2-(3-氯苯基)-1-(4,6-二羟基苯基)乙酮 | 224426-61-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-(3-氯苯基)-1-(4,6-二羟基苯基)乙酮
• 英文名称: 2-(3-chlorophenyl)-1-(4,6-dihydroxyphenyl)ethanone
• 英文别名: Cambridge id 6362821；2-(3-chlorophenyl)-1-(2,4-dihydroxyphenyl)ethanone
• CAS: 224426-61-3
• 化学式: C₁₄H₁₁ClO₃
• 分子量: 262.693
• InChiKey: QFAYWVDOEJIKSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-氯苯基)-1-(4,6-二羟基苯基)乙酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  新型脱氧安息香衍生物的设计，合成及免疫抑制活性

  摘要：

  在寻找具有高功效和低毒性的潜在免疫抑制剂时，合成了一系列新的脱氧安息香素，并对其细胞毒性和免疫抑制活性进行了评估。中合成的化合物，四克脱氧安息香肟（化合物31，32，37，和38）表现出较低的毒性和更高的抑制活性比对其他化合物的抗CD3 /抗CD28共刺激的T细胞增殖。更重要的是，化合物31的细胞毒性比环孢菌素A（CsA）低100倍以上，而且效力更高（31：SI> 684.64，CsA：SI = 235.44）。化合物31的初步抑制机理还通过流式细胞术鉴定了这种化合物，该化合物通过以剂量依赖的方式诱导活化的淋巴结细胞凋亡来发挥免疫抑制活性。另外，通过蛋白质印迹分析检测凋亡的机制。

  DOI：

  10.1002/cmdc.201000107
• 作为产物：
  描述：

  (3-氯苯基)乙酰氯 、 间苯二酚 在 四氯化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以40%的产率得到2-(3-氯苯基)-1-(4,6-二羟基苯基)乙酮
  参考文献：
  名称：

  Use of a Pharmacophore Model for the Design of EGFR Tyrosine Kinase Inhibitors:  Isoflavones and 3-Phenyl-4(1H)-quinolones

  摘要：

  Using a pharmacophore model for ATP-competitive inhibitors interacting with the active site of the EGFR protein tyrosine kinase together with published X-ray crystal data of quercetin (2) in complex with the lick tyrosine kinase and of deschloroflavopiridol (3b) in complex with CDK2, a putative binding mode of the isoflavone genistein (1) was proposed. Then, based on literature data suggesting that a salicylic acid function, which is represented by the 5-hydroxy-4-keto motif in I, could serve as a pharmacophore replacement of a pyrimidine ring, superposition of 1 onto the potent EGFR tyrosine kinase inhibitor 4-(3'-chlorophenylamino)-6,7-dimethoxyquinazoline (4) led to 3'-chloro-5,7-clibydroxyisoflavone (fi) as a target structure which in fact was 10 times more potent than 1. The putative binding mode of 6 suggests a sulfur-aromatic interaction of the m-chlorophenyl moiety with Cys 773 in the "sugar pocket" of the EGFR kinase model. Replacement of the oxygen in the chromenone ring of 6 by a nitrogen atom further improved the inhibitory activity against the EGFR kinase. With IC50 values of 38 and 8 nM, respectively, the quinolones 11 and 12 were the most potent compounds of the series. N-Alkylation of II did not further improve enzyme inhibitory activity but; led to derivatives with cellular activity in the lower micromolar range.

  DOI：

  10.1021/jm980551o

文献信息

• A convenient one-pot synthesis of 7-hydroxy-isoflavones from resorcinol with substituted phenylacetic acids
  作者：Himanshu Singh、Ram Pratap

  DOI：10.1016/j.tetlet.2006.09.034

  日期：2006.11

  7-hydroxy-isoflavones is reported. The acylation of resorcinol with various phenyl acetic acids in molten zinc chloride affords an intermediate deoxybenzoin which without isolation is subjected to cyclization with N,N-dimethylformamide in the presence of boron trifluoride diethyl etherate and methanesulfonyl chloride to afford the 7-hydroxy-isoflavone without the formation of any by-product.

  据报道，温和高效的一锅合成7-羟基异黄酮。在熔融氯化锌中将间苯二酚与各种苯基乙酸酰化，得到中间体脱氧安息香，将其不分离地在三氟化硼二乙基醚化物和甲磺酰氯的存在下，用N，N-二甲基甲酰胺环化，得到7-羟基异黄酮，而无需任何副产物的形成。
• Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
  作者：Jianzhuang Miao、Huaqing Cui、Jing Jin、Fangfang Lai、Hui Wen、Xiang Zhang、Gian Filippo Ruda、Xiaoguang Chen、Dali Yin

  DOI：10.1039/c4cc06762b

  日期：——

  A new class of fluorophores 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) is developed and is suitable as reagents for biological imaging.

  一种新型荧光物质3-烷基-6-甲氧基-7-羟基-香豆素（AMHCs）已开发，并适用于生物成像试剂。
• Use of a Pharmacophore Model for the Design of EGFR Tyrosine Kinase Inhibitors:  Isoflavones and 3-Phenyl-4(1<i>H</i>)-quinolones
  作者：Peter Traxler、Jennifer Green、Helmut Mett、Urs Séquin、Pascal Furet

  DOI：10.1021/jm980551o

  日期：1999.3.1

  Using a pharmacophore model for ATP-competitive inhibitors interacting with the active site of the EGFR protein tyrosine kinase together with published X-ray crystal data of quercetin (2) in complex with the lick tyrosine kinase and of deschloroflavopiridol (3b) in complex with CDK2, a putative binding mode of the isoflavone genistein (1) was proposed. Then, based on literature data suggesting that a salicylic acid function, which is represented by the 5-hydroxy-4-keto motif in I, could serve as a pharmacophore replacement of a pyrimidine ring, superposition of 1 onto the potent EGFR tyrosine kinase inhibitor 4-(3'-chlorophenylamino)-6,7-dimethoxyquinazoline (4) led to 3'-chloro-5,7-clibydroxyisoflavone (fi) as a target structure which in fact was 10 times more potent than 1. The putative binding mode of 6 suggests a sulfur-aromatic interaction of the m-chlorophenyl moiety with Cys 773 in the "sugar pocket" of the EGFR kinase model. Replacement of the oxygen in the chromenone ring of 6 by a nitrogen atom further improved the inhibitory activity against the EGFR kinase. With IC50 values of 38 and 8 nM, respectively, the quinolones 11 and 12 were the most potent compounds of the series. N-Alkylation of II did not further improve enzyme inhibitory activity but; led to derivatives with cellular activity in the lower micromolar range.
• Design, Synthesis, and Immunosuppressive Activity of New Deoxybenzoin Derivatives
  作者：Huan-Qiu Li、Yin Luo、Ran Song、Zi-Lin Li、Tao Yan、Hai-Liang Zhu

  DOI：10.1002/cmdc.201000107

  日期：——

  In the search for potential immunosuppressive agents with high efficacy and low toxicity, a series of new deoxybenzoins were synthesized and evaluated for their cytotoxicity and immunosuppressive activity. Among the synthesized compounds, four deoxybenzoin oximes (compounds 31, 32, 37, and 38) exhibited lower cytotoxicity and higher inhibitory activity toward anti‐CD3/anti‐CD28 co‐stimulated T‐cell

  在寻找具有高功效和低毒性的潜在免疫抑制剂时，合成了一系列新的脱氧安息香素，并对其细胞毒性和免疫抑制活性进行了评估。中合成的化合物，四克脱氧安息香肟（化合物31，32，37，和38）表现出较低的毒性和更高的抑制活性比对其他化合物的抗CD3 /抗CD28共刺激的T细胞增殖。更重要的是，化合物31的细胞毒性比环孢菌素A（CsA）低100倍以上，而且效力更高（31：SI> 684.64，CsA：SI = 235.44）。化合物31的初步抑制机理还通过流式细胞术鉴定了这种化合物，该化合物通过以剂量依赖的方式诱导活化的淋巴结细胞凋亡来发挥免疫抑制活性。另外，通过蛋白质印迹分析检测凋亡的机制。