4-[4-(4-bromo-2-isopropyl-6-methylphenylamino)pyrimidin-4-ylamino]benzonitrile | 943827-02-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[4-(4-bromo-2-isopropyl-6-methylphenylamino)pyrimidin-4-ylamino]benzonitrile
• 英文别名: 4-[[4-(4-Bromo-2-methyl-6-propan-2-ylanilino)pyrimidin-2-yl]amino]benzonitrile
• CAS: 943827-02-9
• 化学式: C₂₁H₂₀BrN₅
• 分子量: 422.327
• InChiKey: ZDEMOVBEHFGPGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[4-(4-bromo-2-isopropyl-6-methylphenylamino)pyrimidin-4-ylamino]benzonitrile 、 丙烯腈 在 palladium diacetate 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙腈 为溶剂， 生成 (Z)-4-{4-[4-(2-cyanovinyl)-2-isopropyl-6-methylphenylamino]pyrimidin-2-ylamino}benzonitrile 、 4-{4-[4-(2-Cyano-vinyl)-2-isopropyl-6-methyl-phenylamino]-pyrimidin-2-ylamino}-benzonitrile
  参考文献：
  名称：

  Synthesis of novel diarylpyrimidine analogues of TMC278 and their antiviral activity against HIV-1 wild-type and mutant strains

  摘要：

  Novel diarylpyrimidines (DAPY), which represent next generation of non-nucleoside reverse transcriptase inhibitors (NNRTIs), were synthesized and their activities against human immunodeficiency virus type I (HIV-1) assessed. Modulations at positions 2 and 6 of the left phenyl ring generated interesting derivatives of TMC278 displaying high potency against wild-type and mutant viruses compared to nevirapine and efavirenz. The pharmacokinetic profile of the best newly synthesized DAPY was evaluated and compared with TMC278 now in phase II clinical trials. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.11.014
• 作为产物：
  描述：

  2-甲基-6-异丙苯胺 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 3.17h， 生成 4-[4-(4-bromo-2-isopropyl-6-methylphenylamino)pyrimidin-4-ylamino]benzonitrile
  参考文献：
  名称：

  Synthesis of novel diarylpyrimidine analogues of TMC278 and their antiviral activity against HIV-1 wild-type and mutant strains

  摘要：

  Novel diarylpyrimidines (DAPY), which represent next generation of non-nucleoside reverse transcriptase inhibitors (NNRTIs), were synthesized and their activities against human immunodeficiency virus type I (HIV-1) assessed. Modulations at positions 2 and 6 of the left phenyl ring generated interesting derivatives of TMC278 displaying high potency against wild-type and mutant viruses compared to nevirapine and efavirenz. The pharmacokinetic profile of the best newly synthesized DAPY was evaluated and compared with TMC278 now in phase II clinical trials. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.11.014