4-[[Ethoxy(3-phenylpropyl)phosphoryl]methyl]benzoic acid | 177169-00-5

• 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: 4-[[Ethoxy(3-phenylpropyl)phosphoryl]methyl]benzoic acid
• CAS: 177169-00-5
• 化学式: C₁₉H₂₃O₄P
• 分子量: 346.363
• InChiKey: KMSWBGCGRJJMKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  516.1±60.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-羟基苯甲脒盐酸盐 、 4-[[Ethoxy(3-phenylpropyl)phosphoryl]methyl]benzoic acid 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 15.0h， 生成 (4-Carbamimidoylphenyl) 4-[[ethoxy(3-phenylpropyl)phosphoryl]methyl]benzoate
  参考文献：
  名称：

  New serine protease inhibitors with leukotriene B4 (LTB4) receptor binding affinity

  摘要：

  A series of new trypsin-like serine protease inhibitors, 1, 2 and 7-23, containing amidinobenzene moiety was found to show potent LTB4-receptor affinity. Among them, compounds 1 and 2 were found to be LTB4 receptor antagonists based on an inhibition assay of human polymorphonuclear neutrophil (PMN) intracellular calcium mobilization induced by LTB4. Compounds 1 and 2, which satisfy the reported structural requirements for good oral activity, are expected to show a balanced dual mode of action, i.e., protease inhibitory activity and LTB4 receptor antagonist activity, in vivo. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00036-9
• 作为产物：
  描述：

  ethyl-3-phenylpropyl-H-phosphinate 在 palladium on activated charcoal 三甲基氯硅烷 、 氢气 、 三乙胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 38.0h， 生成 4-[[Ethoxy(3-phenylpropyl)phosphoryl]methyl]benzoic acid
  参考文献：
  名称：

  New serine protease inhibitors with leukotriene B4 (LTB4) receptor binding affinity

  摘要：

  A series of new trypsin-like serine protease inhibitors, 1, 2 and 7-23, containing amidinobenzene moiety was found to show potent LTB4-receptor affinity. Among them, compounds 1 and 2 were found to be LTB4 receptor antagonists based on an inhibition assay of human polymorphonuclear neutrophil (PMN) intracellular calcium mobilization induced by LTB4. Compounds 1 and 2, which satisfy the reported structural requirements for good oral activity, are expected to show a balanced dual mode of action, i.e., protease inhibitory activity and LTB4 receptor antagonist activity, in vivo. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00036-9

文献信息

• Leukotriene B4 antagonist compounds and method for treatment
  申请人：——

  公开号：US20020128315A1

  公开（公告）日：2002-09-12

  Novel amidinophenol derivatives of formula (IB) 1 and processes for the preparation thereof; compositions containing a compound of formula (IB) as active ingredient useful as antagonists of leukotine B 4 and inhibitors of phospholipase A 2 and/or trypsin; methods for preventing or treating diseases induced by phospholipase A 2 and/or trypsin comprising administering to a patient a compound of formula (IB); and methods for treating diseases induced by leukotine B 4 comprising administering to a patient a compound of formula (IB) or a known amidinophenol derivative of formula (IA) 2

  公式（IB）1的新型氨基酚衍生物及其制备方法；含有公式（IB）化合物作为活性成分的组合物，用作白三烯B4的拮抗剂和磷脂酶A2和/或胰蛋白酶的抑制剂；预防或治疗由磷脂酶A2和/或胰蛋白酶引起的疾病的方法，包括向患者给予公式（IB）化合物；以及治疗由白三烯B4引起的疾病的方法，包括向患者给予公式（IB）化合物或已知的公式（IA）2的氨基酚衍生物。
• Amidinophenol derivatives as protease inhibitors
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0703216A1

  公开（公告）日：1996-03-27

  The compounds of the formula (IB) and processes for the preparation thereof, leukotrieneB₄ antagonist containing the compounds of the formula (IA) or the formula(IB) as active ingredient, and phospholipaseA₂ and/or trypsin antagonist containing the compounds of the formula (IB) as active ingredient (wherein R¹ and R are -COOR⁴ etc; A is alkylene etc; R³ is -CON (R⁷)R⁸ etc; D ring is the formula (i), (ii) etc; T is NH or oxygen; E is bond, -C (R³⁰⁰)=C (R⁴⁰⁰)-; A₀ is bond, alkylene, oxyalkylene, thioalkylene, (substituted)alkenylene; R is -CON (R⁵⁰)R⁶⁰, -N (R⁵⁰)R⁶⁰ etc). [Effect] The compounds of the present invention is useful for prevention or treatment of inflammation, allergy, rheumatoid arthritis, inflammatory bowel diseases, psoriasis, nonsteroidal anti-inflammatory agent-induced stomach diseases, adult respiratory distress syndrome, cardiac infarction, hemodialysis-induced neutropenia etc, prevention and treatment of inflammatory diseases, allergic diseases, disseminated intravascular coagulation, pancreatitis or severity in pancreatitis or multiple organ failure.

  式(IB)化合物及其制备工艺，含有式(IA)或式(IB)化合物作为活性成分的白三烯B₄拮抗剂，以及含有式(IB)化合物作为活性成分的磷脂酶A₂和/或胰蛋白酶拮抗剂（其中R¹和R是-COOR⁴等；A是亚烷基等；R³是-CON (R⁷)R⁸等；D环是式(i)、(ii)等；T是NH或氧；E是键、-C (R³⁰⁰)=C (R⁴⁰⁰)-；A₀ 是键、亚烷基、氧烷基、硫代烷基、（取代）烯基；R 是 -CON (R⁵⁰)R⁶⁰, -N (R⁵⁰)R⁶⁰ 等。） [效果] 本发明的化合物可用于预防或治疗炎症、过敏、类风湿性关节炎、炎症性肠病、银屑病、非甾体类抗炎剂诱发的胃病、成人呼吸窘迫综合征、心肌梗塞、血液透析诱发的中性粒细胞减少症等；预防和治疗炎症性疾病、过敏性疾病、弥散性血管内凝血、胰腺炎或胰腺炎严重程度或多器官功能衰竭。
• US6262114B1
  申请人：——

  公开号：US6262114B1

  公开（公告）日：2001-07-17
• US6583177B2
  申请人：——

  公开号：US6583177B2

  公开（公告）日：2003-06-24
• New serine protease inhibitors with leukotriene B4 (LTB4) receptor binding affinity
  作者：Yoshisuke Nakayama、Kazuhiko Senokuchi、Katsuhito Sakaki、Masashi Kato、Toru Maruyama、Toru Miyazaki、Hidenori Ito、Hisao Nakai、Masanori Kawamura

  DOI：10.1016/s0968-0896(97)00036-9

  日期：1997.5

  A series of new trypsin-like serine protease inhibitors, 1, 2 and 7-23, containing amidinobenzene moiety was found to show potent LTB4-receptor affinity. Among them, compounds 1 and 2 were found to be LTB4 receptor antagonists based on an inhibition assay of human polymorphonuclear neutrophil (PMN) intracellular calcium mobilization induced by LTB4. Compounds 1 and 2, which satisfy the reported structural requirements for good oral activity, are expected to show a balanced dual mode of action, i.e., protease inhibitory activity and LTB4 receptor antagonist activity, in vivo. (C) 1997 Elsevier Science Ltd.