ethyl 3-cyclopropyl-2-(3-methoxybenzyl)-3-oxopropanoate | 87141-68-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 3-cyclopropyl-2-(3-methoxybenzyl)-3-oxopropanoate
• 英文别名: ethyl 3-cyclopropyl-2-[(3-methoxyphenyl)methyl]-3-oxopropanoate
• CAS: 87141-68-2
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: ABWGXLXULYXOAG-UHFFFAOYSA-N

物化性质

• 沸点：
  388.5±27.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  ethyl 3-cyclopropyl-2-(3-methoxybenzyl)-3-oxopropanoate 在 氢氧化钾 、 sodium tetrahydroborate 、 三溴化磷 、 lithium bromide 作用下， 以 乙醇 为溶剂， 生成 1-Cyclopropyl-3-(m-methoxyphenyl)propyl bromide
  参考文献：
  名称：

  Amupitan, Joseph A.; Beddoes, Roy L.; Mills, Owen S., Journal of the Chemical Society. Perkin transactions I, 1983, # 4, p. 759 - 764

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲氧基溴苄 、 3-环丙基-3-羰基-丙酸乙酯 在 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以42%的产率得到ethyl 3-cyclopropyl-2-(3-methoxybenzyl)-3-oxopropanoate
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Triazolopyrimidinone Derivatives as Noncompetitive, Intracellular Antagonists for CC Chemokine Receptors 2 and 5

  摘要：

  CC chemokine receptors 2 (CCR2) and 5 (CCR5) are involved in many inflammatory diseases; however, most CCR2 and CCR5 clinical candidates have been unsuccessful. (Pre)clinical evidence suggests that dual CCR2/CCR5 inhibition might be more effective in the treatment of such multifactorial diseases. In this regard, the highly conserved intracellular binding site in chemokine receptors provides a new avenue for the design of multitarget ligands. In this study, we synthesized and evaluated the biological activity of a series of triazolopyrimidinone derivatives in CCR2 and CCR5. Radioligand binding assays first showed that they bind to the intracellular site of CCR2, and in combination with functional assays on CCR5, we explored structure-affinity/activity relationships in both receptors. Although most compounds were CCR2-selective, 39 and 43 inhibited beta-arrestin recruitment in CCR5 with high potency. Moreover, these compounds displayed an insurmountable mechanism of inhibition in both receptors, which holds promise for improved efficacy in inflammatory diseases.

  DOI：

  10.1021/acs.jmedchem.9b00742

文献信息

• AMUPITAN, J. A.;BEDDOES, R. L.;MILLS, O. S.;SUTHERIAND, J. K., J. CHEM. SOC. PERKIN TRANS., 1983, N 4, 759-763
  作者：AMUPITAN, J. A.、BEDDOES, R. L.、MILLS, O. S.、SUTHERIAND, J. K.

  DOI：——

  日期：——