4-((4'-methoxyphenyl)amino)-7,7-dimethyl-7,8,9,10-tetrahydro-2H-benzo[h]chromen-2-one | 1265218-51-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 4-((4'-methoxyphenyl)amino)-7,7-dimethyl-7,8,9,10-tetrahydro-2H-benzo[h]chromen-2-one
• 英文别名: 4-(4-methoxyanilino)-7,7-dimethyl-9,10-dihydro-8H-benzo[h]chromen-2-one
• CAS: 1265218-51-6
• 化学式: C₂₂H₂₃NO₃
• 分子量: 349.43
• InChiKey: IIKFCESANOLRKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  C₁₅H₁₅ClO₂ 、 甲氧苯胺 以 乙二醇 为溶剂， 反应 1.0h， 生成 4-((4'-methoxyphenyl)amino)-7,7-dimethyl-7,8,9,10-tetrahydro-2H-benzo[h]chromen-2-one
  参考文献：
  名称：

  Antitumor agents 281. Design, synthesis, and biological activity of substituted 4-amino-7,8,9,10-tetrahydro-2H-benzo[h]chromen-2-one analogs (ATBO) as potent in vitro anticancer agents

  摘要：

  In our exploration of new biologically active chemical entities, we designed and synthesized a novel class of antitumor agents, substituted 4-amino-7,8,9,10-tetrahydro-2H-benzo[h]chromen-2-one (ATBO) analogs. We evaluated their cytotoxic activity against seven human tumor cell lines from different tissues, and established preliminary structure-activity relationships (SAR). All analogs, except 8, 9, and 25-27, displayed potent tumor cell growth inhibitory activity. Especially, compounds 15 and 33 with a 4-methoxyphenyl group at position C-4 were extremely potent with ED50 values of 0.008-0.064 and 0.035-0.32 mu M, respectively. Compound 15 was the most potent analog compared with structurally related neo-tanshinlactone (e. g., 1) and 4-amino-2H-benzo[h] chromen-2-one (ABO, e. g., 4) analogs, and thus merits further exploration as an anti-cancer drug candidate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.074

文献信息

• Antitumor agents 281. Design, synthesis, and biological activity of substituted 4-amino-7,8,9,10-tetrahydro-2H-benzo[h]chromen-2-one analogs (ATBO) as potent in vitro anticancer agents
  作者：Yizhou Dong、Kyoko Nakagawa-Goto、Chin-Yu Lai、Susan L. Morris-Natschke、Kenneth F. Bastow、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2010.10.074

  日期：2011.1

  In our exploration of new biologically active chemical entities, we designed and synthesized a novel class of antitumor agents, substituted 4-amino-7,8,9,10-tetrahydro-2H-benzo[h]chromen-2-one (ATBO) analogs. We evaluated their cytotoxic activity against seven human tumor cell lines from different tissues, and established preliminary structure-activity relationships (SAR). All analogs, except 8, 9, and 25-27, displayed potent tumor cell growth inhibitory activity. Especially, compounds 15 and 33 with a 4-methoxyphenyl group at position C-4 were extremely potent with ED50 values of 0.008-0.064 and 0.035-0.32 mu M, respectively. Compound 15 was the most potent analog compared with structurally related neo-tanshinlactone (e. g., 1) and 4-amino-2H-benzo[h] chromen-2-one (ABO, e. g., 4) analogs, and thus merits further exploration as an anti-cancer drug candidate. (C) 2010 Elsevier Ltd. All rights reserved.