(S)-(cyano)(p-bromophenyl)methyl 12β-deoxo-deoxy-artemisinyl ether

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (S)-(cyano)(p-bromophenyl)methyl 12β-deoxo-deoxy-artemisinyl ether
• 英文别名: (2S)-2-(4-bromophenyl)-2-[[(1S,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.04,13.08,13]pentadecan-10-yl]oxy]acetonitrile
• 化学式: C₂₃H₂₈BrNO₄
• 分子量: 462.384
• InChiKey: PYZUEJMPLJDROW-UPLZKIGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dihydroartemisinin 在 Acidic catalyst 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 (S)-(cyano)(p-bromophenyl)methyl 12β-deoxo-deoxy-artemisinyl ether
  参考文献：
  名称：

  Synthesis and cytotoxicity of dihydroartemisinin ethers containing cyanoarylmethyl group

  摘要：

  A new type of ether of dihydroartemisinin containing cyano and aryl groups was prepared and tested for cytotoxicity to A549, P388, L1210 and HT29 cells using the MTT assay. 12k and 121 were the most cytotoxic compounds. 13 lacking the peroxy group showed a 1000-fold less potency than 121. Similarly, the inactive compound 14 indicated that the position of cyano groups was also important. Flow cytometry data showed that the compounds caused an accumulation of P388 cells in the G(1)-phase of the cell cycle. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00538-2

文献信息

• Novel antitumor artemisinin derivatives targeting G1 phase of the cell cycle
  作者：Ying Li、Feng Shan、Jin-Ming Wu、Guang-Shao Wu、Jian Ding、Dong Xiao、Wei-Yi Yang、Ghanem Atassi、Stéphane Léonce、Daniel-Henri Caignard、Pierre Renard

  DOI：10.1016/s0960-894x(00)00578-3

  日期：2001.1

  Modification of artemisinin structure led us to the discovery of a novel class of antitumor compounds. These artemisinin derivatives containing cyano and aryl groups showed potent antiproliferative effect in vitro against P388 and A549 cells. This activity was reflected in P388 murine leukemia by an accumulation of cells in G1 phase, and induction of apoptosis. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and cytotoxicity of dihydroartemisinin ethers containing cyanoarylmethyl group
  作者：Ying Li、Jin-Ming Wu、Feng Shan、Guang-Shao Wu、Jian Ding、Dong Xiao、Jia-Xian Han、Ghanem Atassi、Stéphane Leonce、Daniel-Henri Caignard、Pierre Renard

  DOI：10.1016/s0968-0896(02)00538-2

  日期：2003.3

  A new type of ether of dihydroartemisinin containing cyano and aryl groups was prepared and tested for cytotoxicity to A549, P388, L1210 and HT29 cells using the MTT assay. 12k and 121 were the most cytotoxic compounds. 13 lacking the peroxy group showed a 1000-fold less potency than 121. Similarly, the inactive compound 14 indicated that the position of cyano groups was also important. Flow cytometry data showed that the compounds caused an accumulation of P388 cells in the G(1)-phase of the cell cycle. (C) 2002 Elsevier Science Ltd. All rights reserved.