10β-[2-(N(4),N(8)-di-tert-butoxycarbonylspermidine)-2-oxoethyl]deoxoartemisinin | 1226460-64-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 10β-[2-(N(4),N(8)-di-tert-butoxycarbonylspermidine)-2-oxoethyl]deoxoartemisinin
• 英文别名: tert-butyl N-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-N-[3-[[2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]acetyl]amino]propyl]carbamate
• CAS: 1226460-64-5
• 化学式: C₃₄H₅₉N₃O₉
• 分子量: 653.857
• InChiKey: GXXLHASEPPTDDK-LQYHIAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  10β-[2-(N(4),N(8)-di-tert-butoxycarbonylspermidine)-2-oxoethyl]deoxoartemisinin 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以89%的产率得到10β-[2-(N(1)-spermidine)-2-oxoethyl]deoxoartemisinin dihydrochloride
  参考文献：
  名称：

  Design, synthesis and antimalarial/anticancer evaluation of spermidine linked artemisinin conjugates designed to exploit polyamine transporters in Plasmodium falciparum and HL-60 cancer cell lines

  摘要：

  A series of artemisinin-spermidine conjugates designed to utilise the upregulated polyamine transporter found in cancer cells have been prepared. These conjugates were evaluated against human promyelocytic leukaemia HL-60 cells and chloroquine-sensitive 3D7 Plasmodium falciparum and several show promising anticancer and antimalarial activity. Although some limitations in this vector-based approach are apparent, a number of high potency Boc-protected analogues were identified with activity against malaria parasites as low as 0.21 nM. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.035
• 作为产物：
  描述：

  N1,N5-双-Boc-亚精胺 、 2-((3R, 5aS, 6R, 8aS, 9R,10R, 12R, 12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)acetic acid 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.17h， 以66%的产率得到10β-[2-(N(4),N(8)-di-tert-butoxycarbonylspermidine)-2-oxoethyl]deoxoartemisinin
  参考文献：
  名称：

  Design, synthesis and antimalarial/anticancer evaluation of spermidine linked artemisinin conjugates designed to exploit polyamine transporters in Plasmodium falciparum and HL-60 cancer cell lines

  摘要：

  A series of artemisinin-spermidine conjugates designed to utilise the upregulated polyamine transporter found in cancer cells have been prepared. These conjugates were evaluated against human promyelocytic leukaemia HL-60 cells and chloroquine-sensitive 3D7 Plasmodium falciparum and several show promising anticancer and antimalarial activity. Although some limitations in this vector-based approach are apparent, a number of high potency Boc-protected analogues were identified with activity against malaria parasites as low as 0.21 nM. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.035

文献信息

• Design, synthesis and antimalarial/anticancer evaluation of spermidine linked artemisinin conjugates designed to exploit polyamine transporters in Plasmodium falciparum and HL-60 cancer cell lines
  作者：James Chadwick、Michael Jones、Amy E. Mercer、Paul A. Stocks、Stephen A. Ward、B. Kevin Park、Paul M. O’Neill

  DOI：10.1016/j.bmc.2010.02.035

  日期：2010.4

  A series of artemisinin-spermidine conjugates designed to utilise the upregulated polyamine transporter found in cancer cells have been prepared. These conjugates were evaluated against human promyelocytic leukaemia HL-60 cells and chloroquine-sensitive 3D7 Plasmodium falciparum and several show promising anticancer and antimalarial activity. Although some limitations in this vector-based approach are apparent, a number of high potency Boc-protected analogues were identified with activity against malaria parasites as low as 0.21 nM. (C) 2010 Elsevier Ltd. All rights reserved.