2-benzyloxyethyl 3-aminocrotonate | 112057-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzyloxyethyl 3-aminocrotonate
• 英文别名: 3-amino-but-2-enoic acid 2-benzyloxy-ethyl ester；2-(Benzyloxy)ethyl 3-aminobut-2-enoate；2-phenylmethoxyethyl 3-aminobut-2-enoate
• CAS: 112057-63-3
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: PREAUXZPFMFTLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzyloxyethyl 3-aminocrotonate 、 2-<1-(2-nitrobenzylidene)acetonyl>-2-oxo-1,3,2-dioxaphosphorinane 以 异丙醇 为溶剂， 反应 20.0h， 以72%的产率得到2-benzyloxyethyl 2,6-dimethyl-4-(2-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis and antihypertensive activities of 1,4-dihydropyridine-5-phosphonate derivatives. II.

  摘要：

  合成了一系列1,4-二氢吡啶-5-环状磷酸酯衍生物，作为1,4-二氢吡啶-3,5-二羧酸钙拮抗剂的类似物，并对其抗高血压活性进行了检查。几种化合物在降低正常血压和自发性高血压大鼠（SHR）的血压方面被证明具有优于或可比于硝苯地平的活性。在这些化合物中，甲基2,6-二甲基-5-(2-氧-1,3,2-二氧磷烷-2-基)-4-(2-硝基苯基)-1,4-二氢吡啶-3-羧酸酯（31，DHP-218）在SHR中的活性约为硝苯地平的7倍，并被选为进一步开发和临床评估的候选化合物。讨论了结构-活性关系。

  DOI：

  10.1248/cpb.35.4144

文献信息

• Synthesis and antihypertensive activities of 1,4-dihydropyridine-5-phosphonate derivatives. I.
  作者：IWAO MORITA、SHIN-ICHI TADA、KATSUTOSHI KUNIMOTO、MASAMI TSUDA、MASAHIRO KISE、KIYOSHI KIMURA

  DOI：10.1248/cpb.35.3898

  日期：——

  A series of phosphonate derivatives, designed as analogues of 1, 4-dihydropyridine-3, 5- dicarboxylates in which a phosphonate group was introduced instead of the carboxylate group at the 5-position, was synthesized, and their antihypertensive activities were examined. Among the compounds examined, 5-diallyloxyphosphinyl-1, 4-dihydropyridine-3-carboxylates were most effective in lowering the blood pressure in normotensive rats and spontaneously hypertensive rats (SHR). The phosphonate derivatives are considered to be close analogues of the carboxylate derivatives. The structure-activity relationships are discussed.

  一系列膦酸盐衍生物被设计为1,4-二氢吡啶-3,5-二羧酸盐的类似物，其中在5-位引入了膦酸基团而非羧酸基团，这些化合物被合成并检测了它们的降血压活性。在所研究的化合物中，5-二烯丙氧基膦基-1,4-二氢吡啶-3-羧酸盐在降低正常血压大鼠和自发性高血压大鼠（SHR）的血压方面最为有效。这些膦酸盐衍生物被认为是羧酸盐衍生物的近似类似物。结构-活性关系在此进行了讨论。
• Synthetic Studies on Cardiovascular Agents. IV. Synthesis of Fused Dihydropyridine Derivatives
  作者：YASUNOBU SATO、YASUO SHIMOJI、HIROSHI FUJITA、HIROSHI MIZUNO、SEIJI KUMAKURA

  DOI：10.1248/yakushi1947.98.4_448

  日期：——
• Synthesis and antihypertensive activities of 1,4-dihydropyridine-5-phosphonate derivatives. II.
  作者：IWAO MORITA、KATSUTOSHI KUNIMOTO、MASAMI TSUDA、SHIN-ICHI TADA、MASAHIRO KISE、KIYOSHI KIMURA

  DOI：10.1248/cpb.35.4144

  日期：——

  A series of 1, 4-dihydropyridine-5-cyclic phosphonate derivatives, designed as analogues of 1, 4- dihydropyridine-3, 5-dicarboxylate calcium antagonists, was synthesized and examined for antihypertensive activity. Several compounds were proved to have activities superior or comparable to that of nifedipine in lowering blood pressure in normotensive and spontaneously hypertensive rats (SHR). Among these compounds, methyl 2, 6-dimethyl-5- (2-oxo-1, 3, 2-dioxaphosphorinan-2-yl) -4- (2-nitrophenyl) -1, 4-dihydropyridine-3-carboxylate (31, DHP-218) was approximately 7 times more active than nifedipine in SHR and was selected for further development and clinical evaluation. The structure-activity relationships are discussed.

  合成了一系列1,4-二氢吡啶-5-环状磷酸酯衍生物，作为1,4-二氢吡啶-3,5-二羧酸钙拮抗剂的类似物，并对其抗高血压活性进行了检查。几种化合物在降低正常血压和自发性高血压大鼠（SHR）的血压方面被证明具有优于或可比于硝苯地平的活性。在这些化合物中，甲基2,6-二甲基-5-(2-氧-1,3,2-二氧磷烷-2-基)-4-(2-硝基苯基)-1,4-二氢吡啶-3-羧酸酯（31，DHP-218）在SHR中的活性约为硝苯地平的7倍，并被选为进一步开发和临床评估的候选化合物。讨论了结构-活性关系。