3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one | 405313-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one
• 英文别名: 3,5-Bis[(3,4-dihydroxyphenyl)methylidene]piperidin-4-one
• CAS: 405313-50-0
• 化学式: C₁₉H₁₇NO₅
• 分子量: 339.348
• InChiKey: XXLSPXONMWOWKM-UHFFFAOYSA-N

物化性质

• 沸点：
  693.1±55.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 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：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one 、 苯甲酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以56.15%的产率得到3,5-bis(3,4-dihydroxybenzylidene)-N-benzoylpiperidin-4-one
  参考文献：
  名称：

  Newly Designed and Synthesized Curcumin Analogs within vitroCytotoxicity and Tubulin Polymerization Activity

  摘要：

  Novel curcumin analogs with 4‐piperidone ring were designed, synthesized, and evaluated for their cytotoxic activities against five different cancer cell lines. 3,5‐bis(4‐Hydroxy‐3‐methoxybenzylidene)‐4‐oxo‐N‐phenylpiperidine‐1‐carbothioamide (XIIe) exhibited considerable cytotoxic activity with IC50 values in 1–2.5 μm range. In silico and in vitro, studies were also performed to predict the binding affinity of the target compounds to the β‐chain of tubulin receptor (PDB code 1SA1) and their abilities to affect microtubules polymerization cycle. 3,5‐bis(3‐Iodo‐5‐methoxy‐4‐propoxybenzylidene)‐N‐acetylpiperidin‐4‐one (VIIa) was found to exert 93.3% inhibition of tubulin and destabilization of microtubules in vitro compared to vincristine while, 3,5‐bis(3,4,5‐trimethoxybenzylidene)‐N‐benzoylpiperidin‐4‐one (XIIc) showed high potency in a different way where it exerted 94.8% stabilization of microtubules in vitro compared to positive control paclitaxel.

  DOI：

  10.1111/cbdd.12464
• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 、 3,4-二羟基苯甲醛 在 盐酸 作用下， 以 氯仿 、 水 为溶剂， 反应 50.0h， 以65%的产率得到3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one
  参考文献：
  名称：

  Newly Designed and Synthesized Curcumin Analogs within vitroCytotoxicity and Tubulin Polymerization Activity

  摘要：

  Novel curcumin analogs with 4‐piperidone ring were designed, synthesized, and evaluated for their cytotoxic activities against five different cancer cell lines. 3,5‐bis(4‐Hydroxy‐3‐methoxybenzylidene)‐4‐oxo‐N‐phenylpiperidine‐1‐carbothioamide (XIIe) exhibited considerable cytotoxic activity with IC50 values in 1–2.5 μm range. In silico and in vitro, studies were also performed to predict the binding affinity of the target compounds to the β‐chain of tubulin receptor (PDB code 1SA1) and their abilities to affect microtubules polymerization cycle. 3,5‐bis(3‐Iodo‐5‐methoxy‐4‐propoxybenzylidene)‐N‐acetylpiperidin‐4‐one (VIIa) was found to exert 93.3% inhibition of tubulin and destabilization of microtubules in vitro compared to vincristine while, 3,5‐bis(3,4,5‐trimethoxybenzylidene)‐N‐benzoylpiperidin‐4‐one (XIIc) showed high potency in a different way where it exerted 94.8% stabilization of microtubules in vitro compared to positive control paclitaxel.

  DOI：

  10.1111/cbdd.12464