3,5-bis(3,4,5-trimethoxybenzylidene)piperidin-4-one | 939318-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(3,4,5-trimethoxybenzylidene)piperidin-4-one
• 英文别名: 3,5-Bis[(3,4,5-trimethoxyphenyl)methylidene]piperidin-4-one；3,5-bis[(3,4,5-trimethoxyphenyl)methylidene]piperidin-4-one
• CAS: 939318-25-9
• 化学式: C₂₅H₂₉NO₇
• mdl: MFCD08560181
• 分子量: 455.508
• InChiKey: JBISTWVGSGOQGK-UHFFFAOYSA-N

物化性质

• 熔点：
  251 °C
• 沸点：
  657.2±55.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  草酰氯 、 3,5-bis(3,4,5-trimethoxybenzylidene)piperidin-4-one 在 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 以57%的产率得到1,2-bis[3,5-bis(3,4,5-trimethoxybenzylidene)-4-oxo-piperidin-1-yl]ethane-1,2-dione
  参考文献：
  名称：

  Novel 3,5-bis(arylidene)-4-piperidone dimers: Potent cytotoxins against colon cancer cells

  摘要：

  Two novel series of dimeric 3,5-bis(arylidene)-4-piperidones 7 and 8 were prepared as cytotoxic agents. A specific objective of this study was the discovery of novel compounds displaying potent anti-proliferative activities against colon cancers. Most of the compounds demonstrate potent cytotoxicity against HCT116 and HT29 colon cancer cell lines in which the IC50 values range from low micromolar to nanomolar values. In general, the majority of the compounds showed greater cytotoxicity and some degree of selectivity toward HCT116 cells compared to HT29 cells. Compound 9 in which the amidic carbonyl groups were excised was substantially less potent than 8a in both cell lines suggested that the amide groups are important components of the molecules for exhibiting cytotoxicity. Virtually all the compounds were more potent than a reference drug 5-fluorouracil which is used in treating colon cancers as well as a related enone curcumin. QSAR studies were undertaken and some guidelines for amplification of the project have been formulated. Flow cytometry analysis of a representative potent compound 7f revealed that it induces apoptosis in HCT116 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.055
• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 、 3,4,5-三甲氧基苯甲醛 在 盐酸 作用下， 以 氯仿 、 水 为溶剂， 反应 50.0h， 以91%的产率得到3,5-bis(3,4,5-trimethoxybenzylidene)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

文献信息

• <p>Effects of green synthesised silver nanoparticles (ST06-AgNPs) using curcumin derivative (ST06) on human cervical cancer cells (HeLa) in vitro and EAC tumor bearing mice models</p>
  作者：Kalaimathi Murugesan、Jinsha Koroth、Padma Priya Srinivasan、Amrita Singh、Sanjana Mukundan、Subhas S Karki、Bibha Choudhary、Chhitar M Gupta

  DOI：10.2147/ijn.s202404

  日期：——

  Background: In recent years, green synthesized silver nanoparticles have been increasingly investigated for their anti-cancer potential. In the present study, we aimed at the biosynthesis of silver nanoparticles (AgNPs) using a curcumin derivative, ST06. Although, the individual efficacies of silver nanoparticles or curcumin derivatives have been studied previously, the synergistic cytotoxic effects of curcumin derivative and silver nanoparticles in a single nanoparticulate formulation have not been studied earlier specifically on animal models. This makes this study novel compared to the earlier synthesized curcumin derivative or silver nanoparticles studies. The aim of the study was to synthesize ST06 coated silver nanoparticles (ST06-AgNPs) using ST06 as both reducing and coating agent.Methods: The synthesized nanoparticles AgNPs and ST06-AgNPs were characterised for the particle size distribution, morphology, optical properties and surface charge by using UV-visible spectroscopy, dynamic light scattering (DLS) and transmission electron microscopy (TEM). Elemental composition and structural properties were studied by energy dispersive X-ray spectroscopy (EDX) and X-ray diffraction spectroscopy (XRD). The presence of ST06 as capping agent was demonstrated by Fourier transform infrared spectroscopy (FTIR).Results: The synthesized nanoparticles (ST06-AgNPs) were spherical and had a size distribution in the range of 50-100 nm. UV-Vis spectroscopy displayed a specific silver plasmon peak at 410 nm. The in vitro cytotoxicity effects of ST06 and ST06-AgNPs, as assessed by MTT assay, showed significant growth inhibition of human cervical cancer cell line (HeLa). In addition, studies carried out in EAC tumor-induced mouse model (Ehrlich Ascites carcinoma) using ST06-AgNPs, revealed that treatment of the animals with these nanoparticles resulted in a significant reduction in the tumor growth, compared to the control group animals.Conclusion: In conclusion, green synthesized ST06-AgNPs exhibited superior anti-tumor efficacy than the free ST06 or AgNPs with no acute toxicity under both in vitro and in vivo conditions. The tumor suppression is associated with the intrinsic apoptotic pathway. Together, the results of this study suggest that ST06-AgNPs could be considered as a potential option for the treatment of solid tumors.
• Newly Designed and Synthesized Curcumin Analogs with<i>in vitro</i>Cytotoxicity and Tubulin Polymerization Activity
  作者：Iten M. Fawzy、Khairia M. Youssef、Nasser S. M. Ismail、Joachim Gullbo、Khaled A. M. Abouzid

  DOI：10.1111/cbdd.12464

  日期：2015.7

  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.
• Novel 3,5-bis(arylidene)-4-piperidone dimers: Potent cytotoxins against colon cancer cells
  作者：Swagatika Das、Umashankar Das、Deborah Michel、Dennis K.J. Gorecki、Jonathan R. Dimmock

  DOI：10.1016/j.ejmech.2013.03.055

  日期：2013.6

  Two novel series of dimeric 3,5-bis(arylidene)-4-piperidones 7 and 8 were prepared as cytotoxic agents. A specific objective of this study was the discovery of novel compounds displaying potent anti-proliferative activities against colon cancers. Most of the compounds demonstrate potent cytotoxicity against HCT116 and HT29 colon cancer cell lines in which the IC50 values range from low micromolar to nanomolar values. In general, the majority of the compounds showed greater cytotoxicity and some degree of selectivity toward HCT116 cells compared to HT29 cells. Compound 9 in which the amidic carbonyl groups were excised was substantially less potent than 8a in both cell lines suggested that the amide groups are important components of the molecules for exhibiting cytotoxicity. Virtually all the compounds were more potent than a reference drug 5-fluorouracil which is used in treating colon cancers as well as a related enone curcumin. QSAR studies were undertaken and some guidelines for amplification of the project have been formulated. Flow cytometry analysis of a representative potent compound 7f revealed that it induces apoptosis in HCT116 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.