3-methoxy-4-hydroxyphenylpropenoic acid | 1208246-60-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-methoxy-4-hydroxyphenylpropenoic acid
• 英文别名: 4-hydroxy-3-methoxyphenylpropenoic acid；(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid；2-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
• CAS: 1208246-60-9
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: MWSIBOZRUWYJET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-hydroxyphenylpropenoic acid 、 resiniferonol 9,13,14-orthophenylacetate 生成
  参考文献：
  名称：

  Structure–activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The side chain benzylic methylene

  摘要：

  The side chain benzylic methylene is a critical element for the vanilloid activity of resiniferatoxin (2a, RTX), and introduction of branching, oxygen functions, or isosteric substitution at this center proved detrimental, with a decrease of potency of 2-3 orders of magnitude compared to the natural product. Conversely, only a modest erosion of activity was observed upon a-methylation and alpha-methylenation of the side chain. Surprisingly, introduction of an iodine atom in the guaiacyl moiety of the oxygen isoster 2h led to an unexpected and remarkable (> 1000-fold) increase of potency, affording 2i, a compound that outperforms RTX in terms of vanilloid agonism and represents the first one-digit picomolar ligand of a TRP channel discovered to date. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.035
• 作为产物：
  描述：

  在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以71%的产率得到3-methoxy-4-hydroxyphenylpropenoic acid
  参考文献：
  名称：

  Structure–activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The side chain benzylic methylene

  摘要：

  The side chain benzylic methylene is a critical element for the vanilloid activity of resiniferatoxin (2a, RTX), and introduction of branching, oxygen functions, or isosteric substitution at this center proved detrimental, with a decrease of potency of 2-3 orders of magnitude compared to the natural product. Conversely, only a modest erosion of activity was observed upon a-methylation and alpha-methylenation of the side chain. Surprisingly, introduction of an iodine atom in the guaiacyl moiety of the oxygen isoster 2h led to an unexpected and remarkable (> 1000-fold) increase of potency, affording 2i, a compound that outperforms RTX in terms of vanilloid agonism and represents the first one-digit picomolar ligand of a TRP channel discovered to date. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.035

文献信息

• Photopolymerizable mixture and recording material produced from it
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0155652A2

  公开（公告）日：1985-09-25

  A photopolymerizable mixture is described which contains the following: a binding agent which is soluble or at least capable of swelling in aqueous-alkaline solutions, a photoinitiator or a photoinitiator system and at least one ethylenically unsaturated monomer, whereby at least one monomer contains an aromatic hydroxyl-, mercapto-, sulfonamide- or a mono-N-substituted sulfonamide group, or combinations thereof.

  描述了一种可光聚合的混合物，它包含以下成分：可溶于碱性水溶液或至少能在碱性水溶液中溶胀的结合剂、光引发剂或光引发剂体系以及至少一种乙烯基不饱和单体，其中至少一种单体包含芳香羟基、巯基、磺酰胺基或单-N-取代的磺酰胺基，或它们的组合。
• Pharmaceutical compositions useful in prevention and treatment of beta-amyloid protien-induced disease
  申请人：Kim S.H.L. Darrick

  公开号：US20050239882A1

  公开（公告）日：2005-10-27

  The invention provides methods for treating beta-Amyloid protein-induced disease, pharmaceutical compositions and compounds useful for the same, and the use of these compounds for the manufacture of a medicament for treating the same. More particularly, the invention relates to the use of natural product compounds isolated from turmeric, gingko biloba, and ginger, and synthetic chemical analogues thereof, for the treatment of a beta-Amyloid protein-induced disease.

  本发明提供了治疗β-淀粉样蛋白诱导的疾病的方法、对其有用的药物组合物和化合物，以及使用这些化合物制造治疗该疾病的药物。 银杏叶 和生姜中分离出来的天然产物化合物及其合成化学类似物，用于治疗β-淀粉样蛋白诱发的疾病。
• Methods for treatment of beta-amyloid protein-induced ocular disease
  申请人：Kim S. H. L. Darrick

  公开号：US20060148905A1

  公开（公告）日：2006-07-06

  The invention provides methods for treating beta-amyloid protein-involved ocular disease including age-related macular degeneration and glaucoma, pharmaceutical compositions and compounds useful for the same, and the use of these compounds for the manufacture of a medicament for treating the same. More particularly, the invention relates to the use of natural product compounds isolated from Curcuma sp., Zingiber sp., Ginkgo biloba, Salvia sp., and Rosmarinus sp. and synthetic chemical analogues thereof, for the treatment of a beta-amyloid protein-involved ocular disease.

  本发明提供了治疗β-淀粉样蛋白参与的眼部疾病（包括老年性黄斑变性和青光眼）的方法、药物组合物和对其有用的化合物，以及使用这些化合物制造治疗上述疾病的药物。更具体地说，本发明涉及从以下植物中分离出的天然产物化合物的用途 莪术 sp、 薑 sp、 银杏叶、丹参 和 蔷薇 及其合成化学类似物，用于治疗受β-淀粉样蛋白影响的眼部疾病。
• METHODS FOR TREATMENT OF BETA-AMYLOID PROTEIN-INDUCED OCULAR DISEASE
  申请人：Kim, Darrick S.H.L.

  公开号：EP1895849A1

  公开（公告）日：2008-03-12
• Pharmaceutical compositions useful in prevention and treatment of beta-amyloid protein-induced disease
  申请人：Kim S. H. L. Darrick

  公开号：US20050197393A1

  公开（公告）日：2005-09-08

  The invention provides methods for treating beta-Amyloid protein-induced disease, pharmaceutical compositions and compounds useful for the same, and the use of these compounds for the manufacture of a medicament for treating the same. More particularly, the invention relates to the use of natural product compounds isolated from turmeric, gingko biloba , and ginger, and synthetic chemical analogues thereof, for the treatment of a beta-Amyloid protein-induced disease.