ethyl 2-(m-tolylamino)-6-methyl-4-(4-methylpiperazin-1-yl)furo[2,3-d]pyrimidine-5-carboxylate | 1256270-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: ethyl 2-(m-tolylamino)-6-methyl-4-(4-methylpiperazin-1-yl)furo[2,3-d]pyrimidine-5-carboxylate
• 英文别名: Ethyl 6-methyl-2-(3-methylanilino)-4-(4-methylpiperazin-1-yl)furo[2,3-d]pyrimidine-5-carboxylate
• CAS: 1256270-83-3
• 化学式: C₂₂H₂₇N₅O₃
• 分子量: 409.488
• InChiKey: XHPPPQPVUOYTHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-甲基哌嗪 、 ethyl 4-chloro-6-methyl-2-(m-tolylamino)-furo[2,3-d]pyrimidine-5-carboxylate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以80%的产率得到ethyl 2-(m-tolylamino)-6-methyl-4-(4-methylpiperazin-1-yl)furo[2,3-d]pyrimidine-5-carboxylate
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of some 2,4-diamino-furo[2,3-d]pyrimidine derivatives

  摘要：

  The carbodiimides 2, obtained from aza-Wittig reactions of iminophosphorane 1 with aromatic isocyanates, reacted with ammonia to give ethyl 3,4-dihydro-6-methyl-4-oxo-2-arylamino-furo[2,3-d]pyrimidine-5-carboxylate 3. Further reaction of 3 with POCl3 and various amines generated ethyl 4-alkylamino-2-arylamino-6-methyl-furo[2,3-d]pyrimidine-5-carboxylate 5 in good yields. Their structures were confirmed by H-1 NMR, EI-Ms, IR and elemental analysis. Compound 5b was further analyzed by single crystal X-ray diffraction. Compound 5 exhibited cytotoxicity against two lung cancer cell lines. For example, compound 5a showed the best inhibition activities against A459 with IC50 0.8 mu M. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.122

文献信息

• Efficient synthesis and biological evaluation of some 2,4-diamino-furo[2,3-d]pyrimidine derivatives
  作者：Yang-Gen Hu、Yan Wang、Shi-Ming Du、Xiao-Bao Chen、Ming-Wu Ding

  DOI：10.1016/j.bmcl.2010.08.122

  日期：2010.11

  The carbodiimides 2, obtained from aza-Wittig reactions of iminophosphorane 1 with aromatic isocyanates, reacted with ammonia to give ethyl 3,4-dihydro-6-methyl-4-oxo-2-arylamino-furo[2,3-d]pyrimidine-5-carboxylate 3. Further reaction of 3 with POCl3 and various amines generated ethyl 4-alkylamino-2-arylamino-6-methyl-furo[2,3-d]pyrimidine-5-carboxylate 5 in good yields. Their structures were confirmed by H-1 NMR, EI-Ms, IR and elemental analysis. Compound 5b was further analyzed by single crystal X-ray diffraction. Compound 5 exhibited cytotoxicity against two lung cancer cell lines. For example, compound 5a showed the best inhibition activities against A459 with IC50 0.8 mu M. (C) 2010 Elsevier Ltd. All rights reserved.