p-methoxyphenacyl phenylacetate | 124646-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenacyl phenylacetate
• 英文别名: Acetic acid, 2-phenyl-, [2-(4-methoxyphenyl)-2-oxo]ethyl ester；[2-(4-methoxyphenyl)-2-oxoethyl] 2-phenylacetate
• CAS: 124646-76-0
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: IGXYBLYOQABAJD-UHFFFAOYSA-N

物化性质

• 熔点：
  53-54 °C
• 沸点：
  438.0±25.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  p-methoxyphenacyl phenylacetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.33h， 生成 3-(4-甲氧基苯基)-4-苯基-2H-呋喃-5-酮
  参考文献：
  名称：

  Design of Fluorine-Containing 3,4-Diarylfuran-2(5H)-ones as Selective COX-1 Inhibitors

  摘要：

  We report the design and synthesis of fluorine-containing cyclooxygenase-1 (COX-1)-selective inhibitors to serve as prototypes for the development of a COX-1-targeted imaging agent. Deletion of the SO2CH3 group of rofecoxib switches the compound from a COX-2- to a COX-1-selective inhibitor, providing a 3,4-diarylfuran-2(5H)-one scaffold for structureactivity relationship studies of COX-1 inhibition. A wide range of fluorine-containing 3,4-diarylfuran-2(5H)-ones were designed, synthesized, and tested for their ability to selectively inhibit COX-1 in purified protein and human cancer cell assays. Compounds containing a fluoro-substituent on the C-3 phenyl ring and a methoxy-substituent on the C-4 phenyl ring of the 3,4-diarylfuran-2(5H)-one scaffold were the best COX-1-selective agents of those evaluated, exhibiting IC(50)s in the submicromolar range. These compounds provide the foundation for development of an agent to facilitate radiologic imaging of ovarian cancer expressing elevated levels of COX-1.

  DOI：

  10.1021/ml500344j
• 作为产物：
  描述：

  苯乙酸 、 alpha-溴-4-甲氧基苯乙酮 生成 p-methoxyphenacyl phenylacetate
  参考文献：
  名称：

  Ahluwalia, V. K.; Mehta, Bhupinder; Kumar, Rakesh, Synthetic Communications, 1989, vol. 19, # 3and4, p. 619 - 626

  摘要：

  DOI：

文献信息

• Release of Guests from Encapsulated Masked Hydrophobic Precursors by a Phototrigger
  作者：Nithyanandhan Jayaraj、Pradeepkumar Jagadesan、Shampa R. Samanta、José P. Da Silva、V. Ramamurthy

  DOI：10.1021/ol4019024

  日期：2013.9.6

  Examples of release of organic acids from encapsulated p-methoxyphenacyl esters provided here demonstrate the value of a phototrigger strategy to release chemicals of interest in water from hydrophobic precursors. In this study, a photochemical beta-cleavage process centered on the p-methoxyphenacyl group is exploited to release the acid of interest from a water-soluble capsule made up of octa acid.
• Ahluwalia, V. K.; Mehta, Bhupinder; Kumar, Rakesh, Synthetic Communications, 1989, vol. 19, # 3and4, p. 619 - 626
  作者：Ahluwalia, V. K.、Mehta, Bhupinder、Kumar, Rakesh

  DOI：——

  日期：——
• AHLUWALIA, V. K.;MEHTA, BHUPINDER;KUMAR, RAKESH, SYNTH. COMMUN., 19,(1989) N-4, C. 619-626
  作者：AHLUWALIA, V. K.、MEHTA, BHUPINDER、KUMAR, RAKESH

  DOI：——

  日期：——
• Design of Fluorine-Containing 3,4-Diarylfuran-2(5<i>H</i>)-ones as Selective COX-1 Inhibitors
  作者：Md. Jashim Uddin、Anna V. Elleman、Kebreab Ghebreselasie、Cristina K. Daniel、Brenda C. Crews、Kellie D. Nance、Tamanna Huda、Lawrence J. Marnett

  DOI：10.1021/ml500344j

  日期：2014.11.13

  We report the design and synthesis of fluorine-containing cyclooxygenase-1 (COX-1)-selective inhibitors to serve as prototypes for the development of a COX-1-targeted imaging agent. Deletion of the SO2CH3 group of rofecoxib switches the compound from a COX-2- to a COX-1-selective inhibitor, providing a 3,4-diarylfuran-2(5H)-one scaffold for structureactivity relationship studies of COX-1 inhibition. A wide range of fluorine-containing 3,4-diarylfuran-2(5H)-ones were designed, synthesized, and tested for their ability to selectively inhibit COX-1 in purified protein and human cancer cell assays. Compounds containing a fluoro-substituent on the C-3 phenyl ring and a methoxy-substituent on the C-4 phenyl ring of the 3,4-diarylfuran-2(5H)-one scaffold were the best COX-1-selective agents of those evaluated, exhibiting IC(50)s in the submicromolar range. These compounds provide the foundation for development of an agent to facilitate radiologic imaging of ovarian cancer expressing elevated levels of COX-1.