Brief Article
Journal of Medicinal Chemistry, 2010, Vol. 53, No. 11 4559
141.1, 141.0, 130.0, 127.7, 127.6, 127.5, 127.4, 111.7, 110.8
(C-O-O-C), 63.7 (CH), 62.0 (CH), 57.4 (S-C), 44.4, 44.2,
44.1, 41.5, 41.4, 39.9, 38.1, 38.0, 37.9, 37.2, 36.2, 35.2, 35.1,
30.2, 29.8, 28.7, 28.3, 27.3, 26.4, 25.3. IR (neat)/cm-1 3336
(NH), 2973, 1689 (CdO), 1627 (CdC), 1419, 1164, 1049, 844.
HRMS (ESI): 675.3184 [M þ H]þ, C35H48N4O623NaS requires
675.3192. Anal. C35H48N4O6S requires C: 64.39% H: 7.41%
N: 8.58%. Found C: 64.71% H: 7.64% N: 8.35%
Supporting Information Available: Full experimental details
References
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10β-(3-(Aminomethyl)benzyl)acetamide)deoxoartemisinin Biotin
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DMF (3 mL) and EDIPA (1.1 equiv) was added NHS-SS-Biotin 18
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crystalline solid. 1H NMR (400 MHz, MeOD) δ7.29-7.17 (4H, m,
4 ꢀ CH), 5.51 (1H, s, H-12), 4.63 (1H, m, CH), 4.51-4.32 (7H, m),
4.28 (1H, dd, J = 7.8, 4.4 Hz, CH), 3.45 (2H, t, J = 6.8 Hz, CH2),
3.18 (1H, m, CH), 2.98 (2H, t, J = 7.1 Hz, CH2), 2.90 (1H, dd, J =
12.8, 5.0 Hz, CH2), 2.81 (2H, t, J = 8.5 Hz, CH2), 2.76-1.20 (26 H,
m), 0.97 (3H, d, J = 6.4 Hz, 6-CH3), 0.91 (3H, J = 7.5 Hz, 9-CH3).
13C NMR (100 MHz, MeOD) δ 176.6 (CON), 174.0 (CON), 164.6
(CdO), 139.5, 134.4, 130.1, 127.9, 127.7, 105.3 (C-3), 90.6 (C-12),
75.3, 63.7 (C-S), 62.0 (HN-CH) 54.3 (HN-CH), 46.3, 44.5, 39.8,
39.0, 38.8, 37.9, 37.3, 37.1, 37.0, 36.1, 35.6, 34.7, 30.1, 29.8, 27.4,
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quires C: 57.60% H: 7.13% N: 8.40%. Found C: 57.42% H: 7.28%
N: 8.55%.
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5-Adamantane-3-(amidomethyl)benzylcarbamate-2-spiro-10-
20-4-trioxaspiro[4.5]decane 4-(Sulfamoylbiotin) 26. Trioxolane
amine 16 (88 mg, 0.2 mmol) in anhydrous DMF (5 mL) at 0 °C
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4.57 (2H, s, CH2), 4.43-4.39 (1H, m, CH), 4.36-4.33 (2H, t, J =
5.4 Hz, CH2), 4.20-4.16 (1H, m, CH), 2.24 (2H, td, J = 7.2, 2.0
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180.0 (CONH), 176.1 (NHCO), 168.7 (NHCO), 166.4 (CdO),
141.4 (C-SO2), 140.5 (C-CO2NH), 130.0, 129.7, 129.3, 127.6, 127.5,
127.0, 126.9, 111.6 (O-C-O),110.8 (O-C-O), 63.6 (HN-CH),
61.9 (HN-CH), 57.2 (C-S), 44.9 (CH2), 44.1 (CH2), 44.0 (CH2),
41.4, 41.0, 39.9, 38.0, 37.9, 37.4, 36.2, 36.1, 35.1, 35.0, 29.8, 29.7,
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Acknowledgment. This work was supported by grants from
the BBSRC (UK) (P.O.N., V.B., S.A.W.; BB/C006321/1, BBS/
B/05508, BBS/Q/Q/2004/06032, and BBS/S/P/2003/10353)
and in part by the EU (Antimal. FP6Malaria Drugs Initiative).