2-(4-oxo-3,4-dihydrothieno[3,4-d]pyrimidin-2-yl)methylbenzoic acid | 1262585-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 2-(4-oxo-3,4-dihydrothieno[3,4-d]pyrimidin-2-yl)methylbenzoic acid
• 英文别名: 2-(4-Oxo-3,4-dihydrothieno[3,4-d]pyrimidin-2-yl)methylbenzoic acid；2-[(4-oxo-3H-thieno[3,4-d]pyrimidin-2-yl)methyl]benzoic acid
• CAS: 1262585-96-5
• 化学式: C₁₄H₁₀N₂O₃S
• 分子量: 286.311
• InChiKey: UOWFSGUGTJUFDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-oxo-3,4-dihydrothieno[3,4-d]pyrimidin-2-yl)methylbenzoic acid 在 吡啶 、 sodium methylate 、 乙酸酐 、 三氯氧磷 作用下， 生成 4-methylthio-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
• 作为产物：
  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

文献信息

• Synthesis of substituted 4-oxo-3,4-dihydro-thieno[3,4-d]pyrimidines and comparison of their properties with those of positionally isomeric thienopyrimidinones and benzo isosteres
  作者：A. V. Zadorozhny、A. V. Turov、V. A. Kovtunenko

  DOI：10.1007/s10593-010-0613-z

  日期：2010.12

  compared with analogous substituted 2,3-dimethylthieno[2,3-d][pyrimidinones, thieno[3,2-d]pyrimidinones, and their benzene isosteres. The differences associated with the position of the sulfur atom, are most clearly reflected in the electronic spectra. On the basis of calculated data, the transition from derivatives of 4-oxo-3,4-benzopyrimidines to their analogous thieno isosteres leads to changes in the

  从2-氰基甲基苯甲酸和3-氨基-4-噻吩碳酸甲酯开始合成2-芳基甲基和2-芳基甲基-3-甲基取代的3,4-二氢噻吩并[3,4-d]嘧啶-4-酮，得到通过一种新方法从其盐酸盐中原位提取，可提高所需产物的收率。已将合成的化合物的理化性质和生物学潜力与类似的取代的2,3-二甲基噻吩并[2,3-d]嘧啶酮，噻吩并[3,2-d]嘧啶酮及其苯系等排物进行了比较。与硫原子位置有关的差异在电子光谱中最清楚地反映出来。根据计算的数据，从4-氧代-3,4-苯并嘧啶的衍生物过渡到类似的硫杂环丁烷，导致其生物学活性的变化。
• 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.