3-(4-甲氧基苯基)-1-(2,4,6-三羟基苯基)丙-1-酮 | 76172-68-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 3-(4-甲氧基苯基)-1-(2,4,6-三羟基苯基)丙-1-酮
• 英文名称: 2',4',6'-trihydroxy-4-methoxydihydrochalcone
• 英文别名: 3-(4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one；isosakuranetin dihydrochalcone
• CAS: 76172-68-4
• 化学式: C₁₆H₁₆O₅
• mdl: MFCD00016457
• 分子量: 288.3
• InChiKey: YQNPVOBVGNGYHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2914509090
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  存储条件：2-8°C，密封保存，干燥环境并避免光照。

反应信息

• 作为反应物：
  描述：

  3-(4-甲氧基苯基)-1-(2,4,6-三羟基苯基)丙-1-酮 在 potassium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 2,4,6-trihydroxy-3-[3-(4-methoxyphenyl)propanoyl]-5-methylbenzaldehyde
  参考文献：
  名称：

  An Efficient Regioselective Synthesis of 8-Formylhomoisoflavonoids with Neuroprotective Activity by Enhancing Autophagy

  摘要：

  DOI：

  10.1021/acs.jnatprod.0c00830
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 palladium on activated charcoal 、 氢气 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 16.5h， 生成 3-(4-甲氧基苯基)-1-(2,4,6-三羟基苯基)丙-1-酮
  参考文献：
  名称：

  New homoisoflavonoid analogues protect cells by regulating autophagy

  摘要：

  As a special group of naturally occurring flavonoids, homoisoflavonoids have been discovered as active components of several traditional Chinese medicines for nourishing heart and mind. In this study, twenty homoisoflavonoid analogues, including different substitution groups on rings A and B, as well as heteroaromatic B ring, were synthesized and evaluated for their cardioprotective and neuroprotective activities. In a H2O2-induced H9c2 cardiomyocytes injury assay, nine homoisoflavonoid analogues showed promising activities in the same level as the positive control, diazoxide. Six cardioprotective compounds with representative structure diversities were then evaluated for their neuroprotective effects on MPP+ induced SH-SY5Y cell injury model. Furthermore, autophagy inducing monodansylcadaverine (MDC) fluorescence staining methods and molecular docking studies indicated the action mechanism of these compounds may involve autophagy regulating via class I P13K signaling pathway. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.01.086

文献信息

• Targeting Type 2 Diabetes with <i>C</i>-Glucosyl Dihydrochalcones as Selective Sodium Glucose Co-Transporter 2 (SGLT2) Inhibitors: Synthesis and Biological Evaluation
  作者：Ana R. Jesus、Diogo Vila-Viçosa、Miguel Machuqueiro、Ana P. Marques、Timothy M. Dore、Amélia P. Rauter

  DOI：10.1021/acs.jmedchem.6b01134

  日期：2017.1.26

  Inhibiting glucose reabsorption by sodium glucose co-transporter proteins (SGLTs) in the kidneys is a relatively new strategy for treating type 2 diabetes. Selective inhibition of SGLT2 over SGLT1 is critical for minimizing adverse side effects associated with SGLT1 inhibition. A library of C-glucosyl dihydrochalcones and their dihydrochalcone and chalcone precursors was synthesized and tested as SGLT1/SGLT2

  通过钠葡萄糖共转运蛋白（SGLT）抑制肾脏中的葡萄糖重吸收是治疗2型糖尿病的一种相对较新的策略。相对于SGLT1而言，对SGLT2的选择性抑制对于最小化与SGLT1抑制相关的不利副作用至关重要。合成了C-葡萄糖基二氢查耳酮及其二氢查耳酮和查耳酮前体的文库，并使用基于细胞的葡萄糖吸收荧光测定法测试了它们作为SGLT1 / SGLT2抑制剂的能力。SGLT2的最有效抑制剂（IC 50 = 9–23 nM）是SGLT1的较弱抑制剂（IC 50）= 10–19μM）。他们对葡萄糖转运蛋白的钠依赖性GLUT家族没有影响，最有效的对培养细胞没有急性毒性。通过计算对C-葡萄糖基二氢查耳酮与POPC膜的相互作用进行了建模，从而提供了它不是泛测定干扰化合物的证据。这些结果指向发现是有效且高度选择性的SGLT2抑制剂的结构。
• Base-catalyzed oxidative dearomatization of multisubstituted phloroglucinols: An easy access to C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives
  作者：Wan Gao、Zhong Chen、Yanan Yang、Jianshuang Jiang、Ziming Feng、Xu Zhang、Xiang Yuan、Peicheng Zhang

  DOI：10.1016/j.carres.2019.107756

  日期：2019.10

  An efficient and simple method for the protecting group-free synthesis of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone has been firstly established. This method is compatible with various functional groups, such as benzyl and phenethyl groups, affording a range of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives.

  首先建立了一种有效且简单的无保护基合成C-葡萄糖基3,5,6-三羟基环己-2,4-二烯酮的方法。该方法与各种官能团如苄基和苯乙基兼容，从而提供了一系列的C-葡糖基3,5,6-三羟基环己-2,4-二烯酮衍生物。
• EDDA-catalyzed rapid synthetic routes for biologically interesting polycycles bearing citrans and chalcones: the first total synthesis of sumadain A
  作者：Xue Wang、Yong Rok Lee

  DOI：10.1016/j.tet.2009.10.045

  日期：2009.12

  An efficient and concise synthetic route for biologically interesting polycycles bearing citran and chalcone nuclei was developed starting from a variety of trihydroxybenzenes with substituents on the ring. The key strategies involved an ethylenediamine diacetate-catalyzed cyclization by a domino aldol-type/electrocyclization/H-shift/hetero Diels–Alder reaction of trihydroxybenzenes and citral or trans

  从环上带有取代基的各种三羟基苯开始，开发了一种有效且简捷的合成路线，用于合成具有柑桔和查尔酮核的生物学上令人感兴趣的多环。关键策略包括三羟苯与柠檬醛或反式，反式-反式法呢醛的多米诺骨牌羟醛型/电环化/ H-shift /杂狄尔斯-阿尔德反应对乙二胺二乙酸酯的催化环化作用。该方法已成功地用于合成三种天然产物，去苄基神经核蛋白，胭脂红，苏马丹A及其非天然衍生物。
• Phenolic constituents from seeds of Coptis japonica var. dissecta
  作者：Min Zhi-da、Hiroko Murata、Mizuo Mizuno、Hiroyuki Kojima、Toshiyuki Tanaka、Munekazu Iinuma、Rie Kimura

  DOI：10.1016/s0031-9422(00)81760-4

  日期：——

  Abstract In addition to coumarinolignans (cleomiscosin A aquillochin) and 7,4′-dihydroxy-5-methoxyflavanone, a new dihydrochalcone, 2′,4,4′-trihydroxy-6′-methoxydihydrochalcone, was isolated from the seeds of Coptis japonica var. dissecta. The structure of the dihydrochalcone was confirmed by comparison with relevant synthetic samples.

  摘要 除了香豆素木脂素（cleomiscosin A aquillochin）和7,4'-二羟基-5-甲氧基黄烷酮外，从黄连变种的种子中分离出一种新的二氢查耳酮，2',4,4'-三羟基-6'-甲氧基二氢查耳酮。 . 解剖。通过与相关合成样品的比较，证实了二氢查尔酮的结构。
• 一类A环具有葡萄糖的醌式二氢查尔酮双碳苷化合物，制法与神经保护活性
  申请人：中国医学科学院药物研究所

  公开号：CN111662261B

  公开（公告）日：2023-05-05

  本发明公开了一类A环具有葡萄糖的醌式二氢查尔酮碳苷类化合物及其制备方法与抗脑缺血损伤活性。本发明的化合物具有通式(Ⅰ)所示的结构，其制备方法包括以下步骤：(1)合成2,4,6‑三羟基二氢查尔酮类化合物；(2)合成2,4,6‑三羟基‑3,5‑二葡萄糖基二氢查尔酮碳苷类化合物；(6)合成一类A环具有葡萄糖的醌式二氢查尔酮碳苷类化合物。本发明的化合物制备方法简单并且具有显著的抗脑缺血损伤的作用。