methyl 2-[5-[1-(4-chlorobenzoyl)-2-(2-methylpropyl)-2H-pyridin-4-yl]tetrazol-2-yl]propanoate | 154874-51-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-[5-[1-(4-chlorobenzoyl)-2-(2-methylpropyl)-2H-pyridin-4-yl]tetrazol-2-yl]propanoate
• CAS: 154874-51-8
• 化学式: C₂₁H₂₄ClN₅O₃
• 分子量: 429.906
• InChiKey: BMNMKUVMMSDFKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  589.0±60.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[5-[1-(4-chlorobenzoyl)-2-(2-methylpropyl)-2H-pyridin-4-yl]tetrazol-2-yl]propanoate 在 氨 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 48.0h， 以47%的产率得到2-{5-[1-(4-Chloro-benzoyl)-2-isobutyl-1,2-dihydro-pyridin-4-yl]-tetrazol-2-yl}-propionamide
  参考文献：
  名称：

  Synthesis and antiinflammatory activity of 5-(1,2-dihydropyridyl)-tetrazol-2-acetic acids, esters and amides

  摘要：

  A series of 5-[4-(1,2-dihydropyridyl)]-2H-tetrazol-2-acetic acids 13-19, esters 4-12 and amides 20-22 were synthesized in order to investigate the effect of 1,2-dihydropyridyl substituents (R1 = aryl, alkyl; R2 = phenoxycarbonyl, 4-chlorobenzoyl, hydrogen) on antiinflammatory activity in the carrageenan-induced rat paw edema assay. Compounds possessing a dihydropyridyl C-2 phenyl or n-butyl substituent exhibited, in most cases, more potent activity. The dihydropyridyl N-1 substituent was a determinant of activity in both the acetic acid ester and acetic acid classes of compounds where the relative potency order was 4-chlorobenzoyl > phenoxycarbonyl. The difference in activity between acetic acid esters (R3 = OMe) and the corresponding acetic acids (R3 = OH) was usually small. A dihydropyridyl N-1 substituent is essential for activity since the N-unsubstituted compound 20 was inactive. 2-Methyl-2-{5-[4-(1-phenoxycarbonyl-2-phenyl-1,2-dihydropyridyl)]-2H-tetrazol-2-yl)acetic acid 14 was the most potent antiinflammatory agent in the group, reducing inflammation 75% (75 mg/kg po dose) relative to ibuprofen's 52% inhibition (100 mg/kg po dose) at 5 h.

  DOI：

  10.1016/0223-5234(93)90040-l
• 作为产物：
  描述：

  4-氯苯甲酰氯 以 四氢呋喃 为溶剂， 反应 1.58h， 生成 methyl 2-[5-[1-(4-chlorobenzoyl)-2-(2-methylpropyl)-2H-pyridin-4-yl]tetrazol-2-yl]propanoate
  参考文献：
  名称：

  Synthesis and antiinflammatory activity of 5-(1,2-dihydropyridyl)-tetrazol-2-acetic acids, esters and amides

  摘要：

  A series of 5-[4-(1,2-dihydropyridyl)]-2H-tetrazol-2-acetic acids 13-19, esters 4-12 and amides 20-22 were synthesized in order to investigate the effect of 1,2-dihydropyridyl substituents (R1 = aryl, alkyl; R2 = phenoxycarbonyl, 4-chlorobenzoyl, hydrogen) on antiinflammatory activity in the carrageenan-induced rat paw edema assay. Compounds possessing a dihydropyridyl C-2 phenyl or n-butyl substituent exhibited, in most cases, more potent activity. The dihydropyridyl N-1 substituent was a determinant of activity in both the acetic acid ester and acetic acid classes of compounds where the relative potency order was 4-chlorobenzoyl > phenoxycarbonyl. The difference in activity between acetic acid esters (R3 = OMe) and the corresponding acetic acids (R3 = OH) was usually small. A dihydropyridyl N-1 substituent is essential for activity since the N-unsubstituted compound 20 was inactive. 2-Methyl-2-{5-[4-(1-phenoxycarbonyl-2-phenyl-1,2-dihydropyridyl)]-2H-tetrazol-2-yl)acetic acid 14 was the most potent antiinflammatory agent in the group, reducing inflammation 75% (75 mg/kg po dose) relative to ibuprofen's 52% inhibition (100 mg/kg po dose) at 5 h.

  DOI：

  10.1016/0223-5234(93)90040-l

文献信息

• Synthesis and antiinflammatory activity of 5-(1,2-dihydropyridyl)-tetrazol-2-acetic acids, esters and amides
  作者：EE Knaus、P Kumar

  DOI：10.1016/0223-5234(93)90040-l

  日期：1993.1

  A series of 5-[4-(1,2-dihydropyridyl)]-2H-tetrazol-2-acetic acids 13-19, esters 4-12 and amides 20-22 were synthesized in order to investigate the effect of 1,2-dihydropyridyl substituents (R1 = aryl, alkyl; R2 = phenoxycarbonyl, 4-chlorobenzoyl, hydrogen) on antiinflammatory activity in the carrageenan-induced rat paw edema assay. Compounds possessing a dihydropyridyl C-2 phenyl or n-butyl substituent exhibited, in most cases, more potent activity. The dihydropyridyl N-1 substituent was a determinant of activity in both the acetic acid ester and acetic acid classes of compounds where the relative potency order was 4-chlorobenzoyl > phenoxycarbonyl. The difference in activity between acetic acid esters (R3 = OMe) and the corresponding acetic acids (R3 = OH) was usually small. A dihydropyridyl N-1 substituent is essential for activity since the N-unsubstituted compound 20 was inactive. 2-Methyl-2-5-[4-(1-phenoxycarbonyl-2-phenyl-1,2-dihydropyridyl)]-2H-tetrazol-2-yl)acetic acid 14 was the most potent antiinflammatory agent in the group, reducing inflammation 75% (75 mg/kg po dose) relative to ibuprofen's 52% inhibition (100 mg/kg po dose) at 5 h.