2-ethoxycarbonylmethyl-4,5-dihydro-5-(3-hydroxyphenyl)-1,3-oxazole | 112636-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-ethoxycarbonylmethyl-4,5-dihydro-5-(3-hydroxyphenyl)-1,3-oxazole
• 英文别名: Ethyl 2-[5-(3-hydroxyphenyl)-4,5-dihydro-1,3-oxazol-2-yl]acetate
• CAS: 112636-22-3
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: FIMVJFGAIVKHHS-UHFFFAOYSA-N

物化性质

• 沸点：
  397.9±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-ethoxycarbonylmethyl-4,5-dihydro-5-(3-hydroxyphenyl)-1,3-oxazole 在 盐酸 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.0h， 生成 Ethyl 3-[[2-hydroxy-2-[3-(quinolin-2-ylmethoxy)phenyl]ethyl]amino]-3-oxopropanoate
  参考文献：
  名称：

  Phenylephrine derivatives as leukotriene D4 antagonists

  摘要：

  Two series of phenylephrine derivatives were prepared and tested as inhibitors of leukotriene D4 (LTD4) induced and ovalbumin-induced bronchospasm in the guinea pig. The most potent compound of the urea series, (R)-N,N-diethyl-N-[2-hydroxy-2-[3-(2-quinolinylmethoxy)phenyl]ethyl]-N- methylurea (3, Wy-47,120), was orally active with ED50's of 56 mg/kg vs. LTD4 and 55 mg/kg vs. ovalbumin. When tested as an antagonist of LTD4-induced contraction of isolated guinea pig tracheal strips, 3 was a competitive inhibitor with a p kappa B value of 5.22. In the second series, (R)-3-methyl-5-[3-(2-quinolinylmethoxy)phenyl]-2-oxazolidinone (26, Wy-47,674) had oral ED50's of 36 mg/kg against LTD4 and 95 mg/kg against ovalbumin. Compound 26 selectively antagonized contractile responses of guinea pig trachea evoked by LTD4 (p kappa B = 6.09). In the cat coronary artery, 3 dilated the preparation and blocked the coronary constrictor effect of LTD4. Compound 3 (0.13 mg/kg, iv) also preserved myocardial integrity in rats 48 h after coronary artery ligation. When tested in the rat alcohol-induced gastric lesion model, 3 and 26 manifested a dose-dependent mucosal protection against ethanol.

  DOI：

  10.1021/jm00394a026
• 作为产物：
  描述：

  3-Imino-3-methoxy-propansaeure-aethylester 、 盐酸去甲苯福林 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 2-ethoxycarbonylmethyl-4,5-dihydro-5-(3-hydroxyphenyl)-1,3-oxazole
  参考文献：
  名称：

  Phenylephrine derivatives as leukotriene D4 antagonists

  摘要：

  Two series of phenylephrine derivatives were prepared and tested as inhibitors of leukotriene D4 (LTD4) induced and ovalbumin-induced bronchospasm in the guinea pig. The most potent compound of the urea series, (R)-N,N-diethyl-N-[2-hydroxy-2-[3-(2-quinolinylmethoxy)phenyl]ethyl]-N- methylurea (3, Wy-47,120), was orally active with ED50's of 56 mg/kg vs. LTD4 and 55 mg/kg vs. ovalbumin. When tested as an antagonist of LTD4-induced contraction of isolated guinea pig tracheal strips, 3 was a competitive inhibitor with a p kappa B value of 5.22. In the second series, (R)-3-methyl-5-[3-(2-quinolinylmethoxy)phenyl]-2-oxazolidinone (26, Wy-47,674) had oral ED50's of 36 mg/kg against LTD4 and 95 mg/kg against ovalbumin. Compound 26 selectively antagonized contractile responses of guinea pig trachea evoked by LTD4 (p kappa B = 6.09). In the cat coronary artery, 3 dilated the preparation and blocked the coronary constrictor effect of LTD4. Compound 3 (0.13 mg/kg, iv) also preserved myocardial integrity in rats 48 h after coronary artery ligation. When tested in the rat alcohol-induced gastric lesion model, 3 and 26 manifested a dose-dependent mucosal protection against ethanol.

  DOI：

  10.1021/jm00394a026

文献信息

• 5-Phenyl-2-oxazole derivatives as anti-inflammatory/antiallergic agents
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0226342A1

  公开（公告）日：1987-06-24

  There are disclosed compounds of formula wherein X is N or CR2; Y is O, S, NR2, CHR2 or C(R2)2 when n = 0 or N or CR2 when n is 1; p is 0 to 3, providing that when p is 0, X is N; R' is R2 is hydrogen or lower alkyl; R3 is hydrogen, lower alkyl, phenyl, thienyl, furyl, pyridyl, C(R4)3 or -(CH2)gCOOR2; R4 is halo; X is 0 or S and q is 0 to 3; and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like, in psoriasis, ulcerative colitis, rheumatoid arthritis as well as in other immediate hypersensitivity reactions.

  公开了如下式子的化合物 其中 X 是 N 或 CR2； 当 n = 0 时，Y 是 O、S、NR2、CHR2 或 C(R2)2；当 n 为 1 时，Y 是 N 或 CR2； p 为 0 至 3，当 p 为 0 时，X 为 N； R' 是 R2 是氢或低级烷基 R3 是氢、低级烷基、苯基、噻吩基、呋喃基、吡啶基、 C(R4)3或-(CH2)gCOOR2； R4 是卤代；X 是 0 或 S，q 是 0 至 3； 及其药学上可接受的盐，以及它们在治疗白三烯介导的鼻-支气管阻塞性气道疾病（如过敏性鼻炎、过敏性支气管哮喘等）、银屑病、溃疡性结肠炎、类风湿性关节炎以及其他即时超敏反应中的用途。
• US4681940A
  申请人：——

  公开号：US4681940A

  公开（公告）日：1987-07-21
• Phenylephrine derivatives as leukotriene D4 antagonists
  作者：John H. Musser、Dennis M. Kubrak、Reinhold H. W. Bender、Anthony F. Kreft、Susan T. Nielsen、Allan M. Lefer、Joseph Chang、Alan J. Lewis、James M. Hand

  DOI：10.1021/jm00394a026

  日期：1987.11

  Two series of phenylephrine derivatives were prepared and tested as inhibitors of leukotriene D4 (LTD4) induced and ovalbumin-induced bronchospasm in the guinea pig. The most potent compound of the urea series, (R)-N,N-diethyl-N-[2-hydroxy-2-[3-(2-quinolinylmethoxy)phenyl]ethyl]-N- methylurea (3, Wy-47,120), was orally active with ED50's of 56 mg/kg vs. LTD4 and 55 mg/kg vs. ovalbumin. When tested as an antagonist of LTD4-induced contraction of isolated guinea pig tracheal strips, 3 was a competitive inhibitor with a p kappa B value of 5.22. In the second series, (R)-3-methyl-5-[3-(2-quinolinylmethoxy)phenyl]-2-oxazolidinone (26, Wy-47,674) had oral ED50's of 36 mg/kg against LTD4 and 95 mg/kg against ovalbumin. Compound 26 selectively antagonized contractile responses of guinea pig trachea evoked by LTD4 (p kappa B = 6.09). In the cat coronary artery, 3 dilated the preparation and blocked the coronary constrictor effect of LTD4. Compound 3 (0.13 mg/kg, iv) also preserved myocardial integrity in rats 48 h after coronary artery ligation. When tested in the rat alcohol-induced gastric lesion model, 3 and 26 manifested a dose-dependent mucosal protection against ethanol.