162791-23-3

Basic information

• Product Name: 11-Azaartemisinin
• Synonyms: 11-Azaartemisinin ;(3R,5aS,6R,8aS,9R,12R,12aR)-Decahydro-3,6,9-triMethyl-3,12-epoxy-1,2-dioxepino[4,3-i]isoquinolin-10(3H)-one
• CAS NO: 162791-23-3
• Molecular Formula: C₁₅H₂₃NO₄
• Molecular Weight: 281.34742
• Product Categories: Chiral Reagents;Drug Analogues;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents, Drug Analogues, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 162791-23-3.mol

Chemical Properties

• Boiling Point: 431.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly)
• PKA: 14.49±0.70(Predicted)
• CAS DataBase Reference: 11-Azaartemisinin(CAS DataBase Reference)
• NIST Chemistry Reference: 11-Azaartemisinin(162791-23-3)
• EPA Substance Registry System: 11-Azaartemisinin(162791-23-3)

Safety Data

• Hazardous Substances Data: 162791-23-3(Hazardous Substances Data)

Usage

Uses

A nontoxic analog of Artemisinin

Upstream product

• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 

Relevant articles and documents

Synthesis and reactions of 11-azaartemisinin and derivatives

11-Azaartemisinin was prepared in 45% yield in a one pot, two-step sequence from the reaction of artemisinin with excess ammonia followed by acid treatment. Analogous reactions of artemisinin with primary alkylamines gave N-alkylazaartemisinins in similar yields.

Ring opening of artemisinin (Qinghaosu) and dihydroartemisinin and interception of the open hydroperoxides with formation of N-oxides - A chemical model for antimalarial mode of action

In CH2Cl2 in the presence of benzylamine, artemisinin transfers an oxygen atom from the intermediate open hydroperoxide to tertiary amines to form N-oxides and N-benzyl-11-azadesoxyartemisinin. Base-catalyzed side reactions interfere

Synthesis and anticancer activity of novel aza-artemisinin derivatives

Three series of aza-artemisinin derivatives were synthesized for studies of anticancer activity. The first series of compounds were prepared via copper(I)-catalyzed azide alkyne cycloaddition, so called “click reaction”, starting from propargyl derivative

Syntheses and antimalarial activities of N-substituted 11-azaartemisinins

A two-step reaction sequence between artemisinin and methanolic ammonia followed by treatment with Amberlyst 15 yielded 11-azaartemisinin in 65% yield. Substituting a variety of primary alkyl- and heteroaromatic amines for ammonia in the reaction sequence yields N-substituted 11-azaartemisinins in similar or greater yield. When Amberlyst 15 is replaced by a mixture of sulfuric acid/silica gel, both 11-azaartemisinin and the expected metabolite, 10-azadesoxyartemisinin, are formed in 45% and 15% yields, respectively. In vitro and in vivo test data for a number of novel N-substituted 11- azaartemisinins, against drug-resistant strains of Plasmodium falciparum, show they possess antimalarial activities equal to or greater than that of artemisinin. The most active derivative, N-(2'-acetaldehydo)-11- azaartemisinin, 17, was 26 times more active in vitro and 4 times more active in vivo than artemisinin.

Activities of 11-Azaartemisinin and N-Sulfonyl Derivatives against Asexual and Transmissible Malaria Parasites

Dihydroartemisinin (DHA), either used in its own right or as the active drug generated in vivo from the other artemisinins in current clinical use—artemether and artesunate—induces quiescence in ring-stage parasites of Plasmodium falciparum (Pf). This ind

Synthesis and Anticancer Activity of 11-azaartemisinin Derivatives Bearing 1,2,3-triazole Moiety

[Figure not available: see fulltext.] A series of new compounds were prepared under mild reaction conditions using click reaction of 11-azaartemisinin and various azides. All the synthesized compounds were fully characterized by spectral data and evaluated for their cytotoxic activity against KB and HepG2 cell lines. All synthesized artemisinin derivatives are more active than 11-azaartemisinin. Thirteen of the synthesized compounds displayed good cytotoxic activity against two human cancer cell lines, KB and HepG2, with half maximal inhibitory concentration values in a range of 4.27–70.40 μM. The most active derivative was the best to both KB and HepG2 cell lines with IC50 value of 10.18 and 4.27 μM, respectively.

New products from the reactions of artemisinin with ammonia and amines

Reaction of artemisinin (1) with ammonia, methylamine, dimethylamine, and allylamine afforded five unexpected products 2-6, in addition to the previously reported compounds 7-12. The identities of the new compounds were established from their spectral data, by chemical derivatization and by comparison with published reports. The stereochemistries of compounds 5 and 6 were confirmed by single-crystal X-ray analysis.