5-chloro-N⁴-(2-(isopropylsulfonyl)phenyl)-N²-(8-methoxy-1-methyl-4,5-dihydro-2H-benzo[e]indazol-7-yl)pyrimidine-2,4-diamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-chloro-N⁴-(2-(isopropylsulfonyl)phenyl)-N²-(8-methoxy-1-methyl-4,5-dihydro-2H-benzo[e]indazol-7-yl)pyrimidine-2,4-diamine
• 英文别名: 5-chloro-2-N-(8-methoxy-1-methyl-4,5-dihydro-2H-benzo[e]indazol-7-yl)-4-N-(2-propan-2-ylsulfonylphenyl)pyrimidine-2,4-diamine
• 化学式: C₂₆H₂₇ClN₆O₃S
• 分子量: 539.058
• InChiKey: WAGRWRIWWPGPDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  羟基乙酸 、 5-chloro-N⁴-(2-(isopropylsulfonyl)phenyl)-N²-(8-methoxy-1-methyl-4,5-dihydro-2H-benzo[e]indazol-7-yl)pyrimidine-2,4-diamine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以20 mg的产率得到1-(7-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-8-methoxy-1-methyl-4,5-dihydro-2H-benzo[e]indazol-2-yl)-2-hydroxyethan-1-one
  参考文献：
  名称：

  Novel 2,4-diaminopyrimidines bearing fused tricyclic ring moiety for anaplastic lymphoma kinase (ALK) inhibitor

  摘要：

  In this study, a series of novel 2,4-diaminopyrimidines bearing fused tricyclic ring moiety was described for ALK inhibitor. The pyrazole, imidazole, 1,2,4-triazole, piperazine and phenanthridine moieties were employed at the 2-position of pyrimidine. Among the compounds synthesized, 28, 29, 36, and 42 showed promising anti-ALK activities in enzymatic- and cell-based assays. In vivo H3122 xenograft model study showed that compound 29 effectively suppressed ALK-driven tumor growth, similar to the extent of ceritinib, suggesting that it could be used for a novel ALK inhibitor development. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2017.03.073
• 作为产物：
  描述：

  7-甲氧基-2-萘满酮 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 硝酸 、 sodium hydride 、 一水合肼 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇乙醚 、 乙醇 、 乙酸乙酯 、 mineral oil 为溶剂， 反应 15.0h， 生成 5-chloro-N⁴-(2-(isopropylsulfonyl)phenyl)-N²-(8-methoxy-1-methyl-4,5-dihydro-2H-benzo[e]indazol-7-yl)pyrimidine-2,4-diamine
  参考文献：
  名称：

  Novel 2,4-diaminopyrimidines bearing fused tricyclic ring moiety for anaplastic lymphoma kinase (ALK) inhibitor

  摘要：

  In this study, a series of novel 2,4-diaminopyrimidines bearing fused tricyclic ring moiety was described for ALK inhibitor. The pyrazole, imidazole, 1,2,4-triazole, piperazine and phenanthridine moieties were employed at the 2-position of pyrimidine. Among the compounds synthesized, 28, 29, 36, and 42 showed promising anti-ALK activities in enzymatic- and cell-based assays. In vivo H3122 xenograft model study showed that compound 29 effectively suppressed ALK-driven tumor growth, similar to the extent of ceritinib, suggesting that it could be used for a novel ALK inhibitor development. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2017.03.073