2-Chloro-3-[4-(morpholine-4-carbonyl)anilino]naphthalene-1,4-dione | 1372892-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Chloro-3-[4-(morpholine-4-carbonyl)anilino]naphthalene-1,4-dione
• CAS: 1372892-89-1
• 化学式: C₂₁H₁₇ClN₂O₄
• 分子量: 396.83
• InChiKey: XRXZZRULZPVOIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 4-氨基苯基吗啉-4-基甲酮 以 乙醇 为溶剂， 反应 72.0h， 以25.5%的产率得到2-Chloro-3-[4-(morpholine-4-carbonyl)anilino]naphthalene-1,4-dione
  参考文献：
  名称：

  Design and synthesis of naphthoquinone derivatives as antiproliferative agents and 20S proteasome inhibitors

  摘要：

  Fourteen naphthoquinone derivatives (1-14) were designed based on a putative proteasome inhibitor PI-083. These compounds were synthesized and evaluated against A549, DU145, KB, and KBvin tumor cell lines. Six compounds (2, 4, 8, 9, 10, and 13) showed antiproliferative activities comparable to that of PI-083. Among them, compound 8 was confirmed as a 20S proteasome inhibitor in both in vitro and cell-based assays. These findings endorse further optimization efforts based on this structural phenotype to develop potential anticancer drug candidates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.086

文献信息

• Design and synthesis of naphthoquinone derivatives as antiproliferative agents and 20S proteasome inhibitors
  作者：Kai Xu、Zhiyan Xiao、Yan Bo Tang、Li Huang、Chin-Ho Chen、Emika Ohkoshi、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2012.02.086

  日期：2012.4

  Fourteen naphthoquinone derivatives (1-14) were designed based on a putative proteasome inhibitor PI-083. These compounds were synthesized and evaluated against A549, DU145, KB, and KBvin tumor cell lines. Six compounds (2, 4, 8, 9, 10, and 13) showed antiproliferative activities comparable to that of PI-083. Among them, compound 8 was confirmed as a 20S proteasome inhibitor in both in vitro and cell-based assays. These findings endorse further optimization efforts based on this structural phenotype to develop potential anticancer drug candidates. (C) 2012 Elsevier Ltd. All rights reserved.