N-benzenesulphonyl-3-(1-hydroxyethyl)indole | 701204-60-6

• 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: N-benzenesulphonyl-3-(1-hydroxyethyl)indole
• 英文别名: (RS) 1-(1-benzenesulfonyl-1H-indole-3-yl)ethan-1-ol；1-(1-(Phenylsulfonyl)-1H-indol-3-yl)ethan-1-ol；1-[1-(benzenesulfonyl)indol-3-yl]ethanol
• CAS: 701204-60-6
• 化学式: C₁₆H₁₅NO₃S
• 分子量: 301.366
• InChiKey: SKQUHWWZQJMBOV-UHFFFAOYSA-N

物化性质

• 沸点：
  521.0±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-[1-(苯磺酰基)-1H-吲哚-3-基]乙酮 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 0.03h， 以88%的产率得到N-benzenesulphonyl-3-(1-hydroxyethyl)indole
  参考文献：
  名称：

  An Unusual and Chemoselective Reduction of Ester Grouping in Nsubstituted-3-acetylindoles by Sodium Borohydride

  摘要：

  用K2CO3和四丁基溴化铵(TBAB)作为相转移催化剂，在DMF中处理3-乙酰吲哚1(a-e)与氯乙酸乙酯，生成相应的N取代衍生物，即乙基2-(3-乙酰-1H-吲哚-1-基)乙酸酯2(a-e)。这些衍生物与NaBH4反应时，意外地产生了乙醇衍生物1-(1-(2-羟乙基)-1H-吲哚-3-基)乙酮3(a-e)，这是因为酯基的还原优先于乙酰基。通过在相转移催化条件(PDC)下用2-氯乙醇处理1(a-e)，也能合成后者。1(a-e)在相转移催化条件下与苯磺酰氯反应，生成相应的N-苯磺酰基-3-乙酰吲哚7(a-e)，这些化合物在甲醇中与NaBH4还原后得到相应的羟基衍生物N-苯磺酰基-(α-羟乙基)吲哚8(a-e)。这些反应说明了使用NaBH4还原吲哚中的3-乙酰基的简单性。

  DOI：

  10.2174/157017812800167402

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。
• 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。
• N-ARYLSULFONYL-3-SUBSTITUTED INDOLES HAVING SEROTONIN RECEPTOR AFFINITY, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITION CONTAINING THEM
  申请人：Suven Life Sciences Limited

  公开号：EP1581492A1

  公开（公告）日：2005-10-05
• US7875605B2
  申请人：——

  公开号：US7875605B2

  公开（公告）日：2011-01-25
• An Unusual and Chemoselective Reduction of Ester Grouping in Nsubstituted-3-acetylindoles by Sodium Borohydride
  作者：Muvvala Venkatanarayana、Pramod K. Dubey

  DOI：10.2174/157017812800167402

  日期：2012.3.1

  Treatment of 3-acetylindoles 1(a-e) with ethyl chloroacetate in the presence of K2CO3 and tetrabutylammoniumbromide (TBAB) as phase transfer catalyst in DMF, resulted in the formation of the corresponding N-substituted derivatives, ethyl 2-(3-acetyl-1H-indol-1-yl)acetate 2(a-e) which on reaction with NaBH4 yielded, unexpectedly, ethanol derivatives, 1-(1-(2-hydroxyethyl)-1H-indol-3-yl)ethanone 3(a-e) by the unusual and chemoselective reduction of ester grouping in preference to the acetyl group. Alternative synthesis of the latter was achieved by the treatment of 1(a-e) with 2-chloroethanol under phase transfer catalytic conditions (PTC). 1(a-e), on treatment with benzenesulphonyl chloride, under PTC conditions, yielded the corresponding N-benzenesulphonyl-3- acetylindoles 7(a-e), which on reduction with NaBH4 in methanol afforded the corresponding hydroxy derivatives Nbenzenesulphonyl-( α-hydroxyethyl)indoles 8(a-e). These reactions throw light on the ease of reduction of the 3-acetyl group on indoles with NaBH4.

  用K2CO3和四丁基溴化铵(TBAB)作为相转移催化剂，在DMF中处理3-乙酰吲哚1(a-e)与氯乙酸乙酯，生成相应的N取代衍生物，即乙基2-(3-乙酰-1H-吲哚-1-基)乙酸酯2(a-e)。这些衍生物与NaBH4反应时，意外地产生了乙醇衍生物1-(1-(2-羟乙基)-1H-吲哚-3-基)乙酮3(a-e)，这是因为酯基的还原优先于乙酰基。通过在相转移催化条件(PDC)下用2-氯乙醇处理1(a-e)，也能合成后者。1(a-e)在相转移催化条件下与苯磺酰氯反应，生成相应的N-苯磺酰基-3-乙酰吲哚7(a-e)，这些化合物在甲醇中与NaBH4还原后得到相应的羟基衍生物N-苯磺酰基-(α-羟乙基)吲哚8(a-e)。这些反应说明了使用NaBH4还原吲哚中的3-乙酰基的简单性。