6-(4-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)-1H-pyridin-2-one | 1198088-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(4-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)-1H-pyridin-2-one
• 英文别名: 4-(1,3-benzodioxol-5-yl)-6-(4-methoxyphenyl)-1H-pyridin-2-one
• CAS: 1198088-71-9
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: FTCBDFOYRHINOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  醋谷胺 、 (2E)-3-(2H-1,3-苯并二氧戊环-5-基)-1-(4-甲氧基苯基)丙-2-烯-1-酮 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以9%的产率得到6-(4-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)-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

文献信息

• [EN] 4, 6-DIPHENYLPYRID-2-0NES AGAINST CANCER<br/>[FR] 4,6-DIPHÉNYLPYRID-2-ONES CONTRE LE CANCER
  申请人：SPEAR THERAPEUTICS LTD DE MONT

  公开号：WO2009146910A1

  公开（公告）日：2009-12-10

  A compound for use in the treatment of proliferative disorders, such as cancer, having the following formula:z wherein: R1, R2 and R3 are independently H or lower alkyl; R4, R5, R6, R7 and R8 are independently H, halo, lower alkyl or -O-lower alkyl, provided that at least one is -O-lower alkyl; or at least one pair of R4 to R8, the members of which pair are adjacent to one another on the ring, are conjoined to form-0-(CR14R15)n-O-, where n is 1 or 2 and R14 and R15 are independently H or lower alkyl, and the remainder of R4 to R8 are independently H, halo, lower alkyl or -O-lower alkyl; and R9, R10, R11, R12 and R13 are independently H, halo, lower alkyl or -O-lower alkyl, provided that at least one is -O-lower alkyl; or at least one pair of R9 to R13, the members of which pair are adjacent to one another on the ring, are conjoined to form-O-(CR16R17)m-O-, where m is 1 or 2 and R16 and R17 are independently H or lower alkyl, and the remainder of R9 to R13 are independently H, halo, lower alkyl or -O-lower alkyl.
• 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.