(E)-1-(2,4-Dimethoxyphenyl)-3-(4-propoxyphenyl) prop-2-en-1-one

• 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)-1-(2,4-Dimethoxyphenyl)-3-(4-propoxyphenyl) prop-2-en-1-one
• 英文别名: 1-(2,4-Dimethoxyphenyl)-3-(4-propoxyphenyl)prop-2-en-1-one
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: OLPFAFZFEDCCPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  醋谷胺 、 (E)-1-(2,4-Dimethoxyphenyl)-3-(4-propoxyphenyl) prop-2-en-1-one 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以32%的产率得到6-(2,4-dimethoxyphenyl)-4-(4-propoxyphenyl)-1H-pyridin-2-one
  参考文献：
  名称：

  The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells

  摘要：

  As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP) 1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6-60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing little toxicity towards a non-tumour breast cell line with no CYP expression. Metabolism studies provided evidence supporting the involvement of CYP1 enzymes in the bioactivation of these compounds.

  DOI：

  10.1016/j.bmcl.2019.03.030
• 作为产物：
  描述：

  2,4-二甲氧基苯乙酮 、 4-丙氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 (E)-1-(2,4-Dimethoxyphenyl)-3-(4-propoxyphenyl) prop-2-en-1-one
  参考文献：
  名称：

  The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells

  摘要：

  As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP) 1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6-60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing little toxicity towards a non-tumour breast cell line with no CYP expression. Metabolism studies provided evidence supporting the involvement of CYP1 enzymes in the bioactivation of these compounds.

  DOI：

  10.1016/j.bmcl.2019.03.030

文献信息

• 4-(c2-6alkoxy)-substituted chalcones as therapeutic agents
  申请人：——

  公开号：US20040259957A1

  公开（公告）日：2004-12-23

  The present invention pertains to compounds of the following formula: (1) wherein: R ALK is primary or secondary aliphatic saturated C 2-6 alkyl; each of R B2 , R B3 , R B4 , and R B5 is independently —H, —OH, or —OMe; each of R 1 and R 2 is independently: —H, optionally substituted C 1-4 alkyl, or optionally substituted C 5-20 aryl; R A3 is —H, —OH, —OC(═O)RE, —OS(═O) 2 OH, or —OP(═O)(OH) 2 ; R E is: —H, optionally substituted C 1-6 alkyl, optionally substituted C 3-20 heterocyclyl, or optionally substituted C 5-20 aryl; or a pharmaceutically acceptable salt, solvate, amide, ester, ether, chemically protected form, or prodrug thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, for both diagnosis and treatment of, for example, proliferative conditions, such as cancer, and inflammatory conditions. 1

  本发明涉及以下式的化合物：（1） 其中：RALK是一级或二级脂肪饱和C2-6烷基；RB2、RB3、RB4和RB5中的每一个独立地是—H、—OH或—OMe；R1和R2中的每一个独立地是：—H、可选地取代的C1-4烷基或可选地取代的C5-20芳基；RA3是—H、—OH、—OC(═O)RE、—OS(═O)2OH或—OP(═O)(OH)2；RE是：—H、可选地取代的C1-6烷基、可选地取代的C3-20杂环基或可选地取代的C5-20芳基；或其药学上可接受的盐、溶剂化物、酰胺、酯、醚、化学保护形式或前药。本发明还涉及包含这种化合物的制药组合物，以及这种化合物和组合物的使用，无论是体外还是体内，用于诊断和治疗增生性疾病，例如癌症和炎症性疾病。
• 4-(C2-6 ALKOXY)-SUBSTITUTED CHALCONES AS THERAPEUTIC AGENTS
  申请人：Spear Therapeutics Limited

  公开号：EP1432669B1

  公开（公告）日：2011-03-23
• US7112698B2
  申请人：——

  公开号：US7112698B2

  公开（公告）日：2006-09-26
• [EN] 4-C2-6ALKOXY-SUBSTITUTED CHALCONES AS THERAPEUTIC AGENTS<br/>[FR] CHALCONES SUBSTITUEES PAR 4-(C2-6ALCOXY) EN TANT QU'AGENTS THERAPEUTIQUES
  申请人：CANCER REC TECH LTD

  公开号：WO2003029176A1

  公开（公告）日：2003-04-10

  The present invention pertains to compounds of the following formula: (1) wherein: RALK is primary or secondary aliphatic saturated C2-6alkyl; each of RB2, RB3, RB4, and RB5 is independently -H, -OH, or -OMe; each of R1 and R2 is independently: -H, optionally substituted C1-4alkyl, or optionally substituted C5-20aryl; RA3 is -H, -OH, -OC(=O)RE, -OS(=O)2OH, or -OP(=O)(OH)2; RE is : -H, optionally substituted C1-6alkyl, optionally substituted C3-20heterocyclyl, or optionally substituted C5-20aryl; or a pharmaceutically acceptable salt, solvate, amide, ester, ether, chemically protected form, or prodrug thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, for both diagnosis and treatment of, for example, proliferative conditions, such as cancer, and inflammatory conditions.
• The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells
  作者：Ketan C. Ruparelia、Sabahat Lodhi、Dyan N. Ankrett、Nicola E. Wilsher、Randolph R.J. Arroo、Gerard A. Potter、Kenneth J.M. Beresford

  DOI：10.1016/j.bmcl.2019.03.030

  日期：2019.6

  As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP) 1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6-60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing little toxicity towards a non-tumour breast cell line with no CYP expression. Metabolism studies provided evidence supporting the involvement of CYP1 enzymes in the bioactivation of these compounds.