5-cyano-2-methyl-4-(4-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester | 94640-15-0

• 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: 5-cyano-2-methyl-4-(4-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
• 英文别名: ethyl 5-cyano-2-methyl-6-oxo-4-(4-nitrophenyl)-1,4,5,6-tetrahydropyridine-3-carboxylate；ethyl 3-cyano-6-methyl-4-(4-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 94640-15-0
• 化学式: C₁₆H₁₅N₃O₅
• mdl: MFCD01219337
• 分子量: 329.312
• InChiKey: RGRDVGBNPGHMNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-cyano-2-methyl-4-(4-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 ethyl 5-cyano-2-methyl-6-oxo-4-(4-nitrophenyl)-1,6-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  二氢吡啶（NH4→O）等位衍生物诱导的血管舒张活性的设计，合成及离体研究

  摘要：

  背景：高血压是一种复杂的多因素疾病，是全世界发病率和死亡率的重要原因。合理的药物结构修饰是开发新型降压药物的重要策略。目的：确定硝苯地平和米力农设计的4H-吡喃和2-吡啶酮衍生物作为药效支架的血管舒张作用。方法：所有设计合成的化合物对去甲肾上腺素0.1 µM诱导的离体大鼠主动脉环的收缩均具有血管舒张作用。结果：化合物4a-j，6a-c和8a-c对去甲肾上腺素引起的大鼠主动脉环收缩产生浓度依赖性和内皮依赖性舒张作用。化合物6a，8a，8b，和8c是整个系列中最有效的化合物；然而，它们的效力不及硝苯地平和卡巴胆碱作为阳性对照。结论：设计合成了具有明显血管舒张作用的化合物，可用于新的降压药的开发。

  DOI：

  10.2174/1570180812666151003002501
• 作为产物：
  描述：

  ethyl 6-amino-5-cyano-2-methyl-4-(4-nitrophenyl)-4H-pyran-3-carboxylate 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 5-cyano-2-methyl-4-(4-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  二氢吡啶（NH4→O）等位衍生物诱导的血管舒张活性的设计，合成及离体研究

  摘要：

  背景：高血压是一种复杂的多因素疾病，是全世界发病率和死亡率的重要原因。合理的药物结构修饰是开发新型降压药物的重要策略。目的：确定硝苯地平和米力农设计的4H-吡喃和2-吡啶酮衍生物作为药效支架的血管舒张作用。方法：所有设计合成的化合物对去甲肾上腺素0.1 µM诱导的离体大鼠主动脉环的收缩均具有血管舒张作用。结果：化合物4a-j，6a-c和8a-c对去甲肾上腺素引起的大鼠主动脉环收缩产生浓度依赖性和内皮依赖性舒张作用。化合物6a，8a，8b，和8c是整个系列中最有效的化合物；然而，它们的效力不及硝苯地平和卡巴胆碱作为阳性对照。结论：设计合成了具有明显血管舒张作用的化合物，可用于新的降压药的开发。

  DOI：

  10.2174/1570180812666151003002501

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, ex vivo and in silico studies of 3-cyano-2-pyridone derivatives with vasorelaxant activity
  作者：Fernando Hernández、Arturo Sánchez、Priscila Rendón-Vallejo、César Millán-Pacheco、Yolanda Alcaraz、Francisco Delgado、Miguel A. Vázquez、Samuel Estrada-Soto

  DOI：10.1016/j.ejmech.2013.10.018

  日期：2013.12

  and simple synthesis of 3-cyano-2-pyridone derivatives (6a–f) through 3,4-dihydropyridin-2-one oxidation process is described. A greener method to synthesize 3,4-dihydropyridin-2-one has also been developed by rearranging 4H-pyran (4a–f) derivatives in aqueous medium applying H2SO4 as the catalyst source and microwave irradiation. The vasorelaxant activity of 3-cyano-2-pyridone derivatives (6a–f) was

  描述了通过3,4-二氢吡啶-2--2-氧化方法有效而简单地合成3-氰基-2-吡啶酮衍生物（6a – f）。通过以H 2 SO 4为催化剂源和微波辐射在水介质中重排4 H-吡喃（4a - f）衍生物，还开发了一种更环保的3,4-二氢吡啶-2-酮合成方法。3-氰基-2-吡啶酮衍生物（6a – f）在去甲肾上腺素（0.1μM）预收缩的分离的胸主动脉大鼠环上有或没有内皮（分别为+ E和-E）证明。所有化合物均表现出显着的浓度依赖性和内皮依赖性血管舒张作用，其中硝基衍生物（6a和f）和化合物6d最有效，EC 50分别为7、4.4和5μM。最后，将先前描述的人L型钙通道（LCC）中心孔的3D模型修改为与亚基α-1F亚型1的NCBI序列NP_005174.2一致，将其用于对接大多数活性化合物。6a，d和f发现最低的亲和能结构停靠在由IS6，IS5，IP和IIS6螺旋线相符的同一个空腔中。在由IIS6，I
• ZnO Nanoparticles: An Efficient Reagent, Simple and One-Pot Procedure for Synthesis of Highly Functionalized Dihydropyridine Derivatives
  作者：Marziyeh Khazaei、Mohammad Anary-Abbasinejad、Alireza Hassanabadi、Bahareh Sadeghi

  DOI：10.1155/2012/780470

  日期：——

  A new and efficient one-pot synthesis of dihydropyridones derivatives by four-component reaction between cyanoacetamide, aryl aldehydes, and ethyl acetoacetate with ammonium acetate using nano ZnO is described. The reaction was performed in ethanol under reflux conditions and afforded good yields of products.

  通过在乙醇中回流条件下使用氨基醋酸铵和纳米氧化锌，在氰基乙酰胺、芳基醛和乙酰乙酸乙酯之间进行四组分反应，描述了一种新的高效一锅法合成二氢吡啶酮衍生物的方法，产率良好。
• 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.
• 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].