(2E)-1-(5-chlorothiophen-2-yl)-3-(3-bromo-4-fluorophenyl)prop-2-en-1-one | 1579254-73-1

• 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)-1-(5-chlorothiophen-2-yl)-3-(3-bromo-4-fluorophenyl)prop-2-en-1-one
• 英文别名: (2E)-3-(3-bromo-4-fluorophenyl)-1-(5-chlorothiophen-2-yl)prop-2-en-1-one；(E)-3-(3-bromo-4-fluorophenyl)-1-(5-chlorothiophen-2-yl)prop-2-en-1-one
• CAS: 1579254-73-1
• 化学式: C₁₃H₇BrClFOS
• 分子量: 345.619
• InChiKey: KABFSIJKSSCJLU-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 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：
  45.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙酰基-5-氯噻酚 、 3-溴-4-氟苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以60%的产率得到(2E)-1-(5-chlorothiophen-2-yl)-3-(3-bromo-4-fluorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  杂芳基查耳酮：设计、合成、X 射线晶体结构和生物学评价。

  摘要：

  查耳酮衍生物因其众多的药理活性而受到越来越多的关注。它们结构的变化显示出高度的多样性，这已被证明会导致广泛的生物活动。本研究重点介绍了一些含有 5-氯噻吩部分的卤素取代的查耳酮 3(ai) 的合成、它们的 X 射线晶体结构以及对可能的生物活性（如抗菌、抗真菌和还原能力）的评估。结果表明测试的化合物对所有测试的微生物菌株显示出不同范围的抑制值。苯环上带有对氟取代基的化合物 3c 表现出较高的抗菌活性，而化合物 3e 和 3f 表现出的抗菌活性最低。化合物 3d, 3e,

  DOI：

  10.3390/molecules181012707

文献信息

• Heteroaryl Chalcones: Design, Synthesis, X-ray Crystal Structures and Biological Evaluation
  作者：C. Kumar、Wan-Sin Loh、Chin Ooi、Ching Quah、Hoong-Kun Fun

  DOI：10.3390/molecules181012707

  日期：——

  Changes in their structures have displayed high degree of diversity that has proven to result in a broad spectrum of biological activities. The present study highlights the synthesis of some halogen substituted chalcones 3(a-i) containing the 5-chlorothiophene moiety, their X-ray crystal structures and the evaluation of possible biological activities such as antibacterial, antifungal and reducing power abilities

  查耳酮衍生物因其众多的药理活性而受到越来越多的关注。它们结构的变化显示出高度的多样性，这已被证明会导致广泛的生物活动。本研究重点介绍了一些含有 5-氯噻吩部分的卤素取代的查耳酮 3(ai) 的合成、它们的 X 射线晶体结构以及对可能的生物活性（如抗菌、抗真菌和还原能力）的评估。结果表明测试的化合物对所有测试的微生物菌株显示出不同范围的抑制值。苯环上带有对氟取代基的化合物 3c 表现出较高的抗菌活性，而化合物 3e 和 3f 表现出的抗菌活性最低。化合物 3d, 3e,
• Monoamine oxidase inhibitory activities of heterocyclic chalcones
  作者：Corné Minders、Jacobus P. Petzer、Anél Petzer、Anna C.U. Lourens

  DOI：10.1016/j.bmcl.2015.09.049

  日期：2015.11

  Studies have shown that natural and synthetic chalcones (1,3-diphenyl-2-propen-1-ones) possess monoamine oxidase (MAO) inhibition activities. Of particular importance to the present study is a report that a series of furanochalcones acts as MAO-B selective inhibitors. Since the effect of heterocyclic substitution, other than furan (and more recently thiophene, piperidine and quinoline) on the MAO inhibitory properties of the chalcone scaffold remains unexplored, the aim of this study was to synthesise and evaluate further heterocyclic chalcone analogues as inhibitors of the human MAOs. For this purpose, heterocyclic chalcone analogues that incorporate pyrrole, 5-methylthiophene, 5-chlorothiophene and 6-methoxypyridine substitution were examined. Seven of the nine synthesised compounds exhibited IC50 values <1 mu M for the inhibition of MAO-B, with all compounds exhibiting higher affinities for MAO-B compared to the MAO-A isoform. The most potent MAO-B inhibitor (4h) displays an IC50 value of 0.067 mu M while the most potent MAO-A inhibitor (4e) exhibits an IC50 value of 3.81 mu M. It was further established that selected heterocyclic chalcones are reversible and competitive MAO inhibitors. 4h, however, may exhibit tight-binding to MAO-B, a property linked to its thiophene moiety. We conclude that high potency chalcones such as 4h represent suitable leads for the development of MAO-B inhibitors for the treatment of Parkinson's disease and possibly other neurodegenerative disorders. (C) 2015 Elsevier Ltd. All rights reserved.