2-chloro-10-[(methylthio)methyl]pyrimido[1,2-a]benzimidazol-4(10H)-one | 1430744-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-chloro-10-[(methylthio)methyl]pyrimido[1,2-a]benzimidazol-4(10H)-one
• 英文别名: 2-Chloro-10-(methylsulfanylmethyl)pyrimido[1,2-a]benzimidazol-4-one；2-chloro-10-(methylsulfanylmethyl)pyrimido[1,2-a]benzimidazol-4-one
• CAS: 1430744-96-9
• 化学式: C₁₂H₁₀ClN₃OS
• 分子量: 279.75
• InChiKey: JOWSAMXGLLLRRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  哌嗪 、 2-chloro-10-[(methylthio)methyl]pyrimido[1,2-a]benzimidazol-4(10H)-one 以 乙醇 为溶剂， 反应 3.0h， 以52%的产率得到10-(Methylsulfanylmethyl)-2-piperazin-1-ylpyrimido[1,2-a]benzimidazol-4-one
  参考文献：
  名称：

  Synthesis, in vitro antiplatelet activity and molecular modelling studies of 10-substituted 2-(1-piperazinyl)pyrimido[1,2- a ]benzimidazol-4(10 H )-ones

  摘要：

  The multistep preparation of the new 10-substituted 2-(1-piperazinyl)pyrimido[1,2-a]benzimidazol-4(10H)-ones 6a-o, and of the two isomers 10-ethyl-2-(diethylamino)pyrimido[1,2-a]benzimidazol-4(10H)-one 6p and 10-ethyl-4-(diethylamino)pyrimido[1,2-a]benzimidazol-2(10H)-one 13, as well as the in vitro evaluation of their inhibitory activity on human platelet aggregation induced in platelet-rich plasma by ADP, collagen or the Ca2+ ionophore A23187 were here described. Nine out of fifteen 2-(1-piperazinyl)derivatives (6g-o) showed good inhibitory properties towards all the platelet aggregation agonists used. Moreover, a molecular modelling study has been performed on two of the best compounds of this series (6i and 6o) to confirm in silico their interactions with the catalytic site of human platelet PDE3, using the X-ray data of the PDE3B isoform in complex with an inhibitor. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.026
• 作为产物：
  描述：

  1-[(methylthio)methyl]-1H-benzimidazol-2-amine 在 盐酸 、 乙醇 、 水 、 sodium 、 三氯氧磷 作用下， 反应 5.0h， 生成 2-chloro-10-[(methylthio)methyl]pyrimido[1,2-a]benzimidazol-4(10H)-one
  参考文献：
  名称：

  Synthesis, in vitro antiplatelet activity and molecular modelling studies of 10-substituted 2-(1-piperazinyl)pyrimido[1,2- a ]benzimidazol-4(10 H )-ones

  摘要：

  The multistep preparation of the new 10-substituted 2-(1-piperazinyl)pyrimido[1,2-a]benzimidazol-4(10H)-ones 6a-o, and of the two isomers 10-ethyl-2-(diethylamino)pyrimido[1,2-a]benzimidazol-4(10H)-one 6p and 10-ethyl-4-(diethylamino)pyrimido[1,2-a]benzimidazol-2(10H)-one 13, as well as the in vitro evaluation of their inhibitory activity on human platelet aggregation induced in platelet-rich plasma by ADP, collagen or the Ca2+ ionophore A23187 were here described. Nine out of fifteen 2-(1-piperazinyl)derivatives (6g-o) showed good inhibitory properties towards all the platelet aggregation agonists used. Moreover, a molecular modelling study has been performed on two of the best compounds of this series (6i and 6o) to confirm in silico their interactions with the catalytic site of human platelet PDE3, using the X-ray data of the PDE3B isoform in complex with an inhibitor. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.026

文献信息

• Synthesis, in vitro antiplatelet activity and molecular modelling studies of 10-substituted 2-(1-piperazinyl)pyrimido[1,2- a ]benzimidazol-4(10 H )-ones
  作者：Mario Di Braccio、Giancarlo Grossi、Maria Grazia Signorello、Giuliana Leoncini、Elena Cichero、Paola Fossa、Silvana Alfei、Gianluca Damonte

  DOI：10.1016/j.ejmech.2013.01.026

  日期：2013.4

  The multistep preparation of the new 10-substituted 2-(1-piperazinyl)pyrimido[1,2-a]benzimidazol-4(10H)-ones 6a-o, and of the two isomers 10-ethyl-2-(diethylamino)pyrimido[1,2-a]benzimidazol-4(10H)-one 6p and 10-ethyl-4-(diethylamino)pyrimido[1,2-a]benzimidazol-2(10H)-one 13, as well as the in vitro evaluation of their inhibitory activity on human platelet aggregation induced in platelet-rich plasma by ADP, collagen or the Ca2+ ionophore A23187 were here described. Nine out of fifteen 2-(1-piperazinyl)derivatives (6g-o) showed good inhibitory properties towards all the platelet aggregation agonists used. Moreover, a molecular modelling study has been performed on two of the best compounds of this series (6i and 6o) to confirm in silico their interactions with the catalytic site of human platelet PDE3, using the X-ray data of the PDE3B isoform in complex with an inhibitor. (C) 2013 Elsevier Masson SAS. All rights reserved.