(2-Benzyloxy-6-methyl-3-phenylmethanesulfonylamino-phenyl)-acetic acid | 225096-26-4

• 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: (2-Benzyloxy-6-methyl-3-phenylmethanesulfonylamino-phenyl)-acetic acid
• 英文别名: 2-[3-(Benzylsulfonylamino)-6-methyl-2-phenylmethoxyphenyl]acetic acid
• CAS: 225096-26-4
• 化学式: C₂₃H₂₃NO₅S
• 分子量: 425.505
• InChiKey: CTNHQAKRJQZFPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2-Benzyloxy-6-methyl-3-phenylmethanesulfonylamino-phenyl)-acetic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (2-Hydroxy-6-methyl-3-phenylmethanesulfonylamino-phenyl)-acetic acid
  参考文献：
  名称：

  Phenolic P2/P3 core motif as thrombin inhibitors—Design, synthesis, and X-ray co-crystal structure

  摘要：

  Prototypical thrombin inhibitors were synthesized based on a trisubstituted phenol as a core motif. A naphthylsulfonamide analogue showed excellent antithrombin activity. An X-ray co-crystal structure showed the expected interactions.

  DOI：

  10.1016/j.bmcl.2005.10.082
• 作为产物：
  描述：

  (3-Amino-2-benzyloxy-6-methyl-phenyl)-acetic acid methyl ester 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (2-Benzyloxy-6-methyl-3-phenylmethanesulfonylamino-phenyl)-acetic acid
  参考文献：
  名称：

  Phenolic P2/P3 core motif as thrombin inhibitors—Design, synthesis, and X-ray co-crystal structure

  摘要：

  Prototypical thrombin inhibitors were synthesized based on a trisubstituted phenol as a core motif. A naphthylsulfonamide analogue showed excellent antithrombin activity. An X-ray co-crystal structure showed the expected interactions.

  DOI：

  10.1016/j.bmcl.2005.10.082

文献信息

• US6011047A
  申请人：——

  公开号：US6011047A

  公开（公告）日：2000-01-04
• US6204384B1
  申请人：——

  公开号：US6204384B1

  公开（公告）日：2001-03-20
• [EN] SUBSTITUTED 3-AMINO-2-HYDROXYPHENYLACETAMIDE DERIVATIVES AS ENZYME INHIBITORS (II)<br/>[FR] DERIVES DE 3-AMINO-2-HYDROXYPHENYLACETAMIDE SUBSTITUE UTILISES EN TANT QU'INHIBITEURS (II) D'ENZYME
  申请人：CORVAS INTERNATIONAL, INC.

  公开号：WO1999026920A1

  公开（公告）日：1999-06-03

  (EN) The present invention provides peptide aldehydes having an 3-amino-2-hydroxyphenyl acetamide group as part of the peptide backbone and an arginine group or analog at P1. These compounds are potent and specific or inhibitors of thrombin. Their pharmaceutically acceptable salts, pharmaceutically acceptable compositions thereof, and methods of using them as therapeutic agents for disease states in mammals characterized by abnormal thrombosis are also described. Also described are 3-amino-2-hydroxyphenyl-acetamide derivatives having in history activity towards proteases of the trypsin/chymotrypsin class.(FR) La présente invention concerne des aldéhydes peptidiques comprenant un groupe 3-amino-2-hydroxyphényle acétamide faisant partie du squelette peptidique et un groupe arginine ou analogue sur P1. Ces composés sont des inhibiteurs puissants et spécifiques de la thrombine. L'invention concerne également leurs sels pharmaceutiquement acceptables, leurs compositions pharmaceutiquement acceptables, et leurs procédés d'utilisation en tant qu'agents thérapeutiques destinés à des états pathologiques chez des mammifères caractérisés par une thrombose anormale. L'invention concerne, en outre, des dérivés de 3-amino-2-hydroxyphényl-acétamide présentant une activité connue vis-à-vis de protéases de la catégorie trypsine/chymotripsine.
• Phenolic P2/P3 core motif as thrombin inhibitors—Design, synthesis, and X-ray co-crystal structure
  作者：Stephen Hanessian、Eric Therrien、Willem A.L. van Otterlo、Malken Bayrakdarian、Ingemar Nilsson、Ola Fjellström、Yafeng Xue

  DOI：10.1016/j.bmcl.2005.10.082

  日期：2006.2

  Prototypical thrombin inhibitors were synthesized based on a trisubstituted phenol as a core motif. A naphthylsulfonamide analogue showed excellent antithrombin activity. An X-ray co-crystal structure showed the expected interactions.