4-pyrrolidin-1-yl-11H-thieno[3',4':5,6]pyrimido[1,2-b]isoquinolin-11-one | 1262629-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-pyrrolidin-1-yl-11H-thieno[3',4':5,6]pyrimido[1,2-b]isoquinolin-11-one
• 英文别名: 16-pyrrolidin-1-yl-13-thia-10,17-diazatetracyclo[8.7.0.03,8.011,15]heptadeca-1,3,5,7,11,14,16-heptaen-9-one
• CAS: 1262629-32-2
• 化学式: C₁₈H₁₅N₃OS
• 分子量: 321.403
• InChiKey: HVPUFONRPRKULB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-pyrrolidin-1-yl-11H-thieno[3',4':5,6]pyrimido[1,2-b]isoquinolin-11-one 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以100%的产率得到2-(4-oxo-3,4-dihydrothieno[3,4-d]pyrimidin-2-yl)methylbenzoic acid
  参考文献：
  名称：

  Synthesis of substituted 4-aminothieno[2,3-d]-, 4-aminothieno[3,2-d]- and 4-aminothieno[3,4-d]pyrimidines

  摘要：

  A study was carried out on the nucleophilic cleavage of the lactam bond in 4-amino(pyrrolidino, piperidino, morpolino)thieno[2,3-d]-, -[3,2-d]-, and -[3,4-d]pyrimido[1,2-b]isoquinolin-11-ones. This bond is readily cleaved upon heating in methanolic NaOH at reflux for 1-2 h to give previously unreported 4-amino-2-(o-carboxyphenylmethyl)thienopyrimidines. Replacement of the amine group by an OH group is possible under the reaction conditions, leading to the corresponding, already reported 2-(o-carboxyphenylmethyl)-4-oxothienopyrimidines. Prolonged refluxing (8-12 h) resulted in oxothienopyrimidines as the major products of the transformations of all the thienopyrimido-isoquinolinones studied. Biological activity predictions of these new products were compared in silico.

  DOI：

  10.1007/s10593-012-1095-y
• 作为产物：
  描述：

  2-(4-oxo-3,4-dihydrothieno[3,4-d]pyrimidin-2-yl)methylbenzoic acid 在 吡啶 、 乙酸酐 、 三氯氧磷 作用下， 生成 4-pyrrolidin-1-yl-11H-thieno[3',4':5,6]pyrimido[1,2-b]isoquinolin-11-one
  参考文献：
  名称：

  Condensed isoquinolines. 35*. Synthesis and reactions of 4h-thieno[3′,4′:5,6]pyrimido-[1,2-b]isoquinoline-4,11(5H)-dione

  摘要：

  Derivatives of the previously unknown tetracyclic system 4H-thieno[3',4':5,6] pyrimido[1,2-b]isoquinoline- 4,11(5H)-dione have been synthesized. A comparison of the spectral characteristics and the biological activities of these compounds has been carried out, and also of their positional isomers and benzene isosteres. The differences, associated with the position of the sulfur atom, are most reflected in their electronic spectra.

  DOI：

  10.1007/s10593-010-0608-9

文献信息

• Condensed isoquinolines. 35*. Synthesis and reactions of 4h-thieno[3′,4′:5,6]pyrimido-[1,2-b]isoquinoline-4,11(5H)-dione
  作者：A. V. Zadorozhny、V. A. Kovtunenko、A. V. Turov

  DOI：10.1007/s10593-010-0608-9

  日期：2010.12

  Derivatives of the previously unknown tetracyclic system 4H-thieno[3',4':5,6] pyrimido[1,2-b]isoquinoline- 4,11(5H)-dione have been synthesized. A comparison of the spectral characteristics and the biological activities of these compounds has been carried out, and also of their positional isomers and benzene isosteres. The differences, associated with the position of the sulfur atom, are most reflected in their electronic spectra.
• Synthesis of substituted 4-aminothieno[2,3-d]-, 4-aminothieno[3,2-d]- and 4-aminothieno[3,4-d]pyrimidines
  作者：A. V. Zadorozhny

  DOI：10.1007/s10593-012-1095-y

  日期：2012.10

  A study was carried out on the nucleophilic cleavage of the lactam bond in 4-amino(pyrrolidino, piperidino, morpolino)thieno[2,3-d]-, -[3,2-d]-, and -[3,4-d]pyrimido[1,2-b]isoquinolin-11-ones. This bond is readily cleaved upon heating in methanolic NaOH at reflux for 1-2 h to give previously unreported 4-amino-2-(o-carboxyphenylmethyl)thienopyrimidines. Replacement of the amine group by an OH group is possible under the reaction conditions, leading to the corresponding, already reported 2-(o-carboxyphenylmethyl)-4-oxothienopyrimidines. Prolonged refluxing (8-12 h) resulted in oxothienopyrimidines as the major products of the transformations of all the thienopyrimido-isoquinolinones studied. Biological activity predictions of these new products were compared in silico.