5-cyano-4-(4-methoxy-phenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester | 94640-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-cyano-4-(4-methoxy-phenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
• 英文别名: 5-cyano-4-(4-methoxyphenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic ethyl ester；ethyl 3-cyano-4-(4-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 94640-18-3
• 化学式: C₁₇H₁₈N₂O₄
• 分子量: 314.341
• InChiKey: WMKYXWSDWQAFNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-cyano-4-(4-methoxy-phenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester 在 硝酸 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.08h， 生成 3-amino-4-(4-methoxyphenyl)-6-methyl-2-(3,4,5-trimethoxybenzoyl)furo[2,3-b]pyridine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Thieno[2,3-b]pyridines—A new class of multidrug resistance (MDR) modulators

  摘要：

  To identify new potent multidrug resistance modulators, we have synthesized a series of novel thieno[ 2,3-b]pyridines and furo[2,3-b] pyridines, and examined their stucture-activity relationships. All synthesized compounds were tested to determine BCRP1, P-gp, and MRP1 inhibitor activity, and most potent MDR modulators were also screened for their toxicity, cytotoxicity and Ca2+ channel antagonist activity. Among these compounds, thieno[2,3-b] pyridine (6r) was found to exhibit a potent P-gp inhibitory action with EC50 = 0.3 +/- 0.2 mu M, MRP1 inhibitory action with EC50 = 1.1 +/- 0.1 mu M and BCRP1 inhibitory action with EC50 = 0.2 +/- 0.05 mu M and may represent suitable candidate for further pharmacological studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.023
• 作为产物：
  描述：

  ethyl 6-amino-4-(4-methoxyphenyl)-5-cyano-2-methyl-4H-pyran-3-carboxylate 在 甲酸 作用下， 生成 5-cyano-4-(4-methoxy-phenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  二氢吡啶酮超分子自组装中的非共价相互作用和人肺腺癌细胞系 (A549) 的体外抗癌评估

  摘要：

  非共价相互作用是分子自组装和分子识别的驱动力。晶体学研究提供了单晶结构及其超分子相互作用的信息。对 A549 癌症合成的二氢吡啶酮的体外分析显示对癌细胞系、诱导细胞凋亡和断裂 DNA 链的潜在抑制作用。

  DOI：

  10.1002/cplu.202200444

文献信息

• Synthesis of 3,4-dihydropyridin-2-one derivatives in convergent mode applying bio catalyst vitamin B1 and polymer supported catalyst PEG–SO3H from two different sets of building blocks
  作者：Koyel Pradhan、Pranabes Bhattacharyya、Sanjay Paul、Asish R. Das

  DOI：10.1016/j.tetlet.2012.08.030

  日期：2012.10

  Two highly efficient, green protocols have been developed for the synthesis of 3,4-dihydropyridin-2-one derivatives from different starting materials exploring two reaction specific catalysts, vitamin B1 (VB1), and PEG–SO3H. VB1 catalyzed simple and convenient protocol has been developed for the synthesis of 3,4-dihydropyridin-2-one derivatives by the installation of aldehyde, cyanoacetamide, and 1

  两个高效，绿色协议已经开发了用于3,4-二氢吡啶-2-酮从不同的原料衍生物的探索两个反应特定的催化剂，维生素B合成1（VB 1）和PEG-SO 3 H. VB 1通过安装醛，氰基乙酰胺和1,3-二羰基化合物，已开发出催化简单方便的方案，用于合成3,4-二氢吡啶-2-酮衍生物。此外，通过形成4 H-吡喃核和PEG-SO 3 H催化的一锅法，将醛，丙二腈和1,3-二羰基化合物简单地结合起来，也合成了3,4-二氢吡啶-2-酮衍生物。重排。
• Synthesis, molecular self-assembly and anti-carcinogenic study of 2-pyridone molecules
  作者：Lalhruai Zela、Esther Laltlanmawii、Biki Hazarika、Zothan Siama、Ramesh Kataria、Nachimuthu Senthil Kumar、Balkaran S. Sran、Ved Prakash Singh

  DOI：10.1016/j.molstruc.2024.137970

  日期：2024.7

  4-pyrans obtained from the multicomponent reactions of aromatic aldehyde, malononitrile, and ethyl acetoacetate were used as a starting scaffold for synthesizing 2-pyridone derivatives (). Two catalytic methods were reported for the conversion of 4-pyrans to 3,4-dihydropyridones. The non-aromatic 3,4-dihydropyridones obtained were then oxidized to give the final desired 2-pyridone derivatives (). Crystals

  由芳香醛、丙二腈和乙酰乙酸乙酯的多组分反应获得的4-吡喃被用作合成2-吡啶酮衍生物的起始支架()。报道了两种将 4-吡喃转化为 3,4-二氢吡啶酮的催化方法。然后将获得的非芳香族3,4-二氢吡啶酮氧化，得到最终所需的2-吡啶酮衍生物()。制备合成化合物的晶体并进行单晶X射线晶体学（SCXRD）以获得其结构参数。研究了超分子体系中的非共价相互作用，发现内酰胺基团之间的NH∙∙∙O相互作用是最主要的氢键。还观察到芳环涉及孤对∙∙∙π、CH∙∙∙π和弱π∙∙∙π相互作用以协助超分子框架。还进行了赫什菲尔德表面研究来验证超分子晶体内的相互作用。还通过技术对 2-吡啶酮衍生物 () 进行了分析，以评估其在人肺腺癌 (A549) 中的细胞毒性活性。还发现 5-氰基-2-甲基-4-(3-硝基苯基)-6-氧代-1,6-二氢吡啶-3-甲酸乙酯 () 在合成的化合物中显示出最高的细胞毒性效力。
• Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media
  作者：Pranabes Bhattacharyya、Koyel Pradhan、Sanjay Paul、Asish R. Das

  DOI：10.1016/j.tetlet.2012.06.086

  日期：2012.8

  A green and highly efficient protocol has been developed for the synthesis of 4H-pyran scaffolds installing a one-pot three-component coupling reaction of an aldehyde, malononitrile, and a 1,3-diketo compound using nano structured ZnO as the catalyst in aqueous alcoholic medium. A greener method to synthesize 3,4-dihydropyridin-2-one has also been developed by rearranging 4H-pyran derivatives in aqueous medium applying p-TSOH as the right catalyst source. A wide spectrum of functional groups was tolerated in both the developed synthetic protocols with good to excellent yield of the targeted molecules. (c) 2012 Elsevier Ltd. All rights reserved.
• Zayed, Salem E.; Elmaged, Eiman I. Abou; Metwally, Saud A., Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 10, p. 2175 - 2182
  作者：Zayed, Salem E.、Elmaged, Eiman I. Abou、Metwally, Saud A.、Elnagdi, Mohamed H.

  DOI：——

  日期：——
• Chem-grafted Zn-SSA as an Efficient Heterogeneous Catalyst to Synthesize 2-Pyridinones
  作者：Li Jun Zhang、Xiang Zhang、Zhen Sheng You、Heng Li、Tian Feng、Wei Li Wang

  DOI：10.1007/s10562-016-1806-6

  日期：2016.10

  Chemo-selectivity is always a hard problem in preparing 2-pyridinones. Silica sulfuric acid (SSA) modified with zinc chloride (Zn-SSA) was found to be a high efficient heterogeneous catalyst to solve this problem. Under Zn-SSA and solvent-free conditions, the one-pot cyclocondensation of 1,3-dicarbonyl compounds, malononitrile and arylaldehydes to afford 2-pyridinones was conveniently implemented. The heterogeneous reaction was much efficient and promising in pharmaceutical study and industrial production.Improving chemo-selectivity is always a hard problem in preparing 2-pyridinones. Silica sulfuric acid (SSA) modified with zinc chloride (Zn-SSA) was found to be efficient heterogeneous catalyst to solve this problem. Under Zn-SSA and solvent-free conditions, the one-pot cyclocondensation of 1,3-dicarbonyl compounds, malononitrile and arylaldehydes to afford 2-pyridinones was conveniently implemented. The heterogeneous reaction was much efficient and promising in pharmaceutical study and industrial production.[GRAPHICS].