(2E)-3-(4-chlorophenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one

• 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: (2E)-3-(4-chlorophenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one
• 英文别名: (E)-3-(4-chlorophenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one
• 化学式: C₁₄H₁₁ClO₂
• 分子量: 246.693
• InChiKey: JDYKOSMIPJOGOL-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  盐酸胍 、 (2E)-3-(4-chlorophenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以30%的产率得到4-(4-chlorophenyl)-6-(5-methylfuran-2-yl)pyrimidin-2-amine
  参考文献：
  名称：

  2-Aminopyrimidines as dual adenosine A1/A2A antagonists

  摘要：

  In this study thirteen 2-aminopyrimidine derivatives were synthesised and screened as potential antagonists of adenosine A(1) and A(2A) receptors in order to further investigate the structure activity relationships of this class of compounds. 4-(5-Methylfuran-2-yl)-6[3-(piperidine-1-carbonyl)phenyl] pyrimidin-2-amine (8m) was identified as a compound with high affinities for both receptors, with an A(2A)Ki value of 6.34 nM and an A(1)Ki value of 9.54 nM. The effect of selected compounds on the viability of cultured cells was assessed and preliminary results indicate low cytotoxicity. In vivo efficacy at A(2A) receptors was illustrated for compounds 8k and 8m since these compounds attenuated haloperidol-induced catalepsy in rats. A molecular docking study revealed that the interactions between the synthesised compounds and the adenosine A2A binding site most likely involve Phe168 and Asn253, interactions which are similar for structurally related adenosine A(2A) receptor antagonists. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.035
• 作为产物：
  描述：

  5-甲基-2-乙酰基呋喃 、 4-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以41%的产率得到(2E)-3-(4-chlorophenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  选定的呋喃并呋喃酮作为单胺氧化酶的抑制剂

  摘要：

  查尔酮支架在设计单胺氧化酶抑制剂中的有效性已在前面进行了说明。为了系统地研究杂环取代对这种多功能支架的单胺氧化酶抑制特性的影响，合成了一系列呋喃并呋喃酮。结果表明，这些呋喃取代的苯基丙烯酮对MAO-B表现出中等至良好的抑制活性，但对MAO-A酶的抑制作用弱或没有抑制作用。活性最高的化合物2 E -3-（5-氯呋喃-2-基）-1-（3-氯苯基）丙-2-烯-1-酮的IC 50为抑制MAO-B的值为0.174μM，抑制MAO-A的值为28.6μM。有趣的是，与先前报道的有关查耳酮的数据相反，这些呋喃取代的衍生物起着可逆抑制剂的作用，而动力学分析显示了一种竞争性的结合方式。

  DOI：

  10.1016/j.bmcl.2013.06.050

文献信息

• Selected furanochalcones as inhibitors of monoamine oxidase
  作者：Sarel J. Robinson、Jacobus P. Petzer、Anél Petzer、Jacobus J. Bergh、Anna C.U. Lourens

  DOI：10.1016/j.bmcl.2013.06.050

  日期：2013.9

  The validity of the chalcone scaffold for the design of inhibitors of monoamine oxidase has previously been illustrated. In a systematic attempt to investigate the effect of heterocyclic substitution on the monoamine oxidase inhibitory properties of this versatile scaffold, a series of furanochalcones were synthesized. The results demonstrate that these furan substituted phenylpropenones exhibited

  查尔酮支架在设计单胺氧化酶抑制剂中的有效性已在前面进行了说明。为了系统地研究杂环取代对这种多功能支架的单胺氧化酶抑制特性的影响，合成了一系列呋喃并呋喃酮。结果表明，这些呋喃取代的苯基丙烯酮对MAO-B表现出中等至良好的抑制活性，但对MAO-A酶的抑制作用弱或没有抑制作用。活性最高的化合物2 E -3-（5-氯呋喃-2-基）-1-（3-氯苯基）丙-2-烯-1-酮的IC 50为抑制MAO-B的值为0.174μM，抑制MAO-A的值为28.6μM。有趣的是，与先前报道的有关查耳酮的数据相反，这些呋喃取代的衍生物起着可逆抑制剂的作用，而动力学分析显示了一种竞争性的结合方式。
• Synthesis of Functionalized Cyclopentenes through Catalytic Asymmetric [3+2] Cycloadditions of Allenes with Enones
  作者：Jonathan E. Wilson、Gregory C. Fu

  DOI：10.1002/anie.200503312

  日期：2006.2.20
• 2-Aminopyrimidines as dual adenosine A1/A2A antagonists
  作者：Sarel J. Robinson、Jacobus P. Petzer、Gisella Terre’Blanche、Anél Petzer、Mietha M. van der Walt、Jacobus J. Bergh、Anna C.U. Lourens

  DOI：10.1016/j.ejmech.2015.09.035

  日期：2015.11

  In this study thirteen 2-aminopyrimidine derivatives were synthesised and screened as potential antagonists of adenosine A(1) and A(2A) receptors in order to further investigate the structure activity relationships of this class of compounds. 4-(5-Methylfuran-2-yl)-6[3-(piperidine-1-carbonyl)phenyl] pyrimidin-2-amine (8m) was identified as a compound with high affinities for both receptors, with an A(2A)Ki value of 6.34 nM and an A(1)Ki value of 9.54 nM. The effect of selected compounds on the viability of cultured cells was assessed and preliminary results indicate low cytotoxicity. In vivo efficacy at A(2A) receptors was illustrated for compounds 8k and 8m since these compounds attenuated haloperidol-induced catalepsy in rats. A molecular docking study revealed that the interactions between the synthesised compounds and the adenosine A2A binding site most likely involve Phe168 and Asn253, interactions which are similar for structurally related adenosine A(2A) receptor antagonists. (C) 2015 Elsevier Masson SAS. All rights reserved.