ethyl (4-(1-hydroxy)ethylphenyl)acetate | 58262-39-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (4-(1-hydroxy)ethylphenyl)acetate
• 英文别名: Ethyl [4-(1-hydroxyethyl)phenyl]acetate；ethyl 2-[4-(1-hydroxyethyl)phenyl]acetate
• CAS: 58262-39-8
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: PQWVOQDOGCLIJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (4-(1-hydroxy)ethylphenyl)acetate 在 jones reagent 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 2.83h， 生成 3-(4-Acetyl-phenyl)-4-(4-methanesulfonyl-phenyl)-5H-furan-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a novel class of rofecoxib analogues as dual inhibitors of cyclooxygenases (COXs) and lipoxygenases (LOXs)

  摘要：

  A group of 4-(4-methanesulfonylphenyl)-3-phenyl-2(5H)furanones possessing an acetyl, 3-oxobut-1-ynyl, [hydroxyl(or alkoxy)imino]alkyl, [hydroxyl(or alkoxy)imino]alkynyl, and N-alkoxy(or N-phenoxy)carbonyl-N-hydroxy-N-ethylamino substituents at the para-position of the C-3 phenyl ring of rofecoxib were synthesized. This group of compounds was designed for evaluation as dual inhibitors of cyclooxygenases (COXs) and lipoxygenases (LOXs) that exhibit in vivo anti-inflammatory and analgesic activities. In vitro COX-1/COX-2, and 5-LOX/15-LOX, isozyme inhibition structure-activity relationships identified 3-[4-(1-hydroxyimino)ethylphenyl]-4-(4-methanesulfonylphenyl)-2(5H)furanone (17a) having an optimal combination of COX-2 (COX-2 IC50 = 1.4 microM; COX-2 SI > 71), and 5-LOX and 15 LOX (5-LOX IC50 = 0.28 microM; 15-LOX IC50 = 0.32 microM), inhibitory effects. It was also discovered that 3-[4-(3-hydroxyiminobut-1-ynyl)phenyl]-4-(4-methanesulfonylphenyl)-2(5H)furanone (18a) possesses dual COX-2 (IC50 = 2.7 microM) and 5-LOX (IC50 = 0.30 microM) inhibitor actions. Further in vivo studies employing a rat carrageenan-induced paw edema model showed that the oxime compounds (17a, 18a) were more potent anti-inflammatory agents than the 5-LOX inhibitor caffeic acid, and 15-LOX inhibitor nordihydroguaiaretic acid (NDGA), but less potent than the selective COX-2 inhibitor celecoxib. The results of this investigation showed that incorporation of a para-oxime moiety on the C-3 phenyl ring of rofecoxib provides a suitable template for the design of dual inhibitors of the COX and LOX enzymes.

  DOI：

  10.1016/j.bmc.2006.07.047
• 作为产物：
  描述：

  4-乙酰基苯乙酸乙酯 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以88%的产率得到ethyl (4-(1-hydroxy)ethylphenyl)acetate
  参考文献：
  名称：

  Synthesis and biological evaluation of a novel class of rofecoxib analogues as dual inhibitors of cyclooxygenases (COXs) and lipoxygenases (LOXs)

  摘要：

  A group of 4-(4-methanesulfonylphenyl)-3-phenyl-2(5H)furanones possessing an acetyl, 3-oxobut-1-ynyl, [hydroxyl(or alkoxy)imino]alkyl, [hydroxyl(or alkoxy)imino]alkynyl, and N-alkoxy(or N-phenoxy)carbonyl-N-hydroxy-N-ethylamino substituents at the para-position of the C-3 phenyl ring of rofecoxib were synthesized. This group of compounds was designed for evaluation as dual inhibitors of cyclooxygenases (COXs) and lipoxygenases (LOXs) that exhibit in vivo anti-inflammatory and analgesic activities. In vitro COX-1/COX-2, and 5-LOX/15-LOX, isozyme inhibition structure-activity relationships identified 3-[4-(1-hydroxyimino)ethylphenyl]-4-(4-methanesulfonylphenyl)-2(5H)furanone (17a) having an optimal combination of COX-2 (COX-2 IC50 = 1.4 microM; COX-2 SI > 71), and 5-LOX and 15 LOX (5-LOX IC50 = 0.28 microM; 15-LOX IC50 = 0.32 microM), inhibitory effects. It was also discovered that 3-[4-(3-hydroxyiminobut-1-ynyl)phenyl]-4-(4-methanesulfonylphenyl)-2(5H)furanone (18a) possesses dual COX-2 (IC50 = 2.7 microM) and 5-LOX (IC50 = 0.30 microM) inhibitor actions. Further in vivo studies employing a rat carrageenan-induced paw edema model showed that the oxime compounds (17a, 18a) were more potent anti-inflammatory agents than the 5-LOX inhibitor caffeic acid, and 15-LOX inhibitor nordihydroguaiaretic acid (NDGA), but less potent than the selective COX-2 inhibitor celecoxib. The results of this investigation showed that incorporation of a para-oxime moiety on the C-3 phenyl ring of rofecoxib provides a suitable template for the design of dual inhibitors of the COX and LOX enzymes.

  DOI：

  10.1016/j.bmc.2006.07.047

文献信息

• Quinolines useful in treating cardiovascular disease
  申请人：Collini D. Michael

  公开号：US20050131014A1

  公开（公告）日：2005-06-16

  This invention provides compounds of formula I that are useful in the treatment or inhibition of LXR mediated diseases.

  本发明提供了式I化合物的用途，它们在治疗或抑制LXR介导的疾病中是有用的。
• Quinone derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05180742A1

  公开（公告）日：1993-01-19

  Quinone derivatives of the general formula: ##STR1## (wherein R.sup.1 and R.sup.2 are the same or different, and independently are a hydrogen atom or a methyl or methoxy group, or R.sup.1 and R.sup.2 combine with each other to represent --CH.dbd.CH--CH.dbd.CH--R.sup.3 is a hydrogen atom or a methyl group; R.sup.4 is an aliphatic, aromatic or heterocyclic group which may be substituted; R.sup.5 is a methyl or methoxy group, a hydroxymethyl group which may be substituted or a carboxyl group which may be esterified or amidated; Z is a group represented by --C.dbd.C--, --CH.dbd.CH--, ##STR2## n is an integer of 0 to 10; m is an integer of 0 to 3; k is an integer of 0 to 5, provided, however, that in the case of m being 2 or 3, Z and k can vary arbitrarily within the bracketed repeating units) are novel compounds, possess metabolism ameliorating action for polyunsaturated fatty acids, particularly production inhibitory activity of lipid peroxides (antioxidant activity), thromboxane A.sub.2 receptor antagonism, or production inhibitory activity of 5-lipoxygenase metabolites in mammals, and of use as drugs, such as antiasthmatic, antiallergic agent and cerebral-circulatory metabolism ameliorating agent.

  通式为：##STR1##的醌衍生物（其中R.sup.1和R.sup.2相同或不同，且独立地为氢原子或甲基或甲氧基，或R.sup.1和R.sup.2结合在一起表示--CH.dbd.CH--CH.dbd.CH--R.sup.3为氢原子或甲基；R.sup.4为可以被取代的脂肪、芳香或杂环基团；R.sup.5为甲基或甲氧基、可以被取代的羟甲基或可以酯化或酰胺化的羧基；Z为--C.dbd.C--，--CH.dbd.CH--，##STR2##所表示的基团；n为0到10的整数；m为0到3的整数；k为0到5的整数，但是在m为2或3的情况下，Z和k可以在括号内的重复单元中任意变化）是新颖的化合物，具有改善多不饱和脂肪酸代谢的作用，特别是对脂质过氧化物的产生抑制活性（抗氧化活性）、血栓素A.sub.2受体拮抗作用，或对哺乳动物中5-脂氧合酶代谢产物的产生抑制活性，并可用作药物，如抗哮喘、抗过敏剂和改善脑循环代谢的药剂。
• Quinolines and pharmaceutical compositions thereof
  申请人：Wyeth

  公开号：US07576215B2

  公开（公告）日：2009-08-18

  This invention provides compounds of formula I that are useful in the treatment or inhibition of LXR mediated diseases.

  本发明提供了I式化合物，可用于治疗或抑制LXR介导的疾病。
• QUINOLINES USEFUL IN TREATING CARDIOVASCULAR DISEASE
  申请人：Wyeth, A Corporation of the State of Delaware

  公开号：EP1692111A2

  公开（公告）日：2006-08-23
• US5180742A
  申请人：——

  公开号：US5180742A

  公开（公告）日：1993-01-19