4-amino-2'-hydroxychalcone | 52923-37-2

• 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: 4-amino-2'-hydroxychalcone
• 英文别名: (2E)-3-(4-Aminophenyl)-1-(2-hydroxyphenyl)-2-propen-1-one；(E)-3-(4-aminophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 52923-37-2
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: HUYUKZWGCULPQF-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 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：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-amino-2'-hydroxychalcone 在 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 4'-Aminoflavone
  参考文献：
  名称：

  Ultrasound mediated nano ZnO catalyzed synthesis of new α -aminophosphonates as potential anti-diabetic agents; an in silico ADMET, molecular docking study, α -amylase and α -glucosidase inhibitory activity

  摘要：

  DOI：

  10.1080/00397911.2023.2269583
• 作为产物：
  描述：

  (E)-N-(4-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)phenyl)acetamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-amino-2'-hydroxychalcone
  参考文献：
  名称：

  Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure–activity relationships

  摘要：

  A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-positive), and human colon adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells. Fourteen out of 53 analyzed compounds resulted very active against at least two of the studied tumoral cells. Alkaline single cell gel electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compounds on normal cells. Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A structure-activity relationship analysis of these compounds was performed and for 4- and 3,4-disubstituted derivatives a quantitative correlation was obtained in the case of anti-HT-29 activity. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2007.03.031

文献信息

• Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers
  作者：Mauricio Cabrera、María Laura Lavaggi、Fiorela Croce、Laura Celano、Leonor Thomson、Marcelo Fernández、Cristina Pintos、Stella Raymondo、Mariela Bollati、Antonio Monge、Adela López de Ceráin、Oscar E. Piro、Hugo Cerecetto、Mercedes González

  DOI：10.1016/j.bmc.2010.05.033

  日期：2010.7

  Cancer preventive agents (CPA) are drugs able to suppress the carcinogen metabolic activation or block the formation of ultimate carcinogens. CPA could act through various molecular mechanisms, for example by interfering with the action of procarcinogen. This could be attained by increasing the phase II enzymes levels of quinone reductase (QR) and glutathione S-transferase (GST). New flavonoids, especially chalcones, have been identified as in vivo monofunctional phase II enzymes inducers. Oral administration of chalcone, 4, and both p-methoxy-substituted chalcones, 6 and 14, increased hepatic QR activity with concomitant decrease in CYP1A1 activity, a member of the most important group of phase I enzymes cytochrome P450. Among them, 4 also increased GST activity. While p-bromo-substituted chalcone 8 was the best inducer of QR it decreased hepatic GST expression and cytochrome P450, being the most effective decreasing cytochrome P450-expression. Thienyl-chalcone 20 being the bioisostere of chalcone 4 did not display the same in vivo profile in the phase I level modification. As chalcone 4 its bioisostere, chalcone 20, displayed low DNA strand breakage and absence of mutagenicity. Also, in our preliminary in vivo tumourigenesis/chemopreventive and acute-toxicity studies, chalcones 4, 6 and 8 showed the best behaviours as CPA justifying additional studies that are ongoing. (C) 2010 Elsevier Ltd. All rights reserved.
• Reductive Coupling Reactions of 2-Nitrochalcones and their β-Hydroxy-analogues: New Syntheses of 2-Arylquinoline and 2-Aryl-4-hydroxyquinoline Derivatives
  作者：Ana I. R. N. A. Barros、André F. R. Dias、Artur M. S. Silva

  DOI：10.1007/s00706-007-0647-9

  日期：2007.6

  A one-pot synthesis of novel 2-arylquinolines and 2-aryl-4-hydroxyquinolines was developed from the intramolecular reductive coupling reactions of 2-nitrochalcones and 3-hydroxy-1-phenyl-3-(2-nitrophenyl)-2-propen-1-ones. Depending on the reduction method and on the presence of electron donating substituents on the A ring of 2-nitrochalcones one can modulate the formation of 2-arylquinolines, their N-oxides, and of 2-aminochalcones. The reduction of 3-hydroxy-1-(2-hydroxyphenyl)-3-(2-nitrophenyl)-2-propen-1-ones with stannous chloride in hydrochloric acid gave 2 '-aminoflavones and with ammonium formate and Pd/C yielded 2-(2-hydroxyaryl)-4-hydroxyquinolines.