(E)-1,3-bis(3,4-dihydroxyphenyl)prop-2-en-1-one | 106593-04-8

• 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: (E)-1,3-bis(3,4-dihydroxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3,4,3',4'-tetrahydroxychalcone；3,4,3',4'-tetrahydroxychalcone；3,4,3',4'-tetrahydroxy-trans-chalcone；3,4,3',4'-Tetrahydroxy-trans-chalkon；1,3-Bis(3,4-dihydroxyphenyl)prop-2-en-1-one
• CAS: 106593-04-8
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: DOWSJIIZLUFMFM-DAFODLJHSA-N

物化性质

• 熔点：
  230-231 °C
• 沸点：
  591.9±50.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 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：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-双(甲氧基甲氧基)苯甲醛 在 盐酸 、 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 75.17h， 生成 (E)-1,3-bis(3,4-dihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and evaluation of 2′,4′,6′-trihydroxychalcones as a new class of tyrosinase inhibitors

  摘要：

  In this study, we synthesized a series of hydroxychalcones and examined their tyrosinase inhibitory activity. The results showed that 2',4',6'-trihydroxychalcone (1), 2,2',3,4',6'-pentahydroxychalcone (4), 2',3,4,4,5,6'-hexahydroxychalcone (5), 2',4',6'-trihydroxy- 3,4-dimethoxychalcone (9) and 2,2,4,4',6'-pentahydroxychalcone (15) exhibited high inhibitory effects on tyrosinase with respect to L-tyrosine as a substrate. By the structure activity relationship study, it was suggested that the 2',4',6'-trihydroxyl substructure in the chalcone skeleton were efficacious for the inhibition of tyrosinase activity. And also, the catechol structure on B-ring of chalcones was not advantageous for the inhibitory potency. Furthermore, 15 (IC50 = 1 mu M) was found to show the highest activity out of a set of 15 hydroxychalcones, even better than both 2,2',4,4'-tetrahydroxychalcone (13, IC50 = 5 mu M) and kojic acid (16, IC50 = 12 mu M), which were known as potent tyrosinase inhibitors. Kinetic study revealed that 15 acts as a competitive inhibitor of tyrosinase with K-i value of 3.1 mu M. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.017

文献信息

• [EN] SUBSTITUTED N-ARYL BENZAMIDES AND RELATED COMPOUNDS FOR TREATMENT OF AMYLOID DISEASES AND SYNUCLEINOPATHIES<br/>[FR] N-BENZAMIDES D'ARYLE SUBSTITUÉS ET COMPOSÉS LIÉS POUR TRAITEMENT DES MALADIES AMYLOÏDES ET DES SYNUCLÉINOPATHIES
  申请人：PROTEOTECH INC

  公开号：WO2005113489A1

  公开（公告）日：2005-12-01

  Substituted diaryl compounds of the Formulae (I, II, III), where the variables are as defined in the claims, and their pharmaceutically acceptable derivatives, their synthesis, pharmaceutical compositions containing them, and their use in the treatment of amyloid diseases, including Aß amyloidosis, such as observed in Alzheimer's disease, IAPP amyloidosis, such as observed in type 2 diabetes, and synucleinopathies, such as observed in Parkinson's disease, and the manufacture of medicaments for such treatment are provided.

  根据权利要求中定义的变量，提供了公式（I，II，III）的取代二芳基化合物及其药学上可接受的衍生物，它们的合成，含有它们的药物组合物，以及它们在治疗淀粉样疾病中的用途，包括阿尔茨海默病中观察到的Aß淀粉样病变，如2型糖尿病中观察到的IAPP淀粉样病变，以及在帕金森病中观察到的α-突触核病变，并提供了用于制造这种治疗药物的方法。
• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR THE TREATMENT OF AMYLOID DISEASES AND SYNUCLEINOPATHIES SUCH AS ALZHEIMER'S DISEASE, TYPE 2 DIABETES, AND PARKINSON'S DISEASE<br/>[FR] COMPOSES, COMPOSITIONS ET PROCEDES DE TRAITEMENT DE MALADIES AMYLOIDES ET DE SYNUCLEINOPATHIES, NOTAMMENT DE LA MALADIE D'ALZHEIMER, DU DIABETE DE TYPE 2 ET DE LA MALADIE DE PARKINSON
  申请人：PROTEOTECH INC

  公开号：WO2003101927A1

  公开（公告）日：2003-12-11

  Bis- and tris-dihydroxyaryl compounds and their methylenedioxy analogs and pharmaceutically acceptable esters, their synthesis, pharmaceutical compositions containing them, and their use in the treatment of amyloid diseases, especially Aß amyloidosis, such as observed in Alzheimer's disease, IAPP amyloidosis, such as observed in type 2 diabetes, and synucleinophathies, such as observed in Parkinson's disease, and the manufacture of medicaments for such treatment.

  双-和三-二羟基芳基化合物及其亚甲二氧基类似物和药用可接受酯，它们的合成，含有它们的药物组合物，以及它们在治疗淀粉样疾病，特别是Aß淀粉样病变，如阿尔茨海默病中观察到的，IAPP淀粉样病变，如2型糖尿病中观察到的，以及α-突触核病，如帕金森病中观察到的，以及用于制造用于此类治疗的药物。
• [EN] COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] COMPOSÉS POUR LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES
  申请人：PROTEOTECH INC

  公开号：WO2012118935A1

  公开（公告）日：2012-09-07

  Compounds and their pharmaceutically acceptable salts for treatment of synucleinopathies, such as Parkinson's disease and tauopathies.

  用于治疗α-突触核复合物病和tau蛋白病的化合物及其药用盐。
• Remedies
  申请人：——

  公开号：US20030144316A1

  公开（公告）日：2003-07-31

  The present invention provides a therapeutic agent or prophylactic agent for a disease that requires enhancement of nerve growth factor production, an enhancer for nerve growth factor production, or a food, beverage or feed for enhancing nerve growth factor production, each comprising as an effective ingredient a specified compound or a salt thereof having enhancing activity for nerve growth factor production; a method for enhancing nerve growth factor production, comprising administering to a mammal the above-mentioned compound or a salt thereof; and use of the above-mentioned compound or a salt thereof in the preparation of a therapeutic agent or prophylactic agent for a disease that requires enhancement of nerve growth factor production, an enhancer for nerve growth factor production, or a food, beverage or feed for enhancing nerve growth factor production. In addition, the present invention provides novel compounds having enhancing activity for nerve growth factor production.

  本发明提供了一种治疗剂或预防剂，用于需要增强神经生长因子产生的疾病，用于增强神经生长因子产生的增强剂，或用作增强神经生长因子产生的食品、饮料或饲料，每种包含一种有效成分，即具有增强神经生长因子产生活性的指定化合物或其盐；一种增强神经生长因子产生的方法，包括向哺乳动物投与上述化合物或其盐；以及使用上述化合物或其盐制备需要增强神经生长因子产生的疾病的治疗剂或预防剂，增强神经生长因子产生的增强剂，或用于增强神经生长因子产生的食品、饮料或饲料。此外，本发明提供了具有增强神经生长因子产生活性的新化合物。
• COMPOSITION FOR INDUCING DIFFERENTIATION INTO BEIGE AND BROWN ADIPOCYTES AND METHOD OF INDUCING THE SAME
  申请人：RESEARCH & BUSINESS FOUNDATION SUNGKYUNKWAN UNIVERSITY

  公开号：US20150374643A1

  公开（公告）日：2015-12-31

  A composition for inducing differentiation into beige adipocytes from white adipocytes, including butein, a butein derivative, or a pharmaceutically available salt thereof as an active ingredient, and a method of inducing the differentiation are provided. Increases in expressions of UCP-1 and PRDM4 are confirmed using the active ingredient, that is, the butein or butein derivative, and therefore the composition is expected to be used in preventing or treating obesity, and more basically, for target treatment.

  本发明提供了一种用于将白色脂肪细胞分化为米色脂肪细胞的组合物，包括布丁、布丁衍生物或其药学上可用的盐作为活性成分，并提供了一种诱导分化的方法。使用活性成分即布丁或布丁衍生物，已确认UCP-1和PRDM4表达的增加，因此预计该组合物可用于预防或治疗肥胖症，更基本地，用于目标治疗。