2-acetyl-3ξ-[3]pyridyl-acrylic acid ethyl ester | 54756-29-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-acetyl-3ξ-[3]pyridyl-acrylic acid ethyl ester
• 英文别名: 2-Acetyl-3ξ-[3]pyridyl-acrylsaeure-aethylester；Ethyl 3-oxo-2-[(pyridin-3-yl)methylidene]butanoate；ethyl 3-oxo-2-(pyridin-3-ylmethylidene)butanoate
• CAS: 54756-29-5
• 化学式: C₁₂H₁₃NO₃
• mdl: MFCD27979420
• 分子量: 219.24
• InChiKey: WBDVKMSBTZRIJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetyl-3ξ-[3]pyridyl-acrylic acid ethyl ester 在 manganese(IV) oxide 、 三乙胺 作用下， 以 氯仿 、 正丁醇 为溶剂， 反应 3.5h， 生成 4-Methyl-2-phenyl-6-pyridin-3-yl-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Studies on Cerebral Protective Agents. I. Novel 4-Arylpyrimidine Derivatives with Anti-anoxic and Anti-lipid Peroxidation Activities.

  摘要：

  通过氧化4-芳基-1,4-二氢嘧啶合成了新型4-芳基嘧啶衍生物，并研究了它们对小鼠抗缺氧（AA）活性和大鼠线粒体抗脂质过氧化（ALP）活性的影响。在这些化合物中，乙基6-甲基-2-苯基-4-(4-吡啶基)-5-嘧啶羧酸酯（4b）具有AA活性（10mg/kg，腹腔注射），而乙基6-甲基-4-(3-硝基苯基)-2-苯基-5-嘧啶羧酸酯（4f）具有ALP活性（73%抑制在10μg/ml）。后者化合物（100mg/kg，腹腔注射）对大鼠花生四烯酸引起的脑水肿也有效，其效力与维生素E相当。

  DOI：

  10.1248/cpb.40.1452
• 作为产物：
  描述：

  3-吡啶甲醛 、 乙酰乙酸乙酯 在 哌啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 2-acetyl-3ξ-[3]pyridyl-acrylic acid ethyl ester
  参考文献：
  名称：

  Studies on Cerebral Protective Agents. I. Novel 4-Arylpyrimidine Derivatives with Anti-anoxic and Anti-lipid Peroxidation Activities.

  摘要：

  通过氧化4-芳基-1,4-二氢嘧啶合成了新型4-芳基嘧啶衍生物，并研究了它们对小鼠抗缺氧（AA）活性和大鼠线粒体抗脂质过氧化（ALP）活性的影响。在这些化合物中，乙基6-甲基-2-苯基-4-(4-吡啶基)-5-嘧啶羧酸酯（4b）具有AA活性（10mg/kg，腹腔注射），而乙基6-甲基-4-(3-硝基苯基)-2-苯基-5-嘧啶羧酸酯（4f）具有ALP活性（73%抑制在10μg/ml）。后者化合物（100mg/kg，腹腔注射）对大鼠花生四烯酸引起的脑水肿也有效，其效力与维生素E相当。

  DOI：

  10.1248/cpb.40.1452

文献信息

• Tacripyrines, the First Tacrine−Dihydropyridine Hybrids, as Multitarget-Directed Ligands for the Treatment of Alzheimer’s Disease
  作者：José Marco-Contelles、Rafael León、Cristóbal de los Ríos、Abdelouahid Samadi、Manuela Bartolini、Vincenza Andrisano、Oscar Huertas、Xavier Barril、F. Javier Luque、María I. Rodríguez-Franco、Beatriz López、Manuela G. López、Antonio G. García、María do Carmo Carreiras、Mercedes Villarroya

  DOI：10.1021/jm801292b

  日期：2009.5.14

  Tacripyrines (1-14) have been designed by combining an ACNE inhibitor (tacrine) with a calcium antagonist such as nimodipine and are targeted to develop a multitarget therapeutic strategy to confront AD. Tacripyrines are selective and potent ACNE inhibitors in the nanomolar range. The mixed type inhibition of hAChE activity of compound 11 (IC50 105 +/- 15 nM) is associated to a 30.7 +/- 8.6% inhibition of the proaggregating action of ACNE on the A beta and a moderate inhibition of A beta self-aggregation (34.9 +/- 5.4%). Molecular modeling indicates that binding of compound 11 to the ACNE PAS mainly involves the (R)-11 enantiomer, which also agrees with the noncompetitive inhibition mechanism exhibited by p-methoxytacripyrine 11. Tacripyrines are neuroprotective agents, show moderate Ca2+ channel blocking effect, and cross the blood-brain barrier, emerging as lead candidates for treating AD.
• Synthesis of 6-amino-1,4-dihydropyridines that prevent calcium overload and neuronal death
  作者：Rafael León、Cristóbal de los Ríos、José Marco-Contelles、Manuela G. López、Antonio G. García、Mercedes Villarroya

  DOI：10.1016/j.ejmech.2007.06.001

  日期：2008.3

  The synthesis and pharmacology of 6-amino-1,4-dihydropyridines, such as ethyl 6-amino-4-aryl-5-cyano-1,4-dihydro-2-methyl-3-pyridinecarboxylic acids (3-16) and 2-amino-4-aryl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinenitriles (17-21) are described. Compounds 18 and 21, at the concentration of 0.3 mu M, proved to be the best blockers of the [Ca2+] overload induced by depolarization with high [K+] of SH-SY5Y neuroblastoma cells, with values of 63.8% and 50.4%, respectively. Most of the compounds induced a remarkable neuroprotective effect against toxicity caused by high [K+]-elicited [Ca2+] overload, and against H2O2-generated free radicals, in SH-SY5Y cells. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Preparation of the Pyridalacetones and the Inductive Effect of Nitrogen on the Dehydration of the Intermediate Aldols^*1
  作者：C. S. MARVEL、J. K. STILLE

  DOI：10.1021/jo01362a037

  日期：1957.11
• Studies on Cerebral Protective Agents. I. Novel 4-Arylpyrimidine Derivatives with Anti-anoxic and Anti-lipid Peroxidation Activities.
  作者：Atsushi KUNO、Yoshie SUGIYAMA、Kiyotaka KATSUTA、Toshiharu KAMITANI、Hisashi TAKASUGI

  DOI：10.1248/cpb.40.1452

  日期：——

  Novel 4-arylpyrimidine derivatives were synthesized by the oxidation of 4-aryl-1, 4-dyhydropyrimidines, and their effects on anti-anoxic (AA) activity in mice and anti-lipid peroxidation (ALP) activity in rat mitochondria were investigated. Among these compounds, ethyl 6-methyl-2-phenyl-4-(4-pyridyl)-5-pyrimidinecarboxylate (4b) has AA activity (10mg/kg, i.p.) and ethyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (4f) has ALP activity (73% inhibition at 10<-5>g/ml). The latter compound (100mg/kg, i.p.) was also effective on arachidonate-induced cerebral edema in rats with comparable potency to that of vitamin E.

  通过氧化4-芳基-1,4-二氢嘧啶合成了新型4-芳基嘧啶衍生物，并研究了它们对小鼠抗缺氧（AA）活性和大鼠线粒体抗脂质过氧化（ALP）活性的影响。在这些化合物中，乙基6-甲基-2-苯基-4-(4-吡啶基)-5-嘧啶羧酸酯（4b）具有AA活性（10mg/kg，腹腔注射），而乙基6-甲基-4-(3-硝基苯基)-2-苯基-5-嘧啶羧酸酯（4f）具有ALP活性（73%抑制在10μg/ml）。后者化合物（100mg/kg，腹腔注射）对大鼠花生四烯酸引起的脑水肿也有效，其效力与维生素E相当。