(R)-3-hydroxy-α-<(methyl-2-propanoylamino)methyl>benzenemethanol | 110193-52-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-3-hydroxy-α-<(methyl-2-propanoylamino)methyl>benzenemethanol
• 英文别名: (R)-3-Hydroxy-alpha-[[methyl-(2-propynyl)amino]methyl]benzene methanol；3-[(1R)-1-hydroxy-2-[methyl(prop-2-ynyl)amino]ethyl]phenol
• CAS: 110193-52-7
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: FRKFSHRHMFDLEB-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(氯甲基)喹啉 、 (R)-3-hydroxy-α-<(methyl-2-propanoylamino)methyl>benzenemethanol 在 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以15%的产率得到(R)-2-(Methyl-prop-2-ynyl-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：

  盐酸去氧肾上腺素 、 3-溴丙炔 在 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.0h， 以64%的产率得到(R)-3-hydroxy-α-<(methyl-2-propanoylamino)methyl>benzenemethanol
  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

• Quinoline compounds
  申请人：American Home Products Corporation

  公开号：US04876346A1

  公开（公告）日：1989-10-24

  There are disclosed compounds of the formula ##STR1## wherein X is N or CR.sup.1 Y is O, S, NR.sup.1, CHR.sup.1 or C(R.sup.1).sub.2 when n=O, or N or CR.sup.1 when n=1; p is 0-3; R.sup.1 is hydrogen or lower alkyl; R.sup.2 is H, ##STR2## --SO.sub.2 R.sup.3 or --SO.sub.2 N(R.sup.3).sub.2, lower alkyl, lower alkenyl, lower alkynyl or lower alkyl carbonyl prolinate; R.sup.3 is H, lower alkyl or perfluoro lower alkyl; R.sup.4 is lower alkyl, phenyl, pyridyl or thienyl; R.sup.5 is hydrogen, lower alkyl, phenyl or pyridyl; A is O or NR.sup.1 ; B is OR.sup.1 or N(R.sup.5).sub.2 ; m is 0-2; 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.

  公开了式子为##STR1##的化合物，其中X为N或CR.sup.1，Y为O、S、NR.sup.1、CHR.sup.1或C(R.sup.1).sub.2（当n=O时）或N或CR.sup.1（当n=1时）；p为0-3；R.sup.1为氢或低碳基；R.sup.2为H、##STR2##、--SO.sub.2 R.sup.3或--SO.sub.2 N(R.sup.3).sub.2、低碳基、低烯基、低炔基或低碳基羰基脯氨酸；R.sup.3为H、低碳基或全氟低碳基；R.sup.4为低碳基、苯基、吡啶基或噻吩基；R.sup.5为氢、低碳基、苯基或吡啶基；A为O或NR.sup.1；B为OR.sup.1或N(R.sup.5).sub.2；m为0-2；以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通气道疾病中的应用，如过敏性鼻炎、过敏性支气管哮喘等。
• MUSSER, JOHN H.;KREFT, ANTHONY F.;BENDER, REINHOLD H. W.
  作者：MUSSER, JOHN H.、KREFT, ANTHONY F.、BENDER, REINHOLD H. W.

  DOI：——

  日期：——
• MUSSER, JOHN H.;KUBRAK, DENNIS M.;BENDER, REINHOLD H. W.;KREFT, ANTHONY F+, J. MED. CHEM., 30,(1987) N 11, 2087-2093
  作者：MUSSER, JOHN H.、KUBRAK, DENNIS M.、BENDER, REINHOLD H. W.、KREFT, ANTHONY F+

  DOI：——

  日期：——