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Volumn , Issue 13, 2008, Pages 2133-2135

The antimalarial artemisone is an efficient heme alkylating agent

b Palumed (France)

Author keywords

Alkylation; Artemisone; Heme; Malaria; Trioxane

Indexed keywords

IRON COMPOUNDS; PORPHYRINS;

ALKYLATING AGENTS; ARTEMISININ; ARTEMISONE; HEME; HIGHER YIELD; MALARIA; REDOX ACTIVE METAL CENTERS; REDUCTIVE ACTIVATION; TRIOXANE;

REDOX REACTIONS;

EID: 53249136298 PISSN: 14341948 EISSN: 10990682 Source Type: Journal
DOI: 10.1002/ejic.200800129 Document Type: Article

Times cited : (14)

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- Analytical data for 3: MS (DCI/NH3, m/z, 402.5 [M, H, 419.5 [M, NH4, C 19H31NO6S (401.5, calcd. C 56.84, H 7.78, N 3.49; found C 56.67, H 7.61, N 3.41. 1H NMR (500 MHz, CDCl 3, δ, 5.31 (s, 1 H, 12-H, 4.24 (d, 3J 10-H,9-H, 10.3 Hz, 1 H, 10-H, 3.54-3.49 (m, 2 H, CH2, 3.43-3.38 (m, 2 H, CH2, 3.23 (m, 4 H, 2 CH2, 2.61 (m, 1 H, 9-H, 2.38 (m,1 H, 4-H, 2.03 (m,1 H, 4-H, 1.90 (m, 1 H, 5-H, 1.78-1.73 (m, 2 H, 7-H, 8-H, 1.60 (m,1 H, 8a-H, 1.56-1.44 (m, 1 H, 5-H, 1.40 (s, 3 H, 3-CH3, 0.98 (d, 3J, 6.3 Hz, 3 H, 6-CH 3, 0.83 (d, 3J, 7.2 Hz, 3 H, 9-CH3) ppm. 13C NMR (125.7 MHz, CDCl3, δ, 104.30 (C-3, 92.14 (C-10, 91.03 (C-12, 80.18 (C-12a, 51.91 (N-CH2, 51.46 (C-6a, 47.02 S-CH2
- 13C NMR spectrum reported by Haynes et al. exhibits 18 signals for only 17 different carbon atoms in compound 3 (no assignment was provided); the signal at δ = 174.2 ppm (absent from our spectrum), cannot be likely assigned to a carbon atom of artemisone. Such a chemical shift is usual for a carbonyl function (acid, ester, amide) which does not exist in artemisone. In addition, we detected only two signals at δ = 90-92 ppm, and not three as reported by Haynes et al. These signals have been assigned by 2D correlations to C-10 and C-12 (δ = 92.14 and 91.03 ppm, respectively). The signal of C-12a, at the junction of four cycles, was detected at δ = 80.18 ppm. The article by Haynes et al. does not report any signal at this chemical shift.

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