2,4,2'-trihydroxychalcone | 72704-77-9

• 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: 2,4,2'-trihydroxychalcone
• 英文别名: (E)-3-(2,4-dihydroxyphenyl)-1-(2'-hydroxyphenyl)-2-propen-1-one；2,2',4'-Trihydroxy-chalkon；2.4.2'-trihydroxy-trans-chalcone；2.4.2'-Trihydroxy-trans-chalkon；(E)-3-(2,4-dihydroxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 72704-77-9
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: ZLEFYDUXMWKPSH-SOFGYWHQSA-N

物化性质

• 熔点：
  164-165 °C (decomp)
• 沸点：
  513.8±50.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

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：

  2,4,2'-trihydroxychalcone 生成 2.4.2'-triacetoxy-trans-chalcone
  参考文献：
  名称：

  黄烷酮和相关化合物。一、多羟基查耳酮和-黄烷酮的制备

  摘要：

  许多聚羟基查耳酮和β-黄烷酮已被制备用于黄烷酮的某些还原产物的光谱研究。本研究中制备的大多数化合物都不是新的，仅在似乎需要对其性质进行一些修改的情况下才会提及。描述了八个新的查耳酮和十个新的黄烷酮，以及所有这些的酰基衍生物。Cha1cones.-fi 有相当多的方法可用于制备多羟基查耳酮。尽管具有某些限制，但最普遍适用的方法包括通过碱将适当取代的苯乙酮和适当的苯甲醛缩合。此处描述的大多数化合物是通过该通用程序制备的。在少数情况下发现有必要使用 Russell's2 方法。某些含有 2'-羟基-的查耳酮的制备

  DOI：

  10.1021/ja01208a051
• 作为产物：
  描述：

  2'-hydroxy-2,4-diisopropoxychalcone 在 三氯化硼 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 2.0h， 生成 2,4,2'-trihydroxychalcone
  参考文献：
  名称：

  Tsuchiya; Sato; Akagiri, Pharmazie, 1994, vol. 49, # 10, p. 756 - 758

  摘要：

  DOI：

文献信息

• Diarylalkanes as potent inhibitors of binuclear enzymes
  申请人：Jia Qi

  公开号：US20050267047A1

  公开（公告）日：2005-12-01

  The present invention implements a strategy that combines an enzyme inhibition assay with a chemical dereplication process to identify active plant extracts and the particular compounds—diarylalkanes and/or diarylalkanols within those extracts that specifically inhibit binuclear enzyme function. Included in the present invention are compositions of matter comprised of one or more of diarylalkanes and/or diarylalkanols, which inhibit the activity of binuclear enzymes, particularly tyrosinase and which prevent melanin overproduction. The present invention also provides a method for inhibiting the activity of a binuclear enzyme, particularly tyrosinase and a method for preventing and treating diseases and conditions related to binuclear enzyme function. The present invention further includes a method for preventing and treating melanin overproduction and diseases and conditions of the skin related thereto. The method for preventing and treating diseases and conditions related to binuclear enzyme function and melanin overproduction is comprised of administering to a host in need thereof an effective amount of a composition comprising one or more diarylalkanes and/or diarylalkanols synthesized and/or isolated from one or more plants together with a pharmaceutically acceptable carrier.

  本发明实施了一种策略，将酶抑制测定与化学去重复过程相结合，以识别活性植物提取物和特定化合物——二芳基烷烃和/或二芳基醇，这些化合物特异性地抑制双核酶功能。本发明包括由一种或多种二芳基烷烃和/或二芳基醇组成的物质组合物，其抑制双核酶的活性，特别是酪氨酸酶，并防止黑色素过度产生。本发明还提供了一种抑制双核酶活性的方法，特别是酪氨酸酶，以及一种预防和治疗与双核酶功能相关的疾病和病况的方法。本发明还包括一种预防和治疗黑色素过度产生以及与之相关的皮肤疾病和病况的方法。预防和治疗与双核酶功能和黑色素过度产生相关的疾病和病况的方法包括向需要的宿主施用由一种或多种植物合成和/或分离的一种或多种二芳基烷烃和/或二芳基醇组成的组合物的有效量，以及药用载体。
• DIARYLALKANES AS POTENT INHIBITORS OF BINUCLEAR ENZYMES
  申请人：Unigen, Inc.

  公开号：US20140371491A1

  公开（公告）日：2014-12-18

  The present invention implements a strategy that combines an enzyme inhibition assay with a chemical dereplication process to identify active plant extracts and the particular compounds—diarylalkanes and/or diarylalkanols within those extracts that specifically inhibit binuclear enzyme function. Included in the present invention are compositions of matter comprised of one or more of diarylalkanes and/or diarylalkanols, which inhibit the activity of binuclear enzymes, particularly tyrosinase and which prevent melanin overproduction. The present invention also provides a method for inhibiting the activity of a binuclear enzyme, particularly tyrosinase and a method for preventing and treating diseases and conditions related to binuclear enzyme function. The present invention further includes a method for preventing and treating melanin overproduction and diseases and conditions of the skin related thereto. The method for preventing and treating diseases and conditions related to binuclear enzyme function and melanin overproduction is comprised of administering to a host in need thereof an effective amount of a composition comprising one or more diarylalkanes and/or diarylalkanols synthesized and/or isolated from one or more plants together with a pharmaceutically acceptable carrier.

  本发明实施了一种策略，将酶抑制测定与化学去重过程相结合，以鉴定活性植物提取物及其中特定化合物——二芳基烷烃和/或二芳基烷醇，其特异性抑制双核酶功能。本发明包括由一种或多种二芳基烷烃和/或二芳基烷醇组成的物质组合物，其抑制双核酶的活性，特别是酪氨酸酶，从而防止黑色素过度产生。本发明还提供了一种抑制双核酶活性的方法，特别是酪氨酸酶，并提供了一种预防和治疗与双核酶功能相关的疾病和病症的方法。本发明还包括一种预防和治疗黑色素过度产生及其相关皮肤疾病和病症的方法。预防和治疗与双核酶功能和黑色素过度产生相关的疾病和病症的方法包括向需要的宿主施用一种由一种或多种从一种或多种植物中合成和/或分离出的二芳基烷烃和/或二芳基烷醇组成的组合物的有效量，以及药学上可接受的载体。
• Skin care compositions containing a sugar amine
  申请人：——

  公开号：US20040192649A1

  公开（公告）日：2004-09-30

  Topical skin care compositions containing sugar amines in combination with selected skin care actives and methods of using such compositions to regulate the condition of skin are disclosed. The compositions contain a safe and effective amount of a sugar amine in combination with either a safe and effective amount of a terpene alcohol and a safe and effective amount of a retinoid; a safe and effective amount of a terpene alcohol and a safe and effective amount of a peptide; a safe and effective amount of a retinoid and a safe and effective amount of a peptide; a safe and effective amount of tocopherol sorbate; or a safe and effective amount of a vitamin B 3 compound.

  本发明公开了含糖胺的局部皮肤护理组合物与选定的皮肤护理活性物质的组合，以及使用这种组合物调节皮肤状况的方法。这些组合物含有安全有效量的糖胺与安全有效量的萜烯醇和安全有效量的维甲酸；安全有效量的萜烯醇和安全有效量的肽；安全有效量的维甲酸和安全有效量的肽；安全有效量的生育酚山梨酸酯；或安全有效量的维生素 B3。 3 化合物。
• Chalcones as positive allosteric modulators of α7 nicotinic acetylcholine receptors: A new target for a privileged structure
  作者：Beatriz Balsera、José Mulet、Asia Fernández-Carvajal、Roberto de la Torre-Martínez、Antonio Ferrer-Montiel、José G. Hernández-Jiménez、Judith Estévez-Herrera、Ricardo Borges、Andiara E. Freitas、Manuela G. López、M. Teresa García-López、Rosario González-Muñiz、María Jesús Pérez de Vega、Luis M. Valor、Lucie Svobodová、Salvador Sala、Francisco Sala、Manuel Criado

  DOI：10.1016/j.ejmech.2014.09.039

  日期：2014.10

  The alpha 7 acetylcholine nicotine receptor is a ligand-gated ion channel that is involved in cognition disorders, schizophrenia, pain and inflammation among other diseases. Therefore, the development of new agents that target this receptor has great significance. Positive allosteric modulators might be advantageous, since they facilitate receptor responses without directly interacting with the agonist binding site. Here we report the search for and further design of new positive allosteric modulators having the relatively simple chalcone structure. From the natural product isoliquiritigenin as starting point, chalcones substituted with hydroxyl groups at defined locations were identified as optimal and specific promoters of alpha 7 nicotinic function. The most potent compound (2,4,2',5'-tetrahydroxychalcone, 111) was further characterized showing its potential as neuroprotective, analgesic and cognitive enhancer, opening the way for future developments around the chalcone structure. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Resorcinol-based hemiindigoid derivatives as human tyrosinase inhibitors and melanogenesis suppressors in human melanoma cells
  作者：Brayan Roulier、Inbal Rush、Leticia M. Lazinski、Basile Pérès、Hamza Olleik、Guy Royal、Ayelet Fishman、Marc Maresca、Romain Haudecoeur

  DOI：10.1016/j.ejmech.2022.114972

  日期：2023.1