2-(2-Hydrazinyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)propan-2-ol | 1415660-22-8

• 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-(2-Hydrazinyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)propan-2-ol
• CAS: 1415660-22-8
• 化学式: C₁₃H₁₉N₅O₂S
• 分子量: 309.392
• InChiKey: HELHTDROERAIBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(2-Hydrazinyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)propan-2-ol 、 3-(3-Formyl-indol-1-ylmethyl)-benzonitrile 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以73%的产率得到3-[[3-[(E)-[[6-(2-hydroxypropan-2-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]hydrazinylidene]methyl]indol-1-yl]methyl]benzonitrile
  参考文献：
  名称：

  Design, synthesis and 3D-QSAR analysis of novel 2-hydrazinyl-4-morpholinothieno[3,2-d]pyrimidine derivatives as potential antitumor agents

  摘要：

  A series of 2-hydrazinyl-4-morpholinothieno[3,2-d]pyrimidine derivatives were synthesized and evaluated for their cytotoxic activities against five cancer cell lines. Most of them exhibited moderate to significant cytotoxic activities and high-selectivity against one or more cell lines, and nearly all of them had higher potency than positive controls against MDA-MB-231 cell line. The most promising compound 15f showed strong cytotoxic activities against H460, HT-29 and MDA-MB-231 cell lines, which were 1.7- to 66.5-folds more active than 2-(1H-Indazol-4-yl)-6-((4-(methylsulfonyl)-1-piperazinyl)methyl)-4-(4-morpholinyl)thieno[3,2-d]pyrimidine(GDC-0941). To investigate the SARs of thieno[3,2-d]pyrimidine derivatives in more details, CoMFA (q(2) = 0.436, r(2) = 0.937) and CoMSIA (q(2) = 0.706, r(2) = 0.947) models on H460 cell line were established. The generated 3D-QSAR models can be used for further rational design of novel thienopyrimidines as highly potent and selective cytotoxic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.002
• 作为产物：
  描述：

  2-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)propan-2-ol 在 一水合肼 作用下， 反应 5.0h， 以79%的产率得到2-(2-Hydrazinyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)propan-2-ol
  参考文献：
  名称：

  Design, synthesis and 3D-QSAR analysis of novel 2-hydrazinyl-4-morpholinothieno[3,2-d]pyrimidine derivatives as potential antitumor agents

  摘要：

  A series of 2-hydrazinyl-4-morpholinothieno[3,2-d]pyrimidine derivatives were synthesized and evaluated for their cytotoxic activities against five cancer cell lines. Most of them exhibited moderate to significant cytotoxic activities and high-selectivity against one or more cell lines, and nearly all of them had higher potency than positive controls against MDA-MB-231 cell line. The most promising compound 15f showed strong cytotoxic activities against H460, HT-29 and MDA-MB-231 cell lines, which were 1.7- to 66.5-folds more active than 2-(1H-Indazol-4-yl)-6-((4-(methylsulfonyl)-1-piperazinyl)methyl)-4-(4-morpholinyl)thieno[3,2-d]pyrimidine(GDC-0941). To investigate the SARs of thieno[3,2-d]pyrimidine derivatives in more details, CoMFA (q(2) = 0.436, r(2) = 0.937) and CoMSIA (q(2) = 0.706, r(2) = 0.947) models on H460 cell line were established. The generated 3D-QSAR models can be used for further rational design of novel thienopyrimidines as highly potent and selective cytotoxic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.002