ethyl 2-cyano-3-(pyridin-4-yl)acrylate | 2286-31-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-cyano-3-(pyridin-4-yl)acrylate
• 英文别名: Ethyl 2-cyano-3-(pyridin-4-yl)prop-2-enoate；ethyl 2-cyano-3-pyridin-4-ylprop-2-enoate
• CAS: 2286-31-9
• 化学式: C₁₁H₁₀N₂O₂
• mdl: MFCD00175069
• 分子量: 202.213
• InChiKey: XLQQQEHSYHZOLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  103-105 °C(Solv: ethanol (64-17-5))
• 沸点：
  356.2±32.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  63
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyano-3-(pyridin-4-yl)acrylate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以85%的产率得到ethyl 2-cyano-3-(pyridin-4-yl)propanoate,
  参考文献：
  名称：

  3-亚芳基丙二酸衍生物与三乙胺和其他胺的反应；意外的减少和黑胶

  摘要：

  在热乙醇中将2-氰基-3-（2-甲氧基-5-硝基苯基）丙烯酸乙酯1f暴露于三乙胺导致高产率地形成二氢衍生物2f和乙烯基化合物3f。提供了用于3f的单晶X射线数据。对于各种类似物观察到相似的反应。研究了改变芳基取代基，胺和溶剂的反应。还检查了吡啶基，噻吩基类似物。该研究扩展到包含这种系统，如噻唑烷二酮的环状分子8，3-氰基香豆素9和4-亚芳基-异喹啉-2,4-二酮11。最后一组给出了乙烯基化产物，4-肉桂基-异喹啉二酮和4-羟基化的物质。研究了来自丙二腈，乙酰乙酸乙酯，乙酰丙酮和甲基磺酰乙酸乙酯的亚芳基衍生物的一些实例。肉桂酸乙酯和β-硝基苯乙烯不受影响。由于添加自由基淬灭剂抑制了反应，因此认为该反应可能是自由基介导的。与热条件的影响相反，在254和365 nm的乙醇中1f的辐照产生复杂的混合物。在这项研究中还注意到了一些其他有趣的观察结果：1f与乙醛的乙烯基化反应生成3f；从1f形成3f用

  DOI：

  10.1016/j.tet.2016.03.097
• 作为产物：
  描述：

  4-吡啶甲醛 、 氰乙酸乙酯 在 magnetic core-shell dendritic mesoporous silica nanospheres anchored with N-(2-aminoethyl)-3-aminopropyltrimethoxysilane (Fe₃O₄/SiO₂/DSiO₂-NH₂) 作用下， 以 水 为溶剂， 反应 0.33h， 以89%的产率得到ethyl 2-cyano-3-(pyridin-4-yl)acrylate
  参考文献：
  名称：

  Magnetic core–shell dendritic mesoporous silica nanospheres anchored with diamine as an efficient and recyclable base catalyst

  摘要：

  在这项研究中，通过油水两相分层包覆策略成功合成了二胺功能化的磁芯-壳树枝状介孔硅纳米球。

  DOI：

  10.1039/d0nj04822d

文献信息

• Magnetic core–shell dendritic mesoporous silica nanospheres anchored with diamine as an efficient and recyclable base catalyst
  作者：Surabhi、Javaid Shabir、Padmini Gupta、Digvijay Sah、Subho Mozumdar

  DOI：10.1039/d0nj04822d

  日期：——

  In the present study, diamine-functionalized magnetic core–shell dendritic mesoporous silica nanospheres have been successfully synthesized by an oil–water biphasic stratification-coating strategy.

  在这项研究中，通过油水两相分层包覆策略成功合成了二胺功能化的磁芯-壳树枝状介孔硅纳米球。
• ZrOCl₂·SiO₂-catalyzed synthesis of bis(indoles) via conjugate addition of indole with electron-deficient alkenes in water
  作者：Tayebeh Jari、Mohammad Ali Amrollahi、Zohreh Kheilkordi

  DOI：10.1515/hc-2015-0014

  日期：2015.4.1

  Abstract This report provides a description of an efficient and environmentally benign procedure for the synthesis of bis(indole) derivatives via reaction of indole with electron-deficient alkenes. The remarkable advantages of this method for obtaining bis(indoles) are the simplicity of the experimental procedure, short reaction times, and high yields with the green aspects by avoiding toxic catalysts

  摘要 本报告描述了一种通过吲哚与缺电子烯烃反应合成双（吲哚）衍生物的高效且环境友好的方法。这种获得双（吲哚）的方法的显着优点是实验过程简单，反应时间短，通过避免使用有毒催化剂和溶剂，绿色方面的收率高。
• Noncentrosymmetric Organic Solids with Very Strong Harmonic Generation Response
  作者：Hong Zhao、Yong-Hua Li、Xi-Sen Wang、Zhi-Rong Qu、Li-Zhong Wang、Ren-Gen Xiong、Brendan F. Abrahams、Ziling Xue

  DOI：10.1002/chem.200305425

  日期：2004.5.17

  1-pyridyl-2-ethoxycarbonyl-3-amino-1H-naphtho[2,1-b]pyran-2'-methylacetic acid (5), which likewise crystallizes in a chiral space group. All of compounds are second harmonic generation (SHG) active, and have a very strong SHG response approximately about 8.0, 5.0, 12.0, 6.0, and 1.4 (for 1-5 compounds) times that of urea. Ferroelectric property measurements indicate that compounds 1, 2, 4, and 5 may

  2-萘酚，4-（氨基甲基）吡啶和4-吡啶甲醛的熔融反应在约180摄氏度下产生反式-2,3-二氢-2,3-二（4'-吡啶基）苯并[e]吲哚（ 1）具有两个手性中心，而不是只有一个手性碳中心的预期Betti型反应产物。使用3-吡啶甲醛，4-氰基苯甲醛或3-氰基苯甲醛代替4-吡啶甲醛的相同反应产生了相关的化合物反式-2,3-二氢-2-（4'-吡啶基）-3-（3“-吡啶基）苯并[e]吲哚（2），反式-2,3-二氢-2-（4'-吡啶基）-3-（4“-氰基苯基）苯并[e]吲哚（3）和反式-2,3 -二氢-2-（4'-吡啶基）-3-（3“-氰基苯基）苯并[e]吲哚（4）。该反应以高度的立体选择性进行，反式/顺式比为约98： 2在高温下化合物1，2，化合物3和4在非中心对称空间群（Pca2（1），Pca2（1）和Cc）中结晶，而化合物3具有手性空间群（P2（1））。这些成功的无心堆积结构可能是由于该分子同
• New Route to the Synthesis of Novel Pyrazolo[1,5-a]pyrimidines and Evaluation of their Antimicrobial Activity as RNA Polymerase Inhibitors
  作者：Amira E. M. Abdallah、Galal H. Elgemeie

  DOI：10.2174/1573406418666220302092414

  日期：2022.11

  The current study aimed to synthesize novel pyrazolo[1,5-a]pyrimidines based on 5- aminopyrazoles 3, evaluate their antimicrobial activity, and study the minimum inhibitory concentration (MIC) for the most active compounds. In addition, molecular docking studies and RNA polymerase inhibitory activity were determined.

  Starting with our previously reported 5-aminopyrazoles 3, a number of novel pyrazolo[1,5- a]pyrimidines were synthesized. Due to the similarity of pyrazolopyrimidine derivatives with the purine systems, pyrazolopyrimidines are important in many different biological applications, most notably as anti-tumor, antibacterial, and hepatitis C virus inhibitors. The pharmaceutical applications of the pyrazolopyrimidine derivatives were explained in several approved drugs like Indiplon, Zaloplan, and Ocinaplon.

  To prepare a novel antimicrobial agent, namely pyrazolo[1,5-a]pyrimidine, reveal their structures using different spectral data, the minimum inhibitory concentration (MIC) for the most active compounds was evaluated, and both the molecular docking and the RNA polymerase inhibitory activity were determined.

  A number of different pyrazolopyrimidines namely 2-(phenylamino)-6,11-dihydrobenzo[g]pyrazolo [1,5-a]quinazoline-3-carboxamides (5a-c), (E)-5,7-dimethyl-2-(phenylamino)-6-(phenyldiazenyl)pyrazolo-[1,5- a]pyrimidine-3-carboxamides (7a-c), 7-amino-2-(phenylamino) pyrazolo[1,5-a]pyrimidine-3-carboxamides (11af), 7-amino-2-(phenylamino)-5-(2-thienyl)pyrazolo[1,5-a]pyrimidine-3-carboxamides (14-f) and ethyl 7-amino-3- carbamoyl-2-(phenylamino)-5-(4-pyridyl)pyrazolo[1,5-a]pyrimidine-6-carboxylate derivatives (14g-i) were synthesized through the reaction of 5-aminopyrazoles 3 with a variety of chemical reagents. On the other hand, the evaluation of the antimicrobial activity for all the prepared compounds was screened through different strains as Gram-positive bacteria, such as staphylococcus aureus and Streptococcus mutans, and Gram-negative bacteria, such as Escherichia coli, Pseudomonas aeruginosa, and klebsiella. The antifungal activity was determined by Candids Albicans fungal strain, and the MIC of the most active compounds was measured. The molecular docking was recorded, and the RNA polymerase inhibitory activity was estimated for the high docking score compounds.

  Compounds 5a, 5b, 5c, 7a, 7b, 7c, 11d, 14b, and 14h were the most active compounds against some of the bacterial and fungal tested strains. MIC was determined for the most active tested compounds. As an antimicrobial agent, compound 7b was the most potent, with a high docking score and RNA polymerase inhibitory activity (IC50= 0.213 μg/ml) compared to Rifampicin (IC50= 0.244 μg/ml). The reactivity of the latter compound was attributed to the presence of 4-Br-C6H4 moiety. The results demonstrated that docking studies on the most active compounds in the RNA polymerase active site were consistent with in vitro assays.

  The resultant novel bioactive pyrazolo[1,5-a]pyrimidine derivatives were synthesized based on 5- aminopyrazole derivatives 3. The current study evaluated the antimicrobial activity for all the prepared compounds, followed by the determination of the MIC for the most potent active compounds. The molecular docking study was performed, and it was appropriate with the in vitro activity. The RNA polymerase inhibitory activity was assessed for the most active antimicrobial compounds with a high docking score (7b, 7c, 14a, 14b, 14e, 14i). Compound 7b was the most potent compound inhibiting RNA polymerase enzyme compared to the reference drug Rifampicin.

  The novel prepared heterocyclic systems are extremely important in a variety of domains, especially biological and pharmacological ones.

  目的：本研究旨在基于5-氨基吡唑3合成新型吡唑并[1,5-a]嘧啶，评估其抗微生物活性，并研究最活性化合物的最小抑菌浓度（MIC）。此外，还进行了分子对接研究和RNA聚合酶抑制活性测定。 背景：从我们先前报道的5-氨基吡唑3开始，合成了许多新型吡唑并[1,5-a]嘧啶。由于吡唑并嘧啶衍生物与嘌呤系统相似，吡唑并嘧啶在许多不同的生物应用中非常重要，特别是作为抗肿瘤、抗菌和丙型肝炎病毒抑制剂。吡唑并嘧啶衍生物的药物应用已在多种批准药物中得到解释，如Indiplon、Zaloplan和Ocinaplon。 方法：通过5-氨基吡唑3与各种化学试剂的反应，合成了许多不同的吡唑并嘧啶，包括2-(苯氨基)-6,11-二氢苯并[g]吡唑并[1,5-a]喹唑啉-3-羧酰胺（5a-c）、（E）-5,7-二甲基-2-(苯氨基)-6-(苯基偶氮基)吡唑并[1,5-a]嘧啶-3-羧酰胺（7a-c）、7-氨基-2-(苯氨基)吡唑并[1,5-a]嘧啶-3-羧酰胺（11af）、7-氨基-2-(苯氨基)-5-(2-噻吩基)吡唑并[1,5-a]嘧啶-3-羧酰胺（14-f）和乙酸乙酯7-氨基-3-羧酰胺基-2-(苯氨基)-5-(4-吡啶基)吡唑并[1,5-a]嘧啶-6-羧酸酯衍生物（14g-i）。另一方面，通过不同菌株的筛选，如金黄色葡萄球菌和链球菌等革兰氏阳性细菌，以及大肠杆菌、铜绿假单胞菌和克雷伯菌等革兰氏阴性细菌，对所有制备的化合物的抗微生物活性进行了评估。用Candids Albicans真菌菌株确定了抗真菌活性，并测量了最活性化合物的最小抑菌浓度。记录了分子对接，并评估了RNA聚合酶抑制活性高的对接分数化合物。 结果：化合物5a、5b、5c、7a、7b、7c、11d、14b和14h对某些细菌和真菌菌株具有最活性。测定了最活性的化合物的MIC。作为抗微生物剂，化合物7b是最有效的，具有较高的对接分数和RNA聚合酶抑制活性（IC50= 0.213μg/ml），与利福平（IC50= 0.244μg/ml）相比。后一种化合物的反应性归因于4-Br-C6H4基团的存在。结果表明，在RNA聚合酶活性位点上，最活性化合物的对接研究与体外试验一致。 结论：基于5-氨基吡唑衍生物3，合成了新型生物活性吡唑并[1,5-a]嘧啶衍生物。本研究评估了所有制备化合物的抗微生物活性，随后测定了最强活性化合物的MIC。进行了分子对接研究，并与体外活性相符。对RNA聚合酶抑制活性高的最活性抗微生物化合物（7b、7c、14a、14b、14e、14i）进行了评估。化合物7b是抑制RNA聚合酶酶的最有效化合物，与参考药物利福平相比。 其他：所制备的新型杂环系统在许多领域，特别是生物和药理学领域中非常重要。
• Abdelhamid; Zohdi; Ziada, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 3, p. 202 - 209
  作者：Abdelhamid、Zohdi、Ziada

  DOI：——

  日期：——