2-((4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetic acid | 97980-65-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-((4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetic acid
• 英文别名: Flavon-7-oxyessig；2-(4-oxo-2-phenylchromen-7-yl)oxyacetic acid
• CAS: 97980-65-9
• 化学式: C₁₇H₁₂O₅
• 分子量: 296.279
• InChiKey: YEHGDIWRWAAVCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-((4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetic acid 在 乙醇 、 硫酸 作用下， 生成 乙酯黄酮
  参考文献：
  名称：

  Da Re; Colleoni, Annali di Chimica, 1959, vol. 49, p. 1632,1636

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酯黄酮 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以43 %的产率得到2-((4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetic acid
  参考文献：
  名称：

  作为潜在 P450 2A6 抑制剂的黄酮基酯和酸的设计、合成和生物学研究

  摘要：

  作为戒烟并预防吸烟相关疾病和死亡的潜在手段，在本研究中，我们的目标是研究 P450 2A6 对尼古丁代谢的抑制作用。吸烟是许多疾病和残疾的主要原因，几乎损害身体的每个器官。据美国疾病控制与预防中心 (CDC) 报告，超过 1600 万美国人患有由吸烟引起的疾病。平均而言，吸烟者的预期寿命比不吸烟者短约 10 年。戒烟可以大大降低与吸烟相关的疾病（包括癌症）的发病率。 7000多种卷烟烟雾成分中至少有70种是已知的致癌物质，其中包括多环芳烃、N-亚硝胺和芳香胺。尼古丁是导致烟草成瘾和精神药理学作用的化合物。细胞色素 P450 酶负责许多烟草成分（包括尼古丁）的 I 相代谢。尼古丁主要由细胞色素 P450s 2A6 和 2A13 代谢为可替宁。这种新陈代谢减少了血液中可用尼古丁的含量，导致吸烟行为增加，从而接触烟草毒物和致癌物。在此，我们报告了许多新型黄酮基酯和酸的合成和 P450 2A6 抑

  DOI：

  10.1021/acs.chemrestox.3c00249

文献信息

• Synthesis and biological evaluation of Complex I inhibitor R419 and its derivatives as anticancer agents in HepG2 cells
  作者：Yaping Huang、Geng Sun、Pengfei Wang、Rui Shi、Yanchun Zhang、Xiaoan Wen、Hongbin Sun、Caiping Chen

  DOI：10.1016/j.bmcl.2018.07.006

  日期：2018.9

  In this study, Complex I inhibitor R419 was firstly revealed to have significant anticancer activity against HepG2 cells (IC50 = 5.2 ± 0.9 μM). Based on this finding, a series of R419 derivatives were synthesized and biologically evaluated. As results, 9 derivatives were found to have obvious anticancer activity. Among them, H20 exhibited the most potent activity (IC50 = 2.8 ± 0.4 μM). Mechanism study

  在这项研究中，首次发现复合物I抑制剂R419对HepG2细胞具有显着的抗癌活性（IC 50  = 5.2±0.9μM）。基于此发现，合成了一系列R419衍生物并对其进行了生物学评估。结果，发现9种衍生物具有明显的抗癌活性。其中，H20表现出最强的活性（IC 50  = 2.8±0.4μM）。机制研究表明，H20导致细胞ATP严重耗竭，剂量依赖性激活的AMPK，Bcl-2 / Bax比例降低并导致坏死性细胞死亡。最重要的是，H20对复合物I表现出明确的抑制活性。
• Synthesis and biological evaluation of CX-659S and its related compounds for their inhibitory effects on the delayed-type hypersensitivity reaction
  作者：Masanori Tobe、Yoshiaki Isobe、Yuso Goto、Fumihiro Obara、Masami Tsuchiya、Junko Matsui、Kosaku Hirota、Hideya Hayashi

  DOI：10.1016/s0968-0896(00)00126-7

  日期：2000.8

  In order to find novel nonsteroidal compounds possessing an inhibitory activity against delayed-type hypersensitivity (DTH) reactions, we conducted random screening using a picryl chloride (PC)-induced contact hypersensitivity reaction (CHR) in mice, and found compound 1 as a lead compound. Then we synthesized and evaluated an extensive series of 5-carboxamidouracil derivatives focused on both the

  为了找到对延迟型超敏反应（DTH）反应具有抑制活性的新型非甾体化合物，我们使用氯化吡啶（PC）诱导的小鼠接触超敏反应（CHR）在小鼠中进行了随机筛选，发现化合物1为铅复合。然后，我们合成并评估了一系列广泛的针对尿嘧啶和抗氧化部分的5-羧酰胺基尿嘧啶衍生物。其中，我们发现受阻酚部分对于展示其活性是必要的。特别地，发现具有维生素E的部分结构的化合物28a-28c通过口服和局部给药都具有针对DTH反应的有效活性。化合物28c对脂质过氧化具有抗氧化活性，IC50为5.9 microM。
• Compounds for immunopotentiation
  申请人：Novartis Vaccines and Diagnostics, Inc.

  公开号：EP2277595A2

  公开（公告）日：2011-01-26

  Compounds of formula I: wherein R1 to R5 are defined herein, for use in modulating an immune response in a subject, wherein said use comprises administering said compound to said subject, are disclosed.

  式 I 的化合物： 其中 R1 至 R5 在本文中定义，用于调节受试者的免疫反应，其中所述用途包括向所述受试者施用所述化合物。
• Synthesis and anti-inflammatory in vitro, in silico, and in vivo studies of flavone analogues
  作者：Manjulatha Khanapur、Nishal K. Pinna、Jaishree Badiger

  DOI：10.1007/s00044-015-1317-9

  日期：2015.6

  Chrysin and 7-hydroxy flavone were prepared by Baker-Venkatraman rearrangement followed by esterification at 7th position and replacement of ester with acetamide linking to different heterocyclic moieties synthesized 13a-g and 14a-g series of flavones analogues. These were screened against COX-2 and COX-1 enzymes for inhibition by in vitro assay and COX-2 for in silico docking studies. The compound 14a was found to be most active with IC50 of 3.11 A mu M concentration, with highest binding energy of -12.4 kcal/mole and 77.2 and 80.5 % inhibition at 3 and 5 h post-carrageenan induced in paw oedema.
• Synthesis of carboxylated flavonoids as new leads for LTD4 antagonists
  作者：ME Zwaagstra、H Timmerman、RS Abdoelgafoer、MQ Zhang

  DOI：10.1016/s0223-5234(97)89849-2

  日期：1996.1

  A series of 3'- and 5'-carboxylated chalcones, 6- or 8-carboxylated flavones and 6-carboxylated flavanones, -flavanols and -flavans were prepared. The compounds were tested for their inhibitory activities against leukotriene D-4 (LTD(4)) induced contraction of guinea-pig ileum. A new and convenient synthetic route to 3-acetyl-2-hydroxybenzoic acid (1d), a key intermediate for the synthesis of 3'-carboxy-2'-hydroxychalcones and 8-carboxylated flavones, was developed. The activities of the tested compounds ranged from 0 to 63% inhibition at 10(-5) M drug concentration against a single challenge of 10(-8) M LTD(4). Several compounds were tested in a radioligand binding assay against [H-3]LTD(4) on guinea-pig lung membrane. The quinoline-containing chalcone 12 and flavone 17 were found to exhibit significant but weak affinities for LTD(4) receptors with pK(D)-values of 4.95 and 4.83, respectively, and are interesting lead structures for the development of rigid LTD(4) antagonists. In contrast, the rest of the compounds tested in the binding assay did not show significant displacement of the radioligand, implying that for these compounds the functional activity is probably not caused by competitive antagonism at the LTD(4) receptor. The exact mechanism of the relaxant activity remains unclear.