2-(3-苄基苯基)丙酸 | 118202-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(3-苄基苯基)丙酸
• 英文名称: 2-(3-benzylphenyl)propanoic acid
• 英文别名: α-(3-benzylphenyl)propionic acid methyl ester；Methyl 2-(3-benzylphenyl)propanoate
• CAS: 118202-02-1
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: WBKKVKSVSQONEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-苄基苯基)丙酸 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以2.41 g的产率得到脱氧酮洛芬
  参考文献：
  名称：

  2-Arylpropionic CXC Chemokine Receptor 1 (CXCR1) Ligands as Novel Noncompetitive CXCL8 Inhibitors

  摘要：

  The CXC chemokine CXCL8/IL-8 plays a major role in the activation and recruitment of polymorphonuclear (PMN) cells at inflammatory sites. CXCL8 activates PMNs by binding the seven-transmembrane (7-TM) G-protein-coupled receptors CXC chemokine receptor 1 (CXCR1) and CXC chemokine receptor 2 (CXCR2). (R)-Ketoprofen (1) was previously reported to be a potent and specific noncompetitive inhibitor of CXCL8-induced human PMNS chemotaxis. We report here molecular modeling studies showing a putative interaction site of 1 in the TM region of CXCR1. The binding model was confirmed by alanine scanning mutagenesis and photoaffinity labeling experiments. The molecular model driven medicinal chemistry optimization of 1 led to a new class of potent and specific inhibitors of CXCL8 biological activity. Among these, repertaxin (13) was selected as a clinical candidate drug for prevention of post-ischemia reperfusion injury.

  DOI：

  10.1021/jm049082i
• 作为产物：
  描述：

  3-羟基苯乙酸 在 四(三苯基膦)钯 、 硫酸 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 2-(3-苄基苯基)丙酸
  参考文献：
  名称：

  2-Arylpropionic CXC Chemokine Receptor 1 (CXCR1) Ligands as Novel Noncompetitive CXCL8 Inhibitors

  摘要：

  The CXC chemokine CXCL8/IL-8 plays a major role in the activation and recruitment of polymorphonuclear (PMN) cells at inflammatory sites. CXCL8 activates PMNs by binding the seven-transmembrane (7-TM) G-protein-coupled receptors CXC chemokine receptor 1 (CXCR1) and CXC chemokine receptor 2 (CXCR2). (R)-Ketoprofen (1) was previously reported to be a potent and specific noncompetitive inhibitor of CXCL8-induced human PMNS chemotaxis. We report here molecular modeling studies showing a putative interaction site of 1 in the TM region of CXCR1. The binding model was confirmed by alanine scanning mutagenesis and photoaffinity labeling experiments. The molecular model driven medicinal chemistry optimization of 1 led to a new class of potent and specific inhibitors of CXCL8 biological activity. Among these, repertaxin (13) was selected as a clinical candidate drug for prevention of post-ischemia reperfusion injury.

  DOI：

  10.1021/jm049082i

文献信息

• PROCESS FOR PREPARING ALPHA-(3-BENZYLPHENYL)PROPIONIC ACID DERIVATIVE
  申请人：NIPPON PETROCHEMICALS COMPANY, LIMITED

  公开号：EP0306538A1

  公开（公告）日：1989-03-15

  A process for preparing a-(3-benzylphenyl)propionic acid or its derivative, a precursor of ketoprofen (trade name), which comprises dehydrogenating a by-product oil fraction formed in the production of ethylbenzene using synthetic zeolite as an alkylating catalyst, and carbonylating the product with carbon monoxide or the like. This precursor can be easily converted into ketoprofen, a useful medicine as an anti-inflammatory agent.

  一种制备 a-(3-苄基苯基)丙酸或其衍生物，即酮洛芬（商品名）前体的工艺，包括使用合成沸石作为烷基化催化剂对乙苯生产过程中形成的副产品油馏分进行脱氢，并用一氧化碳或类似物质对产品进行羰基化。这种前体可以很容易地转化成酮洛芬，它是一种有用的消炎药。
• (Vinylphenyl)phenylmethane and method for producing (benzoylphenyl)propionic acid
  申请人：NIPPON PETROCHEMICALS COMPANY, LIMITED

  公开号：EP0283038B1

  公开（公告）日：1991-06-12
• SHIMIZU, ISOO;MATSUMURA, YASUO;ARAI, YUTAKA
  作者：SHIMIZU, ISOO、MATSUMURA, YASUO、ARAI, YUTAKA

  DOI：——

  日期：——
• US4922052A
  申请人：——

  公开号：US4922052A

  公开（公告）日：1990-05-01
• US4999450A
  申请人：——

  公开号：US4999450A

  公开（公告）日：1991-03-12