2′,5′-dihydroxy-4-methoxychalcone | 6342-92-3

• 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′,5′-dihydroxy-4-methoxychalcone
• 英文别名: 2',5'-Dihydroxy-4-methoxy-chalkon；1-(2,5-dihydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 6342-92-3
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: FUQGIYDZGLORRC-UHFFFAOYSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  528.2±50.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-bromophenyl)semicarbazide 、 2′,5′-dihydroxy-4-methoxychalcone 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以57%的产率得到1-[1-(2,5-dihydroxyphenyl)-3-(4-methoxyphenyl)allylidene]-4-(4-bromophenyl)semicarbazide
  参考文献：
  名称：

  某些新型苯基取代的氨基脲化合物的合成及药理筛选

  摘要：

  在本研究中，我们合成了查尔酮和氨基脲连接的查洛尔基衍生物，并通过MS，IR和1 H NMR技术确认了标题化合物。通过最大电击（MES）诱发癫痫发作方法确定抗惊厥活性。腹膜内给药后，大多数化合物表现出显着的抗惊厥活性。结果表明氢键对活性的重要性。在本研究中，5e，5h，5i，6e，6h和6i成为最活跃的分子，显示出明显的抗惊厥活性。

  DOI：

  10.1007/s00044-009-9277-6
• 作为产物：
  描述：

  2'-hydroxy-5'-methoxymethoxyacetophenone 在 盐酸 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 2′,5′-dihydroxy-4-methoxychalcone
  参考文献：
  名称：

  Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists

  摘要：

  Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.037

文献信息

• CHALCONSEMICARBAZONE: A NEW SCAFFOLD FOR ANTIEPILEPTIC DRUG DISCOVERY
  作者：HEMENDRA PRATAP SINGH、C S CHAUHAN、S N PANDEYA、CHANDRA SHEKHAR SHARMA

  DOI：10.4067/s0717-97072010000100024

  日期：——

  having broad spectrum activity. On the bases of work done in this area we have applied hybridization of pharmacophore strategy of drug design and developed a new pharmacophore. We have also designed a scheme for synthesizing such pharmacophore and performed their pharmacological screening for the protection of seizures, behavioral study and CNS activity. The compound 1-[1-(2,4-dihydroxyphenyl)-3-(2-h

  摘要在我们对癫痫药发现领域的调查中，我们发现可用的常规抗癫痫药对60-80％的患者和特定类型的癫痫发作有效，并具有各种不良副作用。但是目前，新型的芳基半卡巴zone出现在具有广谱活性的癫痫药物发现中作为新的药效团。在这一领域的工作基础上，我们应用了药效基团杂交的药物设计策略，并开发了一种新的药效基团。我们还设计了合成此类药效团的方案，并进行了药理学筛选，以保护癫痫发作，行为研究和CNS活性。化合物1- [1-（2，在所有模型中，4-二羟基苯基）-3-（2-羟基苯基）亚烷基] -4-（2-氟苯基）氨基脲（8）成为最活跃的原型分子。关键词：氨基脲，光度计，抗癫痫引言癫痫是一个统称，包括40多种不同类型的人类癫痫发作。在任何一次世界人口中，大约有1％（全球超过5000万人）患有这种严重的神经系统疾病。尽管当前的药物可在许多患者中提供足够的癫痫发作控制，但据粗略估计，多达28-30％的患者未使用有
• Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists
  作者：Guoning Zhang、Shuainan Liu、Wenjuan Tan、Ruchi Verma、Yuan Chen、Deyang Sun、Yi Huan、Qian Jiang、Xing Wang、Na Wang、Yang Xu、Chiwai Wong、Zhufang Shen、Ruitang Deng、Jinsong Liu、Yanqiao Zhang、Weishuo Fang

  DOI：10.1016/j.ejmech.2017.02.037

  日期：2017.3

  Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Synthesis and pharmacological screening of some novel chalconyl derivatives of substituted phenyl semicarbazide
  作者：Hemendra Pratap Singh、S. N. Pandeya、C. S. Chauhan、Chandra Shekhar Sharma

  DOI：10.1007/s00044-009-9277-6

  日期：2011.1

  In the present study, we have synthesized chalcone and semicarbazide-linked chalonyl derivatives and the titled compounds confirmed by MS, IR, and 1H NMR techniques. The anticonvulsant activity was determined by maximal electroshock (MES) induced seizure method. A majority of the compounds exhibited significant anticonvulsant activity after intraperitoneal administration. The results show the importance

  在本研究中，我们合成了查尔酮和氨基脲连接的查洛尔基衍生物，并通过MS，IR和1 H NMR技术确认了标题化合物。通过最大电击（MES）诱发癫痫发作方法确定抗惊厥活性。腹膜内给药后，大多数化合物表现出显着的抗惊厥活性。结果表明氢键对活性的重要性。在本研究中，5e，5h，5i，6e，6h和6i成为最活跃的分子，显示出明显的抗惊厥活性。