2-Chlor-3-isovalerylamino-naphthochinon-(1.4) | 101103-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Chlor-3-isovalerylamino-naphthochinon-(1.4)
• 英文别名: N-(3-chloro-1,4-dioxo-1,4-dihydro-[2]naphthyl)-isovaleramide；N-(3-Chlor-1,4-dioxo-1,4-dihydro-[2]naphthyl)-isovaleramid；2-Chlor-3-isovalerylamino-[1,4]naphthochinon；N-(3-chloro-1,4-dioxonaphthalen-2-yl)-3-methylbutanamide
• CAS: 101103-03-1
• 化学式: C₁₅H₁₄ClNO₃
• 分子量: 291.734
• InChiKey: RYJVJXCXLHBXRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  447.6±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-3-氯-1,4-萘醌 、 异戊酰氯 反应 0.58h， 生成 2-Chlor-3-isovalerylamino-naphthochinon-(1.4) 、 N-(3-chloro-1,4-dioxonaphthalen-2-yl)-3-methyl-N-(3-methylbutanoyl)butanamide
  参考文献：
  名称：

  Synthesis and MEK1 inhibitory activities of imido-Substituted 2-chloro-1,4-naphthoquinones

  摘要：

  Mitogen activated protein kinases are of interest as research tools and as therapeutic target for certain physiological disorders. In this study, we found 2-chloro-3-(N-succinimidyl)-1,4-naphthoquinone 6 to be a selective inhibitor of MEK1 with an IC50 of 0.38 muM. An open-chain homologue, 10, showed selective cytotoxicity against renal cancer in the NCI in vitro tumor screeninQ. Structure-activity relationship study of eight compounds showed the cyclic imido-substituted chloro-1,4-naphthoquinone as more potent and selective MEK1 inhibitors than the open chain homologues. The imido-substituted chloro-1,4-naphthoquinones were synthesized in a straightforward fashion by refluxing 2-amino-3-chloro-1,4-naphthoquinone with the appropriate acid chloride or diacyl dichloride. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00267-0