(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(5-chloro-2-hydroxyphenyl)prop-2-en-1-one | 28328-71-4

• 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: (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(5-chloro-2-hydroxyphenyl)prop-2-en-1-one
• 英文别名: 5'-Chlor-2'-hydroxy-3,4-methylendioxychalkon；5'-chloro-2'-hydroxy-3,4-methylenedioxy-trans-chalcone；5'-Chlor-2'-hydroxy-3,4-methylendioxy-trans-chalkon；3-(Benzo[1,3]dioxol-5-yl)-1-(5-chloro-2-hydroxyphenyl)-2-propen-1-one；(E)-3-(1,3-benzodioxol-5-yl)-1-(5-chloro-2-hydroxyphenyl)prop-2-en-1-one
• CAS: 28328-71-4
• 化学式: C₁₆H₁₁ClO₄
• 分子量: 302.714
• InChiKey: YPGXNIHFYIFXQL-DAFODLJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-羟基-5-氯苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以80%的产率得到(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(5-chloro-2-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  CDK inhibitors having flavone structure

  摘要：

  本发明涉及一种新的黄酮衍生物，其药用可接受的盐、水合物、溶剂合物和异构体，可用作对 Cyclin Dependent Kinase (CDK) 的抑制剂，以及其制备方法和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

文献信息

• Discovery of 2′-hydroxychalcones as autophagy inducer in A549 lung cancer cells
  作者：Fang-Wu Wang、Sheng-Qing Wang、Bao-Xiang Zhao、Jun-Ying Miao

  DOI：10.1039/c3ob42429d

  日期：——

  A series of 2′-hydroxychalcone derivatives was synthesized and the effects of all the compounds on growth of A549 lung cancer cell were investigated.

  合成了一系列2'-羟基茚酮衍生物，并研究了所有化合物对A549肺癌细胞生长的影响。
• New Compounds. Some New Chalcones
  作者：Charles K. Bradsher、Frances C. Brown、Willis B. Blue

  DOI：10.1021/ja01178a600

  日期：1949.10
• Ozawa et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 1178,1182
  作者：Ozawa et al.

  DOI：——

  日期：——
• US6500846B1
  申请人：——

  公开号：US6500846B1

  公开（公告）日：2002-12-31
• 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.