N-methyl-3,5-bis(3-nitrophenylmethylene)-4-piperidone | 303789-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-methyl-3,5-bis(3-nitrophenylmethylene)-4-piperidone
• 英文别名: 3,5-bis(3-nitrobenzylidene)-1-methylpiperidin-4-one；1-Methyl-3,5-bis(3'-nitrobenzylidene)4-piperidone；1-methyl-3,5-bis[(3-nitrophenyl)methylidene]piperidin-4-one
• CAS: 303789-15-3
• 化学式: C₂₀H₁₇N₃O₅
• mdl: MFCD02693644
• 分子量: 379.372
• InChiKey: BXKGLLLSZMXQNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-methyl-3,5-bis(3-nitrophenylmethylene)-4-piperidone 在 盐酸 、 tin(ll) chloride 作用下， 以 水 为溶剂， 反应 6.0h， 以2.17 g的产率得到N-methyl-3,5-bis-(3-aminobenzylidene)-4-piperidone
  参考文献：
  名称：

  具有抗肿瘤活性的3,5-二(3-氨基苯亚甲基)-4-哌啶酮衍生物及其制备方法

  摘要：

  本发明涉及两个具有抗肿瘤活性的3,5-二(3-氨基苯基)亚甲基-4-哌啶酮化合物及其制备方法，属于抗肿瘤药物及其制备方法技术领域。其制备方法是通过4-哌啶酮与间硝基苯甲醛进行克莱森-施密特缩合反应得到中间体，再用还原剂进行还原得到发明产物A和B。该化合物抗肿瘤活性好，可避免现在使用的抗肿瘤药的基因毒性，对正常细胞的毒性小。制备方法操作简便，反应条件温和，合成产率高，利于其在抗肿瘤领域的广泛推广。

  公开号：

  CN105669537A
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 间硝基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 N-methyl-3,5-bis(3-nitrophenylmethylene)-4-piperidone
  参考文献：
  名称：

  微波辐射合成吡喃并[3,2- c ]吡啶衍生物的有效方法

  摘要：

  通过以下反应合成了一系列吡喃并[3,2- c ]吡啶衍生物3,5-二亚苄基-哌啶-4-一和丙二腈在N，N-二甲基甲酰胺在微波辐射下。构建吡喃并[3,2- c ]吡啶骨架是一种简单，高效，有前途的合成方法。J.杂环化​​学，（2009）。

  DOI：

  10.1002/jhet.152

文献信息

• An Efficient and Chemoselective Synthesis of 1,6-Naphthyridines and Pyrano[3,2-c]pyridines under Microwave Irradiation
  作者：Shu-Jiang Tu、Zheng-Guo Han、Bo Jiang、Shu Yan、Xiao-Hong Zhang、Shan-Shan Wu、Wen-Juan Hao、Xu-Dong Cao、Feng Shi、Ge Zhang、Ning Ma

  DOI：10.1055/s-0028-1088052

  日期：2009.5

  6-naphthyridines and pyrano[3,2-c]pyridines were selectively synthesized via microwave-assisted reactions controlled by the nature of the solvent. This has resulted in an efficient and promising synthetic method for constructing the 1,6-naphthyridine and pyrano[3,2-c]pyridine skeletons. solvent-dependent chemoselectivity - 1,6-naphthyridines - pyrano[3,2-c]pyridines

  通过受溶剂性质控制的微波辅助反应，有选择地合成了一系列的1,6-萘啶和吡喃并[3,2- c ]吡啶。这导致了一种有效且有前途的合成方法，用于构建1,6-萘吡啶和吡喃并[3,2- c ]吡啶骨架。 溶剂依赖性化学选择性-1,6-萘吡啶-吡喃并[3,2- c ]吡啶
• Magnetic Graphene Oxide Anchored Sulfonic Acid as a Novel Nanocatalyst for the Synthesis of N-aryl-2-amino-1,6-naphthyridines
  作者：Shahnaz Rostamizadeh、Mina Rezgi、Nasrin Shadjou、Mohammad Hasanzadeh

  DOI：10.1002/jccs.201300167

  日期：2013.11

  Magnetic graphene oxide functionalized with sulfonic acid (Fe3O4‐GO‐SO3H) was used as a new recyclable nanocatalyst for one‐pot synthesis of N‐aryl‐2‐amino‐1,6‐naphthyridine derivatives under solvent free conditions. The catalyst could be easily recovered from the reaction mixture by an external magnet and reused without significant decrease in activity even after 4 runs. This nanocatalyst exhibited

  磺酸功能化的磁性氧化石墨烯（Fe 3 O 4 -GO-SO 3 H）被用作一种新的可回收纳米催化剂，用于在无溶剂条件下一锅法合成N-芳基-2-氨基-1,6-萘啶衍生物。可以容易地通过外部磁体从反应混合物中回收催化剂，并且即使在4次运行后，活性也不会显着降低地重复使用。该纳米催化剂显示出比其他市售磺酸催化剂更好的活性。
• Quinine-catalyzed enantioselective tandem conjugate addition/intramolecular cyclization of malononitrile and 1,4-dien-3-ones
  作者：Zhi-Peng Hu、Jian Li、Xiao-Gang Yin、Xue-Jing Zhang、Ming Yan

  DOI：10.3998/ark.5550190.0014.301

  日期：——

  An organocatalytic tandem conjugate addition / intramolecular cyclization of malononitrile and conformationally restricted 1,4-dien-3-ones has been developed. A series of cinchona alkaloids and their derivatives were examined as the catalysts. Quinine was found to be the most efficient catalyst in the absence of any additive. The reaction gave 2-amino-4H-pyrans with high yield and excellent enantiopurity

  已开发出丙二腈和构象受限的 1,4-二烯-3-酮的有机催化串联共轭加成/分子内环化。研究了一系列金鸡纳生物碱及其衍生物作为催化剂。在没有任何添加剂的情况下，奎宁被发现是最有效的催化剂。该反应仅使用 5 mol% 奎宁作为催化剂，以高收率和优异的对映纯度得到 2-氨基-4H-吡喃。
• An efficient and stereoselective synthesis of pyrazolo[4,3-<i>c</i>]pyridine derivatives under microwave heating
  作者：Ju-Hua Peng、Wen-Juan Hao、Shu-Jiang Tu

  DOI：10.1002/jhet.169

  日期：2009.9

  A practical, inexpensive, and rapid method for the stereoselective synthesis of pyrazolo[4,3-c]pyridine derivatives via microwave-assisted reactions of 3,5-diarylidenepiperidin-4-ones with phenylhydrazine in ethylene glycol. This method has the advantages of good yield, operational simplicity, and simple purification procedure. J. Heterocyclic Chem., (2009).

  一种实用，廉价，快速的方法，可通过3,5-二芳基亚哌啶4-酮与微波的微波辅助反应立体选择性合成吡唑并[4,3- c ]吡啶衍生物乙二醇中的苯肼。该方法具有收率高，操作简便，纯化步骤简单的优点。J.杂环化​​学，（2009）。
• Diarylidene‐<i>N</i>‐Methyl‐4‐Piperidones and Spirobibenzopyrans as Antioxidant and Anti‐Inflammatory Agents
  作者：Siva Kumar Rokkam、Javier A. Mas‐Rosario、Bishnu P. Joshi、Mayank Joshi、Angshuman Roy Choudhury、Swayamsiddha Kar、Nageswara Rao Golakoti、Michelle E. Farkas

  DOI：10.1002/cbdv.202300822

  日期：2023.9

  Curcumin has antioxidant properties resulting from its radical scavenging ability and inhibition of inflammation‐associated factors. However, its lack of solubility, instability, and poor bioavailability are impediments to its therapeutic use. As potential alternatives, we synthesized and performed chemical analysis of thirty diarylidene‐N‐methyl‐4‐piperidone (DANMP), diheteroarylidene‐N‐methyl‐4‐piperidone (DHANMP), and spirobibenzopyran (SBP) derivatives, one of which was also characterized by single crystal X‐ray diffraction. All compounds were evaluated for antioxidant activity via 2,2‐Diphenyl‐1‐picrylhydrazyl (DPPH) radical scavenging assay and for drug‐like properties in silico. A subset of five compounds was investigated in terms of aqueous solubilities, which were significantly improved compared to that of curcumin. In vitro assessments of cellular and anti‐inflammatory effects were conducted via real time polymerase chain reaction (RT‐PCR) and Griess assays to evaluate the presence of inflammatory/activated (M1) markers and production of nitric oxide (NO) species, which are associated with inflammation. The five compounds reduced levels of markers and NO to extents similar to or better than curcumin in inflamed cells, and showed no adverse effects on cell viability. We show that these compounds possess anti‐inflammatory properties and may be used as curcumin‐substitutes with improved characteristics.

  摘要 姜黄素具有清除自由基和抑制炎症相关因子的抗氧化特性。然而，其缺乏溶解性、不稳定性和较差的生物利用度阻碍了它的治疗用途。作为潜在的替代品，我们合成了 30 种二芳基-N-甲基-4-哌啶酮（DANMP）、二异芳基-N-甲基-4-哌啶酮（DHANMP）和螺苯并吡喃（SBP）衍生物并进行了化学分析，其中一种衍生物还通过单晶 X 射线衍射进行了表征。通过 2,2-二苯基-1-苦基肼（DPPH）自由基清除试验评估了所有化合物的抗氧化活性，并对其类似药物的性质进行了硅学研究。对五个化合物的水溶性进行了研究，与姜黄素相比，这些化合物的水溶性得到了显著改善。通过实时聚合酶链式反应（RT-PCR）和格里耶斯测定法对细胞和抗炎效果进行了体外评估，以评估炎症/活化（M1）标志物的存在以及与炎症相关的一氧化氮（NO）的产生。在炎症细胞中，这五种化合物降低标记物和一氧化氮水平的程度与姜黄素相似或优于姜黄素，而且对细胞活力没有不良影响。我们的研究表明，这些化合物具有抗炎特性，可用作姜黄素的替代品，并具有更好的特性。