SYNTHESIS OF CHIRAL ZILEUTON, A POTENT AND SELECTIVE INHIBITOR OF 5-LIPOXYGENASE

被引:52
作者
HSIAO, CN
KOLASA, T
机构
[1] Abbott Laboratories, Department 45L / AP 10, Process Chemistry
关键词
D O I
10.1016/S0040-4039(00)79043-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Coupling and intramolecular Wittig reaction of N-benzyloxy-D-alanine anhydride (13) and (2-Mercaptophenyl)methyltriphenylphosphonium bromide (3) were used as key steps to prepare (+)-enantiomer of zileuton (1), a potent and selective inhibitor of 5-lipoxygenase.
引用
收藏
页码:2629 / 2632
页数:4
相关论文
共 13 条
[1]  
AKIYAMA M, 1979, TETRAHEDRON LETT, V19, P2599
[2]  
ARNOLDI A, 1988, SYNTHESIS-STUTTGART, P155
[3]   ADDITION OF ORGANOLITHIUM COMPOUNDS TO N-THP PROTECTED NITRONE [J].
BASHA, A ;
RATAJCZYK, JD ;
BROOKS, DW .
TETRAHEDRON LETTERS, 1991, 32 (31) :3783-3786
[5]  
CARTER GW, 1989, LEUKOTRIENES PROSTAN, P50
[6]  
CASHMAN J R, 1988, Drugs of Today, V24, P723
[7]  
CHANG SC, 1984, J CHROMATOGR, V289, P53
[8]   INVERSION OF STEROSPECIFICITY IN HYDROLYSIS BY ALPHA-CHYMOTRYPSIN - ACETOXYL SUBSTITUENT [J].
COHEN, SG ;
CROSSLEY, J ;
KLEE, LH ;
KHEDOURI, E ;
ZAND, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (11) :1685-&
[9]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[10]   INHALATION CHALLENGE WITH SULFIDOPEPTIDE LEUKOTRIENES IN HUMAN-SUBJECTS [J].
DRAZEN, JM .
CHEST, 1986, 89 (03) :414-419