2-chloro-3-[3-(2-oxo-pyrrolidin-1-yl)-propylamino]-[1,4]naphthoquinone | 1044642-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-[3-(2-oxo-pyrrolidin-1-yl)-propylamino]-[1,4]naphthoquinone
• 英文别名: 2-Chloro-3-[3-(2-oxopyrrolidin-1-yl)propylamino]naphthalene-1,4-dione
• CAS: 1044642-92-3
• 化学式: C₁₇H₁₇ClN₂O₃
• 分子量: 332.787
• InChiKey: XCYPTXXOANJQED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 1-(3-氨基丙基)-2-吡咯烷酮 以 乙醇 为溶剂， 反应 72.0h， 以43.6%的产率得到2-chloro-3-[3-(2-oxo-pyrrolidin-1-yl)-propylamino]-[1,4]naphthoquinone
  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

• Diamine derivatives of quinone and uses thereof
  申请人：Padia K. Janak

  公开号：US20050032794A1

  公开（公告）日：2005-02-10

  Diamine derivatives of quinones, and related compounds, including salts thereof, that modulate the levels of gene expression in cellular systems, such as cancer cells, are disclosed, along with methods for preparing such compounds and derivatives, as well as pharmaceutical compositions containing these compounds and derivatives as active ingredients. Methods of using these as compounds and derivatives as therapeutic agents are also described.

  公开了喹喔醌的二胺衍生物及相关化合物，包括其盐，这些化合物在细胞系统（如癌细胞）中调节基因表达水平，同时公开了制备这些化合物和衍生物的方法，以及含有这些化合物和衍生物作为活性成分的药物组合物。还描述了将这些化合物和衍生物用作治疗剂的方法。
• 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.