1,5-bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadien-3-ylidenmalononitrile | 1246023-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,5-bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadien-3-ylidenmalononitrile
• 英文别名: 2-[1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-ylidene]propanedinitrile
• CAS: 1246023-94-8
• 化学式: C₂₂H₁₈N₂O₄
• 分子量: 374.396
• InChiKey: FEWPBIMTTNBKSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one 、 丙二腈 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以76%的产率得到1,5-bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadien-3-ylidenmalononitrile
  参考文献：
  名称：

  New antitumoral agents I: In vitro anticancer activity and in vivo acute toxicity of synthetic 1,5-bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadien-3-one and derivatives

  摘要：

  This paper describes a new method for the preparation of 1,5-bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadien-3-one 1 and its derivatives 2-5. This set of synthetic compounds exhibited high antitumoral activities regarding in vitro screening against several human tumor cell lines as lung carcinoma NCI-460, melanoma UACC-62, breast MCF-7, colon HT-29, renal 786-O, ovarian OVCAR-03 and ovarian expressing the resistance phenotype for adriamycin NCI-ADR/ RES, prostate PC-3, and leukemia K-562. Compounds were also tested against murine tumor cell line B16F10 melanoma and lymphocytic leukemia L1210 as well as to their effect toward normal macrophages. Specific activity against colon cancer cells HT-29 was observed for all tested compounds and suggests further studies with models of colon cancer. Compounds 1, 2, and 4 showed significant cytotoxic activity with IC(50) values <= 2.3 mu M for all human cancer cell lines. Intraperitoneal acute administration of compound 1 and 2 showed very low toxicity rate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.026