3-(3-chlorophenyl)-7-hydroxy-4H-chromen-4-one | 224426-56-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-(3-chlorophenyl)-7-hydroxy-4H-chromen-4-one
• 英文别名: 3-(3-chlorophenyl)-7-hydroxychromen-4-one
• CAS: 224426-56-6
• 化学式: C₁₅H₉ClO₃
• 分子量: 272.688
• InChiKey: RQYVHBZWMYJJAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  243.5-246.5 °C
• 沸点：
  483.5±45.0 °C(Predicted)
• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-chlorophenyl)-7-hydroxy-4H-chromen-4-one 在 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 3-(3-chlorophenyl)-7-[4-(piperazin-1-yl)butoxy]-4H-1-benzopyran-4-one bis[hydrochloride]
  参考文献：
  名称：

  Novel Basic Isoflavones as Inhibitors of Bone Resorption

  摘要：

  A number of aminoalkoxy analogues of ipriflavone (=7-(1-methylethoxy)isoflavone) were prepared and examined for their capacity to inhibit bone resorption induced by bovine parathyroid hormone fragment 1 - 34. Good-to-high activities were found for 7-(aminoalkoxy)isoflavone. analogues. Their activity was influenced by a number of structural features, among which the length of the basic side chain, the basicity of the amino group, and the nature and position of substituents on the 3-phenyl ring. 4'-(Aminoalkoxy)ipriflavone derivatives were less active.

  DOI：

  10.1002/1522-2675(20010815)84:8<2417::aid-hlca2417>3.0.co;2-n
• 作为产物：
  描述：

  (3-氯苯基)乙酰氯 在 三氟化硼乙醚 、 四氯化锡 、 甲基磺酰氯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 3-(3-chlorophenyl)-7-hydroxy-4H-chromen-4-one
  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。
• Novel Basic Isoflavones as Inhibitors of Bone Resorption
  作者：Maurizio Delcanale、Gabriele Amari、Elisabetta Armani、Milco Lipreri、Maurizio Civelli、Elisabetta Galbiati、Massimo Giossi、Paola Lorenza Caruso、Patrizia Crivori、Pierre-Alain Carrupt、Bernard Testa

  DOI：10.1002/1522-2675(20010815)84:8<2417::aid-hlca2417>3.0.co;2-n

  日期：2001.8.15

  A number of aminoalkoxy analogues of ipriflavone (=7-(1-methylethoxy)isoflavone) were prepared and examined for their capacity to inhibit bone resorption induced by bovine parathyroid hormone fragment 1 - 34. Good-to-high activities were found for 7-(aminoalkoxy)isoflavone. analogues. Their activity was influenced by a number of structural features, among which the length of the basic side chain, the basicity of the amino group, and the nature and position of substituents on the 3-phenyl ring. 4'-(Aminoalkoxy)ipriflavone derivatives were less active.
• 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.