n-propyl 3-aminocrotonate | 53055-18-8

• 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: n-propyl 3-aminocrotonate
• 英文别名: 2-Butenoic acid, 3-amino-, propyl ester；propyl (E)-3-aminobut-2-enoate
• CAS: 53055-18-8
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: DIWWDNJUKATEGY-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  n-propyl 2-(3-nitrobenzylidene)acetoacetate 、 n-propyl 3-aminocrotonate 生成 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid dipropyl ester
  参考文献：
  名称：

  MEYER H.; BOSSERT F.; WEHINGER E.; STOEPEL K.; VATER W., ARZNEIMITTEL-FORSCH., 1981, 31, NO 3, 407-409

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酸正丙酯 在 乙酸铵 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 n-propyl 3-aminocrotonate
  参考文献：
  名称：

  亲脂性硝基咪唑-1,4-二氢吡啶类化合物作为钙通道拮抗剂的合成，3D结构研究和药理活性。

  摘要：

  QSAR研究表明硝苯地平类似物的效力取决于亲脂性，DHP环上每个位置的电子术语和分离的术语。DHP的C3，C4和C5位置的取代模式变化会改变效能，组织选择性和1,4-DHP环的构象。在该项目中，硝苯地平新衍生物的一组烷基酯类似物，其中第4位的邻硝基苯基被1-甲基-5-硝基-2-咪唑基取代基取代，第6位的甲基为合成并被豚鼠回肠纵向平滑肌的高K +收缩评估为钙通道拮抗剂，并将其评估为钙通道拮抗剂。不对称酯的结果表明，C3酯取代基中取代基的延长增加了活性。当长度的增加伴随着障碍的增加时，活性降低。结果表明，所有化合物与参考药物硝苯地平相比，活性更高或相似。

  DOI：

  10.1016/j.bmc.2006.03.016

文献信息

• Structure−Activity Relationships of 4-(Phenylethynyl)-6-phenyl-1,4- dihydropyridines as Highly Selective A₃ Adenosine Receptor Antagonists
  作者：Ji-long Jiang、A. Michiel van Rhee、Louis Chang、Abraham Patchornik、Xiao-duo Ji、Patricia Evans、Neli Melman、Kenneth A. Jacobson

  DOI：10.1021/jm970091j

  日期：1997.8.1

  (Trifluoromethyl)-, nitro-, and other benzyl esters substituted with electron-withdrawing groups were specific for A3 receptors with nanomolar Ki values and selectivity as high as 37000-fold. A functionalized congener bearing an [(aminoethyl)amino]carbonyl group was also prepared as an intermediate in the synthesis of biologically active conjugates.

  4-(苯乙炔基)-6-苯基-1,4-二氢吡啶衍生物是人 A3 腺苷受体的选择性拮抗剂，与 [125I]AB-MECA (N6-(4-amino-3-碘苄基）-5'-（N-甲基氨基甲酰基）腺苷）在亚微摩尔范围内。在本研究中，综合探讨了二氢吡啶环不同位置（3-和5-酰基取代基、4-芳基取代基和1-甲基）的构效关系。利用1-乙氧基甲基和5-[2-(三甲基甲硅烷基)乙基]酯基团的联合保护，在5位形成游离羧酸，允许各种取代。确定新类似物对克隆人 A3 腺苷受体的选择性与大鼠脑 A1 和 A2A 受体上放射性配体的结合。腺苷受体的结构活性分析表明，4 位的吡啶基、呋喃基、苯并呋喃基和噻吩基最多只能对 A3 腺苷受体产生中等选择性。与4-苯乙烯基取代的二氢吡啶不同，4-苯乙炔基的环取代（例如4-硝基）没有提供增强的选择性。在二氢吡啶环的 3 位，酯对 A3 受体的选择性比密切相关的硫酯、酰胺和酮衍生物高得多。环状
• Synthesis of 3-[(2,3-dihydro-1,1,3-trioxo-1,2-benzisothiazol-2-yl)alkyl] 1,4-dihydropyridine-3,5-dicarboxylate derivatives as calcium channel modulators
  作者：Carlos E. Sunkel、Miguel Fau de Casa-Juana、Luis Santos、Antonio G. Garcia、Cristina R. Artalejo、Mercedes Villarroya、M. Antonia Gonzalez-Morales、Manuela G. Lopez、Javier Cillero

  DOI：10.1021/jm00091a008

  日期：1992.6

  1,4-Dihydropyridine (DHP) derivatives with a 1,2-benzisothiazol-3-one 1,1-dioxide group, linked through an alkylene bridge to the C-3 carboxylate of the DHP ring, with both vasconstricting and vasorelaxant properties were obtained. In blocking Ca2+-evoked contractions of K+-depolarized rabbit aortic strips, compounds 12 and 41 were 10-fold more potent than nifedipine; 27 other compounds were 1-4-fold more potent. Their vascular versus cardiac selectivity was very pronounced; for instance, the selectivity index for compound 41 was 70-fold higher than that of nifedipine. This was also true for the vasoconstricting compound 22, which was as potent as Bay K 8644 in enhancing the Ca2+-evoked contractions of rabbit aorta strips, yet it had poor inotropic activity in rabbit left atria. Oral adminstration of compounds 38, 40, 43, and 53 (20 mg/kg) caused a 35-37% decrease in systolic blood pressure in spontaneously hypertensive rats (SHR); these effects were similar to those of nifedipine. However, iv administration of these compounds to anesthetized SHR caused a decrease in blood pressure which was more pronounced and long-lasting than that of nifedipine. When administered iv at 100-mu-g/kg, the vasoconstricting compound 22 caused a 40% increase in systolic and diastolic blood pressure. Compound 22 exhibited an unusually interesting feature over the other five Ca2+ DHP agonists: it had diester substitutions at the C-3 and C-5 positions of the DHP ring. Overall, compounds processing these properties might be useful in treating clinical cardiovascular conditions in which DHP Ca2+ antagonists or agonists are indicated.