3-(4-hydroxy-3-allylphenyl)acrylic acid | 52507-50-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4-hydroxy-3-allylphenyl)acrylic acid
• 英文别名: 3-allyl-4-hydroxy-cinnamic acid；β-(4-Oxy-3-allyl-phenyl)-acrylsaeure；3-Allyl-4-hydroxy-zimtsaeure；3-(4-hydroxy-3-prop-2-enylphenyl)prop-2-enoic acid
• CAS: 52507-50-3
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: MAYTXVQHJNLZKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  3-(4-hydroxy-3-allylphenyl)acrylic acid 在 sodium hydroxide 作用下， 生成 3-Allyl-4-acetoxy-zimtsaeureazid
  参考文献：
  名称：

  DE2324584

  摘要：

  公开号：
• 作为产物：
  描述：

  4-羟基肉桂酸甲酯 在 potassium carbonate 、 N,N-二乙基苯胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 9.5h， 生成 3-(4-hydroxy-3-allylphenyl)acrylic acid
  参考文献：
  名称：

  Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis

  摘要：

  The tumor microenvironment is characterized by hypoxia, low-nutrient levels, and acidosis. A natural product chemistry-based approach was used to discover small molecules that modulate adaptive responses to a hypoxic microenvironment through the hypoxia-inducible factor (HIF)-1 signaling pathways. Five compounds, such as baccharin (3), beturetol (4), kaempferide (5), isosakuranetin (6), and drupanin (9), that modulate HIF-1-dependent luciferase activity were identified from Brazilian green propolis using reporter assay. Compounds 3, 9 and 5 reduced HIF-1-dependent luciferase activity. The cinnamic acid derivatives 3 and 9 significantly inhibited expression of the HIF-1 alpha protein and HIF-1 downstream target genes such as glucose transporter 1, hexokinase 2, and vascular endothelial growth factor A. They also exhibited significant anti-angiogenic effects in the chick chorioallantoic membrane (CAM) assay at doses of 300 ng/CAM. On the other hand, flavonoids 4 and 6 induced HIF-1-dependent luciferase activity and expression of HIF-1 target genes under hypoxia. The contents (g/100 g extract) of the HIF-1-modulating compounds in whole propolis ethanol extracts were also determined based on liquid chromatography-electrospray ionization mass spectrometry as 1.6 (3), 14.2 (4), 4.0 (5), 0.7 (6), and 0.7 (9), respectively. These small molecules screened from Brazilian green propolis may be useful as lead compounds for the development of novel therapies against ischemic cardiovascular disease and cancer based on their ability to induce or inhibit HIF-1 activity, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.060

文献信息

• [EN] PHENYLALKANOIC ACID AND PHENYLOXYALKANOIC ACID DERIVATIVES AS HPPAR ACTIVATORS<br/>[FR] ACIDE PHENYLALKANOIQUE ET DERIVES D'ACIDE PHENYLOXYALKANOIQUE EN TANT QU'ACTIVATEURS DE HPPAR
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2004000315A1

  公开（公告）日：2003-12-31

  The present invention provides a compound of formula (I):wherein:R1 and R2 are independently H or C1-3 alkyl;X represents a O or (CH2)n where n is 0, 1 or 2;R3and R4 independently represent H, C1-3 alkyl, -OCH3, -CF3, allyl, or halogen;X1 represents O, S, SO2, SO, or CH2;R5 and R6 independently represent hydrogen, C1-6 alkyl (including branched alkyl and optionally substituted by one or more halogens or C1-6alkoxy), or together with the carbon atom to which they are bonded form a 3-6 membered cycloalkyl ring;R7 represents a phenyl or a 6 membered heteroaryl group containing 1, 2 or 3 nitrogen atoms wherein the phenyl or heteroaryl group is substituted by 1, 2 or 3 moieties selected from the group consisting of halogen, C1-6 alkoxy, C1-6 alkyl, CF3, hydroxy, or phenyl (which may be optionally substituted by one or more C1-3 alkyl, -OC1-3 alkyl, CN, acetyl, hydroxy, halogen or CF3).

  本发明提供了一种具有以下结构的化合物(I)：其中：R1和R2分别独立地表示H或C1-3烷基；X代表O或(CH2)n，其中n为0、1或2；R3和R4独立地表示H、C1-3烷基、-OCH3、-CF3、烯丙基或卤素；X1代表O、S、SO2、SO或 ；R5和R6独立地表示氢、C1-6烷基（包括支链烷基，并且可以选择性地被一个或多个卤素或C1-6烷氧基取代），或者与它们键合的碳原子一起形成一个3-6环状烷基环；R7表示苯基或含有1、2或3个氮原子的6元杂芳基，其中苯基或杂芳基被选自卤素、C1-6烷氧基、C1-6烷基、 、羟基或苯基（可以选择性地被一个或多个C1-3烷基、-OC1-3烷基、CN、乙酰基、羟基、卤素或 取代）的1、2或3个取代基取代。
• Phenylalkanoic acid and phenyloxyalkanoic acid derivatives as hppar activators
  申请人：Bell Richard

  公开号：US20060089394A1

  公开（公告）日：2006-04-27

  A compound of formula (I) or a pharmaceutically acceptable salt, solvate, or hydrolysable ester thereof, wherein:

  化合物的公式（I）或其药学上可接受的盐、溶剂化合物或可水解酯，其中：
• N-cinnamylcarbamic acid esters
  申请人：Ciba-Geigy Corporation

  公开号：US04014920A1

  公开（公告）日：1977-03-29

  Amines of the formula ##SPC1## Wherein R.sub.1 is lower alkyl, lower alkoxy or amino, R.sub.2 is hydrogen or lower alkyl, R.sub.3 is hydrogen, lower alkyl, carboxyl or lower alkoxycarbonyl, R.sub.4 is hydrogen or lower alkyl, R.sub.5 is lower alkyl, aryl-lower alkyl or optionally functionally modified carboxy-lower alkyl and R.sub.6 denotes halogen, trifluoromethyl, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy, nitro, lower alkoxymethyl, carbamoyl, N-lower alkylcarbamoyl, nitrile, lower alkinyloxy or hydrogen, and their salts block cardiac and vascular .beta.-receptors the are useful in the treatment of arrhythenias and angina pectoris and as intermediates for, especially for pharmaceutically active substances.

  化合物的胺式##SPC1##其中R.sub.1是低烷基，低烷氧基或氨基，R.sub.2是氢或低烷基，R.sub.3是氢，低烷基，羧基或低烷氧羰基，R.sub.4是氢或低烷基，R.sub.5是低烷基，芳基-低烷基或可选择性功能修饰的羧基-低烷基，R.sub.6表示卤素，三氟甲基，低烷基，低烯基，低烷氧基，低烯基氧基，硝基，低烷氧甲基，氨基甲酰，N-低烷基氨基甲酰，腈，低炔氧基或氢，并且它们的盐可以阻断心脏和血管的β-受体，对于治疗心律失常和心绞痛以及作为特别是药物活性物质的中间体是有用的。
• Amines and processes for their manufacture
  申请人：Ciba-Geigy Corporation

  公开号：US04038414A1

  公开（公告）日：1977-07-26

  Amines of the formula ##STR1## wherein R.sub.1 is lower alkyl, lower alkoxy or amino, R.sub.2 is hydrogen or lower alkyl, R.sub.3 is hydrogen, lower alkyl, carboxyl or lower alkoxycarbonyl, R.sub.4 is hydrogen or lower alkyl, R.sub.5 is lower alkyl, aryl-lower alkyl or optionally functionally modified carboxy-lower alkyl and R.sub.6 denotes halogen, trifluoromethyl, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy, nitro, lower alkoxymethyl, carbamoyl, N-lower alkylcarbamoyl, nitrile, lower alkinyloxy or hydrogen, and their salts block cardiac and vascular .beta.-receptors the are useful in the treatment of arrhythenias and angina pectoris and as intermediates for, especially for pharmaceutically active substances.

  式为##STR1##的胺，其中R.sub.1是低烷基，低烷氧基或氨基，R.sub.2是氢或低烷基，R.sub.3是氢，低烷基，羧基或低烷氧羰基，R.sub.4是氢或低烷基，R.sub.5是低烷基，芳基-低烷基或可选功能修饰的羧基-低烷基，R.sub.6表示卤素，三氟甲基，低烷基，低烯基，低烷氧基，低烯基氧基，硝基，低烷氧甲基，氨基甲酰，N-低烷基氨基甲酰，腈，低炔氧基或氢，及其盐可阻塞心脏和血管的β-受体，适用于治疗心律失常和心绞痛，并作为中间体，特别是用于药物活性物质。
• Mills; Adams, Journal of the American Chemical Society, 1923, vol. 45, p. 1852
  作者：Mills、Adams

  DOI：——

  日期：——