4-dimethylamino-2',5'-dihydroxychalcone | 571165-77-0

• 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-dimethylamino-2',5'-dihydroxychalcone
• 英文别名: 4'-dimethylamino-2,5-dihydroxychalcone；DMADHC；(2E)-1-(2,5-dihydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one；(E)-1-(2,5-dihydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one
• CAS: 571165-77-0
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: MHVFCVMAJIDJMY-WEVVVXLNSA-N

物化性质

• 熔点：
  147-149 °C
• 沸点：
  535.7±50.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-dimethylamino-2',5'-dihydroxychalcone 在 氢氧化钾 、 双氧水 、 sodium carbonate 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 4'-(dimethylamino)-2,6-(3,6,9-trioxoundecane-1,11-dioxy)-flavone
  参考文献：
  名称：

  黄酮衍生物与碱金属和碱土金属阳离子的络合光谱研究

  摘要：

  合成并表征了一种新型的含氟离子载体，其特征在于黄酮类半冠醚[4'-（二甲基氨基）-3,6-（四甘醇）黄酮]和黄酮套索状冠醚。与碱金属和碱土金属阳离子络合后的光物理变化是通过增强阳离子诱导的分子内电荷转移过程来解释的，这是由于结合的阳离子与黄酮的羰基之间的相互作用而引起的。准冠或准穴体的大小和形状以及结合的阳离子的电荷密度控制着光物理变化的幅度。根据不同阳离子与大环配体之间的稳定常数的确定，2+阳离子。

  DOI：

  10.1039/a904825a
• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 barium dihydroxide 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 4-dimethylamino-2',5'-dihydroxychalcone
  参考文献：
  名称：

  Cytotoxic 2′,5′-dihydroxychalcones with unexpected antiangiogenic activity

  摘要：

  A series of 2',5'-dihydroxychalcones were synthesized and evaluated for cytotoxicity against tumor cell lines and human umbilical venous endothelial cells (HUVEC). It was found that chalcones with electron-withdrawing substituents on the B ring exhibited potent cytotoxicity against a variety of tumor cell lines while compounds with electron-releasing groups ere less potent in general. Those compounds with B ring replaced by extended or heteroaromatic rings exhibited significant bioactivity. Several compounds were shown to have marked cytotoxic selectivity towards HUVECs. Especially, among the synthesized compounds. 2-chloro-2'.5'dihydroxychalcone (2-3) showed the highest selectivity index up to 66 in comparison to HCT 116 cells. This Compound also exhibited strong inhibitory effects on the HUVEC tube formation in an in vitro model. When administered into BDF1 mice bearing Lewis lung carcinoma cells at 50 mg kg(-1) day (-1), 2-3 was found to inhibit the growth of tumor mass by 60.5%. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01443-5

文献信息

• Synthesis, Biological Evaluation and In Silico Metabolic and Toxicity Prediction of Some Flavanone Derivatives
  作者：Narayana Subbiah Hari Narayana Moorthy、Rahul Jitendra Singh、Hemendra Pratap Singh、Sayan Dutta Gupta

  DOI：10.1248/cpb.54.1384

  日期：——

  flavone) possess various pharmacological activities and due to its xanthine-oxidase enzyme inhibitory effect it also has superoxide-scavenging activities. A series of 2-phenyl-2,3-dihydrochromon-4-one derivatives (flavanone derivatives) were synthesized from chalcones by cyclization method and their activities were evaluated against some gram positive and gram-negative bacteria. IR, NMR and CHN analysis

  黄酮化学上是花青素，以游离态或与单宁有关的糖苷（类黄酮）存在。类黄酮（黄酮的衍生物）具有多种药理活性，并且由于其具有黄嘌呤氧化酶抑制作用，因此还具有超氧化物清除活性。通过环化法从查耳酮合成了一系列的2-苯基-2,3-二氢色子-4-酮衍生物（黄酮衍生物），并评估了它们对某些革兰氏阳性和革兰氏阴性细菌的活性。IR，NMR和CHN分析证实了合成化合物的结构。抗菌研究的结果表明，化合物2b，2e，2f和2h具有对抗许多细菌菌株的活性。其中，化合物（2h）对所有菌株viz具有显着的活性。对金黄色葡萄球菌，S。sonnei，大肠杆菌，鼠伤寒沙门氏菌和霍乱弧菌的抑制浓度为25微克/毫升。化合物2f对大肠杆菌和鼠伤寒沙门氏菌的最低抑菌浓度为200微克/毫升，对S. sonnei，痢疾链球菌和霍乱弧菌的最小抑菌浓度为25微克/毫升。在计算机上对合成的化合物进行代谢和毒性研究，预测结果表明具有羟基官能团的化合
• A Novel Optochemical Sensor for Fe³⁺by an Intramolecular Charge-transfer Fluorescence Probe: 4-Dimethylamino-2′,5′-dihydroxychalcone
  作者：Wenyan Wang、Yanli Wei、Shaomin Shuang、Chuan Dong

  DOI：10.1246/cl.2009.348

  日期：2009.4.5

  4-Dimethylamino-2′,5′-dihydroxychalcone (DMADHC), a typical compound that exhibits excited-state intramolecular charge-transfer (ICT) characteristics and possesses good photophysical properties, is synthesized and used as fluoroionophore for a Fe3+ sensitive optochemical sensor. The sensor shows a linear response toward Fe3+ in the concentration range of 3.984×10−7–1.135×10−5 M with a limit of detection of 8.223×10−9 M. It exhibits excellent selectivity for Fe3+ over a large number of cations such as alkali, alkaline earth, and transitional-metal ions.

  4-Dimethylamino-2′,5′-dihydroxychalcone (DMADHC) 是一种典型的化合物，具有激发态分子内电荷转移（ICT）特性和良好的光物理性质。该传感器在 3.984×10-7-1.135×10-5 M 的浓度范围内对 Fe3+ 呈线性响应，检测限为 8.223×10-9 M。
• Cytotoxic 2′,5′-dihydroxychalcones with unexpected antiangiogenic activity
  作者：Nguyen-Hai Nam、Yong Kim、Young-Jae You、Dong-Ho Hong、Hwan-Mook Kim、Byung-Zun Ahn

  DOI：10.1016/s0223-5234(02)01443-5

  日期：2003.2

  A series of 2',5'-dihydroxychalcones were synthesized and evaluated for cytotoxicity against tumor cell lines and human umbilical venous endothelial cells (HUVEC). It was found that chalcones with electron-withdrawing substituents on the B ring exhibited potent cytotoxicity against a variety of tumor cell lines while compounds with electron-releasing groups ere less potent in general. Those compounds with B ring replaced by extended or heteroaromatic rings exhibited significant bioactivity. Several compounds were shown to have marked cytotoxic selectivity towards HUVECs. Especially, among the synthesized compounds. 2-chloro-2'.5'dihydroxychalcone (2-3) showed the highest selectivity index up to 66 in comparison to HCT 116 cells. This Compound also exhibited strong inhibitory effects on the HUVEC tube formation in an in vitro model. When administered into BDF1 mice bearing Lewis lung carcinoma cells at 50 mg kg(-1) day (-1), 2-3 was found to inhibit the growth of tumor mass by 60.5%. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• The complexation of flavone derivatives with alkali and alkaline earth metal cations studied by spectroscopic methods
  作者：Huaping Li、Hongzhi Xie、Penfei Wang、Shikang Wu

  DOI：10.1039/a904825a

  日期：——

  A new kind of fluoroionophore, typified by flavone quasi-crown ether [4′-(dimethylamino)-3,6-(tetraethylene glycol)flavone] and flavone lariat-crown ether, were synthesized and characterized. The photophysical changes upon complexation with alkali and alkaline earth metal cations are explained in terms of the enhancement of a cation-induced intramolecular charge transfer process, which results from

  合成并表征了一种新型的含氟离子载体，其特征在于黄酮类半冠醚[4'-（二甲基氨基）-3,6-（四甘醇）黄酮]和黄酮套索状冠醚。与碱金属和碱土金属阳离子络合后的光物理变化是通过增强阳离子诱导的分子内电荷转移过程来解释的，这是由于结合的阳离子与黄酮的羰基之间的相互作用而引起的。准冠或准穴体的大小和形状以及结合的阳离子的电荷密度控制着光物理变化的幅度。根据不同阳离子与大环配体之间的稳定常数的确定，2+阳离子。