Arteether

Artemotil (β-Arteether) is a fast acting blood schizonticide specifically indicated for the treatment of chloroquine-resistant Plasmodium falciparum malaria and cerebral malaria cases. Target:Artemotil is a semi-synthetic derivative of artemisinin, a natural product of the Chinese plant Artemisia annua.

Artemotil is an artemisinin derivative.|Artemotil, also known as β-arteether, is a semi-synthetic derivative of artemisinin and a fast acting blood schizonticide specifically indicated for the treatment of chloroquine-resistant Plasmodium falciparum malaria and cerebral malaria cases.

Artemisinin (100 g.) and polyhydroxy catalyst, phloroglucinol (400 mg.) were stirred in ethanol. Sodium borohydride (65 mg.) was added slowly to the reaction mixture and the same was stirred for 2 hours at room temperature (20-23° C.). After completion of the reduction step, chlorotrimethysilane (0.8 ml) was added and the reaction mixture was further stirred for 2 hours at room temperature to complete the reaction. Work up and purification of the crude product by preparative TLC yielded 74percent w/w a mixture of alpha and beta arteether.Artemisinin (100 g.) and polyhydroxy catalyst, dextrose (500 mg.) were stirred in ethanol (10 ml) for 5 minutes. Sodium borohydride (65 mg.) was added slowly to the reaction mixture and the same was stirred for 1.25 hours at room temperature (20-23° C.). After completion of the reduction step, p-toluene sulphonic acid (300 mg.) was added and the reaction mixture was completed in 4 hours at room temperature. After usual work up and purification by preparative TLC, the impure reaction product yielded 53percent w/w a mixture of alpha and beta arteether.Dihydroartemisinin (25 g, 0.088 mole), ethanol (75 ml) and triethyl ortho formate (50 ml / 44.55 g = 0.301 mole) were stirred at ambient temperature for 15 minutes. The reaction mixture was cooled to 10-15°C and acetyl chloride (0.24 ml / 0.265 g =0.0034 mole) was added. Stirring was continued at 10-15°C for another 3hs or till the end of the reaction (monitoring by TLC). The reaction mixture was diluted with sodium bicarbonate solution (0.25g in 150 ml water). The reaction mass was then cooled to 0°C-5°C and stirred for 2 hours. The precipitated product was filtered and washed with ethanol: water (1 :1, 2 X 25 ml). The product was suck-dried and then recrystallised from ethanol: water (1:1) to get the title product as white crystalline solid. Yield: 19.6g, (71.38percent); m.p.: 81°C-84°C; [α]D20: +155° to +157° (2percent solution in dehydrated ethanol). HPLC purity > 99percent1HNMR : δ 0.91 (doublet, 3H), δ 0.96 (doublet, 3H), δ 1.16-1.18 (triplet, 3H), δ 1.21-1.34 (multiplet, 3H), δ 1.44 (singlet, 3H), δ 1.47-1.62 (multiplet, 2H), δ 1.65-1.66 (multiplet, IH), δ 1.7-1.91 (multiplet, 3H), δ 2.01-2.06 (multiplet, IH), δ 2.32-2.38 (multiplet, IH), δ 2.62-2.64 (multiplet, IH), δ 3.43 3.86 (multiplet, 2H), δ 4.80 (doublet, IH), δ 5.41 (singlet, IH)Artemisinin (100 g.) and polyhydroxy catalyst, galactose (300 mg.) were stirred in ethanol (5 ml) for 5 minutes. Sodium borohydride (60 mg.) was added slowly to the reaction mixture and the same was stirred for 1.5 hours at room temperature (20-23° C.). After completion of the reduction step, liquid acid catalyst chlorotrimethysilane (0.35 ml) was added and the reaction mixture was further stirred for 2 hours to complete the reaction. After usual work up and purification by preparative TLC, the impure reaction product afforded 62percent w/w of a mixture of alpha and beta arteether

Derivative of Artemisinin. Antimalarial

Molecular Weight:312.4
XLogP3:3.4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:312.19367399
Monoisotopic Mass:312.19367399
Topological Polar Surface Area:46.2
Heavy Atom Count:22
Complexity:443
Defined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes