(3E,5E)-3,5-bis(4-bromobenzylidene)-4-piperidone hydrochloride | 1381948-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3E,5E)-3,5-bis(4-bromobenzylidene)-4-piperidone hydrochloride
• 英文别名: (3E,5E)-3,5-bis[(4-bromophenyl)methylidene]piperidin-4-one;hydrochloride
• CAS: 1381948-43-1
• 化学式: C₁₉H₁₅Br₂NO*ClH
• 分子量: 469.603
• InChiKey: CAGAJDOCSGTLLK-XETSTSIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 、 对溴苯甲醛 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (3E,5E)-3,5-bis(4-bromobenzylidene)-4-piperidone hydrochloride
  参考文献：
  名称：

  一种姜黄素衍生物及其制备方法和应用

  摘要：

  本发明提供了一种具有式I所示结构的姜黄素衍生物和其应用，属于药物合成技术领域，本发明提供的姜黄素衍生物对卵巢癌细胞株HO‑8910PM具有抑制作用，通过诱导细胞凋亡而杀死癌细胞，本发明提供的姜黄素衍生物(3E，5E)‑3,5‑双(4‑卤素‑苯亚甲基)哌啶‑4‑酮盐酸盐，生物利用率高，可将其用于制备抗卵巢癌的药物。本发明还提供了具有式I所示结构的姜黄素衍生物的制备方法，本发明提供的制备方法制备得到的姜黄素衍生物纯度可达99％以上。

  公开号：

  CN109734658A

文献信息

• Synthesis and evaluation of curcumin-related compounds for anticancer activity
  作者：Xingchuan Wei、Zhi-Yun Du、Xi Zheng、Xiao-Xing Cui、Allan H. Conney、Kun Zhang

  DOI：10.1016/j.ejmech.2012.04.005

  日期：2012.7

  Sixty-one curcumin-related compounds were synthesized and evaluated for their anticancer activity toward cultured prostate cancer PC-3 cells, pancreas cancer Panc-1 cells and colon cancer HT-29 cells. Inhibitory effects of these compounds on the growth of PC-3. Panc-1 and HT-29 cells were determined by the MTT assay. Compounds E10, F10, FN1 and FN2 exhibited exceptionally potent inhibitory effects on the growth of cultured PC-3, Panc-1 and HT-29 cells. The IC50 for these compounds was lower than 1 mu M in all three cell lines. E10 was 72-, 46- and 117-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. F10 was 69-, 34- and 72-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. FN1 and FN2 had about the same inhibitory effect as E10 and F10 toward Panc-1 cells but were less active than E10 and F10 toward PC-3 and HT-29 cells. The active compounds were potent stimulators of apoptosis. The present study indicates that E10, F10, FN1 and FN2 may have useful anticancer activity. (C) 2012 Elsevier Masson SAS. All rights reserved.