2-[(2-oxo-2H-chromen-4-yl)oxy]acetic acid | 462094-45-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-[(2-oxo-2H-chromen-4-yl)oxy]acetic acid
• 英文别名: 2-((2-oxo-2H-chromen-4-yl)oxy)acetic acid；2-(2-oxochromen-4-yl)oxyacetic acid
• CAS: 462094-45-7
• 化学式: C₁₁H₈O₅
• mdl: MFCD09837287
• 分子量: 220.182
• InChiKey: HCADRKLBKXNECB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(2-oxo-2H-chromen-4-yl)oxy]acetic acid 在 吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 2-(2-oxo-2H-chromen-4-yloxymethylcarbonyl)hydrazine-1-carbothioamide
  参考文献：
  名称：

  Syntheses on the basis of 2H-chromen-2-one and 2H-chromene-2-thione

  摘要：

  4-Hydroxy-2H-chromen-2-one and 4-hydroxy-2H-chromene-2-thione reacted with allyl bromide, 1,1,3-trichloroprop-l-ene, and 1,3-dichlorobut-2-ene to give the corresponding ethers, which were oxidized to (2-oxo-2H-chromen-4-yloxy)acetic acid with potassium permanganate, and various derivatives of that acid were obtained. 3-(3,3-Dichloroprop-2-enyl)-7-hydroxy-4-methyl-2H-chromen-2-one and 3-(3,3-dichloroprop2-enyl)-7-hydroxy-4-methyl-2H-chromene-2-thione were synthesized, and some their transformations were studied.

  DOI：

  10.1134/s1070428006070244
• 作为产物：
  描述：

  4-烯丙氧基香豆素 在 potassium permanganate 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以65%的产率得到2-[(2-oxo-2H-chromen-4-yl)oxy]acetic acid
  参考文献：
  名称：

  Syntheses on the basis of 2H-chromen-2-one and 2H-chromene-2-thione

  摘要：

  4-Hydroxy-2H-chromen-2-one and 4-hydroxy-2H-chromene-2-thione reacted with allyl bromide, 1,1,3-trichloroprop-l-ene, and 1,3-dichlorobut-2-ene to give the corresponding ethers, which were oxidized to (2-oxo-2H-chromen-4-yloxy)acetic acid with potassium permanganate, and various derivatives of that acid were obtained. 3-(3,3-Dichloroprop-2-enyl)-7-hydroxy-4-methyl-2H-chromen-2-one and 3-(3,3-dichloroprop2-enyl)-7-hydroxy-4-methyl-2H-chromene-2-thione were synthesized, and some their transformations were studied.

  DOI：

  10.1134/s1070428006070244

文献信息

• Synthesis of novel 4-hydroxycoumarin derivatives: evaluation of antimicrobial, antioxidant activities and its molecular docking studies
  作者：M. Govindhan、K. Subramanian、K. Chennakesava Rao、K. Easwaramoorthi、P. Senthilkumar、P. T. Perumal

  DOI：10.1007/s00044-015-1448-z

  日期：2015.12

  evaluated for their antimicrobial and total antioxidant activity using in vitro well diffusion method and phosphomolybdenum method, respectively. Amongst all the compounds, 4c has shown potential antimicrobial and antioxidant activity against the standard. All compounds have exhibited good binding energies from −4.46 to −5.70 kcal/mol against 24-kDa DNA gyrase B fragment from E. coli (PDB ID-1KZN) in molecular

  通过用各种胺处理2-（2-oxo-2H-chromen-4-yloxy）乙酸3合成了一系列新颖的4-羟基香豆素衍生物4a-n。由相应的酯2的水解得到酸3，该酯由4-羟基香豆素1和溴乙酸乙酯制备。所有合成的化合物4a–n使用光谱技术进行表征。分别使用体外孔扩散法和磷钼法评估了合成的化合物4a–n的抗菌和总抗氧化活性。在所有化合物中，4c对标准显示出潜在的抗微生物和抗氧化活性。在分子对接研究中，所有化合物对大肠杆菌的24 kDa DNA促旋酶B片段（PDB ID-1KZN）均表现出从-4.46至-5.70 kcal / mol的良好结合能，其中4c显示出最大结合能。
• Synthesis and evaluation of 4-substituted coumarins as novel acetylcholinesterase inhibitors
  作者：Seyyede Faeze Razavi、Mehdi Khoobi、Hamid Nadri、Amirhossein Sakhteman、Alireza Moradi、Saeed Emami、Alireza Foroumadi、Abbas Shafiee

  DOI：10.1016/j.ejmech.2013.03.021

  日期：2013.6

  that Phe330 is responsible for ligand recognition and trafficking by forming π-cation interaction with benzylpiperidine moiety. Furthermore, the formation of an additional π–π interaction between coumarin moiety and Trp279 of peripheral anionic site could stabilize the ligand in the active site resulting in more potent inhibition of the enzyme.

  设计并合成了一系列4-羟基香豆素衍生物，作为新的乙酰胆碱酯酶（AChE）抑制剂，可以考虑将其用于阿尔茨海默氏病治疗。在19种从香豆素衍生的化合物中，对电的乙酰胆碱酯酶（eel AChE）和马血清丁酰胆碱酯酶（eq BChE）进行了测试，其中N-（1-苄基哌啶-4-基）乙酰胺衍生物4m表现出最高的AChE抑制活性（IC 50  = 1.2μM ）和良好的选择性（37倍）。最有效化合物的对接研究4m，表明Phe330负责通过与苄基哌啶部分形成π-阳离子相互作用来进行配体识别和运输。此外，香豆素部分与外围阴离子位点的Trp279之间形成额外的π-π相互作用可以使配体稳定在活性位点，从而更有效地抑制该酶。
• Design, Synthesis and Acetylcholinesterase and Butylcholinesterase Inhibition Activity of Novel 1-(Alkyl)-3-(2-oxo-2H-chromenyloxy Acetamido) methylpyridinium Salts
  作者：Mehri Abdollahi fard、Mohammadreza Manafi、Manijeh Motevalian、Seyed Saied Homami

  DOI：10.2174/1570178617999200818165935

  日期：2021.7