R-(-)-α-methyl-6-hydroxy-2-naphthalene acetic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: R-(-)-α-methyl-6-hydroxy-2-naphthalene acetic acid
• 英文别名: (R)-O-Desmethyl Naproxen；(2R)-2-(6-hydroxynaphthalen-2-yl)propanoic acid
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: XWJUDDGELKXYNO-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  R-(-)-α-methyl-6-hydroxy-2-naphthalene acetic acid 生成 R-(-)-α-methyl-6-(2-quinolinylmethoxy)-2-naphthaleneacetic acid
  参考文献：
  名称：

  Quinoline substituted naphthalenepropionic acid derivatives as

  摘要：

  给定的化合物公式为##STR1##，其中a是烷基，含有3-19个碳原子，二次烷基烯丙基，二卤代烯丙基，二苯基烯丙基，低炔基，##STR2## W是--CR.sub.2 O--，--CH.dbd.CH--或--CH.dbd.CHCH.sub.2 O-- X是N或CR；Z是##STR3## R是氢或低烷基；Y是##STR4## R.sup.1是氢，低烷基或苯基；R.sup.2是氢或低烷基；或者R.sup.1和R.sup.2一起形成苯环，可以选择地被卤素取代；R.sup.3是--OR，##STR5## -- NHSO.sub.2 R.sup.4；R.sup.4是苯基或低烷基取代的苯基；R.sup.5是卤素；以及它们的药用盐，以及它们在治疗白三烯介导的鼻支气管阻塞气道疾病中的用途，例如过敏性鼻炎，过敏性支气管哮喘等，在牛皮癣，溃疡性结肠炎，类风湿性关节炎以及其他即时超敏反应中。

  公开号：

  US05084575A1
• 作为产物：
  描述：

  (R)-萘普生 在 水 、 氢溴酸 作用下， 反应 2.0h， 以96%的产率得到R-(-)-α-methyl-6-hydroxy-2-naphthalene acetic acid
  参考文献：
  名称：

  Two-colour screening in combinatorial chemistry: prospecting for enantioselectivity in a library of steroid-based receptors

  摘要：

  The screening of resin-bound combinatorial libraries with pairs of dye-tagged substrates is a powerful strategy for discovering selective receptors. However, implementation has been hampered by a lack of complementary but chemically similar dyes. We now show that the well-established Disperse Red 1 and the recently-introduced Bristol Blue 1 can be used in parallel to synthesise 'pseudoenantiomeric' analogues of N-acetyl-alpha-amino acids and of the anti-inflammatory drug Naproxen. A steroid-based receptor library has been prepared and screened with these substrates. Preliminary results suggest that some members may be highly enantioselective receptors for N-acetyl-alpha-amino acids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.018

文献信息

• Quinoline substituted naphthalenepropionic acid derivatives as
  申请人：American Home Products Corporation

  公开号：US05084575A1

  公开（公告）日：1992-01-28

  There are disclosed compounds of the formula ##STR1## wherein a is alkyl 3-19 carbon atoms, diloweralkyl allyl, diahaloallyl, diphenylallyl, lower alkynyl, ##STR2## W is --CR.sub.2 O--, --CH.dbd.CH-- or --CH.dbd.CHCH.sub.2 O-- X is N or CR; Z is ##STR3## R is hydrogen or lower alkyl; Y is ##STR4## R.sup.1 is hydrogen, lower alkyl or phenyl; R.sup.2 is hydrogen or lower alkyl; or R.sup.1 and R.sup.2 taken together form a benzene ring, optionally substituted by halo; R.sup.3 is --OR, ##STR5## -- NHSO.sub.2 R.sup.4 ; R.sup.4 is phenyl or loweralkyl substituted phenyl; R.sup.5 is halo; and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as alelrgic rhinitis, allergic bronchial asthma and the like, in psoriasis, ulcerative colitis, rheumatoid arthritis as well as in other immediate hypersensitivity reactions.

  给定的化合物公式为##STR1##，其中a是烷基，含有3-19个碳原子，二次烷基烯丙基，二卤代烯丙基，二苯基烯丙基，低炔基，##STR2## W是--CR.sub.2 O--，--CH.dbd.CH--或--CH.dbd.CHCH.sub.2 O-- X是N或CR；Z是##STR3## R是氢或低烷基；Y是##STR4## R.sup.1是氢，低烷基或苯基；R.sup.2是氢或低烷基；或者R.sup.1和R.sup.2一起形成苯环，可以选择地被卤素取代；R.sup.3是--OR，##STR5## -- NHSO.sub.2 R.sup.4；R.sup.4是苯基或低烷基取代的苯基；R.sup.5是卤素；以及它们的药用盐，以及它们在治疗白三烯介导的鼻支气管阻塞气道疾病中的用途，例如过敏性鼻炎，过敏性支气管哮喘等，在牛皮癣，溃疡性结肠炎，类风湿性关节炎以及其他即时超敏反应中。
• Quinolinylmethoxy naphthalenepropionic acid derivatives as
  申请人：American Home Products Corporation

  公开号：US05250693A1

  公开（公告）日：1993-10-05

  There are disclosed compounds of the formula ##STR1## wherein R is hydrogen or lower alkyl; Y is ##STR2## or a pharmaceutically acceptable salt thereof, and its 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.

  公开了化合物的结构式为##STR1##其中R是氢或较低的烷基；Y是##STR2##或其药学上可接受的盐，并且其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，牛皮癣，溃疡性结肠炎，类风湿性关节炎以及其他即时型超敏反应中的用途。
• Naphthalenepropionic acid derivatives as anti-inflammatory/anti-allergic
  申请人：American Home Products Corporation

  公开号：US04960892A1

  公开（公告）日：1990-10-02

  There are disclosed compounds of the formula ##STR1## wherein A is alkyl of 3-19 carbon atoms, diloweralkyl allyl, dihaloallyl, diphenylallyl, lower alkynyl, ##STR2## X is N or CR; Z is ##STR3## R is hydrogen or lower alkyl; R.sup.1 is hydrogen, lower alkyl or phenyl; R.sup.2 is hydrogen or loweralkyl; or R.sup.1 and R.sup.2 taken together form a benzene ring; 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.

  公开了以下化合物的结构式##STR1##其中A是3-19个碳原子的烷基，二次烷基烯丙基，二卤代烯丙基，二苯基烯丙基，低炔基，##STR2##X是N或CR；Z是##STR3##R是氢或低烷基；R.sup.1是氢，低烷基或苯基；R.sup.2是氢或低烷基；或者R.sup.1和R.sup.2一起形成苯环；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，类风湿性关节炎以及其他即时超敏反应中的用途。
• Efficient demethylation of aromatic methyl ethers with HCl in water
  作者：Jeroen Bomon、Mathias Bal、Tapas Kumar Achar、Sergey Sergeyev、Xian Wu、Ben Wambacq、Filip Lemière、Bert F. Sels、Bert U. W. Maes

  DOI：10.1039/d0gc04268d

  日期：——

  A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could

  芳族甲基醚与无机酸（HCl或H 2 SO 4）作为催化剂在高温加压水中进行绿色，高效且廉价的脱甲基反应，可高产率提供相应的芳族醇（酚，邻苯二酚，邻苯三酚）。考虑到4-丙基邻苯二酚反应产物的各种应用，选择4-丙基愈创木酚作为模型。该脱甲基反应可以容易地扩大规模，并且来自木材和丁香油的可生物再生的4-丙基愈创木酚也可以用作原料。所开发方法的绿色度与通过进行定量和定性的Green Metrics分析，评估了最先进的脱甲基反应。该方法在多种含（生物可再生）底物的芳族甲基醚上具有多功能性，可产生高达99％的相应芳族醇，在大多数情况下，仅需简单提取即可进行后处理。
• Naphthalenepropionic acid derivatives
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0301813B1

  公开（公告）日：1990-08-08