A PRACTICAL AND GENERAL-SYNTHESIS OF (+)-CARBOXYALKYLDEOXOARTEMISININS

被引:26
作者
JUNG, M
FREITAS, ACC
MCCHESNEY, JD
ELSOHLY, HN
机构
[1] UNIV MISSISSIPPI, SCH PHARM, DEPT MED CHEM, UNIVERSITY, MS 38677 USA
[2] UNIV MISSISSIPPI, SCH PHARM, DEPT PHARMACOGNOSY, UNIVERSITY, MS 38677 USA
关键词
D O I
10.3987/COM-93-S(B)9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dye-sensitized photoxygenation of olefinic alcohols of dihydroartemisinates (4a-c) and direct oxidation of olefinic deoxoartemisinins (5a-c) have led to the preparation of carboxyalkyldeoxoartemisinins (6a-c), which are water-soluble and chemically more stable antimalarial agents.
引用
收藏
页码:23 / 29
页数:7
相关论文
共 35 条
[1]   ON THE CONVERSION OF DIHYDROARTEMISINIC ACID INTO ARTEMISININ [J].
ACTON, N ;
ROTH, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3610-3614
[2]   THE TOTAL SYNTHESIS OF (+)-ARTEMISININ AND (+)-9-DESMETHYLARTEMISININ [J].
AVERY, MA ;
JENNINGSWHITE, C ;
CHONG, WKM .
TETRAHEDRON LETTERS, 1987, 28 (40) :4629-4632
[3]   SIMPLIFIED ANALOGS OF THE ANTIMALARIAL ARTEMISININ - SYNTHESIS OF 6,9-DESMETHYLARTEMISININ [J].
AVERY, MA ;
JENNINGSWHITE, C ;
CHONG, WKM .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1792-1795
[4]   TRICYCLIC ANALOGS OF ARTEMISININ - SYNTHESIS AND ANTIMALARIAL ACTIVITY OF (+)-4,5-SECOARTEMISININ AND (-)-5-NOR-4,5-SECOARTEMISININ [J].
AVERY, MA ;
CHONG, WKM ;
BUPP, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (21) :1487-1489
[5]   NUCLEAR OVERHAUSER EFFECT SPECTROSCOPY (NOESY) AND 3JHH COUPLING MEASUREMENTS IN THE DETERMINATION OF THE CONFORMATION OF THE SESQUITERPENE ANTIMALARIAL ARTEETHER IN SOLUTION [J].
BAKER, JK ;
ELSOHLY, HN ;
HUFFORD, CD .
SPECTROSCOPY LETTERS, 1990, 23 (01) :111-122
[6]   ARTEETHER, A NEW ANTIMALARIAL DRUG - SYNTHESIS AND ANTIMALARIAL PROPERTIES [J].
BROSSI, A ;
VENUGOPALAN, B ;
GERPE, LD ;
YEH, HJC ;
FLIPPENANDERSON, JL ;
BUCHS, P ;
LUO, XD ;
MILHOUS, W ;
PETERS, W .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (03) :645-650
[7]  
BUSTOS DA, 1989, HETEROCYCLES, V29, P2273
[8]   A LARGE-SCALE EXTRACTION TECHNIQUE OF ARTEMISININ FROM ARTEMISIA-ANNUA [J].
ELSOHLY, HN ;
CROOM, EM ;
ELFERALY, FS ;
ELSHEREI, MM .
JOURNAL OF NATURAL PRODUCTS, 1990, 53 (06) :1560-1564
[9]  
HAYNES RK, 1992, SYNLETT, P481