(E)-2-氰基乙基3-氨基丁-2-烯酸酯 | 88977-32-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (E)-2-氰基乙基3-氨基丁-2-烯酸酯
• 英文名称: 2-cyanoethyl 3-aminocrotonate
• 英文别名: (E)-2-Cyanoethyl 3-AMinobut-2-enoate；2-cyanoethyl (E)-3-aminobut-2-enoate
• CAS: 88977-32-6
• 化学式: C₇H₁₀N₂O₂
• 分子量: 154.169
• InChiKey: QTKRICXKOUIGOK-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-氰基乙基3-氨基丁-2-烯酸酯 以 乙醇 、 溶剂黄146 为溶剂， 反应 9.0h， 生成 bis(2-cyanoethyl) 2,6-dimethyl-4-(2-nitrosophenyl)pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Goerlitzer; Baltrusch; Goessnitzer, Pharmazie, 2000, vol. 55, # 1, p. 35 - 41

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氰基乙酰乙酸乙酯 在 ammonium hydroxide 、 溶剂黄146 作用下， 反应 2.0h， 以71%的产率得到(E)-2-氰基乙基3-氨基丁-2-烯酸酯
  参考文献：
  名称：

  Effect of Acyl Chain Length and Branching on the Enantioselectivity of Candida rugosa Lipase in the Kinetic Resolution of 4-(2-Difluoromethoxyphenyl)-Substituted 1,4-Dihydropyridine 3,5-Diesters

  摘要：

  Since 2,6-dimethyl-4-aryl-1,4-dihydropyridine 3,5-diesters themselves are not hydrolyzed by commercially available hydrolases, derivatives with spacers containing a hydrolyzable group were prepared. Seven acyloxymethyl esters of 5-methyl- and 5-(2-propoxyethyl) 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate were synthesized and subjected to Candida rugosa lipase (CRL) catalyzed hydrolysis in wet diisopropyl ether. A methyl ester at the 5-position and a long or branched acyl chain at C3 gave the highest enantiomeric ratio (E values). The most stereoselective reaction (E = 21) was obtained with 3-[(isobutyryloxy)methyl] 5-methyl 4-(2-difluoromethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, and this compound was used to prepare both enantiomers of 3-methyl 5-(2-propoxyethyl) 4-[2-(difluoromethoxy)phenyl]2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate. The absolute configuration of the enzymatically produced carboxylic acid was established to be 4R by X-ray crystallographic analysis of its 1-(R)-phenylethyl amide.

  DOI：

  10.1021/jo0104025

文献信息

• 1,4-Dihydropyridines as antagonists of platelet activating factor. 1. Synthesis and structure-activity relationships of 2-(4-heterocyclyl)phenyl derivatives
  作者：Kelvin Cooper、M. Jonathan Fray、M. John Parry、Kenneth Richardson、John Steele

  DOI：10.1021/jm00095a005

  日期：1992.8

  A novel class of 2-(4-heterocyclylphenyl)-1,4-dihydropyridines (2-38) possessing antagonist activity against platelet activating factor (PAF) was prepared by the Hantzsch synthesis from a variety of ethyl 4'-heterocyclic-substituted benzoylacetates, aryl or heteroaryl aldehydes, and substituted 3-aminocrotonamides or 3-aminocrotonate esters. Structure-activity relationships were evaluated where PAF

  利用多种4'-杂环取代的苯甲酰乙酸乙酯通过Hantzsch合成方法制备了一类对血小板活化因子（PAF）具有拮抗活性的2-（4-杂环基苯基）-1,4-二氢吡啶（2-38） ，芳基或杂芳基醛，以及取代的3-氨基巴豆酰胺或3-氨基巴豆酸酯。评估了结构活性关系，其中通过测定抑制PAF诱导的兔洗涤血小板聚集所需的化合物浓度（IC50）在体外测量PAF拮抗剂活性，并通过确定保护小鼠的口服剂量（ED50）在体内测量PAF拮抗剂活性致命注射PAF。发现二氢吡啶2位上的取代基对于体外和体内活性均很重要，而4位和5位的结构变化具有更大的灵活性。最有效的化合物是4-（2-氯苯基）-1,4-二氢-3-（乙氧羰基）-6-甲基-2- [4-（2-甲基咪唑并[4,5-c]吡啶-1-基）苯基] -5- [N-（2-吡啶基）氨基甲酰基]吡啶（17，UK-74,505），IC50 = 4.3 nM，ED50 = 0.26 mg
• Design and Synthesis of Novel α_1a Adrenoceptor-Selective Dihydropyridine Antagonists for the Treatment of Benign Prostatic Hyperplasia
  作者：Dhanapalan Nagarathnam、John M. Wetzel、Shou Wu Miao、Mohammad R. Marzabadi、George Chiu、Wai C. Wong、Xingfang Hong、James Fang、Carlos Forray、Theresa A. Branchek、William E. Heydorn、Raymond S. L. Chang、Theodore Broten、Terry W. Schorn、Charles Gluchowski

  DOI：10.1021/jm980506g

  日期：1998.12.1

  We report the synthesis and evaluation of novel alpha(1a) adrenoceptor subtype-selective antagonists. Systematic modification of the lipophilic 4,4-diphenylpiperidinyl moiety of the dihydropyridine derivatives 1 and 2 provided several highly selective and potent alpha(1a), antagonists. From this series, we identified the 4-(methoxycarbonyl)-4-phenylpiperidine analogue SNAP 5540 (-) [(-)-63] for further characterization. When examined in an isolated human prostate tissue assay, this compound was found to have a K-i of 2.8 nM, in agreement with the cloned human receptor binding data (K-i = 2.42 nM). Further evaluation of the compound in isolated dog prostate tissue showed a K-i of 3.6 nM and confirmed it to be a potent antagonist (K-b = 1.6 nM). In vivo, this compound effectively blocked the phenylephrine-stimulated increase in intraurethral pressure (IUP) in mongrel dogs, at doses which did not significantly affect the arterial pressure (diastolic blood pressure, DBP), with a DBP K-b/IUP K-b ratio of 16. In addition, (-)-63 also showed greater than 40 000-fold selectivity over the rat L-type calcium channel and 200-fold selectivity over several G protein-coupled receptors, including histamine and serotonin subtypes. These findings prove that alpha(1a) adrenoceptor-subtype selective antagonists such as (-)-63 may be developed as uroselective agents for an improved treatment of BPH over nonselective alpha(1) antagonists such as prazosin and terazosin, with fewer side effects.
• Meyer; Wehinger; Bossert, Arzneimittel-Forschung/Drug Research, 1983, vol. 33, # 1, p. 106 - 112
  作者：Meyer、Wehinger、Bossert、Scherling

  DOI：——

  日期：——
• AN IMPROVED SYNTHESIS OF HIGH-PURITY FELODIPINE
  作者：Sai-Hay Yiu、Edward E. Knaus

  DOI：10.1080/00304949609355911

  日期：1996.2
• Candida Rugosa Lipase-catalyzed Kinetic Resolution of 3-(Isobutyryloxy)methyl 4-[2-(Difluoromethoxy)phenyl]-2-methyl-5,5-dioxo-1,4-dihydrobenzothieno[3,2-b]pyridine-3-carboxylate
  作者：A. Sobolev、R. Zhalubovskis、M. C. R. Franssen、B. Vigante、B. Chekavichus、G. Duburs、Ae. de Groot

  DOI：10.1023/b:cohc.0000044578.17992.95

  日期：2004.7