3,5-bis(4-fluorobenzylidene)piperidin-4-one hydrochloride | 1379669-18-7

• 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: 3,5-bis(4-fluorobenzylidene)piperidin-4-one hydrochloride
• 英文别名: 3,5-bis(4-fluorobenzylidene)-4-piperidone hydrochloride；3,5-bis[(4-fluorophenyl)methylidene]piperidin-4-one;hydrochloride
• CAS: 1379669-18-7
• 化学式: C₁₉H₁₅F₂NO*ClH
• 分子量: 347.792
• InChiKey: PUZKKRJRMQXSCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 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：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,5-bis(4-fluorobenzylidene)piperidin-4-one hydrochloride 在 potassium carbonate 作用下， 以1.4 g的产率得到H-4073
  参考文献：
  名称：

  CLEFMA—An anti-proliferative curcuminoid from structure–activity relationship studies on 3,5-bis(benzylidene)-4-piperidones

  摘要：

  3,5-Bis(benzylidene)-4-piperidones are being advanced as synthetic analogs of curcumin for anti-cancer and anti-inflammatory properties. We performed structure-activity relationship studies, by testing several synthesized 3,5-bis(benzylidene)-4-piperidones for anti-proliferative activity in lung adenocarcinoma H441 cells. Compared to the lead compound 1, or 3,5-bis(2-fluorobenzylidene)-4-piperidone, five compounds were found to be more potent (IC50 <30 mu M), and 16 compounds possessed reduced cell-killing efficacy (IC50 >50 mu M). Based on the observations, we synthesized 4-[3,5-bis(2-chlorobenzyl-idene-4-oxo-piperidine-1-yl)-4-oxo-2-butenoic acid] (29 or CLEFMA) as a novel analog of 1. CLEFMA was evaluated for anti-proliferative activity in H441 cells, and was found to be several folds more potent than compound 1. We did not find apoptotic cell population in flow cytometry, and the absence of apoptosis was confirmed by the lack of caspase cleavage. The electron microscopy of H441cells indicated that CLEFMA and compound 1 induce autophagic cell death that was inhibited by specific autophagy inhibitor 3-methyladenine. The results suggest that the potent and novel curcuminoid, CLEFMA, offers an alternative mode of cell death in apoptosis-resistant cancers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.055
• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 、 对氟苯甲醛 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 4.67h， 生成 3,5-bis(4-fluorobenzylidene)piperidin-4-one hydrochloride
  参考文献：
  名称：

  Synthesis and antimicrobial activity of new 3,5-diarylidene-4-piperidone derivatives

  摘要：

  我们合成了三个系列的杂芳香族类似物（二十七个化合物），它们都带有 合成并评估了它们对六种微生物菌株的抗菌活性。 对六种微生物菌株的抗菌活性进行了评估。其中包括 3,5-二苄基-1-(3,5-二氯-2-羟基苯磺酰基)哌啶-4-酮 5e 对黑曲霉和烟曲霉显示出最佳的抗真菌活性。 和烟曲霉的抗真菌活性最好。合成化合物的结构阐释是根据各种光谱测定的 根据各种光谱方法确定了合成化合物的结构。

  DOI：

  10.2298/jsc151112043s