3,5-bis((E)-3,4,5-trimethoxybenzylidene)-1-methylpiperidin-4-one | 1195795-93-7

• 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((E)-3,4,5-trimethoxybenzylidene)-1-methylpiperidin-4-one
• 英文别名: (3E,5E)-3,5-bis(3,4,5-trimethoxybenzylidene)-1-methylpiperidin-4-one；(3Ε,5Ε)-1-methyl-3,5-di(3,4,5-trimethoxybenzylidene)piperidin-4-one；1-methyl-3,5-bis((E)-3,4,5-trimethoxybenzylidene)piperidin-4-one；(3E,5E)-1-methyl-3,5-bis[(3,4,5-trimethoxyphenyl)methylidene]piperidin-4-one
• CAS: 1195795-93-7
• 化学式: C₂₆H₃₁NO₇
• 分子量: 469.535
• InChiKey: OGEWTDITEXRGCF-GCBPPVMSSA-N

物化性质

• 熔点：
  151-152 °C(Solv: ethanol (64-17-5))
• 沸点：
  644.0±55.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-bis((E)-3,4,5-trimethoxybenzylidene)-1-methylpiperidin-4-one 在 四氯苯醌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 (E)-7-methyl-2-(methylthio)-9-(3,4,5-trimethoxybenzylidene)-5-(3,4,5-trimethoxyphenyl)-6,7,8,9-tetrahydropyrimido[4,5-b][1,6]naphthyridin-4(3H)-one
  参考文献：
  名称：

  微波辅助合成具有潜在抗肿瘤活性的嘧啶并[4,5- b ] [1,6]萘啶-4（3 H）-酮

  摘要：

  的6,7,8,9-四氢嘧啶并[4,5- b ] [1,6]萘啶-4（3 H ^，5 ħ，10 ħ） -酮4，图5a -克和它们的氧化形式6，图7a -克从6-氨基-2-甲硫基-4（3无催化剂反应获得ħ） -酮3和（ë）-3,5-双（亚苄基）-1-烷基-4-哌啶酮1，图2a – g在微波辐射下及其随后的氧化过程中，p-氯苯胺。在美国国家癌症研究所（NCI）中评估了18种新化合物，其中化合物4g对57种癌细胞具有显着活性，体外试验中最重要的GI 50值范围为1.48至9.92μM。

  DOI：

  10.1016/j.ejmech.2012.11.037
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 mineral oil 为溶剂， 反应 12.5h， 生成 3,5-bis((E)-3,4,5-trimethoxybenzylidene)-1-methylpiperidin-4-one
  参考文献：
  名称：

  Design, synthesis, anti-lung cancer activity, and chemosensitization of tumor-selective MCACs based on ROS-mediated JNK pathway activation and NF-κB pathway inhibition

  摘要：

  EF24 and F35 both were effective monocarbonyl curcumin analogues (MCACs) with excellent anti-tumor activity, however, drug defect such as toxicity may limit their further development. To get anti-lung cancer drugs with high efficiency, low toxicity and chemosensitization, a series of analogues based on EF24 and F35 were designed and synthesized. A number of compounds were found to exhibit cytotoxic activities selectively towards lung cancer cells compared to normal cells. Among these compounds, 5B was considered as an optimal anti-tumor agent for lung cancer cells with IC50 values ranging from 1.0 to 1.7 mu M, selectivity index (SI, as a logarithm of a ratio of IC50 value for normal and cancer cells) were all above 1.1, while the SI of EF24 and F35 were less than 0.8. Consistent with selectivity in vitro, 5B was observed to show lower toxicity in acute toxicity experiment than EF24 and F35 respectively. Further, 5B was found to exert anti-tumor effects through ROS-mediated activation of JNK pathway and inhibition of NF-kappa B pathway. 5B could significantly enhance the sensitivity of A549 cells to cisplatin or 5-Fu. These findings suggested that 5B was an effective and less toxic MCAC and provided a promising candidate for anti-tumor drugs. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.03.051

文献信息

• Small Molecule Stimulators of Steroid Receptor Coactivator-3 and Methods of Their Use as Cardioprotective and/or Vascular Regenerative Agents
  申请人：Baylor College of Medicine

  公开号：US20200071300A1

  公开（公告）日：2020-03-05

  Small molecule stimulators of steroid receptor coactivator-3 (SRC-3) and methods of their use as cardioprotective agents are provided. The small molecule stimulators are useful for promoting cardiac protection and repair and vascular regeneration after myocardial infarction. The compounds are also useful in preventing cardiac hypertrophy and collagen deposition and improving cardiac post-infarction function.

  提供了类固醇受体共激活因子-3（SRC-3）的小分子激活剂以及它们作为心脏保护剂的使用方法。这些小分子激活剂有助于促进心脏保护和修复，以及在心肌梗死后促进血管再生。这些化合物还可用于预防心肌肥大和胶原沉积，改善心肌梗死后的心脏功能。
• [EN] SMALL MOLECULE STIMULATORS OF STEROID RECEPTOR COACTIVATOR PROTEINS AND THEIR USE IN THE TREATMENT OF CANCER<br/>[FR] STIMULATEURS À PETITES MOLÉCULES DES PROTÉINES CO-ACTIVATRICES DES RÉCEPTEURS DE STÉROÏDES ET MÉTHODES POUR LES UTILISER
  申请人：BAYLOR COLLEGE MEDICINE

  公开号：WO2016109470A1

  公开（公告）日：2016-07-07

  Small molecule stimulators of steroid receptor coactivator (SRC) family proteins are provided, as well as methods for their use in treating or preventing cancer. Also provided are methods for stimulating SRC family proteins in a cell.

  提供了激活类固醇受体共激活蛋白（SRC）家族蛋白的小分子刺激剂，以及它们在治疗或预防癌症中的使用方法。还提供了在细胞中刺激SRC家族蛋白的方法。
• 一种姜黄素类似物在制备抗肿瘤药物中的应用
  申请人：温州医科大学

  公开号：CN107737124A

  公开（公告）日：2018-02-27

  一种姜黄素类似物在制备抗肿瘤药物中的应用，其特征在于，所述的姜黄素类似物的结构如下式所示，所述的抗肿瘤药物用于选择性杀伤肿瘤细胞而对正常细胞无毒性，可以作为一种有潜力的抗肿瘤药物。
• Small molecule stimulators of steroid receptor coactivator-3 and methods of their use as cardioprotective and/or vascular regenerative agents
  申请人：Baylor College of Medicine

  公开号：US10875841B2

  公开（公告）日：2020-12-29

  Small molecule stimulators of steroid receptor coactivator-3 (SRC-3) and methods of their use as cardioprotective agents are provided. The small molecule stimulators are useful for promoting cardiac protection and repair and vascular regeneration after myocardial infarction. The compounds are also useful in preventing cardiac hypertrophy and collagen deposition and improving cardiac post-infarction function.

  本研究提供了类固醇受体辅激活剂-3（SRC-3）的小分子刺激剂及其用作心脏保护剂的方法。 这些小分子刺激剂有助于促进心肌梗塞后的心脏保护和修复以及血管再生。 这些化合物还能防止心脏肥大和胶原沉积，改善心肌梗塞后的功能。
• Small molecule stimulators of steroid receptor coactivator proteins and their use in the treatment of cancer
  申请人：BAYLOR COLLEGE OF MEDICINE

  公开号：US11312676B2

  公开（公告）日：2022-04-26

  Small molecule stimulators of steroid receptor coactivator (SRC) family proteins are provided, as well as methods for their use in treating or preventing cancer. Also provided are methods for stimulating SRC family proteins in a cell.

  本研究提供了类固醇受体辅激活剂（SRC）家族蛋白的小分子刺激剂，以及将其用于治疗或预防癌症的方法。还提供了刺激细胞中 SRC 家族蛋白的方法。