9-Dimethylcarbamoyl-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester | 86610-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 9-Dimethylcarbamoyl-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 9-(dimethylcarbamoyl)-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate
• CAS: 86610-89-1
• 化学式: C₁₅H₂₁N₃O₄
• 分子量: 307.349
• InChiKey: BACGLSCSGLXGMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-Dimethylcarbamoyl-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 Potassium; 9-dimethylcarbamoyl-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylate
  参考文献：
  名称：

  氮桥头化合物。38.新型抗过敏的4H-吡啶并[1,2-a]嘧啶-4-酮。3。

  摘要：

  6-甲基-4-氧代-6,7,8,9-四氢-4H-吡啶并[1,2-a]嘧啶-3-羧酸（4）对大鼠原尿被动皮肤过敏反应的弱抗过敏活性通过将适当的官能团引入到吡啶并嘧啶环的9位上，可以增强α-β。最具活性的9-取代的吡啶并嘧啶羧酸在9位上含有肟，苯氨基或（苯基氨基）硫代氧甲基。9-苯基羧酰胺基和9-苯基肼基部分可被视为吡啶并嘧啶酮系列中的生物等排基团。在9-（芳基氨基）二氢吡啶并嘧啶系列中，结构-活性关系研究揭示了与9-（芳基肼基）四氢吡啶并嘧啶类似的关系。生物学活性归因于6S对映异构体。9位的单取代芳基氨基部分对于静脉内活性是必需的。活性最高的化合物9-[（（3-乙酰基苯基）氨基] -6-甲基-4-氧代-6,7,8,9-四氢-4H-吡啶基[1,2-a]嘧啶-3-羧酸（40）在被动性皮肤过敏反应（PCA）测试中的活性是参考铬酸葡萄糖酸钠（DSCG）的三倍。

  DOI：

  10.1021/jm00364a025
• 作为产物：
  描述：

  6-甲基-4-氧代-6,7,8,9-四氢吡啶并[1,6-a]嘧啶-3-羧酸乙酯 在 丙酮 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 9-Dimethylcarbamoyl-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Structural studies on 6-methyl-9-carbamoyl-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-ones by1H,13C and15N NMR spectroscopy

  摘要：

  AbstractSeveral 6‐methyl‐9‐carbamoyltetrahydro‐4H‐pyrido[1,2‐α]pyrimidin‐4‐ones have been prepared using phosgene iminium chloride. These compounds can exist in equilibrium as the cis (3A) imine ⇌ (3B) enamine ⇌ trans (3C) imine. 1H, 13C and 15N NMR prove that the cis‐ and trans‐imine isomers are predominant in the equilibrium. 1H NMR data reveal that the share of the 3B enamine form is negligible at measurable concentrations. The isomeric ratio 3A:3C is time dependent and can be monitored by measuring the CH3C‐6 and (CH3)2N signals. The 13C NMR data show that doublets in the range 42–45 ppm for C‐9 are only compatible with the imine forms 3A and 3C. The SCS values of the CH3C‐6 and OCN(CH3)2 groups were calculated and used for identification of the cis and trans isomers. 15N NMR data show that the N‐1 chemical shift of the imine is approximately − 140 ppm for compound 3, whereas that of a fixed enamine is around − 267.8. This provides additional support for the predominance of the imine tautomers in the equilibrium 3A ⇌ 3B ⇌ 3C. 15N data allow the stereoisomers 3A and 3C to be distinguished.

  DOI：

  10.1002/mrc.1270200408

文献信息

• Structural studies on 6-methyl-9-carbamoyl-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-ones by1H,13C and15N NMR spectroscopy
  作者：Gábor Tóth、Carlos de La Cruz、István Bitter、István Hermecz、Béla Pete、Zoltán Mészáros

  DOI：10.1002/mrc.1270200408

  日期：1982.12

  AbstractSeveral 6‐methyl‐9‐carbamoyltetrahydro‐4H‐pyrido[1,2‐α]pyrimidin‐4‐ones have been prepared using phosgene iminium chloride. These compounds can exist in equilibrium as the cis (3A) imine ⇌ (3B) enamine ⇌ trans (3C) imine. 1H, 13C and 15N NMR prove that the cis‐ and trans‐imine isomers are predominant in the equilibrium. 1H NMR data reveal that the share of the 3B enamine form is negligible at measurable concentrations. The isomeric ratio 3A:3C is time dependent and can be monitored by measuring the CH3C‐6 and (CH3)2N signals. The 13C NMR data show that doublets in the range 42–45 ppm for C‐9 are only compatible with the imine forms 3A and 3C. The SCS values of the CH3C‐6 and OCN(CH3)2 groups were calculated and used for identification of the cis and trans isomers. 15N NMR data show that the N‐1 chemical shift of the imine is approximately − 140 ppm for compound 3, whereas that of a fixed enamine is around − 267.8. This provides additional support for the predominance of the imine tautomers in the equilibrium 3A ⇌ 3B ⇌ 3C. 15N data allow the stereoisomers 3A and 3C to be distinguished.
• Nitrogen bridgehead compounds. 38. New antiallergic 4H-pyrido[1,2-a]pyrimidin-4-ones. 3
  作者：Istvan Hermecz、Tibor Breining、Lelle Vasvari-Debreczy、Agnes Horvath、Zoltan Meszaros、Istvan Bitter、Christine DeVos、Ludovic Rodriguez

  DOI：10.1021/jm00364a025

  日期：1983.10

  The weak antiallergic activity of 6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (4) on the rat reaginic passive cutaneous anaphylaxis test was enhanced by the introduction of appropriate functional groups into position 9 of the pyridopyrimidine ring. The most active 9-substituted pyridopyrimidinecarboxylic acids contained an oxime, a phenylamino, or a (phenylamino)thioxomethyl

  6-甲基-4-氧代-6,7,8,9-四氢-4H-吡啶并[1,2-a]嘧啶-3-羧酸（4）对大鼠原尿被动皮肤过敏反应的弱抗过敏活性通过将适当的官能团引入到吡啶并嘧啶环的9位上，可以增强α-β。最具活性的9-取代的吡啶并嘧啶羧酸在9位上含有肟，苯氨基或（苯基氨基）硫代氧甲基。9-苯基羧酰胺基和9-苯基肼基部分可被视为吡啶并嘧啶酮系列中的生物等排基团。在9-（芳基氨基）二氢吡啶并嘧啶系列中，结构-活性关系研究揭示了与9-（芳基肼基）四氢吡啶并嘧啶类似的关系。生物学活性归因于6S对映异构体。9位的单取代芳基氨基部分对于静脉内活性是必需的。活性最高的化合物9-[（（3-乙酰基苯基）氨基] -6-甲基-4-氧代-6,7,8,9-四氢-4H-吡啶基[1,2-a]嘧啶-3-羧酸（40）在被动性皮肤过敏反应（PCA）测试中的活性是参考铬酸葡萄糖酸钠（DSCG）的三倍。