2-(benzo[d][1,3]dioxol-5-yl)-6-chloro-3-hydroxy-4H-chromen-4-one | 260063-86-3

• 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: 2-(benzo[d][1,3]dioxol-5-yl)-6-chloro-3-hydroxy-4H-chromen-4-one
• 英文别名: 2-(Benzo[1,3]dioxol-5-yl)-6-chloro-3-hydroxy-4H-chromen-4-one；2-(1,3-benzodioxol-5-yl)-6-chloro-3-hydroxychromen-4-one
• CAS: 260063-86-3
• 化学式: C₁₆H₉ClO₅
• 分子量: 316.697
• InChiKey: YCSHECRLWLRDMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(benzo[d][1,3]dioxol-5-yl)-6-chloro-3-hydroxy-4H-chromen-4-one 、 三溴化硼 、 甲醇 以 二氯甲烷 为溶剂， 反应 2.0h， 以to give 7 mg of the title compound in a yield of 72%的产率得到6-chloro-2-(3,4-dihydroxy-phenyl)-3-hydroxy-chromen-4-one
  参考文献：
  名称：

  CDK inhibitors having flavone structure

  摘要：

  本发明涉及一种新型黄酮衍生物，其药学上可接受的盐、水合物、溶剂化物和异构体，可用作抑制细胞周期素依赖性激酶(CDK)的抑制剂，其制备方法，以及包含该化合物作为活性成分的抗癌剂或治疗神经退行性疾病的药物组合物。

  公开号：

  US06500846B1
• 作为产物：
  描述：

  (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(5-chloro-2-hydroxyphenyl)prop-2-en-1-one 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以67%的产率得到2-(benzo[d][1,3]dioxol-5-yl)-6-chloro-3-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  SAR Studies and Biological Characterization of a Chromen-4-one Derivative as an Anti-Trypanosoma brucei Agent

  摘要：

  Chemical modulation of the flavonol 2-(benzo[d] [1,3]dioxo1-5-y1)-chromen-4-one (1), a promising anti-Trypanosomatid agent previously identified, was evaluated through a phenotypic screening approach. Herein, we have performed structure activity relationship studies around hit compound 1. The pivaloyl derivative (13) showed significant anti-T. brucei activity (EC50 = 1.1 1iM) together with a selectivity index higher than 92. The early in vitro ADME-tox properties (cytotoxicity, mitochondria] toxicity, cytochrome P450 and hERG inhibition) were determined for compound 1 and its derivatives, and these led to the identification of some liabilities. The 1,3-benzodioxole moiety in the presented compounds confers better in vivo pharmacokinetic properties than those of classical flavonols. Further studies using different delivery systems could lead to an increase of compound blood levels.

  DOI：

  10.1021/acsmedchemlett.8b00565

文献信息

• NOVEL CDK INHIBITORS HAVING FLAVONE STRUCTURE
  申请人：LG CHEMICAL LIMITED

  公开号：EP1109800A1

  公开（公告）日：2001-06-27
• US6500846B1
  申请人：——

  公开号：US6500846B1

  公开（公告）日：2002-12-31
• [EN] NOVEL CDK INHIBITORS HAVING FLAVONE STRUCTURE<br/>[FR] NOUVEAUX INHIBITEURS DE KINASE DEPENDANTE DES CYCLINES (CDK) PRESENTANT UNE STRUCTURE FLAVONE
  申请人：LG CHEMICAL LTD

  公开号：WO2000012496A1

  公开（公告）日：2000-03-09

  The present invention relates to a novel flavone derivative, pharmaceutically acceptable salt, hydrate, solvate and isomer thereof which is useful as an inhibitor against Cyclin Dependent Kinase (CDK), a process for preparation thereof, and a composition of anti-cancer agent or agent for treating neurodegenerative disease comprising this compound as an active ingredient.
• SAR Studies and Biological Characterization of a Chromen-4-one Derivative as an Anti-<i>Trypanosoma brucei</i> Agent
  作者：Chiara Borsari、Nuno Santarem、Sara Macedo、María Dolores Jiménez-Antón、Juan J. Torrado、Ana Isabel Olías-Molero、María J. Corral、Annalisa Tait、Stefania Ferrari、Luca Costantino、Rosaria Luciani、Glauco Ponterini、Sheraz Gul、Maria Kuzikov、Bernhard Ellinger、Birte Behrens、Jeanette Reinshagen、José María Alunda、Anabela Cordeiro-da-Silva、Maria Paola Costi

  DOI：10.1021/acsmedchemlett.8b00565

  日期：2019.4.11

  Chemical modulation of the flavonol 2-(benzo[d] [1,3]dioxo1-5-y1)-chromen-4-one (1), a promising anti-Trypanosomatid agent previously identified, was evaluated through a phenotypic screening approach. Herein, we have performed structure activity relationship studies around hit compound 1. The pivaloyl derivative (13) showed significant anti-T. brucei activity (EC50 = 1.1 1iM) together with a selectivity index higher than 92. The early in vitro ADME-tox properties (cytotoxicity, mitochondria] toxicity, cytochrome P450 and hERG inhibition) were determined for compound 1 and its derivatives, and these led to the identification of some liabilities. The 1,3-benzodioxole moiety in the presented compounds confers better in vivo pharmacokinetic properties than those of classical flavonols. Further studies using different delivery systems could lead to an increase of compound blood levels.
• CDK inhibitors having flavone structure
  申请人：LG Chemical, Ltd.

  公开号：US06500846B1

  公开（公告）日：2002-12-31

  The present invention relates to a novel flavone derivative, pharmaceutically acceptable salt, hydrate, solvate and isomer thereof which is useful as an inhibitor against Cyclin Dependent Kinase (CDK), a process for preparation thereof, and a composition of anti-cancer agent or agent for treating neurodegenerative disease comprising this compound as an active ingredient.

  本发明涉及一种新型黄酮衍生物，其药学上可接受的盐、水合物、溶剂化物和异构体，可用作抑制细胞周期素依赖性激酶(CDK)的抑制剂，其制备方法，以及包含该化合物作为活性成分的抗癌剂或治疗神经退行性疾病的药物组合物。