(2E)-3-(3-chlorophenyl)-1-(furan-2-yl)prop-2-en-1-one | 135950-62-8

• 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-(3-chlorophenyl)-1-(furan-2-yl)prop-2-en-1-one
• 英文别名: (E)-3-(3-chlorophenyl)-1-(furan-2-yl)prop-2-en-1-one
• CAS: 135950-62-8
• 化学式: C₁₃H₉ClO₂
• 分子量: 232.666
• InChiKey: DSWLLQZGSLGKPU-VOTSOKGWSA-N

物化性质

• 沸点：
  361.5±42.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-(3-chlorophenyl)-1-(furan-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22%的产率得到4-(3-chlorophenyl)-6-(furan-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：

  2-乙酰基呋喃 、 3-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以50%的产率得到(2E)-3-(3-chlorophenyl)-1-(furan-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  五元单杂环的查耳酮衍生物的NMR化学位移研究和芳香度指标的确定

  摘要：

  通过将噻吩，吡咯和呋喃的相应醛与m-和n-醛缩醛缩合制得五元单杂环化合物的一系列查耳酮衍生物（E）-1-芳基-3-杂芳基丙烯-1-酮对位取代的苯乙酮。杂环的乙酰基化合物与m和p取代的苯甲醛的类似缩合产生了另一系列查尔酮衍生物，（E）-1-杂芳基-3-芳基丙-1-酮。在13 c。化学位移值（δ Ç确定查尔酮衍生物的），以查明它们是否与Hammettσ值相关。一个很好的相关性，特别是对β-C为两个系列，被发现为13 c。化学位移值（δ ç与哈米特σ值的查耳酮衍生物的）。绘制了杂环化合物β-C的化学位移值与苯衍生物的化学位移值的关系图。发现所得的斜率接近芳香性指数的值。

  DOI：

  10.1002/bkcs.11749

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。
• Inhibitory potential of some chalcones on cathepsins B, H and L
  作者：Shweta Garg、Neera Raghav

  DOI：10.1039/c5ra12856k

  日期：——

  Cathepsins, intracellular proteases, are known to be involved in a number of physiological processes such as degradation of extracellular proteins, prohormone processing, progressions of atherosclerosis etc.

  卡特普辛是细胞内蛋白酶，已知参与多种生理过程，如降解细胞外蛋白、前激素加工、动脉粥样硬化进展等。
• Studies of NMR Chemical Shifts of Chalcone Derivatives of Five‐membered Monoheterocycles and Determination of Aromaticity Indices
  作者：Eun Jeong Jeong、In‐Sook Han Lee

  DOI：10.1002/bkcs.11749

  日期：2019.7

  (E)‐1‐heteroaryl‐3‐arylpropen‐1‐ones. The 13C chemical shift values (δC) of the chalcone derivatives were determined in order to find if they correlated with the Hammett σ values. A good correlation, especially for the β‐C for both series, was found for the 13C chemical shift values (δC) of the chalcone derivatives with the Hammett σ values. The chemical shift values of the β‐C of the heterocyclic compounds

  通过将噻吩，吡咯和呋喃的相应醛与m-和n-醛缩醛缩合制得五元单杂环化合物的一系列查耳酮衍生物（E）-1-芳基-3-杂芳基丙烯-1-酮对位取代的苯乙酮。杂环的乙酰基化合物与m和p取代的苯甲醛的类似缩合产生了另一系列查尔酮衍生物，（E）-1-杂芳基-3-芳基丙-1-酮。在13 c。化学位移值（δ Ç确定查尔酮衍生物的），以查明它们是否与Hammettσ值相关。一个很好的相关性，特别是对β-C为两个系列，被发现为13 c。化学位移值（δ ç与哈米特σ值的查耳酮衍生物的）。绘制了杂环化合物β-C的化学位移值与苯衍生物的化学位移值的关系图。发现所得的斜率接近芳香性指数的值。
• 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.