artemether | 82638-05-9

• 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: artemether
• 英文别名: (1R,4S,5R,8S,9R,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
• CAS: 82638-05-9
• 化学式: C₁₆H₂₆O₅
• 分子量: 298.379
• InChiKey: SXYIRMFQILZOAM-LRNQLFNOSA-N

物化性质

• 沸点：
  357.5±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  artemether 在 Amberlyst A-21 、 (乙氧基羰基甲基)三苯基氯化膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.03h， 以45%的产率得到Acetic acid (3aS,4R,6aS,7R,10R,10aR)-8-methoxy-4,7-dimethyl-octahydro-furo[3,2-i]isochromen-10-yl ester
  参考文献：
  名称：

  Kalita, Biswajit; Barua, Nabin C.; Bez, Ghanashyam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 10, p. 2622 - 2624

  摘要：

  DOI：
• 作为产物：
  描述：

  青蒿素 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 26.0h， 生成 artemether
  参考文献：
  名称：

  Antimalarial activity of new water-soluble dihydroartemisinin derivatives

  摘要：

  The usefulness of sodium artesunate (3), a water-soluble derivative of artemisinin (1), is impaired by its poor stability in aqueous solution. To overcome the ease of hydrolysis of the ester group in 3, a new series of derivatives of dihydroartemisinin (2) was prepared in which the solubilizing moiety, which contains a carboxylate group, is joined to dihydroartemisinin by an ether rather than an ester linkage. The new derivatives were prepared in good yield by treatment of dihydroartemisinin with an appropriate alcohol under boron trifluoride etherate catalysis at room temperature. All major condensation products are the beta isomer. Hydrolysis of the esters with 2.5% KOH/MeOH gave the corresponding potassium salts, which were converted to free acids (8b-d) by acidification. The derivatives were tested in vitro against two clones of human malaria, Plasmodium falciparum D-6 (Sierra Leone clone) and W-2 (Indochina clone). No cross-resistance to the antimalarial agents mefloquine, chloroquine, pyrimethamine, sulfadoxine, and quinine was observed. In general, the new compounds are more effective against the W-2 than the D-6 strain. Esters (5a-d) possess activity comparable to that of the parent compounds 1 and 2; however, conversion of the esters to their corresponding carboxylates (7a-d) or acids (8b-d), with the exception of artelinic acid (8d), drastically decreases the antimalarial activities in both cell lines. Artelinic acid, which is both soluble and stable in 2.5% K2CO3 solution, possesses superior in vivo activity against Plasmodium berghei than artemisinin or artesunic acid.

  DOI：

  10.1021/jm00394a037

文献信息

• Electronically stabilized versions of the antimalarial acetal trioxanes artemether and artesunate
  作者：Gary H. Posner、William A. Maio、Alvin S. Kalinda

  DOI：10.1016/j.bmc.2008.03.010

  日期：2008.5

  From 9-substituted DHA, several new artemisinin-derived C-10 acetal ethers and esters were prepared with either a 9-fluoro or a 9-sulfonyl substituent. The very strong inductive electron-withdrawing C-9 substituent is shown to retard considerably C-10 ionization (acid-promoted etherification) of 9-fluoro-DHA and 9-sulfonyl-DHA. (C) 2008 Elsevier Ltd. All rights reserved.
• LIN, AI JENG;KLAYMAN, DANIEL L.;MILHOUS, WILBUR K., J. MED. CHEM., 30,(1987) N 11, 2147-2150
  作者：LIN, AI JENG、KLAYMAN, DANIEL L.、MILHOUS, WILBUR K.

  DOI：——

  日期：——
• METHODS OF CANCER TREATMENT
  申请人：Ferro Therapeutics, Inc.

  公开号：US20200138829A1

  公开（公告）日：2020-05-07

  The present disclosure relates to a method of treating a subject with cancer with a ferroptosis inducer, including use of the ferroptosis inducer in combination with a second therapeutic agent.