3-((4-aminophenyl)(4-hydroxy-2-oxochroman-3-yl)methyl)-4-hydroxy-2H-chromen-2-one | 405228-14-0

• 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: 3-((4-aminophenyl)(4-hydroxy-2-oxochroman-3-yl)methyl)-4-hydroxy-2H-chromen-2-one
• 英文别名: 3,3'-((4-aminophenyl)methylene)bis(4-hydroxy-2H-chromen-2-one)；4-hydroxy-3-((4-hydroxy-2-oxo-2H-chromen-3-yl)(4-aminophenyl)methyl)-2Hchromen-2-one；3,3′-((4-aminophenyl)methylene)bis(4-hydroxy-2Hchromen-2-one)；3-[(4-Aminophenyl)-(4-hydroxy-2-oxochromen-3-yl)methyl]-4-hydroxychromen-2-one
• CAS: 405228-14-0
• 化学式: C₂₅H₁₇NO₆
• 分子量: 427.413
• InChiKey: XVQFMBJIJAQGRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  126.9
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-((4-aminophenyl)(4-hydroxy-2-oxochroman-3-yl)methyl)-4-hydroxy-2H-chromen-2-one 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3,3'-((4-((5-(2-bromophenyl)-1,3,4-thiadiazol-2-yl)amino)phenyl)methylene)bis(4-hydroxy-2H-chromen-2-one)
  参考文献：
  名称：

  杂双香豆素与噻二唑作为脲酶的新抑制剂的设计，合成，体外评价，分子对接和ADME性能研究。

  摘要：

  混合双-香豆素衍生物1 - 18合成并评价它们的体外尿素酶抑制潜力。所有化合物均显示出出色的脲酶抑制潜能，IC 50值（最大抑菌浓度的一半）在0.12 SD 0.01和38.04 SD 0.63 µM（SD标准偏差）之间。与标准硫脲相比（IC 50  =  21.40±0.21 µM）。在这些衍生物中，化合物7（IC 50  =  0.29±0.01），9（IC 50  =  2.4±0.05），10（IC 50  =  2.25±0.05）和16 与硫脲相比（IC 50 =  21.40±0.21 µM）（IC 50  = 0.12±0.01）是脲酶的更好抑制剂。为了发现结构与活性之间的关系，还进行了分子对接以及吸收，分布，代谢和排泄（ADME）研究。各种光谱学技术（例如1 H NMR，13 C NMR和EI-MS）用于表征所有合成的类似物。测试所有化合物的细胞毒性，发现无毒。 

  DOI：

  10.1016/j.bioorg.2019.103235
• 作为产物：
  描述：

  4-hydroxycoumarin 在 盐酸 、 铁粉 作用下， 以 乙醇 、 水 为溶剂， 反应 3.5h， 生成 3-((4-aminophenyl)(4-hydroxy-2-oxochroman-3-yl)methyl)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Amberlyst 15 通过双 C-C 偶联催化 4-羟基香豆素和醛的双香豆素甲烷的设计和合成：为存储器件引入香豆素基薄膜有机纳米材料

  摘要：

  在 Amberlyst 15 催化剂存在下，在乙醇-水 (1:1) 的回流条件下，通过一系列醛与 4-羟基香豆素缩合，研究了一种有效的一锅法合成各种双香豆素基甲烷衍生物的方法。这种一锅多米诺骨牌 Knoevenagel 缩合/迈克尔加成反应提供了优异的双香豆素甲烷衍生物收率，具有反应时间短、反应介质环保、后处理简单、催化剂可回收和免色谱纯化等许多优点。此外，合成的化合物被用于开发具有特殊兴趣的双香豆基亚甲基基纳米结构材料，并通过紫外-可见光、荧光光谱、扫描电子显微镜和原子力显微镜成像进行了研究。我们的 UV-Vis 和荧光研究表明，一些有机化合物在薄膜中以 H 聚集体的形式组织。我们还调查了一些选择性化合物的薄膜的I-V特性，这些化合物在所研究的薄膜上表现出一次写入多次读取的存储器切换行为。 图形概要

  DOI：

  10.1007/s11164-022-04841-3

文献信息

• Synthesis, in vitro evaluation and molecular docking studies of biscoumarin thiourea as a new inhibitor of α-glucosidases
  作者：Nik Khairunissa Nik Abdullah Zawawi、Muhammad Taha、Norizan Ahmat、Nor Hadiani Ismail、Abdul Wadood、Fazal Rahim、Ashfaq Ur Rehman

  DOI：10.1016/j.bioorg.2015.09.004

  日期：2015.12

  Biscoumarin analogs 1-18 have been synthesized, characterized by EI-MS and H-1 NMR and evaluated for a-glucosidase inhibitory potential. All compounds showed variety of alpha-glucosidase inhibitory potential ranging in between 13.5 +/- 0.39 and 104.62 +/- 0.3 mu M when compared with standard acarbose having IC50 value 774.5 +/- 1.94 mu M. The binding interactions of the most active analogs were confirmed through molecular docking. The compounds showed very good interactions with enzyme. All synthesized compounds 1-18 are new. Our synthesized compounds can further be studied to developed lead compounds. (C) 2015 Elsevier Inc. All rights reserved.
• Design, Synthesis, and Biological Activity of Novel Dicoumarol Glucagon-like Peptide 1 Conjugates
  作者：Jing Han、Lidan Sun、Yingying Chu、Zheng Li、Dandan Huang、Xiaoyun Zhu、Hai Qian、Wenlong Huang

  DOI：10.1021/jm4017448

  日期：2013.12.27

  Twelve novel dicoumarol glucagon-like peptide 1 (GLP-1) conjugates were designed, synthesized, and tested for biological activity. All derivatives retained receptor activation efficacy, and exhibited improved albumin affinity and in vitro stability in rat plasma. The in vivo elimination half-lives of 13c and 131 (22.07 and 18.78 h, respectively) were much longer than those of the GLP-1 receptor agonists exendin-4 (2.82 h) and liraglutide (12.53 h). The prolonged in vivo antidiabetic effects of 13c and 13l on db/db mice were confirmed by the hypoglycemic efficacy test and the multiple intraperitoneal glucose tolerance test. Importantly, a once daily administration of 13c to db/db mice for 7 weeks provided long-term beneficial effects by lowering glycated hemoglobin (HbAlc) levels to 5.05%, which was lower than with liraglutide treatment (5.41%). These results suggest that 13c is a promising long-lasting GLP-1 mimetic that may be suitable for clinical use following further research.
• [EN] COUMARIN-BASED COMPOUNDS<br/>[FR] COMPOSÉS À BASE DE COUMARINE
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2010075280A2

  公开（公告）日：2010-07-01

  Compounds including those of the Formula I where X, R1, R2 and subscript t are as defined herein, useful as γ-secretase inhibitors, are provided, as are compositions comprising the compounds, as well as methods for use of the compounds for treating or preventing neurodegenerative diseases, such as, for instance, Alzheimer's disease.