ethyl (2-methyl-6-4'-nitrophenyl)nicotinate | 100970-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl (2-methyl-6-4'-nitrophenyl)nicotinate
• 英文别名: ethyl (2-methyl-6-p-nitrophenyl)nicotinate；Ethyl 2-methyl-6-(4-nitrophenyl)nicotinate；ethyl 2-methyl-6-(4-nitrophenyl)pyridine-3-carboxylate
• CAS: 100970-07-8
• 化学式: C₁₅H₁₄N₂O₄
• mdl: MFCD08446619
• 分子量: 286.287
• InChiKey: GFBBEVJAEBSTTJ-UHFFFAOYSA-N

物化性质

• 熔点：
  71-73 °C(Solv: methanol (67-56-1))
• 沸点：
  408.1±45.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2-methyl-6-4'-nitrophenyl)nicotinate 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 (Z)-2-methyl-N'-(1-methyl-2-oxoindolin-3-ylidene)-6-(4-nitrophenyl)nicotinohydrazide
  参考文献：
  名称：

  Protective effect of novel substituted nicotine hydrazide analogues against hypoxic brain injury in neonatal rats via inhibition of caspase

  摘要：

  In hypoxic-ischemic injury of the brain of neonates, the level of caspase-3 was found to be aberrantly activated. Its overexpression leads to the alteration of cytoskeleton protein fodrin and loss of DNA repair enzyme which ultimately results in neurological impairment and disability. Concerning this, the present study was intended to develop novel nicotine hydrazide analogues as caspase inhibitors via efficient synthetic route. These compounds were subsequently tested for inhibitory activity against caspase-3 and -7 where they exhibit highly potent activity against caspase-3 revealing compound 5k as most potent inhibitor (IC50 = 19.4 +/- 2.5 mu M). In Western blot analysis, 5k considerably inhibits the overexpression of caspase-3. The aryl nicotinate of compound 5k, as indicated by molecular docking was found to engage His121 and critical enzyme thiols, i.e., Cys163 of caspase-3 for its potent activity. Moreover, histopathological examination of brain tissues and hippocampus neurons showed that compound 5k considerably improves the brain injury and exert neuroprotective effects in hypoxic-ischemic (HI). In brain homogenate, 5k significantly improves the activity of MDA, SOD, GSH-Px, CAT and T-AOC to exert its beneficial effect against oxidative stress induced by HI injury. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.04.031
• 作为产物：
  描述：

  4-硝基苯甲酰氯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 ethyl (2-methyl-6-4'-nitrophenyl)nicotinate
  参考文献：
  名称：

  Consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz syntheses of tri- and tetrasubstituted pyridines

  摘要：

  修改后的Sonogashira炔酮合成与Bagley-Bohlmann-Rahtz吡啶合成的串联反应，以一锅法给出了新颖的连续三元和四元组分偶联-Bagley-Bohlmann-Rahtz (cBBR)合成方法，用于合成三取代和四取代吡啶。通过这些过程，可以轻松地以适度到中等产率获得15种不同取代的3-乙氧羰基-2-甲基吡啶。

  DOI：

  10.1515/znb-2016-0046

文献信息

• Microwave-assisted regioselective one-pot synthesis of trisubstituted pyridine scaffolds using K₅CoW₁₂O₄₀.3H₂O under solvent free conditions
  作者：Srinivas Kantevari、Mahankhali Venu Chary、Srinivasu V. N. Vuppalapati、N. Lingaiah

  DOI：10.1002/jhet.5570450424

  日期：2008.7

  A highly efficient, microwave-assisted, regioselective synthesis of 2,3-disubstituted-6-arylpyridines and new series of 7,7-dimethyl-2-aryl-5,6,7,8-tetrahydroquinoline-5-ones from enaminones in the presence of K5CoW12O40.3H2O (1.0 mol %) as heterogeneous catalyst under solvent free conditions is reported.

  高效的微波辅助区域选择性合成的2,3-二取代的6-芳基吡啶和新的7,7-二甲基2-芳基5,6,7,8-四氢喹啉5-酮从氨基酮中合成。据报道在无溶剂条件下存在K 5 CoW 12 O 40 .3H 2 O（1.0 mol％）作为非均相催化剂。
• Domino synthesis of functionalized pyridine carboxylates under gallium catalysis: Unravelling the reaction pathway and the role of the nitrogen source counter anion
  作者：Dinesh Kumar、Himanshu Sharma、Nirjhar Saha、Asit K. Chakraborti

  DOI：10.1002/asia.202200304

  日期：2022.8

  domino Michael-cyclodehydration-aromatization multicomponent reaction for the synthesis of functionalized pyridines from enaminones, 1,3-diketones, and NH4OAc under solvent-free condition is reported. The method is simple, high-yielding, and operates under mild conditions with a wide substrate scope. The use of different ammonium salts as a nitrogen source was investigated and the decisive role of the acetate

  报道了在无溶剂条件下由烯胺酮、1,3-二酮和 NH 4 OAc 合成官能化吡啶的 GaI 3催化多米诺迈克尔环脱水芳构化多组分反应。该方法简单、收率高、操作条件温和、底物范围广。研究了使用不同的铵盐作为氮源，并确定了醋酸盐抗衡阴离子的决定性作用。
• A highly efficient regioselective one-pot synthesis of 2,3,6-trisubstituted pyridines and 2,7,7-trisubstituted tetrahydroquinolin-5-ones using K5CoW12O40·3H2O as a heterogeneous recyclable catalyst
  作者：Srinivas Kantevari、Mahankhali Venu Chary、Srinivasu V.N. Vuppalapati

  DOI：10.1016/j.tet.2007.10.014

  日期：2007.12

  A systematic investigation into the regioselective one-pot, three-component condensation of enaminones la-g, beta-dicarbonyl compounds 2a-c, and ammonium acetate in the presence of a catalytic amount of K5CoW12O40 center dot 3H(2)O (0.01 equiv or 1.0 mol %) under solvent free conditions, as well as in refluxing isopropanol, has been reported. The reaction was highly efficient to produce 2,3,6-trisubstituted pyridines 3a-g, 4a-g, and novel 2,7,7-trisubstituted-5,6,7,8-tetrahydroquinoline-5-ones 5a-g in excellent yields. The present procedure offers advantages of short reaction time, simple work-up, and the catalyst exhibited remarkable reusable activity. (c) 2007 Elsevier Ltd. All rights reserved.
• A facile synthesis of 2,3-disubstituted-6-arylpyridines from enaminones using montmorillonite K10 as solid acid support
  作者：G. Jagath Reddy、D. Latha、C. Thirupathaiah、K. Srinivasa Rao

  DOI：10.1016/j.tetlet.2004.11.071

  日期：2005.1

  A facile synthesis of 2.3-disubstituted-6-arylpyridines from enaminones using montmorillonite K10 as solid acid support is reported herein. (C) 2004 Published bv Elsevier Ltd.
• Kotschetkow et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 1657; engl. Ausg. S. 1632
  作者：Kotschetkow et al.

  DOI：——

  日期：——