82596-30-3

Basic information

• Product Name: anhydrodihydroartemisinin
• Synonyms: anhydrodihydroartemisinin;(+)-9,10-AnhydrodehydroarteMisinin;(3R,5aS,6R,8aS,12R,12aR)-3,4,5,5a,6,7,8,8a-Octahydro-3,6,9-triMethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin;9,10-Anhydro-10-deoxoarteMisinin;9,10-AnhydrodehydroarteMisinin;Anhydrod
• CAS NO: 82596-30-3
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33278
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 82596-30-3.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: anhydrodihydroartemisinin(CAS DataBase Reference)
• NIST Chemistry Reference: anhydrodihydroartemisinin(82596-30-3)
• EPA Substance Registry System: anhydrodihydroartemisinin(82596-30-3)

Safety Data

• Hazardous Substances Data: 82596-30-3(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Anhydrodihydroartemisinin is a semisynthetic derivative of Artersiminin (A777500). Anhydrodihydroartemisinin is a decomposition product of Artesunate (A777800) and Dihydroartemisinin (D448360). Anhydrodihydroartemisinin showed antimalarial activity although much weaker than its parent compound.

Upstream product

• 39093-93-1 thiomorpholine 1,1-dioxide 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 71939-50-9 dihydroartemisinin 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 
• 2759-28-6 1-phenylmethylpiperazine 
• 255731-10-3 10α-(trimethylsilyloxy)dihydroartemisinin 
• 140658-34-0 10β-(trimethylsilyloxy)dihydroartemisinin 
• 163381-14-4 (5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl benzoate 
• 151-10-0 1,3-Dimethoxybenzene 
• 82596-25-6 10α-dihydroartemisinyl benzoate 
• 621-23-8 1,2,3-trimethoxybenzene 
• 75887-51-3 dihydroartemisinin acetate 
• 3976-69-0 Methyl (R)-3-hydroxybutyrate 
• 53562-86-0 (S)-3-hydroxybutyric acid methyl ester 

Downstream Products

• 255730-18-8 4-[(3R,5aS,6R,8aS,9R,10R,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl]thiomorpholine 1,1-dioxide 
• 458535-73-4 10β-benzenesulfonyl-9-epi-dihydroartemisinin 
• 128052-60-8 C₂₁H₂₇BrFNO₄ 
• 127997-42-6 C₂₁H₂₇BrFNO₄ 
• 127997-43-7 C₂₁H₂₈BrNO₄ 
• 75887-54-6 artemotil 
• 101020-89-7 dehydroqinghaosu 

Relevant articles and documents

Stereoselective Access to Antimelanoma Agents by Hybridization and Dimerization of Dihydroartemisinin and Artesunic acid

A library of five hybrids and six dimers of dihydroartemisinin and artesunic acid has been synthetized in a stereo-controlled manner and evaluated for the anticancer activity against metastatic melanoma cell line (RPMI7951). Among novel derivatives, three artesunic acid dimers showed antimelanoma activity and cancer selectivity, being not toxic on normal human fibroblast (C3PV) cell line. Among the three dimers, the one bearing 4-hydroxybenzyl alcohol as a spacer showed no cytotoxic effect (CC50>300 μM) and high antimelanoma activity (IC50=0.05 μM), which was two orders of magnitude higher than that of parent artesunic acid, and of the same order of commercial drug paclitaxel. In addition, this dimer showed cancer-type selectivity towards melanoma compared to prostate (PC3) and breast (MDA-MB-231) tumors. The occurrence of a radical mechanism was hypothesized by DFO and EPR analyses. Qualitative structure activity relationships highlighted the role of artesunic acid scaffold in the control of toxicity and antimelanoma activity.

Evaluation and optimization of synthetic routes from dihydroartemisinin to the alkylamino-artemisinins artemiside and artemisone: A test of N-glycosylation methodologies on a lipophilic peroxide

10-Alkylamino-artemisinins including artemiside and artemisone display enhanced activities against malaria. Earlier, dihydroartemisinin (DHA) TMS ether was converted by trimethylsilyl bromide into the 10-β-bromide that with amine nucleophiles provided the amino-artemisinins. In an attempt to develop more economic approaches, direct N-glycosylation of DHA was examined but 2-deoxyartemisinin was invariably obtained. However, hydroxyl group activation by conversion into the 10β-halide in non-polar solvents with anhydrous HCl and Group I and II metal halides, oxalyl chloride or thionyl chloride with catalytic DMSO, and oxalyl bromide did succeed. The β-halides were converted in situ by thiomorpholine into artemiside, and by thiomorpholine-1,1-dioxide into artemisone respectively in scalable reactions. Hydrogen peroxide-acetonitrile or the urea-hydrogen peroxide complex efficiently oxidized the sulfide artemiside to the sulfone artemisone. Overall, a generalized approach to 10-alkylamino-artemisinins is now available.

C1O-modified artemisinin derivatives: Efficient heme-alkylating agents

(Chemical Equation Presented) Discussion is reopened regarding C10-substituted derivatives of the peroxide-based antimalarial agent artemisinin (see picture); they are shown to react readily with iron(II)-heme to provide heme-drug adducts in high yields.