2-[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid phenethyl ester | 61312-48-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid phenethyl ester
• 英文别名: 2-phenylethyl (2E)-2-[(3-nitrophenyl)methylidene]-3-oxobutanoate
• CAS: 61312-48-9
• 化学式: C₁₉H₁₇NO₅
• 分子量: 339.348
• InChiKey: NMYXYYJBJVESLU-QGOAFFKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-amino-3-butylthiophene-2-carboxylate 、 2-[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid phenethyl ester 、 叔丁醇 以57%的产率得到
  参考文献：
  名称：

  ADACHI, IKUO;YAMAMORI, TERUO;HIRAMATSU, YOSHIHARU;SAKAI, KATSUNORI;MIHARA+, CHEM. AND PHARM. BULL., 36,(1988) N1, C. 4389-4402

  摘要：

  DOI：

文献信息

• Studies on dihydropyridines. III. Synthesis of 4,7-dihydrothieno(2,3-b)pyridines with vasodilator and antihypertensive activities.
  作者：IKUO ADACHI、TERUO YAMAMORI、YOSHIHARU HIRAMATSU、KATSUNORI SAKAI、SHIN-ICHI MIHARA、MASARU KAWAKAMI、MASAO MASUI、OSAMU UNO、MOTOHIKO UEDA

  DOI：10.1248/cpb.36.4389

  日期：——

  A series of 4-aryl-4, 7-dihydrothieno [2, 3-b] pyridine-5-carboxylate derivatives (I) was synthesized and tested for binding affinity to Ca2+ channels in rat cerebral cortex membranes, coronary vasodilator effect in isolated guinea pig hearts, and antihypertensive activity in spontaneously hypertensive rats.Several compounds had potent coronary vasodilator and antihypertensive activities.The structure-ctivity relationships of the series indicated that a lipophilic 3-alkyl substituent with moderate bulkiness was effective for enhancing the pharmacological potencies.Among them, methyl 4, 7-dihydro-3-isobuty1-6-methy1-4-(3-nitrophenyl) thieno [2, 3-b] pyridine-5-carboxylate (S-312) was selected as a promising cardiovascular agent.The relationship between the absolute configuration of S-312 and its biological activities is also presented.

  合成了一系列4-芳基-4, 7-二氢噻吩[2, 3-b]吡啶-5-羧酸酯衍生物(I)，并测试了它们对大鼠大脑皮层膜中Ca2+通道的结合亲和力、在离体豚鼠心脏中的冠状动脉扩张作用以及在自发性高血压大鼠中的抗高血压活性。若干化合物具有强大的冠状动脉扩张和抗高血压活性。该系列的结构-活性关系表明，具有适中体积的脂溶性3-烷基取代基对增强药理效能是有效的。其中，甲基4, 7-二氢-3-异丁基-6-甲基-4-(3-硝基苯基)噻吩[2, 3-b]吡啶-5-羧酸酯(S-312)被选为一个有前景的心血管药物。还介绍了S-312的绝对构型与其生物活性之间的关系。
• ADACHI, IKUO;YAMAMORI, TERUO;HIRAMATSU, YOSHIHARU;SAKAI, KATSUNORI;MIHARA+, CHEM. AND PHARM. BULL., 36,(1988) N1, C. 4389-4402
  作者：ADACHI, IKUO、YAMAMORI, TERUO、HIRAMATSU, YOSHIHARU、SAKAI, KATSUNORI、MIHARA+

  DOI：——

  日期：——