N-(4-methoxyphenyl)-N-methyl-4-nitronaphthalen-1-amine | 1083178-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(4-methoxyphenyl)-N-methyl-4-nitronaphthalen-1-amine
• CAS: 1083178-70-4
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: SWECFNSQUUYHCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-溴-4-硝基萘 、 N-甲基-P-氨基苯甲醚 在 三叔丁基膦 、 palladium diacetate 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 生成 N-(4-methoxyphenyl)-N-methyl-4-nitronaphthalen-1-amine
  参考文献：
  名称：

  Discovery of (naphthalen-4-yl)(phenyl)methanones and N-methyl-N-phenylnaphthalen-1-amines as new apoptosis inducers using a cell- and caspase-based HTS assay

  摘要：

  We report the discovery of a series of (naphthalen-4-yl)(phenyl)methanones as potent inducers of apoptosis using our proprietary cell- and caspase-based ASAP HTS assay. Through SAR studies, a group of N-methyl-N-phenylnaphthalen-1-amines also were identified as potent inducers of apoptosis. (1-(Dimethylamino) naphthalen-4-yl)(4-(dimethylamino)phenyl)methanone (2a), one of the most potent analogs, had EC(50) values of 37, 49 and 44 nM in T47D, HCT116 and SNU398 cells, respectively. Compound 2a also was highly active in a growth inhibition assay with an GI(50) value of 34 nM in T47D cells. Functionally, compound 2a arrested HCT116 cells in G(2)/M followed by induction of apoptosis and inhibited tubulin polymerization. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.088

文献信息

• Discovery of (naphthalen-4-yl)(phenyl)methanones and N-methyl-N-phenylnaphthalen-1-amines as new apoptosis inducers using a cell- and caspase-based HTS assay
  作者：Songchun Jiang、Candace Crogan-Grundy、John Drewe、Ben Tseng、Sui Xiong Cai

  DOI：10.1016/j.bmcl.2008.09.088

  日期：2008.11

  We report the discovery of a series of (naphthalen-4-yl)(phenyl)methanones as potent inducers of apoptosis using our proprietary cell- and caspase-based ASAP HTS assay. Through SAR studies, a group of N-methyl-N-phenylnaphthalen-1-amines also were identified as potent inducers of apoptosis. (1-(Dimethylamino) naphthalen-4-yl)(4-(dimethylamino)phenyl)methanone (2a), one of the most potent analogs, had EC(50) values of 37, 49 and 44 nM in T47D, HCT116 and SNU398 cells, respectively. Compound 2a also was highly active in a growth inhibition assay with an GI(50) value of 34 nM in T47D cells. Functionally, compound 2a arrested HCT116 cells in G(2)/M followed by induction of apoptosis and inhibited tubulin polymerization. (C) 2008 Elsevier Ltd. All rights reserved.