2-Ethyl-4,5-dihydro-5-[3-[(2-quinolinyl)methoxy]phenyl]-1,3-oxazole | 110205-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-Ethyl-4,5-dihydro-5-[3-[(2-quinolinyl)methoxy]phenyl]-1,3-oxazole
• 英文别名: 2-Ethyl-5-[3-(quinolin-2-ylmethoxy)phenyl]-4,5-dihydro-1,3-oxazole
• CAS: 110205-31-7
• 化学式: C₂₁H₂₀N₂O₂
• 分子量: 332.402
• InChiKey: JFFXCTBSQURQOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  43.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Ethyl-4,5-dihydro-5-[3-[(2-quinolinyl)methoxy]phenyl]-1,3-oxazole 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以8%的产率得到2-Amino-1-[3-(quinolin-2-ylmethoxy)phenyl]ethanol
  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：

  盐酸去甲苯福林 在 caesium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 64.0h， 生成 2-Ethyl-4,5-dihydro-5-[3-[(2-quinolinyl)methoxy]phenyl]-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-[3-[[2-quinolyl]methoxy]phenyl]-1,3-oxazoles
  申请人：American Home Products Corporation

  公开号：US04681940A1

  公开（公告）日：1987-07-21

  There are disclosed compounds of the formula ##STR1## wherein X is N or CR.sup.2 Y is O, S, NR.sup.2, CHR.sup.2 or C(R.sup.2).sub.2 when n=0, or N or CR.sup.2 when n=1; p is 0-3; R.sup.1 is ##STR2## R.sup.2 is hydrogen or lower alkyl; R.sup.3 is hydrogen, lower alkyl, phenyl, thienyl, furyl, pyridyl, ##STR3## --C(R.sup.4).sub.3 or --(CH.sub.2).sub.p COOR.sup.2 ; R.sup.4 is halo; Z is O or S; and the pharmaceutically acceptable salts thereof, and their use in the treatment of luekotriene-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.

  已公开的化合物的化学式为##STR1##其中X是N或CR.sup.2，Y是O、S、NR.sup.2、CHR.sup.2或C(R.sup.2).sub.2（当n=0时），或N或CR.sup.2（当n=1时）；p为0-3；R.sup.1是##STR2##R.sup.2是氢或低碳烷基；R.sup.3是氢、低碳烷基、苯基、噻吩基、呋喃基、吡啶基、##STR3##--C(R.sup.4).sub.3或--(CH.sub.2).sub.p COOR.sup.2；R.sup.4是卤素；Z是O或S；以及其药用盐，以及它们在治疗白三烯介导的鼻支气管阻塞症状，如过敏性鼻炎、过敏性支气管哮喘等，牛皮癣、溃疡性结肠炎、类风湿关节炎以及其他即时过敏反应中的用途。
• 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.