1-乙酰基-1,4-二氢-4-苯基吡啶-3-羧酸乙酯 | 350032-39-2

• 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
• 中文名称: 1-乙酰基-1,4-二氢-4-苯基吡啶-3-羧酸乙酯
• 英文名称: ethyl 1-acetyl-4-phenyl-1,4-dihydropyridine-3-carboxylate
• 英文别名: ethyl 1-acetyl-1,4-dihydro-4-phenylpyridine-3-carboxylate；ethyl 1-acetyl-4-phenyl-4H-pyridine-3-carboxylate
• CAS: 350032-39-2
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: IRGOTZUTWXIEMX-UHFFFAOYSA-N

物化性质

• 沸点：
  420.4±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙酰基-1,4-二氢-4-苯基吡啶-3-羧酸乙酯 在 吡啶 、 高氯酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 6-Acetoxy-4-phenyl-benzo[4,5]furo[2,3-b]pyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Evaluation of the First Cytostatically Active 1-Aza-9-oxafluorenes as Novel Selective CDK1 Inhibitors with P-Glycoprotein Modulating Properties

  摘要：

  The first series of synthetic 1-aza-9-oxafluorenes with cytostatic activities in the micromolar range was evaluated as cyclin-dependent kinase (CDK1) inhibitors. Activity was found to be selective in comparison to the inhibition of other kinases within the CDK family. Compounds were shown to inhibit the membrane-efflux pump P-glycoprotein responsible for multidrug resistance in cancer cells. First structure-activity relationships are discussed.

  DOI：

  10.1021/jm021090g
• 作为产物：
  描述：

  烟酸乙酯 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 生成 1-乙酰基-1,4-二氢-4-苯基吡啶-3-羧酸乙酯
  参考文献：
  名称：

  Synthesis and first biological evaluation of 1-aza-9-oxafluorenes as novel lead structures for the development of small-sized cytostatics

  摘要：

  A first series of novel 1-aza-9-oxafluorenes has been prepared from 3-carbonyl substituted 1,4-dihydropyridines and p-benzoquinone as small-sized cytostatics. Biological evaluation has been carried out in various cancer cell-lines. First structure-activity relationships proved the 4-phenyl substituent to be more favorable than the 4-methyl substituent. Cytostatic properties are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00769-7

文献信息

• Evaluation of Novel Substituted Furopyridines as Inhibitors of Protein Kinases Related to Tau Pathology in Alzheimer´s Disease
  作者：N. Schade、P. Koch、F. Ansideri、V. Krystof、M. Holzer、A. Hilgeroth

  DOI：10.2174/1573406417666210601144510

  日期：2021.9.10

  ATP-competition assays with determined affinity constants for the most active compounds. Results: The compounds were prepared in simple two-component reactions of substituted 1,4- dihydropyridines and respective quinones to obtain various substitutions of the molecular furopyridine scaffold. The substituent effects on the determined kinase inhibitory properties of cdk1, cdk2, Fyn, JNK3 and gsk-3β are discussed

  背景：阿尔茨海默病 (AD) 的特征是由两个病理标志引起的进行性神经元变性，过度磷酸化的 tau 蛋白聚集成 tau 细丝和淀粉样前体蛋白衍生的β淀粉样肽聚集成细胞外淀粉样斑块。迄今为止，所有寻找有效药物的尝试都在临床试验中失败。AD 是一种多因素疾病，因此仅针对一种 AD 相关结构的选择性药物可能是不够的。 目的：我们构建了具有各种取代模式的新型呋喃吡啶，以评估它们作为与 tau 病理学相关的酶的蛋白激酶抑制剂。 方法：合成并纯化呋喃吡啶衍生物。蛋白激酶抑制特性在 ATP 竞争试验中确定，对最活跃的化合物具有确定的亲和力常数。 结果：通过取代的1,4-二氢吡啶和各自的醌的简单双组分反应制备化合物以获得分子呋喃吡啶支架的各种取代。讨论了取代基对确定的 cdk1、cdk2、Fyn、JNK3 和 gsk-3β 激酶抑制特性的影响。 结论：根据长度、性质和其中的取代基定位，发现各种3-取代对蛋白
• Regioselective Formation of Novel Functionalized 1-Aza-9-oxafluorenes
  作者：Andreas Hilgeroth、Kristin Brachwitz、Ute Baumeister

  DOI：10.3987/com-00-9141

  日期：——

  A small series of novel 1-aza-9-oxafluorenes have been prepared by regioselective cycloaddition reaction of p-benzoquinone to the sterically unhindered side of unsymmetrically substituted N-acyl-l,4-dihydropyridines (1). The stereochemistry of the products is discussed on the basis of X-Ray crystal structure analysis of one starting structure (la). The formation of pyridine derivatives by possible redox reaction of the adducts was not observed. Rotameric properties of the N-acyl-1,4-dihydropyridines are demonstrated by H-1 and C-13 NMR spectroscopy, thus stabilizing the 1,4-dihydropyridine system towards competing oxidation by the quinone.
• First Rotameric Anti Dimers and 3,9-Diazatetraasteranes from Unsymmetrically Substituted N-Acyl and N-Acyloxy-4-aryl-1,4-dihydropyridines
  作者：Andreas Hilgeroth、Frank W. Heinemann、Ute Baumeister

  DOI：10.3987/com-01-9423

  日期：——

  A series of unsymmetrically substituted N-acyl- and N-acyloxy-1,4-dihydropyridines (1) have been photochemically investigated. On irradiating the crystals of one derivative (la) containing centrosymmetrical pairs of molecules with a distance of 3.894(3) Angstrom between the potentially reacting double bonds favorable for a photodimerisation reaction, the formation of an anti-dimer (2a) was observed. Two other solid derivatives (1b, c) merely decomposed on irradiation to give substituted pyridine compound (3). Solution irradiation of 1,4-dihydropyridines (1) led to the centrosymmetric cage compounds 3,9-diazatetraasteranes (4) and to anti dimers (2) as main products, both existing as rotamers. Symmetric as well as rotameric properties of selected compounds (4) have been demonstrated by X-Ray crystal structure analysis and H-1 NMR spectroscopy.