2',4',6'-trihydroxychalcone

• 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
• 英文名称: 2',4',6'-trihydroxychalcone
• 英文别名: pinocembrin chalcone；2′,4′,6′-trihydroxychalcone；(E)-3-Phenyl-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one；3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: LOYXTWZXLWHMBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2',4',6'-trihydroxychalcone 在 碘 作用下， 以 三乙二醇 为溶剂， 反应 2.0h， 以62%的产率得到白杨素
  参考文献：
  名称：

  Synthesis, characterization and molecular docking studies of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives as potential antimicrobial agents

  摘要：

  A series of novel 2-amino 3-cyano 4-aryl pyrano[2,3H]chrysin derivatives (3a-m) were efficiently synthesized by one-pot three-component reaction of aromatic aldehydes, malononitrile and chrysin and characterized by H-1 NMR, C-13 NMR and mass spectral data. All the newly synthesized compounds were evaluated for their in vitro antimicrobial activity (antibacterial and antifungal). Among the tested compounds, 3a, 3g, 3h, 3j and 3k showed potent antibacterial activity compared to ciprofloxacin and the compounds 3a, 3g, 3h, 3i and 3k showed excellent antifungal activity compared to itrazole. The compounds 3a, 3g, 3h and 3k exhibited potent antimicrobial activity against all the selected pathogenic bacteria and fungi and emerged as potential molecules for further development. In addition, molecular modeling studies also performed to delineate the putative binding mode of these compounds. All of these chrysin derivatives (3a-m) obeyed the Lipinski's "rule of five" and have drug-likeness. Docking scores with appreciable binding energy values also exactly correlated with the experimental antimicrobial activity. The chemscore estimated by GOLD software was found to have a good correlation with the experimental inhibitory activity.Docking of compound 3g with proteinA series of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives (3a-m) has been synthesized and evaluated for their antimicrobial activity along with molecular modeling studies.

  DOI：

  10.1007/s00044-015-1396-7
• 作为产物：
  描述：

  松属素 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以55%的产率得到2',4',6'-trihydroxychalcone
  参考文献：
  名称：

  僵木的生物活性甲酰化类黄酮：分离，合成和X射线晶体学

  摘要：

  两个新的类黄酮，rac -6-甲酰基-5,7-二羟基黄酮（1）和2'，6'-二羟基-4'-甲氧基-3'-甲基查尔酮（2），以及五个已知的衍生物，rac -8-甲酰基-5,7-二羟基黄酮（3），4'，6'-二羟基-2'-甲氧基-3'-甲基二氢查耳酮（4），rac -7-羟基-5-甲氧基-6-甲基黄酮（5），3 ' -甲酰基-2'，4'，6'-三羟基- 5'-methyldihydrochalcone（6），和3'-甲酰基-2'，4'，6'- trihydroxydihydrochalcone（7）中，从叶分离尤金尼亚刚性的。的单独的（S）-和（R）-对映体1和3，以及相应的甲酰化黄酮8（6-甲酰基-5,7-二羟基黄酮）和9（8-甲酰基-5,7-二羟基黄酮），以及2'，4'，6'-三羟基查耳酮（10），3'-甲酰基-2'，4'，6'-三羟基查耳酮（11）和相应的3'-甲酰基-2'，4'，6'-

  DOI：

  10.1021/acs.jnatprod.6b00474

文献信息

• Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives
  作者：Chunling Hu、Zongbao Zhou、Yuanhang Xiang、Xiaoying Song、Hong Wang、Kaiqi Tao、Xiaochuan Ye

  DOI：10.1007/s00044-017-2054-z

  日期：2018.1

  Thirty dihydroflavonol derivatives (D1–D30) were designed and synthesized, meanwhile the synthesized compounds were characterized on the basis of spectroscopic analyzes. Their inhibitory activity against the pro-inflammatory inducible interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophages were evaluated and

  设计并合成了三十种二氢黄酮醇衍生物（D1 - D30），同时在光谱分析的基础上对合成的化合物进行了表征。它们对脂多糖（LPS）刺激的鼠RAW 264.7巨噬细胞中促炎性诱导白介素1β（IL-1β），白介素6（IL-6）和肿瘤坏死因子-α（TNF-α）的抑制活性为评估并显示出各种效率。化合物D1 - D30在20μM的浓度下对RAW 264.7细胞无毒作用；其中，化合物D9，D13和D19通过降低IL-1β，IL-6和TNF-α表现出最佳的抗炎活性。此外，初步讨论了它们的结构-活性关系。
• 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。
• Discovery of a Unique Flavonoid Biosynthesis Mechanism in Fungi by Genome Mining
  作者：Wei Zhang、Xuan Zhang、Dandan Feng、Yajing Liang、Zhenying Wu、Siyu Du、Yu Zhou、Ce Geng、Ping Men、Chunxiang Fu、Xuenian Huang、Xuefeng Lu

  DOI：10.1002/anie.202215529

  日期：2023.3.13

  Plant flavonoids are synthesized by type III PKS followed by chalcone isomerase (CHI) and flavone synthase (FNS). Now a unique flavonoid biosynthesis mechanism has been identified in fungi by genome mining. The chalcone skeleton is assembled by an NRPS-PKS hybrid enzyme, and subsequent conversion into a flavone is catalyzed by new types of CHI and FNS. This finding provides new insight into the microbial

  植物类黄酮由 III 型 PKS 合成，随后是查耳酮异构酶 (CHI) 和黄酮合酶 (FNS)。现在，通过基因组挖掘在真菌中发现了一种独特的类黄酮生物合成机制。查尔酮骨架由 NRPS-PKS 杂合酶组装，随后转化为黄酮由新型 CHI 和 FNS 催化。这一发现为有价值的植物类黄酮的微生物生产提供了新的见解。
• Shinoda; Sato, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1928, vol. 48, p. 111
  作者：Shinoda、Sato

  DOI：——

  日期：——
• Rosenmund; Rosenmund, Chemische Berichte, 1928, vol. 61, p. 2611
  作者：Rosenmund、Rosenmund

  DOI：——

  日期：——