7-(3-fluorophenyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione | 1217272-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 7-(3-fluorophenyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione
• 英文别名: 7-(3-Fluorophenyl)-1,3-dimethylpurine-2,6-dione
• CAS: 1217272-92-8
• 化学式: C₁₃H₁₁FN₄O₂
• 分子量: 274.254
• InChiKey: SUIVXUQQRXEQJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(3-fluorophenyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione 、 4-bromo-3-methoxy-N,N-dimethylaniline 在 copper(l) iodide 、 palladium diacetate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以57%的产率得到8-(4-(dimethylamino)-2-methoxyphenyl)-7-(3-fluorophenyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione
  参考文献：
  名称：

  Fluorescent phosphoinositide 3-kinase inhibitors suitable for monitoring of intracellular distribution

  摘要：

  The monitoring of the drug behavior and distribution in biological system can provide information whether drug reaches its desired target, and a biological rationale for the design of new therapeutics. We have developed a family of potent fluorescent PI3K alpha inhibitors in which part of the fluorophore was engineered to be a pharmacophore capable of inhibiting PI3K alpha. These xanthine derivatives are characterized by a donor-acceptor molecular structure, and changes in the electronic properties of the two variation points at R-1 and R-2 give rise to notable bathochromic shifts in the lambda(em), (abs) and increase the value of Phi(F). Further, we illustrated the use of E2 (PI3K alpha/IC50 = 0.068 mu M, T47D cell viability: IC50 = 0.9 mu M) to block cancer cell proliferation and to monitor its subcellular localization by fluorescence microscopy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.025
• 作为产物：
  描述：

  茶碱 、 3-氟苯基硼酸 在 吡啶 、 copper diacetate 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以44%的产率得到7-(3-fluorophenyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione
  参考文献：
  名称：

  Development of New Fluorescent Xanthines as Kinase Inhibitors

  摘要：

  An efficient and versatile synthetic approach for the preparation of highly substituted xanthine derivatives has been developed by a combination of direct N7- and C8-arylation. With this method, diverse xanthine analogues were prepared and potent kinase inhibitors could be identified. For example, compound 8a Inhibits PI3Ks and proliferation in T47D tumor cells. In addition, these xanthine-based kinase inhibitors exhibited significant fluorescence emission in a concentration-dependent response.

  DOI：

  10.1021/ol100011n