methyl p-[(10-dihydroartemisininoxy)methyl]benzoate

• 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: methyl p-[(10-dihydroartemisininoxy)methyl]benzoate
• 英文别名: methyl 4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoate
• 化学式: C₂₄H₃₂O₇
• 分子量: 432.514
• InChiKey: LMZFUTLREPSZGJ-NKBQRIFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl p-[(10-dihydroartemisininoxy)methyl]benzoate 以60的产率得到
  参考文献：
  名称：

  Novel antimalarial dihydroartemisinin derivatives

  摘要：

  本发明涉及新颖的双氢青蒿素衍生物，包括其药学上可以接受的盐，其在疟疾感染的预处理和后处理中具有治疗效果。

  公开号：

  US04791135A1
• 作为产物：
  描述：

  4-(羟甲基)苯甲酸甲酯 、 dihydroartemisinin 在 4-(羟甲基)苯甲酸甲酯 作用下， 以89的产率得到methyl p-[(10-dihydroartemisininoxy)methyl]benzoate
  参考文献：
  名称：

  Novel antimalarial dihydroartemisinin derivatives

  摘要：

  本发明涉及新颖的双氢青蒿素衍生物，包括其药学上可以接受的盐，其在疟疾感染的预处理和后处理中具有治疗效果。

  公开号：

  US04791135A1

文献信息

• Novel antimalarial dihydroartemisinin derivatives
  申请人：The United States of America as represented by the Secretary of the Army

  公开号：US04791135A1

  公开（公告）日：1988-12-13

  This invention relates to novel dihydroartemisinin derivatives, including their pharmaceutically-acceptable salts, which are therapeutically-effective in the pre- and post-treatment of malarial infections.

  本发明涉及新颖的双氢青蒿素衍生物，包括其药学上可以接受的盐，其在疟疾感染的预处理和后处理中具有治疗效果。
• A one-pot conversion of artemisinin to its ether derivatives
  作者：Chandan Singh、Pallavi Tiwari

  DOI：10.1016/s0040-4039(02)01607-6

  日期：2002.9

  A one-pot preparation of artemether, arteether and related antimalarial compounds from artemisinin, using NaBH4/ Amberlyst-15, is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Effects of highly active novel artemisinin–chloroquinoline hybrid compounds on β-hematin formation, parasite morphology and endocytosis in Plasmodium falciparum
  作者：Tzu-Shean Feng、Eric M. Guantai、Margo Nell、Constance E.J. van Rensburg、Kanyile Ncokazi、Timothy J. Egan、Heinrich C. Hoppe、Kelly Chibale

  DOI：10.1016/j.bcp.2011.04.018

  日期：2011.8

  4-Aminoquinolines were hybridized with artemisinin and 1,4-naphthoquinone derivatives via the Ugi-four-component condensation reaction, and their biological activities investigated. The artemisinin-containing compounds 6a-c and its salt 6c-citrate were the most active target compounds in the antiplasmodial assays. However, despite the potent in vitro activities, they also displayed cytotoxicity against a mammalian cell-line, and had lower therapeutic indices than chloroquine. Morphological changes in parasites treated with these artemisinin-containing hybrid compounds were similar to those observed after addition of artemisinin. These hybrid compounds appeared to share mechanism(s) of action with both chloroquine and artemisinin: they exhibited potent beta-hematin inhibitory activities; they caused an increase in accumulation of hemoglobin within the parasites that was intermediate between the increase observed with artesunate and chloroquine; and they also appeared to inhibit endocytosis as suggested by the decrease in the number of transport vesicles in the parasites. No cross-resistance with chloroquine was observed for these hybrid compounds, despite the fact that they contained the chloroquinoline moiety. The hybridization strategy therefore appeared to be borrowing the best from both classes of antimalarials. (C) 2011 Elsevier Inc. All rights reserved.