2-({[(4-hydroxyphenyl)carbamoyl]methyl}sulfamoyl)benzoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-({[(4-hydroxyphenyl)carbamoyl]methyl}sulfamoyl)benzoic acid
• 英文别名: SCP-123；SCP-M1；2-{[(4-Hydroxyphenylcarbamoyl)methyl]sulfamoyl}benzoic acid；2-[[2-(4-hydroxyanilino)-2-oxoethyl]sulfamoyl]benzoic acid
• 化学式: C₁₅H₁₄N₂O₆S
• 分子量: 350.352
• InChiKey: SORCZKVIGXLCNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-({[(4-hydroxyphenyl)carbamoyl]methyl}sulfamoyl)benzoic acid 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以99%的产率得到SCP-123ss
  参考文献：
  名称：

  First Multigram Preparation of SCP-123, A Novel Water-Soluble Analgesic

  摘要：

  A short multigram process for the preparation of the analgesic compound SCP-123 (4) and its sodium salt has been developed.

  DOI：

  10.1021/op900113b
• 作为产物：
  描述：

  SCP-1 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.33h， 以80%的产率得到2-({[(4-hydroxyphenyl)carbamoyl]methyl}sulfamoyl)benzoic acid
  参考文献：
  名称：

  Analgesic compounds, their synthesis and pharmaceutical compositions containing them

  摘要：

  本发明揭示了一些新的镇痛化合物，这些化合物是通过N-酰化的4-羟基苯胺衍生物的水解制备而成，还揭示了它们的合成方法和包含它们的药物组合物。这些化合物出人意料地具有高度的镇痛活性，且对肝脏毒性影响较小，因此在慢性疼痛的治疗中比传统的非甾体抗炎药（NSAIDs）更加有用。

  公开号：

  US06806291B1

文献信息

• Analgesic compounds, their synthesis and pharmaceutical compositions containing them
  申请人：The Foundation for the LSU Health Sciences Center

  公开号：US06806291B1

  公开（公告）日：2004-10-19

  New analgesic compounds, which are prepared by the hydrolysis of N-acylated 4-hydroxyphenylamine derivatives, their synthesis and pharmaceutical compositions containing them are disclosed. These compounds surprisingly possess high analgesic activity with little hepatotoxic effect, making them more useful than conventional non-steroidal anti-inflammatory drugs (NSAIDs) in the treatment of chronic pain.

  本发明揭示了一些新的镇痛化合物，这些化合物是通过N-酰化的4-羟基苯胺衍生物的水解制备而成，还揭示了它们的合成方法和包含它们的药物组合物。这些化合物出人意料地具有高度的镇痛活性，且对肝脏毒性影响较小，因此在慢性疼痛的治疗中比传统的非甾体抗炎药（NSAIDs）更加有用。
• Compositions and methods for ameliorating pain and reducing fever
  申请人：The Board of Supervisors of Louisiana State University and Agricultural and Mechanical College

  公开号：US11007199B2

  公开（公告）日：2021-05-18

  This invention is directed to compositions, methods and kits that can be used for the treatment or amelioration of pain and fever.

  本发明涉及可用于治疗或改善疼痛和发烧的组合物、方法和试剂盒。
• Synthesis and in vivo evaluation of non-hepatotoxic acetaminophen analogs
  作者：Anthony L. Vaccarino、Dennis Paul、Pranab K. Mukherjee、Elena B. Rodríguez de Turco、Victor L. Marcheselli、Liang Xu、Mark L. Trudell、J.M. Minguez、M.P. Matía、Carlos Sunkel、Julio Alvarez-Builla、Nicolas G. Bazan

  DOI：10.1016/j.bmc.2006.07.054

  日期：2007.3

  A series of acetaminophen (APAP) analogs, 2-(1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)-N-(4-hydroxyphenyl)alkanecarboxamides, bearing a heterocyclic moiety linked to the p-acylaminophenol fragment, were prepared in a general project to develop APAP analogs with modulated pharmacokinetic profiles. Unexpectedly, the products described maintained the in vivo analgesic profile, while the characteristic hepatotoxicity of APAP was consistently reduced. One of the products, 5a, was studied in vivo in comparison with APAP. Compound 5a displayed an analgesic efficacy comparable to that of APAP. A relatively high acute oral dose of 5a (6 mmol/kg) produced no measurable toxicity, whereas the equimolar dose of APAP increased transaminase activity, depleted hepatic and renal glutathione, and resulted in mortality. In human hepatocytes (HEPG-2) and in human primary cultures of normal liver cells, APAP, but not 5a, was associated with apoptotic cell death, Fas-ligand up-regulation, and CAR (constitutive androstane receptor) activation, contributing to a favorable safety profile of 5a as an orally delivered analgesic. (c) 2006 Elsevier Ltd. All rights reserved.
• ANALGESIC COMPOUNDS, THEIR SYNTHESIS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Board of Supervisors of Louisiana State University and Agricultural and Mechanical College

  公开号：EP1682496B1

  公开（公告）日：2009-04-08
• COMPOSITIONS AND METHODS FOR AMELIORATING PAIN
  申请人：The Board of Supervisors of Louisiana State University and Agricultural and Mechanical Colleg

  公开号：US20200179393A1

  公开（公告）日：2020-06-11

  This invention is directed to compositions, methods and kits that can be used for the treatment or amelioration of pain.