1-(4-hydroxy-2-methoxyphenyl)-1-propanone | 873397-07-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-hydroxy-2-methoxyphenyl)-1-propanone
• 英文别名: 1-(4-hydroxy-2-methoxy-phenyl)-propan-1-one；1-(4-Hydroxy-2-methoxy-phenyl)-propan-1-on；1-(4-Hydroxy-2-methoxyphenyl)propan-1-one
• CAS: 873397-07-0
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: VZONHROZKCUBKK-UHFFFAOYSA-N

物化性质

• 熔点：
  117 °C(Solv: benzene (71-43-2))
• 沸点：
  340.2±22.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxy-2-methoxyphenyl)-1-propanone 在 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 72.0h， 生成 2-[3-Methoxy-4-(2-methylprop-2-enoyl)phenoxy]acetic acid
  参考文献：
  名称：

  Ethacrynic acid as a lead structure for the development of potent urease inhibitors

  摘要：

  摘要 合成了乙烯酰基酸及其一系列类化合物，并随后评估了它们对豌豆尿素酶的抑制作用。乙烯酰基酸即使在低浓度下也显示出对该酶非常强的抑制活性。对于乙烯酰基酸，抑制潜力随着乙烯酰基酸和酶的预孵育时间的增加而增强，然而对于其他一些化合物，较长的预孵育时间会显著降低其活性。我们证明了我们化合物中的α,β-不饱和羰基单元对抑制该酶是必不可少的，可能是由于它能够与豌豆尿素酶活性位点中的半胱氨酸残基结合。

  DOI：

  10.1016/j.crci.2013.03.020
• 作为产物：
  描述：

  2,4-二羟基苯丙酮 在 盐酸 、 potassium carbonate 、 溶剂黄146 、 丙酮 作用下， 生成 1-(4-hydroxy-2-methoxyphenyl)-1-propanone
  参考文献：
  名称：

  Beer et al., Journal of the Chemical Society, 1954, p. 3672,3675

  摘要：

  DOI：

文献信息

• Synthesis and evaluation of aromatic methoxime derivatives against five postharvest phytopathogenic fungi of fruits. Main structure–activity relationships
  作者：Iván Cortés、Melina G. di Liberto、Teodoro S. Kaufman、Marcos G. Derita、Andrea B.J. Bracca

  DOI：10.1016/j.foodchem.2020.126701

  日期：2020.8

  concentrations and minimum fungicidal concentrations of each compound were defined and the main structure-activity relationships were determined. Although other congeners were more potent, drug likeliness considerations pointed to the methoxime derived from 2,4-dihydroxypropiophenone as the compound with the most suitable profile. The morphology of the colonies of the fungal strains treated with the methoxime

  检查了二十四个芳香族甲肟库对五种代表性的收获后植物病原真菌的抗真菌活性。小组成员包括数位青霉，意大利青霉，根霉，灰葡萄孢和莫尼利尼亚毛果，这些都因影响收获的水果而在世界范围内造成相关的经济损失。确定了每种化合物的最小抑菌浓度和最小杀真菌浓度，并确定了主要的构效关系。尽管其他同类药物更有效，但从药物相似性的角度出发，认为衍生自2,4-二羟基苯乙酮的甲氧肟是最合适的化合物。
• Ethacrynic acid analogues lacking the α,β-unsaturated carbonyl unit—Potential anti-metastatic drugs
  作者：Romy F.J. Janser、Ranjith K. Meka、Zack E. Bryant、Enoch A. Adogla、Elizabeth K. Vogel、Jaimie L. Wharton、Cynthia M. Tilley、Catherine N. Kaminski、Seth L. Ferrey、Severine Van slambrouck、Wim F.A. Steelant、Ingo Janser

  DOI：10.1016/j.bmcl.2010.01.144

  日期：2010.3

  A series of ethacrynic acid analogues, lacking the alpha,beta-unsaturated carbonyl unit, was synthesized and subsequently evaluated for their ability to inhibit the migration of human breast cancer cells, MCF-7/AZ. Several of the analogues were already active in the low micromolar range, whereas ethacrynic acid itself shows no potential to inhibit the migration of these cancer cells. Preliminary studies show that the presence of one or more methoxy groups at the phenyl ring of ethacrynic acid is important in order for the ethacrynic acid analogues to demonstrate an inhibitory effect on the migration. (C) 2010 Elsevier Ltd. All rights reserved.
• Nakazawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 836
  作者：Nakazawa

  DOI：——

  日期：——
• Ethacrynic acid as a lead structure for the development of potent urease inhibitors
  作者：Ingo Janser、Caitlyn M. Vortolomei、Ranjith K. Meka、Courtney A. Walsh、Romy F.J. Janser

  DOI：10.1016/j.crci.2013.03.020

  日期：2013.7

  Résumé Ethacrynic acid and a series of its analogues were synthesized and subsequently evaluated for their inhibitory effect on jack bean urease. Ethacrynic acid showed, even at low concentrations, very potent inhibitory activity against the enzyme. For ethacrynic acid, the inhibition potential increased with increasing preincubation time of ethacrynic acid and enzyme, whereas for some other compounds a higher preincubation time lead to a significant reduction of their activity. We could demonstrate that the α,β-unsaturated carbonyl unit of our compounds is mandatory to inhibit the enzyme, possibly due to its ability to bind to cysteine residues in the active site of the jack bean urease.

  摘要 合成了乙烯酰基酸及其一系列类化合物，并随后评估了它们对豌豆尿素酶的抑制作用。乙烯酰基酸即使在低浓度下也显示出对该酶非常强的抑制活性。对于乙烯酰基酸，抑制潜力随着乙烯酰基酸和酶的预孵育时间的增加而增强，然而对于其他一些化合物，较长的预孵育时间会显著降低其活性。我们证明了我们化合物中的α,β-不饱和羰基单元对抑制该酶是必不可少的，可能是由于它能够与豌豆尿素酶活性位点中的半胱氨酸残基结合。
• Beer et al., Journal of the Chemical Society, 1954, p. 3672,3675
  作者：Beer et al.

  DOI：——

  日期：——