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.
• Synthesis, study of 3D structures, and pharmacological activities of lipophilic nitroimidazolyl-1,4-dihydropyridines as calcium channel antagonist
  作者：Ramin Miri、Katayoun Javidnia、Hasti Sarkarzadeh、Bahram Hemmateenejad

  DOI：10.1016/j.bmc.2006.03.016

  日期：2006.7.15

  replaced by a phenyl substituent, were synthesized and evaluated as calcium channel antagonist using the high K+ contraction of guinea-pig ileal longitudinal smooth muscle. The results for asymmetrical esters showed that lengthening of the substituent in C3 ester substituent increased activity. When increasing of the length is accompanied by increasing the hindrance, the activity decreased. The results

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

  DOI：——

  日期：——