蒿乙醚 | 131175-88-7

• 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
• 中文名称: 蒿乙醚
• 英文名称: α,β-arteether
• 英文别名: arteether；10-Ethoxydecahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin；(1R,4S,5R,8S,9R,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
• CAS: 131175-88-7
• 化学式: C₁₇H₂₈O₅
• 分子量: 312.406
• InChiKey: NLYNIRQVMRLPIQ-APPDHFLQSA-N

物化性质

• 沸点：
  372.4±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  2
• 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：

  蒿乙醚 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44%的产率得到Acetic acid (3aS,4R,6aS,7R,10R,10aR)-8-ethoxy-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 蒿乙醚
  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

• [EN] SINGLE POT CONVERSION OF ARTEMISININ INTO ARTEETHER<br/>[FR] CONVERSION D'ARTEMISINE EN ARTEETHER EN FOUR MONOCELLULAIRE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2004050662A1

  公开（公告）日：2004-06-17

  The present invention provides a method for the preparation of arteether from artemisinin in one pot in just about 4 hours comprising reduction of artemisinin into dihydroartemisinin by less quantity of sodium borohydride in ethanol at room temperature in the presence of a novel polyhydroxy catalyst, acylation of dihydroartemisinin in the presence of an acid catalyst, extraction of arteether from an aqueous reaction mixture using 1% ethyl acetate in n-hexane followed by workup and purification of the impure arteether to yield 80-86% (w/w) pure alpha, beta arteether.

  该发明提供了一种从青蒿素制备缬草酯的方法，该方法在一个锅中仅需约4小时，包括在室温下在乙醇中使用少量硼氢化钠将青蒿素还原为二氢青蒿素，在新型多羟基催化剂的存在下，通过酸催化剂对二氢青蒿素进行酰化，使用1%乙酸乙酯在正己烷中从水相反应混合物中提取缬草酯，然后进行处理和纯化以得到80-86%（质量百分比）纯度的α，β缬草酯。
• 一锅法制备α,β-蒿乙醚原料药的方法
  申请人：张家港威胜生物医药有限公司

  公开号：CN110835349A

  公开（公告）日：2020-02-25

  本发明属于α,β‑蒿乙醚原料药制备技术领域，具体涉及一锅法制备α,β‑蒿乙醚原料药的方法。该方法包括如下步骤：S1青蒿素在催化剂的催化作用下发生还原反应制得双氢青蒿素；S2所述双氢青蒿素以原低碳酸酯或硼酸酯为催化剂的条件下发生醚化反应，得到α,β‑蒿乙醚原料药混合物；所述醚化反应的溶剂为非极性有机溶剂与乙醇的组合；反应体系的pH值为1‑4。本发明提供的一锅法直接从青蒿素制备α，β‑蒿乙醚原料药不经过出双氢青蒿素中间体，直接得到合格α，β‑蒿乙醚原料药；反应体系回收率大于98％。
• FMO3 inhibitors for treating pain
  申请人：Akron Molecules GmbH

  公开号：EP2674161A1

  公开（公告）日：2013-12-18

  The present invention relates to new therapies to treat pain and related diseases, as well as pharmaceutical compounds for use in said therapies.

  本发明涉及治疗疼痛和相关疾病的新疗法，以及用于上述疗法的药物化合物。
• Compositions of pharmaceutical actives containing diethylene glycol monoethyl ether or other alkyl derivatives
  申请人：THEMIS MEDICARE LIMITED

  公开号：US10940205B2

  公开（公告）日：2021-03-09

  The present invention relates to pharmaceutical compositions of various pharmaceutical actives, especially lyophilic and hydrophilic actives containing Diethylene glycol monoethyl ether or other alkyl derivatives thereof as a primary vehicle and/or to pharmaceutical compositions utilizing Diethylene glycol monoethyl ether or other alkyl derivatives thereof as a primary vehicle or as a solvent system in preparation of such pharmaceutical compositions. The pharmaceutical compositions of the present invention are safe, non-toxic, exhibits enhanced physical stability compared to conventional formulations containing such pharmaceutical actives and are suitable for use as injectables for intravenous and intramuscular administration, as well as for use as a preformed solution/liquid for filling in and preparation of capsules, tablets, nasal sprays, gargles, dermal applications, gels, topicals, liquid oral dosage forms and other dosage forms.

  本发明涉及各种药物活性物质的药物组合物，特别是含有二乙二醇单乙醚或其 他烷基衍生物作为主要载体的冻干和亲水活性物质，和/或涉及利用二乙二醇单乙醚或其 他烷基衍生物作为主要载体或作为制备此类药物组合物的溶剂系统的药物组合物。本发明的药物组合物安全、无毒，与含有此类药物活性成分的传统制剂相比，具有更强的物理稳定性，适合用作静脉注射和肌肉注射的注射剂，也适合用作预制溶液/液体，用于填充和制备胶囊、片剂、鼻腔喷雾剂、漱口水、皮肤应用、凝胶、外用药、口服液剂型和其他剂型。
• 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.