naringenin | 120980-69-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: naringenin
• 英文别名: 4'-methyl-5,7-dihydroxyflavanone；(+/-)-2,3-dihydro-5,7-dihydroxy-2-(4-methylphenyl)-4H-1-benzopyran-4-one；PTP inhibitor, 4m；5,7-dihydroxy-2-(4-methylphenyl)-2,3-dihydrochromen-4-one
• CAS: 120980-69-0
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: FIUQSEYGBLVZQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  196-197 °C(Solv: ethanol (64-17-5))
• 沸点：
  519.4±50.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  naringenin 、 1-溴-3-甲基-2-丁烯 在 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.0h， 生成 5-Hydroxy-7-(3-methylbut-2-enoxy)-2-(4-methylphenyl)-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  甘草素衍生物抗阿尔茨海默病活性的设计、合成和胆碱酯酶抑制试验

  摘要：

  海洋环境是发现功能材料的丰富资源，海藻因其在生物学和医学中的潜在用途而受到认可。甘草素已从马尾藻中分离和鉴定。为了寻找新的抗阿尔茨海默病活性，我们设计并合成了 32种 7-异戊二烯氧基-2,3-二氢黄烷酮衍生物 ( 3a-3p ) 和 5-羟基-7-异戊二烯氧基-2,3-二氢黄烷酮衍生物 ( 4a- 4p）作为基于甘草素作为先导化合物的胆碱酯酶抑制剂。对乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BuChE) 的抑制筛选表明，所有合成的化合物在体外均具有有效的 AChE 抑制活性，但对 BuChE 的抑制活性减弱至较弱. 动力学研究表明，化合物 4o 通过双重结合位点能力抑制 AChE。此外，所有化合物均显示出自由基清除作用。最后，4o在AChE活性位点的分子对接模拟与所得药理结果吻合较好。

  DOI：

  10.1016/j.bmcl.2021.128306
• 作为产物：
  描述：

  (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-prop-2-en-1-one 在 氢碘酸 作用下， 以 溶剂黄146 为溶剂， 以71%的产率得到naringenin
  参考文献：
  名称：

  Efficient One‐Pot Synthesis of Hydroxyflavanones by Cyclization andO‐Demethylation of Methoxychalcones

  摘要：

  An efficient one-pot method for the synthesis of hydroxyflavanones is described. Methoxychalcones are treated with 36% HBr to afford cyclization and regioselective O-demethylation products (2a-i) while cyclization and complete O-demethylation products (3a-e) are obtained in the presence of 45% HI.

  DOI：

  10.1080/00397910801991465

文献信息

• Synthesis and Antidiabetic Activity of 5,7-Dihydroxyflavonoids and Analogs
  作者：Liu-Shuan Chang、Chun-Bao Li、Nan Qin、Mei-Na Jin、Hong-Quan Duan

  DOI：10.1002/cbdv.201100049

  日期：2012.1

  essential for the antidiabetic activity of flavonoids, we synthesized two series of flavonoids, 5,7‐dihydroxyflavanones and 5,7‐dihydroxyflavones. In a screening for potential antidiabetic activity, most of the flavonoids showed a remarkable in vitro activity, and compounds 1f, 2d, and 3c were significantly more effective than the positive control, metformin. The biological activity was mainly affected

  在一项评估黄酮类化合物抗糖尿病活性所必需的结构元素的研究中，我们合成了两个系列的黄酮类化合物，5,7-二羟基黄烷酮和 5,7-二羟基黄酮。在筛选潜在的抗糖尿病活性时，大多数黄酮类化合物显示出显着的体外活性，化合物 1f、2d 和 3c 明显比阳性对照二甲双胍更有效。生物活性主要受黄酮骨架环B部分结构修饰的影响。结果表明，5,7-二羟基黄酮类化合物可被认为是开发新的抗糖尿病先导化合物的有希望的候选物。
• Zhao, Dong-Hai; Sui, Xin; Qu, You-Le, Asian Journal of Chemistry, 2011, vol. 23, # 3, p. 1129 - 1132
  作者：Zhao, Dong-Hai、Sui, Xin、Qu, You-Le、Yang, Li-Ye、Wang, Xian、Guan, Li-Ping

  DOI：——

  日期：——
• Compositions Comprising A Polypeptide Having Cellulolytic Enhancing Activity And A Bicyclic Compound And Uses Thereof
  申请人：Quinlan Jason

  公开号：US20130217077A1

  公开（公告）日：2013-08-22

  The present invention relates to compositions comprising: a polypeptide having cellulolytic enhancing activity and a bicyclic compound. The present invention also relates to methods of using the compositions.
• METHODS FOR INHIBITING MUSCLE ATROPHY
  申请人：Adams Christopher M.

  公开号：US20140228333A1

  公开（公告）日：2014-08-14

  In one aspect, the invention relates to methods for treating muscle atrophy by providing to an animal in need thereof an effective amount of a compound. The compound can modulate the expression levels of multiple mRNA of a muscle atrophy signature. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
• HTS Assay for Identifying Small Molecule Inhibitors of RAD52 and Uses of Identified Small Molecule Inhibitors for Treatment and Prevention of BRCA-Deficient Malignancies
  申请人：University of Iowa Research Foundation

  公开号：US20180209956A1

  公开（公告）日：2018-07-26

  Disclosed are methods, compositions, kits, and systems for identifying small-molecule drugs for treating cancer in a subject. The disclosed methods, compositions, kits, and systems may be utilized to identify small-molecule inhibitors of radiation sensitive protein 52 (RAD52) in order to treat cancer in a subject, such as breast cancer in a subject having a BRCA1-deficient, BRCA2-deficient, and/or PALB2-deficient phenotype by administering the identified small-molecule inhibitors to the subject.