Ethyl 4-[6-(4,5-dihydro-1,3-thiazol-2-yl)-2,2-dimethyl-3-oxo-1,4-benzoxazin-4-yl]butanoate | 205818-56-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: Ethyl 4-[6-(4,5-dihydro-1,3-thiazol-2-yl)-2,2-dimethyl-3-oxo-1,4-benzoxazin-4-yl]butanoate
• CAS: 205818-56-0
• 化学式: C₁₉H₂₄N₂O₄S
• 分子量: 376.477
• InChiKey: VYSGXQYXWLXTCL-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  589.8±60.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  93.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二甲胺 、 Ethyl 4-[6-(4,5-dihydro-1,3-thiazol-2-yl)-2,2-dimethyl-3-oxo-1,4-benzoxazin-4-yl]butanoate 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以90%的产率得到4-[6-(4,5-dihydro-1,3-thiazol-2-yl)-2,2-dimethyl-3-oxo-1,4-benzoxazin-4-yl]-N,N-dimethylbutanamide
  参考文献：
  名称：

  Synthesis by microwave irradiation of a substituted benzoxazine parallel library with preferential relaxant activity for guinea pig trachealis

  摘要：

  An efficient, facile, and practical parallel combinatorial synthesis of substituted-benzoxazines under microwave irradiation was described. The procedure involved the use of a microwave oven especially designed for organic synthesis suitable for parallel synthesis of solution libraries. A demonstration 19-membered library of substituted N,N-dimethyl- and N-methyl-benzoxazine amide derivatives, structurally related to the potassium channel opener cromakalim, was generated by both conventional and microwave procedures, achieving a reduction from 7 h to 30-36 min in library generation time for the microwave approach. All the synthesized compounds were tested using the in vitro models of rat aorta and guinea pig trachea rings pre-contracted with phenylephrine and carbachol, respectively. All N,N-dimethyl amide derivatives showed a relaxant activity higher on guinea pig trachea rings than on rat aorta rings. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.05.003
• 作为产物：
  描述：

  2,2-Dimethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile 在 sodium hydride 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 Ethyl 4-[6-(4,5-dihydro-1,3-thiazol-2-yl)-2,2-dimethyl-3-oxo-1,4-benzoxazin-4-yl]butanoate
  参考文献：
  名称：

  新的1，4-苯并恶嗪衍生物钾通道开放剂的合成及其血管舒张活性。

  摘要：

  作为寻找新的钾通道开放剂的一部分，描述了衍生自克罗马卡林的苯并吡喃骨架的新的1,4-苯并恶嗪衍生物的合成和血管舒张活性。几种新的1,4-苯并恶嗪衍生物具有明显的血管舒张活性，其总体药理行为类似于CRK（1f，1i，2d，2e，2f和2i）。

  DOI：

  10.1016/s0968-0896(02)00091-3

文献信息

• Synthesis and vasorelaxant activity of new 1,4-benzoxazine derivatives potassium channel openers
  作者：Giuseppe Caliendo、Elisa Perissutti、Vincenzo Santagada、Ferdinando Fiorino、Beatrice Severino、Roberta d'Emmanuele di Villa Bianca、Laura Lippolis、Aldo Pinto、Raffaella Sorrentino

  DOI：10.1016/s0968-0896(02)00091-3

  日期：2002.8

  As part of a search for new potassium channel openers, the synthesis and vasorelaxant activity of new 1,4-benzoxazine derivatives derived from transformation of the benzopyran skeleton of cromakalim were described. Several new 1,4-benzoxazine derivatives were provided with significant vasorelaxant activity with an overall pharmacological behavior similar to CRK (1f, 1i, 2d, 2e, 2f and 2i).

  作为寻找新的钾通道开放剂的一部分，描述了衍生自克罗马卡林的苯并吡喃骨架的新的1,4-苯并恶嗪衍生物的合成和血管舒张活性。几种新的1,4-苯并恶嗪衍生物具有明显的血管舒张活性，其总体药理行为类似于CRK（1f，1i，2d，2e，2f和2i）。
• Synthesis by microwave irradiation of a substituted benzoxazine parallel library with preferential relaxant activity for guinea pig trachealis
  作者：Giuseppe Caliendo、Elisa Perissutti、Vincenzo Santagada、Ferdinando Fiorino、Beatrice Severino、Donatella Cirillo、Roberta d’Emmanuele di Villa Bianca、Laura Lippolis、Aldo Pinto、Raffaella Sorrentino

  DOI：10.1016/j.ejmech.2004.05.003

  日期：2004.10

  An efficient, facile, and practical parallel combinatorial synthesis of substituted-benzoxazines under microwave irradiation was described. The procedure involved the use of a microwave oven especially designed for organic synthesis suitable for parallel synthesis of solution libraries. A demonstration 19-membered library of substituted N,N-dimethyl- and N-methyl-benzoxazine amide derivatives, structurally related to the potassium channel opener cromakalim, was generated by both conventional and microwave procedures, achieving a reduction from 7 h to 30-36 min in library generation time for the microwave approach. All the synthesized compounds were tested using the in vitro models of rat aorta and guinea pig trachea rings pre-contracted with phenylephrine and carbachol, respectively. All N,N-dimethyl amide derivatives showed a relaxant activity higher on guinea pig trachea rings than on rat aorta rings. (C) 2004 Elsevier SAS. All rights reserved.