3-(3,4-二羟基苯基)-1-(2-羟基-4-甲氧基苯基)丙-2-烯-1-酮 | 152340-67-5

• 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-(3,4-二羟基苯基)-1-(2-羟基-4-甲氧基苯基)丙-2-烯-1-酮
• 英文名称: (E)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 英文别名: calythropsin
• CAS: 152340-67-5
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: IULVGTQOZKYHCS-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 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：
  87
• 氢给体数：
  3
• 氢受体数：
  5

制备方法与用途

Calythropsin 是一种具有细胞毒性的查尔酮，其对有丝分裂和微管蛋白聚合的作用较弱。

反应信息

• 作为反应物：
  描述：

  3-(3,4-二羟基苯基)-1-(2-羟基-4-甲氧基苯基)丙-2-烯-1-酮 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以13.6%的产率得到2-(3,4-dihydroxyphenyl)-3-hydroxy-7-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  非瑟酮衍生物的设计、合成和生物活性评价作为潜在的抗 LPS 诱导的急性肺损伤的抗炎药

  摘要：

  急性肺损伤 (ALI) 是一种由炎症引起的常见且危及生命的疾病。然而，对于 ALI，有效的药物治疗很少见。天然产物被认为是药物发现的重要来源，这表明在天然产物中寻找新的抗炎药物是一种可行的方法。受非瑟酮各种生物活性的启发，我们报道了一系列非瑟酮衍生物的设计和合成，这些衍生物还评估了它们在 J774A.1 巨噬细胞中的抗炎活性。所得衍生物大部分在体外实验中均能有效抑制IL-6和TNF-α的释放，且无细胞毒性。最有希望的化合物5b在体内表现出显着LPS 诱导的小鼠 ALI 模型中的抗炎活性。总的来说，这项研究可以为治疗 ALI 提供新的候选者。

  DOI：

  10.1016/j.bmc.2021.116456
• 作为产物：
  描述：

  3,4-二(四氢吡喃-2-氧基)苯甲醛 在 barium dihydroxide 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 23.0h， 生成 3-(3,4-二羟基苯基)-1-(2-羟基-4-甲氧基苯基)丙-2-烯-1-酮
  参考文献：
  名称：

  3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors

  摘要：

  A novel series of 3,4-dihydroxychalcones was synthesized to evaluate their effects against 5-lipoxygenase and cyclooxygenase. Almost all compounds exhibited potent inhibitory effects on 5-lipoxygenase with antioxidative effects, and some also inhibited cyclooxygenase. The 2',5'-disubstituted 3,4-dihydroxychalcones with hydroxy or alkoxy groups exhibited optimal inhibition of cyclooxygenase. We found that 2',5'-dimethoxy-3,4-dihydroxychalcone (37; HX-0836) inhibited cyclooxygenase to the same degree as flufenamic acid and 6-lipoxygenase, more than quercetin. Finally, these active inhibitors of 5-lipoxygenase inhibited arachidonic acid-induced mouse ear edema more than phenidone.

  DOI：

  10.1021/jm00076a019

文献信息

• Reactivity assessment of chalcones by a kinetic thiol assay
  作者：Sabine Amslinger、Nafisah Al-Rifai、Katrin Winter、Kilian Wörmann、Rebekka Scholz、Paul Baumeister、Martin Wild

  DOI：10.1039/c2ob27163j

  日期：——

  The electrophilic nature of chalcones (1,3-diphenylprop-2-en-1-ones) and many other α,β-unsaturated carbonyl compounds is crucial for their biological activity, which is often based on thiol-mediated regulation processes. To better predict their biological activity a simple screening assay for the assessment of the second-order rate constants (k2) in thia-Michael additions was developed. Hence, a clear structure–activity relationship of 16 differentially decorated hydroxy-alkoxychalcones upon addition of cysteamine could be established. Moreover, amongst other naturally occurring α,β-unsaturated carbonyl compounds k2 values for curcumin and cinnamaldehyde were gained while cinnamic acids or esters gave no or very slow reactions.

  查耳酮（1,3-二苯基丙-2-烯-1-酮）和许多其他α,β-不饱和羰基化合物的亲电性质对其生物活性至关重要，而生物活性通常是基于硫醇介导的调节过程。为了更好地预测它们的生物活性，我们开发了一种简单的筛选方法，用于评估噻-迈克尔加成反应的二阶速率常数（k2）。因此，在添加半胱胺后，16 种不同装饰的羟基烷氧基查耳酮的结构-活性关系得以明确。此外，在其他天然存在的 α、β-不饱和羰基化合物中，姜黄素和肉桂醛的 k2 值得到了提高，而肉桂酸或酯类则没有反应或反应非常缓慢。
• Catechin and gingerol loaded nanomedicine
  申请人：King Abdulaziz University

  公开号：US11129797B1

  公开（公告）日：2021-09-28

  A nanomedicine for the treatment of obesity comprising either noble metal nanoparticles having surface ligands comprising a mixture comprising (+)-catechin (2R,3S) and gingerol or particles of a carbon nanomaterial having an adsorbed mixture comprising (+)-catechin (2R,3S) and gingerol. Also provided are a method for making the noble metal nanomedicine and the carbon nanomedicine. The nanomedicine is used in a method of treating obesity.

  一种用于治疗肥胖症的纳米药物，该药物包含贵金属纳米颗粒，其表面配体包含(+)-儿茶素（2R,3S）和姜酚的混合物，或者包含吸附了(+)-儿茶素（2R,3S）和姜酚混合物的碳纳米材料颗粒。此外，还提供了一种制造贵金属纳米药物和碳纳米药物的方法。该纳米药物可用于治疗肥胖症。
• Method for making a noble metal nanomedicine
  申请人：King Abdulaziz University

  公开号：US11234940B1

  公开（公告）日：2022-02-01

  A nanomedicine for the treatment of obesity comprising either noble metal nanoparticles having surface ligands comprising a mixture comprising (+)-catechin (2R,3S) and gingerol or particles of a carbon nanomaterial having an adsorbed mixture comprising (+)-catechin (2R,3S) and gingerol. Also provided are a method for making the noble metal nanomedicine and the carbon nanomedicine. The nanomedicine is used in a method of treating obesity.

  一种用于治疗肥胖症的纳米药物，该药物包含贵金属纳米颗粒，其表面配体包含(+)-儿茶素（2R,3S）和姜酚的混合物，或者包含吸附了(+)-儿茶素（2R,3S）和姜酚混合物的碳纳米材料颗粒。此外，还提供了一种制造贵金属纳米药物和碳纳米药物的方法。该纳米药物可用于治疗肥胖症。
• Metal nanoparticle medicine with a mixture of natural ligands
  申请人：King Abdulaziz University

  公开号：US11219605B1

  公开（公告）日：2022-01-11

  A nanomedicine for the treatment of obesity comprising either noble metal nanoparticles having surface ligands comprising a mixture comprising (+)-catechin (2R,3S) and gingerol or particles of a carbon nanomaterial having an adsorbed mixture comprising (+)-catechin (2R,3S) and gingerol. Also provided are a method for making the noble metal nanomedicine and the carbon nanomedicine. The nanomedicine is used in a method of treating obesity.

  一种用于治疗肥胖症的纳米药物，该药物包含贵金属纳米颗粒，其表面配体包含(+)-儿茶素（2R,3S）和姜酚的混合物，或者包含吸附了(+)-儿茶素（2R,3S）和姜酚混合物的碳纳米材料颗粒。此外，还提供了一种制造贵金属纳米药物和碳纳米药物的方法。该纳米药物可用于治疗肥胖症。
• Carbon nanomedicine with natural ligands
  申请人：King Abdulaziz University

  公开号：US11311492B1

  公开（公告）日：2022-04-26

  A nanomedicine for the treatment of obesity comprising either noble metal nanoparticles having surface ligands comprising a mixture comprising (+)-catechin (2R,3S) and gingerol or particles of a carbon nanomaterial having an adsorbed mixture comprising (+)-catechin (2R,3S) and gingerol. Also provided are a method for making the noble metal nanomedicine and the carbon nanomedicine. The nanomedicine is used in a method of treating obesity.

  本发明涉及一种用于治疗肥胖症的纳米药物，其成分包括：要么包含具有表面配体的贵金属纳米粒子，所述表面配体由混合物组成，所述混合物包括(+)-儿茶素(2R,3S)和姜酚；要么包含碳纳米材料颗粒，所述颗粒吸附有由混合物组成的混合物，所述混合物包括(+)-儿茶素(2R,3S)和姜酚。本发明还提供了一种制备所述贵金属纳米药物和碳纳米药物的方法。该纳米药物用于治疗肥胖症的方法。