8-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-5,9-dimethoxyphenanthridin-6(5H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-5,9-dimethoxyphenanthridin-6(5H)-one
• 英文别名: 8-[[5-Chloro-4-(2-propan-2-ylsulfonylanilino)pyrimidin-2-yl]amino]-5,9-dimethoxyphenanthridin-6-one；8-[[5-chloro-4-(2-propan-2-ylsulfonylanilino)pyrimidin-2-yl]amino]-5,9-dimethoxyphenanthridin-6-one
• 化学式: C₂₈H₂₆ClN₅O₅S
• 分子量: 580.064
• InChiKey: YRWVTRIPDNRHAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  8-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-5,9-dimethoxyphenanthridin-6(5H)-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以63%的产率得到8-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-9-methoxyphenanthridin-6(5H)-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：

  4-甲氧基-3-硝基苯甲酸 在 盐酸 、 草酰氯 、 palladium on activated carbon 、 氢气 、 palladium diacetate 、 溶剂黄146 、 三乙胺 、 silver(l) oxide 作用下， 以 甲醇 、 乙二醇乙醚 、 二氯甲烷 为溶剂， 反应 75.25h， 生成 8-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-5,9-dimethoxyphenanthridin-6(5H)-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

文献信息

• Novel 2,4-diaminopyrimidines bearing fused tricyclic ring moiety for anaplastic lymphoma kinase (ALK) inhibitor
  作者：Raghavendra Achary、Gangadhar Rao Mathi、Dong Ho Lee、Chang Soo Yun、Chong Ock Lee、Hyoung Rae Kim、Chi Hoon Park、Pilho Kim、Jong Yeon Hwang

  DOI：10.1016/j.bmcl.2017.03.073

  日期：2017.5

  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.