在医学中的用途。本发明还涉及其中涉及的新中间体及其制备过程。
• [EN] COMPOSITIONS AND METHODS FOR TARGETING RECEPTORS EXPRESSED IN THE GUT<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE CIBLAGE DE RÉCEPTEURS EXPRIMÉS DANS L'INTESTIN
  申请人：SENSOR PHARMACEUTICALS INC

  公开号：WO2016014797A1

  公开（公告）日：2016-01-28

  The invention relates to novel compounds and pharmaceutical preparations thereof, as well as methods of making and using these compounds. The invention further relates to methods of treating or preventing disease using the novel compounds of the invention.

  这项发明涉及新化合物及其药物制剂，以及制备和使用这些化合物的方法。该发明还涉及使用该发明的新化合物治疗或预防疾病的方法。
• Organocatalytic aldol reaction of indole-3-carbaldehydes with ketones: synthesis of chiral 3-substituted indoles
  作者：Qi-Xiang Guo、Wei Wen、Li-Na Fu、Shun-En Zhang、Lan-Xi Zhang、Yu-Wan Liu、Biao Xu、Yan Xiong

  DOI：10.1016/j.tetlet.2013.06.056

  日期：2013.8

  An efficient aldol reaction of indole-3-carbaldehydes with ketones is described. O-TBS-protected l-threonine promoted the aldol addition of ketones to indole-3-carbaldehydes affording 3-indolylmethanols with good to excellent yields and diastereoselectivities, and excellent enantioselectivities.

  描述了吲哚-3-甲醛与酮的有效醛醇缩合反应。O-TBS保护的1-苏氨酸促进了吲哚-3-甲醛中醛酮的羟醛加成，从而提供了3-吲哚基甲醇，具有良好至优异的产率和非对映选择性，以及优异的对映选择性。
• N-arylsulfonyl-3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical composition containing them
  申请人：Ramakrishna Satya Nirogi Venkata

  公开号：US20060223890A1

  公开（公告）日：2006-10-05

  N-arylsulfonyl-3-substituted indole compounds, derivatives, analogs, tautomeric forms, stereoisomers, geometric forms, N-oxides, polymorphs and pharmaceutically acceptable salts.

  N-芳基磺酰基-3-取代吲哚化合物，衍生物，类似物，互变异构体，立体异构体，几何异构体，N-氧化物，多晶形式和药学上可接受的盐。
• Design, synthesis and biological evaluation of heteroaryl diketohexenoic and diketobutanoic acids as HIV-1 integrase inhibitors endowed with antiretroviral activity
  作者：R. Di Santo、R. Costi、M. Artico、R. Ragno、G. Greco、E. Novellino、C. Marchand、Y. Pommier

  DOI：10.1016/j.farmac.2005.03.008

  日期：2005.5

  Highly active anti-retroviral therapy (HAART) using reverse transcriptase (RT) and protease (PR) inhibitors and, more recently, inhibitors of the fusion is currently the best clinical approach in combating acquired immunodeficiency syndrome (AIDS), caused by infection from human immunodeficiency virus type 1 (HIV-1). However, this therapy does not completely eradicate the virus, so that resistant strains easily emerge. The above problem calls urgently for research on inhibitors of further viral targets such as integrase (IN), the third enzyme produced by HIV. Recently, our research group was engaged in studies on conformationally restrained cinnamoyl compounds related to curcumin as anti-IN agents. Compounds containing both a 3,4,5-trihydroxyphenyl group and a carboxylic acid function were potent IN inhibitors active against viral replication. More recently, a promising new class of inhibitors synthesized by Merck Company has emerged, which contain aryldiketoacid (ADK) functionality. The ADKs selectively inhibited the stand transfer (ST) step of integration and were proven to be effective IN inhibitors in vivo. Our interest in the field of IN inhibitors led us to design pyrrole and indole derivatives containing both a cinnamoyl moiety and a diketoacid group. A number of the cited derivatives were proven potent IN inhibitors, which selectively inhibited the ST step at submicromolar concentrations and were effective against virus replication in HIV-1 infected cells.