2-[4-(1-羟乙基)苯基]乙酸 | 855935-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[4-(1-羟乙基)苯基]乙酸
• 英文名称: (4-(1-hydroxy)ethylphenyl)acetic acid
• 英文别名: [4-(1-Hydroxy-aethyl)-phenyl]-essigsaeure；[4-(1-Hydroxyethyl)phenyl]acetic acid；2-[4-(1-hydroxyethyl)phenyl]acetic acid
• CAS: 855935-31-8
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: NPHZIWZSJCUWKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-[4-(1-羟乙基)苯基]乙酸 在 jones reagent 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.33h， 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 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 生成 2-[4-(1-羟乙基)苯基]乙酸
  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

• Precise Alkoxyamine Design to Enable Automated Tandem Mass Spectrometry Sequencing of Digital Poly(phosphodiester)s
  作者：Kévin Launay、Jean‐Arthur Amalian、Eline Laurent、Laurence Oswald、Abdelaziz Al Ouahabi、Alexandre Burel、Florent Dufour、Christine Carapito、Jean‐Louis Clément、Jean‐François Lutz、Laurence Charles、Didier Gigmes

  DOI：10.1002/anie.202010171

  日期：2021.1.11

  sequence of long poly(phosphodiester)s was previously achieved by introducing an alkoxyamine spacer between information sub‐segments. However, MS/MS decoding had to be performed manually to safely identify useful fragments of low abundance compared to side‐products from the amide‐based alkoxyamine used. Here, alternative alkoxyamines were designed to prevent side‐reactions and enable automated MS/MS sequencing

  以前，通过在信息子片段之间引入烷氧基胺间隔基，可实现迈向可靠读取长聚磷酸二酯序列编码信息的重要一步。但是，与使用酰胺基烷氧基胺的副产品相比，必须手动执行MS / MS解码，以安全地鉴定有用的低丰度片段。在这里，替代烷氧基胺旨在防止副反应并实现自动MS / MS测序。准备了不同的苯乙烯基-TEMPO间隔基，以增加自由基的离域作用和结构的刚度。通过EPR研究了它们的解离行为，并使用含有链内苄基环的间隔基获得了最佳结果，在合成或测序过程中没有副反应。使用MS-DECODER软件对这些聚合物进行自动解码，
• Conception and Evaluation of a Library of Cleavable Mass Tags for Digital Polymers Sequencing
  作者：Thibault Schutz、Isaure Sergent、Georgette Obeid、Laurence Oswald、Abdelaziz Al Ouahabi、Paul N. W. Baxter、Jean‐Louis Clément、Didier Gigmes、Laurence Charles、Jean‐François Lutz

  DOI：10.1002/anie.202310801

  日期：2023.11.6

  phosphoramidite monomers was synthesized herein for facilitating the mass spectrometry (MS) sequencing of digital poly(phosphodiester)s. These molecules contain a cleavable alkoxyamine group and various side-chain substituents with a distinct mass signature. When incorporated periodically in the polymers, these new molecules enable a controlled MS fragmentation and an easy identification of the resulting

  本文合成了一组最佳的亚磷酰胺单体，以促进数字聚（磷酸二酯）的质谱（MS）测序。这些分子含有可裂解的烷氧基胺基团和具有独特质量特征的各种侧链取代基。当定期掺入聚合物中时，这些新分子能够实现受控的 MS 碎片并轻松识别所得碎片。
• Synthese von p-Acetylphenyl-fetts�uren, p-[(?)-Oxy�thylphenyl]-fetts�uren, der p-Methylatrolactins�ure und des Dehydrochols�ureamids des p-Aminoacetophenons
  作者：L. Schmid、H. Schultes、M. Wichtl

  DOI：10.1007/bf00900429

  日期：——
• Synthesis and biological evaluation of a novel class of rofecoxib analogues as dual inhibitors of cyclooxygenases (COXs) and lipoxygenases (LOXs)
  作者：Qiao-Hong Chen、P.N. Praveen Rao、Edward E. Knaus

  DOI：10.1016/j.bmc.2006.07.047

  日期：2006.12

  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.