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Res. Rev."},{"key":"10.1016\/j.bmcl.2007.12.074_bib2_3","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1016\/S1054-3589(08)60952-7","volume":"37","author":"Cumming","year":"1997","journal-title":"Adv. Pharmacol."},{"key":"10.1016\/j.bmcl.2007.12.074_bib2_4","doi-asserted-by":"crossref","first-page":"1681","DOI":"10.3987\/REV-98-505","volume":"51","author":"Bhattacharya","year":"1999","journal-title":"Heterocycles"},{"key":"10.1016\/j.bmcl.2007.12.074_bib2_5","doi-asserted-by":"crossref","first-page":"1661","DOI":"10.1016\/S0020-7519(02)00195-9","volume":"32","author":"Borstnik","year":"2002","journal-title":"Int. J. Parasitol."},{"key":"10.1016\/j.bmcl.2007.12.074_bib2_6","doi-asserted-by":"crossref","first-page":"329","DOI":"10.1016\/j.actatropica.2003.10.006","volume":"89","author":"Ploypradith","year":"2004","journal-title":"Acta Trop."},{"key":"10.1016\/j.bmcl.2007.12.074_bib2_7","doi-asserted-by":"crossref","first-page":"2945","DOI":"10.1021\/jm030571c","volume":"47","author":"O\u2019Neill","year":"2004","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2007.12.074_bib2_8","doi-asserted-by":"crossref","first-page":"425","DOI":"10.1002\/med.10066","volume":"24","author":"Tang","year":"2004","journal-title":"Med. Res. Rev."},{"key":"10.1016\/j.bmcl.2007.12.074_bib2_9","first-page":"866","volume":"5","author":"Jefford","year":"2004","journal-title":"Curr. Opin. Invest. Drugs"},{"key":"10.1016\/j.bmcl.2007.12.074_bib2_10","doi-asserted-by":"crossref","first-page":"487","DOI":"10.1016\/j.drudis.2007.04.009","volume":"12","author":"Jefford","year":"2007","journal-title":"Drug Discov. Today"},{"key":"10.1016\/j.bmcl.2007.12.074_bib3_1","first-page":"1","volume":"211","author":"Asthana","year":"1997","journal-title":"J. Parasitic Diseases"},{"key":"10.1016\/j.bmcl.2007.12.074_bib3_2","first-page":"1960","volume":"366","author":"Jambou","year":"2005","journal-title":"Res. Lett."},{"issue":"24","key":"10.1016\/j.bmcl.2007.12.074_bib4","doi-asserted-by":"crossref","first-page":"7227","DOI":"10.1021\/jm060826x","volume":"49","author":"Singh","year":"2006","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2007.12.074_bib5","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1002\/1099-0690(20021)2002:1<113::AID-EJOC113>3.0.CO;2-N","author":"Haynes","year":"2002","journal-title":"Eur. J. Org. Chem."},{"key":"10.1016\/j.bmcl.2007.12.074_bib6","unstructured":"This work has been covered in an Indian patent: Singh, C.; Chaudhary, S.; Puri, S. K. Indian Patent Appl. No. 0391 DEL 2006, Filing Date 13-02-2006."},{"key":"10.1016\/j.bmcl.2007.12.074_bib7","doi-asserted-by":"crossref","first-page":"645","DOI":"10.1021\/jm00398a026","volume":"31","author":"Brossi","year":"1988","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2007.12.074_bib8_1","first-page":"38","volume":"15","author":"Li","year":"1980","journal-title":"Yao Hsueh Tung Pao"},{"key":"10.1016\/j.bmcl.2007.12.074_bib8_2","unstructured":"Li, Y.; Yu, P.; Chen, Y.; Ji, R. HuaXue XueBao 1982, 40, 557\u2013561; Chem. Abstr. 1982, 98, 4420h. (b) General procedure for esterification of dihydroartemisinin (compound 7a as representative). To a solution of dihydroartemisinin (0.50g, 1.75mmol) and biphenyl-4-carbonyl chloride (1.14g, 3 equiv, 5.25mmol) dissolved in dry dichloromethane (30mL) was added triethylamine (0.73ml, 3 equiv, 5.29mmol) dropwise at 0\u00b0C. The mixture was stirred at the same temperature for 2h. The reaction mixture was then quenched with saturated sodium bicarbonate solution (25mL) and extracted with dichloromethane (3\u00d7 25mL). The organic layer was washed with 10% aqueous HCl solution (2\u00d7 20mL), then with water, dried over anhyd Na2SO4 and concentrated under reduced pressure. The crude product on column chromatography over silica gel using ethyl acetate\/hexane (1:25) as eluant gave pure 7a (465mg, 57%) as a white solid. (c) Selected spectral data. Compound 7a: White solid; FT-IR (KBr, cm\u22121): 2932.3, 2876.9, 1729.0, 1608.1, 1452.4, 1378.2, 1269.4, 1201.8, 1130.6, 1087.8, 1016.9, 754.2; 1H NMR (200MHz, CDCl3) \u03b4 0.94 (d, 3H, J=7.1Hz, CH3), 0.98 (d, 3H, J=5.8Hz, CH3), 1.25\u20132.10 (m, 10H), 1.43 (s, 3H, CH3), 2.32\u20132.46 (m, 1H), 2.74\u20132.80 (m, 1H), 5.54 (s, 1H, C12\u2013H), 6.03 (d, 1H, J=9.8Hz, C10\u2013H), 7.38\u20137.51 (m, 3H), 7.60\u20137.68 (m, 4H), 8.18 (d, 2H, J=8.4Hz); FABMS (m\/z): 465 [M+H]+; ESMS (m\/z): 482 [M+NH4]+, 487 [M+Na]+; Anal. Calcd for (C28H32O6\u00b70.1H2O): C 72.38 H 6.94; Found C 72.11 H 6.96. Compound 7b: White solid; FT-IR (KBr, cm\u22121): 2931.5, 2875.8, 1748.8, 1487.4, 1452.0, 1379.1, 1243.1, 1141.1, 1099.7, 1019.8, 756.3; 1H NMR (200MHz, CDCl3) \u03b4 0.74 (d, 3H, J=7.0Hz, CH3), 0.95 (d, 3H, J=5.1Hz, CH3), 1.17\u20132.07 (m, 10H), 1.45 (s, 3H, CH3), 2.30\u20132.44 (m, 1H), 2.52\u20132.63 (m, 1H), 3.75 (s, 2H), 5.44 (s, 1H, C12\u2013H), 5.80 (d, 1H, J=9.8Hz, C10\u2013H), 7.29\u20137.59 (m, 9H); 13C NMR (50MHz, CDCl3) \u03b4 12.37 (CH3), 20.60 (CH3), 22.38 (CH2), 24.99 (CH2), 26.39 (CH3), 32.30 (CH), 34.49 (CH2), 36.64 (CH2), 37.66 (CH), 41.31(CH2), 45.68 (CH), 51.98 (CH), 80.55 (C), 91.97 (CH), 92.71 (CH), 104.89 (C), 127.46 (CH), 127.66 (CH), 129.15 (CH), 130.23 (CH), 133.03 (C), 140.49 (C), 141.20 (C), 170.76 (C); ESMS (m\/z): 501 [M+Na]+; Anal. Calcd for (C29H34O6): C 72.77 H 7.16; Found C 72.47 H 7.53. Compound 7c: White solid; FT-IR (KBr, cm\u22121): 1774.7, 1637.8, 1480.8, 1438.5, 1379.1, 1218.0, 1131.9, 1103.4, 1013.8, 770.4; 1H NMR (200MHz, CDCl3) \u03b4 0.77 (d, 3H, J=7.1Hz, CH3), 0.96 (d, 3H, J=5.3Hz, CH3), 1.25\u20132.07 (m, 10H), 1.44 (s, 3H, CH3), 2.30\u20132.44 (m, 1H), 2.50\u20132.57 (m, 1H), 4.67 (s, 2H), 5.44 (s, 1H, C12\u2013H), 5.80 (d, 1H, J=9.8Hz, C10\u2013H), 6.87\u20137.62 (m, 9H); 13C NMR (50MHz, CDCl3) \u03b4 12.38 (CH3), 20.60 (CH3), 22.37 (CH2), 24.98 (CH2), 26.32 (CH3), 32.18 (CH), 34.47 (CH2), 36.61 (CH2), 37.68 (CH), 45.64 (CH), 51.93 (CH), 66.08 (CH2), 80.49 (C), 91.99 (CH), 93.07 (CH), 104.96 (C), 113.22 (CH), 122.59 (CH), 127.50 (CH), 128.45 (CH), 128.93 (CH), 130.04 (CH), 131.67 (CH), 138.43 (C), 155.08 (C), 168.32 (C); ESMS (m\/z): 512 [M+Na]+; Anal. Calcd for (C29H34O7): C 70.43 H 6.93; Found C 70.28 H 7.15. Compound 7d: White solid; FT-IR (KBr, cm\u22121): 2928.9, 2874.4, 1774.3, 1607.4, 1519.4, 1488.0, 1452.0, 1379.4, 1354.4, 1273.2, 1178.5, 1133.1, 1103.1, 1081.8, 1013.2, 764.3; 1H NMR (200MHz, CDCl3) \u03b4 0.83 (d, 3H, J=7.0Hz, CH3), 0.96 (d, 3H, J=5.1Hz, CH3), 1.17\u20132.07 (m, 10H), 1.43 (s, 3H, CH3), 2.31\u20132.44 (m, 1H), 2.55\u20132.62 (m, 1H), 4.70 and 4.80 (2\u00d7d, 2H, J=16.1Hz, COCH2O), 5.46 (s, 1H, C12\u2013H), 5.91 (d, 1H, J=9.8Hz, C10\u2013H), 6.96\u20137.55 (m, 9H); ESMS (m\/z): 517 [M+Na]+; HR-EIMS for (C29H34O7): Measured 494.2326, Calculated 494.2305; Anal. Calcd for (C29H34O7\u00b70.1H2O): C 70.43 H 6.93; Found C 70.21 H 6.94. Compound 7e: White solid; mp 85\u201387\u00b0C; FT-IR (KBr, cm\u22121): 3020.4, 2910.3, 1742.5, 1451.9, 1368.5, 1219.4, 1133.5, 1098.3, 1022.0, 769.0; 1H NMR (200MHz, CDCl3) \u03b4 0.82 (d, 3H, J=7.1Hz, CH3), 0.96 (d, 3H, J=5.6Hz, CH3), 1.25\u20132.01 (m, 25H), 1.42 (s, 3H, CH3), 2.29\u20132.43 (m, 1H), 2.53\u20132.59 (m, 1H), 5.42 (s, 1H, C12\u2013H), 5.75 (d, 1H, J=9.7Hz, C10\u2013H); 13C NMR (50MHz, CDCl3) \u03b4 12.58 (CH3), 20.63 (CH3), 22.42 (CH2), 24.97 (CH2), 26.29 (CH3), 28.28 (3\u00d7CH), 32.37 (CH2), 34.53(CH2), 36.87 (3\u00d7CH2), 37.64 (CH), 38.98 (3\u00d7CH2), 41.20 (CH), 45.73 (CH), 52.07 (CH), 80.58 (C), 91.94 (CH), 104.71 (C), 176.63 (C); ESMS (m\/z): 469 [M+Na]+; Anal. Calcd for (C26H38O6): C 69.92 H 8.57; Found: C 69.48 H 8.46. Compound 7f: White solid; mp 115\u2013117\u00b0C; FT-IR (KBr, cm\u22121): 2914.3, 1751.0, 1452.2, 1401.9, 1375.0, 1267.5, 1161.1, 1096.0, 1020.3; 1H NMR (200MHz, CDCl3) \u03b4 0.87 (d, 3H, J=7.0Hz, CH3), 0.96 (d, 3H, J=5.6Hz, CH3), 1.25\u20132.08 (m, 25H), 1.42 (s, 3H, CH3), 2.15\u20132.23 (m, 2H), 2.29\u20132.45 (m, 1H), 2.50\u20132.61 (m, 1H), 5.43 (s, 1H, C12\u2013H), 5.77 (d, 1H, J=9.8Hz, C10\u2013H); 13C NMR (50MHz, CDCl3) \u03b4 12.84 (CH3), 20.62 (CH3), 22.38 (CH2), 25.01 (CH2), 26.34 (CH3), 29.00 (3\u00d7CH), 31.98 (CH), 33.21 (C), 34.54 (CH2), 36.63 (CH2), 37.12 (3\u00d7CH2), 37.68 (CH), 42.73 (3\u00d7CH2), 45.77 (CH), 49.18 (CH2), 51.99 (CH), 80.51 (C), 91.76 (CH), 91.96 (CH), 104.75 (C), 170.92 (C); FABMS (m\/z): 461 [M+H]+; ESMS (m\/z): 483 [M+Na]+; Anal. Calcd for (C27H40O6): C 70.40 H 8.75; Found C 70.87 H 9.09. Compound 7g: White solid; mp 73\u201375\u00b0C; FT-IR (KBr, cm\u22121) 2909.7, 2855.5, 1742.2, 1452.4, 1411.7, 1377.5, 1251.0, 1150.0, 1099.7, 1021.8, 757.0; 1H NMR (200MHz, CDCl3) \u03b4 0.83 (d, 3H, J=6.9Hz, CH3), 0.96 (d, 3H, J=5.0Hz, CH3), 1.25\u20132.06 (m, 25H), 1.43 (s, 3H, CH3), 2.24\u20132.37 (m, 1H), 2.46\u20132.57 (m, 3H), 5.44 (s, 1H, C12\u2013H), 5.78 (d, 1H, J=9.8Hz, C10\u2013H); 13C NMR (50MHz, CDCl3) \u03b4 12.46 (CH3), 20.60 (CH3), 22.37 (CH2), 24.99 (CH2), 26.33 (CH3), 28.24 (2\u00d7CH), 31.90 (2\u00d7CH2), 32.17 (3\u00d7CH), 34.51 (CH2), 36.62 (CH2), 37.64 (CH), 38.56 (2\u00d7CH2), 39.24 (2\u00d7CH2), 41.36 (CH), 45.70 (CH), 51.97 (CH), 80.50 (C), 91.84 (CH), 92.00 (CH), 104.78 (C), 172.58 (C); FABMS (m\/z): 461 [M+H]+; ESMS (m\/z): 478 [M+NH4]+, 483 [M+Na]+; Anal. Calcd for (C27H40O6): C 70.40 H 8.75; Found C 70.12 H 9.10. Compound 7h: White solid; FT-IR (KBr, cm\u22121): 2920.0, 2853.7, 1751.5, 1591.3, 1457.0, 1378.5, 1352.1, 1161.9, 1096.4, 1022.0; 1H NMR (200MHz, CDCl3) \u03b4 0.86 (d, 3H, J=7.0Hz, CH3), 0.95 (d, 3H, J=5.6Hz, CH3), 1.25\u20132.10 (m, 27H), 1.43 (s, 3H, CH3), 2.15\u20132.24 (m, 2H), 2.36\u20132.45 (m, 1H), 2.53\u20132.59 (m, 1H), 5.43 (s, 1H, C12\u2013H), 5.77 (d, 1H, J=9.8Hz, C10\u2013H); 13C NMR (50MHz, CDCl3) \u03b4 12.85 (CH3), 20.63 (CH3), 22.39 (CH2), 24.99 (CH2), 26.35 (CH3), 29.01 (3\u00d7CH), 31.99 (CH), 33.22 (C), 34.53 (CH2), 35.15 (CH2), 36.64 (CH2), 37.13 (3\u00d7CH2), 37.69 (CH), 42.74 (3\u00d7CH2), 45.78 (CH), 49.19 (CH2), 52.00 (CH), 80.52 (C), 91.77 (CH), 91.97 (CH), 104.76 (C), 170.93 (C); FABMS (m\/z): 475 [M+H]+; ESMS (m\/z): 497 [M+Na]+; Anal. for (C28H42O6): Calcd C 70.86 H 8.92; Found C 70.57 H 8.99. Compound 7i: White solid; FT-IR (KBr, cm\u22121) 2943.8, 1750.1, 1596.9, 1451.5, 1353.0, 1276.0, 1190.4, 1139.1, 1100.8, 1015.9, 744.8; 1H NMR (200MHz, CDCl3) \u03b4 0.80 (d, 3H, J=7.1Hz, CH3), 0.96 (d, 3H, J=5.6Hz, CH3), 1.25\u20132.09 (m, 10H), 1.47 (s, 3H, CH3), 2.27\u20132.48 (m, 1H), 2.68\u20132.74 (m, 1H), 4.99 (s, 1H, benzylic H), 5.46 (s, 1H, C12\u2013H), 5.87 (d, 1H, J=9.8Hz, C10\u2013H), 7.32\u20137.45 (m, 4H), 7.65\u20137.82 (m, 4H); 13C NMR (50MHz, CDCl3) \u03b4 12.69 (CH3), 20.61 (CH3), 22.34 (CH2), 25.01 (CH2), 26.39 (CH3), 32.35 (CH), 34.48 (CH2), 36.67 (CH2), 37.63 (CH), 45.78 (CH), 51.96 (CH), 53.61 (CH), 80.52 (C), 91.99 (CH), 93.31 (CH), 104.87 (C), 120.33 (CH), 120.48 (CH) 126.21 (CH), 126.79 (CH), 127.66 (CH), 127.82 (CH), 128.60 (CH), 140.49 (C), 140.78 (C), 141.90 (C), 169.87 (C); FABMS (m\/z): 476 [M]+, 477[M+H]+; ESMS (m\/z): 499 [M+Na]+; Anal. Calcd for (C29H32O6): C 73.09 H 6.77; Found C 73.38 H 6.73. Compound 7j: White solid; FT-IR (KBr, cm\u22121) 2929.9, 2877.2, 1747.2, 1653.9, 1529.6, 1450.4, 1350.9, 1275.6, 1216.2, 1145.2, 1097.4, 1014.1, 755.9; 1H NMR (200MHz, CDCl3) \u03b4 0.84 (d, 3H, J=7.1Hz, CH3), 0.98 (d, 3H, J=5.3Hz, CH3), 1.25\u20132.08 (m, 10H), 1.45 (s, 3H, CH3), 2.31\u20132.38 (m, 1H), 2.53\u20132.63 (m, 1H), 2.79 (dd, 1H, J=16.12Hz, 6.55Hz), 2.96 (dd, 1H, J=16.4Hz, 7.56Hz), 4.44 (br t, 1H, benzylic H), 5.50 (s, 1H, C12\u2013H), 5.92 (d, 1H, J=9.8Hz, C10\u2013H), 7.28\u20137.41 (m, 4H), 7.51\u20137.58 (m, 2H), 7.75 (d, 2H, J=7.4Hz); 13C NMR (50MHz, CDCl3) \u03b4 12.61 (CH3), 20.65 (CH3), 22.46 (CH2), 25.03 (CH2), 26.38 (CH3), 32.11 (CH), 34.53 (CH2), 36.63 (CH2), 37.72 (CH), 39.10 (CH2), 43.77 (CH), 45.68 (CH), 51.98 (CH), 80.55 (C), 91.90 (CH), 92.77 (CH), 104.90 (C), 120.30 (CH), 120.42 (CH), 124.77 (CH), 124.94 (CH), 127.68 (CH), 127.88 (CH), 128.01 (CH), 141.20 (C), 146.41 (C), 146.66 (C), 171.88 (C); ESMS (m\/z): 508 [M+NH4]+, 513 [M+Na]+; Anal. Calcd for (C30H34O6): C 73.45 H 6.99; Found C 73.30 H 6.95."},{"key":"10.1016\/j.bmcl.2007.12.074_bib9_1","series-title":"Chemotherapy and Drug Resistance in Malaria","first-page":"64","author":"Peters","year":"1970"},{"key":"10.1016\/j.bmcl.2007.12.074_bib9_2","unstructured":"In vivo antimalarial efficacy test. The blood schizontocidal activity of the test compounds was evaluated in rodent model using multidrug-resistant strain of Plasmodium yoelii nigeriensis. Multidrug-resistant Plasmodium yoelii nigeriensis used in this study is resistant to chloroquine, mefloquine and halofantrine. The colony bred Swiss mice of either sex (20\u00b12g) were inoculated intraperitoneally with 1\u00d7105 P. yoelii (MDR) parasites on day zero, and treatment was administered to group of five mice at each dose, from day 0 to 3, once daily. The drug dilutions of all compounds were prepared in groundnut oil so as to contain the required amount of the drug (0.6mg\/kg for a dose of 48mg\/kg, 0.3mg for a dose of 24mg\/kg, 0.15mg for a dose of 12mg\/kg) in 0.1mL and administered orally for each dose. Parasitaemia level was recorded from thin blood smears on day 4 and subsequently twice a week until day 28. The animals which did not develop patent infection until day 28 were recorded as cured.15 Mice treated with \u03b2-arteether served as positive control."},{"key":"10.1016\/j.bmcl.2007.12.074_bib10_1","unstructured":"Also in our programme on synthetic 1,2,4-trioxanes, we had observed that trioxane built around these moieties showed promising antimalarial activity: Singh, C.; Kanchan, R.; Puri, S. K. Indian Patent Appl. No. 1554 DEL 99, 1999."},{"key":"10.1016\/j.bmcl.2007.12.074_bib10_2","unstructured":"Singh, C.; Tiwari, P.; Puri, S. K. U.S. Patent 6,737,438 B2, 2004."},{"issue":"3","key":"10.1016\/j.bmcl.2007.12.074_bib10_3","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1021\/jm0610043","volume":"50","author":"Singh","year":"2007","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2007.12.074_bib11_1","doi-asserted-by":"crossref","first-page":"1052","DOI":"10.1021\/jm0109816","volume":"45","author":"Hindley","year":"2002","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2007.12.074_bib11_2","doi-asserted-by":"crossref","first-page":"4321","DOI":"10.1021\/jm020142z","volume":"45","author":"Avery","year":"2002","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2007.12.074_bib11_3","doi-asserted-by":"crossref","first-page":"1060","DOI":"10.1021\/jm020461q","volume":"46","author":"Posner","year":"2003","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2007.12.074_bib11_4","doi-asserted-by":"crossref","first-page":"1423","DOI":"10.1021\/jm030947m","volume":"47","author":"Grellepois","year":"2004","journal-title":"J. Med. Chem."},{"issue":"9","key":"10.1016\/j.bmcl.2007.12.074_bib11_5","doi-asserted-by":"crossref","first-page":"2731","DOI":"10.1021\/jm058288w","volume":"49","author":"Paik","year":"2006","journal-title":"J. Med. Chem."},{"issue":"10","key":"10.1016\/j.bmcl.2007.12.074_bib11_6","doi-asserted-by":"crossref","first-page":"2516","DOI":"10.1021\/jm070149m","volume":"50","author":"Posner","year":"2007","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2007.12.074_bib12_1","unstructured":"100% suppression of parasitamia means no parasites were detected in 50 oil immersion microscopic fields (parasites if at all present were below the detection limit). The parasites present below the detection limit can multiply and eventually can be detected during observation on subsequent days. In such cases though the drug is providing near 100% suppression of the parasitaemia on day 4 it will not provide full protection to the treated mice in the 28 day survival assay."},{"key":"10.1016\/j.bmcl.2007.12.074_bib12_2","unstructured":"100% protection means none of the treated mice developed patent infection during the 28 days observation period and hence were recorded as cured. Similarly 60% protection means only 3 out of 5 mice were cured."},{"key":"10.1016\/j.bmcl.2007.12.074_bib15","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1006\/expr.1999.4465","volume":"94","author":"Puri","year":"2000","journal-title":"Expl. 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