4-(3-Hydroxy-4-oxo-4H-chromen-2-yl)benzoic acid

• 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: 4-(3-Hydroxy-4-oxo-4H-chromen-2-yl)benzoic acid
• 英文别名: 4-(3-hydroxy-4-oxo-4H-1-benzopyran-2-yl)benzoic acid；4-(3-Hydroxy-4-oxo-chromen-2-yl)benzoic acid；4-(3-hydroxy-4-oxochromen-2-yl)benzoic acid
• 化学式: C₁₆H₁₀O₅
• 分子量: 282.252
• InChiKey: ATXHVCLKKGQFDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-Hydroxy-4-oxo-4H-chromen-2-yl)benzoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.8h， 生成
  参考文献：
  名称：

  Fluorescence detection of endogenous bisulfite in liver cancer cells using an effective ESIPT enhanced FRET platform

  摘要：

  探针 L-HF1 具有较大的（伪）斯托克斯位移和较高的 FRET 效率，是在新型 ESIPT 增强 FRET 平台上设计的，用于检测 HSO3-/SO32-。

  DOI：

  10.1039/c6cc06459k
• 作为产物：
  描述：

  2'-hydroxy-4-carboxychalcone 在 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 4-(3-Hydroxy-4-oxo-4H-chromen-2-yl)benzoic acid
  参考文献：
  名称：

  Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies

  摘要：

  To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened forin vitroagainst mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis,H-1-,C-13-NMR) and mass spectrometry (EI-MS). The structure of compound15was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibioticsi.e.Cefixime and Clotrimazole. Amongst the series, the compounds2, 4, 5, 6, 7, 10, 11, 14and22exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound2(IC50= 0.280 +/- 0.010 mu g/ml) was found almost sixfold and derivative5(IC50= 0.230 +/- 0.020 mu g/ml) about sevenfold more active as compared to standard Kojic acid (IC50=1.79 +/- 0.6 mu g/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma

  DOI：

  10.1080/07391102.2020.1805364

文献信息

• 一种以半川菁及黄酮醇为荧光团的二氧化硫 衍生物比例荧光探针及其应用
  申请人：山东大学

  公开号：CN106518855B

  公开（公告）日：2019-03-26

  本发明公开了一种以半川菁及黄酮醇为荧光团的二氧化硫衍生物比例荧光探针，所述荧光探针是由黄酮醇荧光团与半川菁荧光团通过非共轭连接而成，命名为L‑HF1，其化学结构式如式(I)所示。本发明还公开了所述荧光探针在检测液体或细胞中的二氧化硫衍生物的应用。实验证实本发明的探针可以选择性的与二氧化硫衍生物作用，使测试体系由红色变为无色，使得检测肉眼可辨，并且荧光由红色变为绿色，这些现象可以通过紫外吸收仪及荧光分光光度计进行分析。同时，本发明公开的该荧光探针可实现对微量二氧化硫衍生物的高灵敏度检测，具有重要的应用价值。
• 10.1021/acs.biomac.4c00542
  作者：Li, Zhezhe、Wang, Suzhen、Zhao, Lili、Feng, Shaofeng、Che, Hailong

  DOI：10.1021/acs.biomac.4c00542

  日期：——

  As one of the gaseous signals in living cells, carbon monoxide (CO) not only participates in many biological activities but also serves as a therapeutic agent for the treatment of diseases. However, the limited applicability of CO in gas therapy emerges from the inconvenience of direct administration of CO. Here we reported the construction of guanidinylated CO-releasing micelles, which are composed

  一氧化碳 （CO） 作为活细胞中的气态信号之一，不仅参与许多生物活动，而且还作为治疗疾病的治疗剂。然而，CO 在气体治疗中的适用性有限，这是由于直接给予 CO 的不便。在这里，我们报道了胍酰化 CO 释放胶束的构建，其由基于聚碳酸三亚甲基酯 （PTMC） 的 CO 供体组成。体外研究表明，光照射下的胶束可诱导癌症死亡，而未观察到对正常细胞的明显毒性。此外，由于与细胞表面的特异性相互作用，胍基团的功能化提高了胶束的细胞摄取效率，从而协同增加了系统的抗癌能力。胍功能化的 CO 释放胶束为构建 CO 释放纳米载体提供了一种新策略，有望在气体治疗中得到应用。
• Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies
  作者：Jamshaid Ashraf、Ehsan Ullah Mughal、Amina Sadiq、Maryam Bibi、Nafeesa Naeem、Anser Ali、Anam Massadaq、Nighat Fatima、Asif Javid、Muhammad Naveed Zafar、Bilal Ahmad Khan、Muhammad Faizan Nazar、Amara Mumtaz、Muhammad Nawaz Tahir、Masoud Mirzaei

  DOI：10.1080/07391102.2020.1805364

  日期：2021.12.12

  To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened forin vitroagainst mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis,H-1-,C-13-NMR) and mass spectrometry (EI-MS). The structure of compound15was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibioticsi.e.Cefixime and Clotrimazole. Amongst the series, the compounds2, 4, 5, 6, 7, 10, 11, 14and22exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound2(IC50= 0.280 +/- 0.010 mu g/ml) was found almost sixfold and derivative5(IC50= 0.230 +/- 0.020 mu g/ml) about sevenfold more active as compared to standard Kojic acid (IC50=1.79 +/- 0.6 mu g/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma
• Fluorescence detection of endogenous bisulfite in liver cancer cells using an effective ESIPT enhanced FRET platform
  作者：Dong-Peng Li、Zhao-Yang Wang、Hao Su、Jun-Ying Miao、Bao-Xiang Zhao

  DOI：10.1039/c6cc06459k

  日期：——

  Probe L-HF1, which featured large (pseudo) Stokes shifts and high FRET efficiency, was designed on a new ESIPT enhanced FRET platform for the detection of HSO₃⁻/SO₃²⁻.

  探针 L-HF1 具有较大的（伪）斯托克斯位移和较高的 FRET 效率，是在新型 ESIPT 增强 FRET 平台上设计的，用于检测 HSO3-/SO32-。