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
来源：
TETRAHEDRON LETTERS | 1992年 / 33卷 / 19期
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 50 条
  • [21] Reduction of the multiple organ injury and dysfunction caused by endotoxemia in 5-lipoxygenase knockout mice and by the 5-lipoxygenase inhibitor zileuton
    Collin, M
    Rossi, A
    Cuzzocrea, S
    Patel, NSA
    Di Paola, R
    Hadley, J
    Collino, M
    Sautebin, L
    Thiemermann, C
    JOURNAL OF LEUKOCYTE BIOLOGY, 2004, 76 (05) : 961 - 970
  • [22] Intracolonic administration of zileuton, a selective 5-lipoxygenase inhibitor, accelerates healing in a rat model of chronic colitis
    Bertran, X
    Mane, J
    FernandezBanares, F
    Castella, E
    Bartoli, R
    Ojanguren, I
    Esteve, M
    Gassull, MA
    GUT, 1996, 38 (06) : 899 - 904
  • [23] PHARMACOKINETICS OF THE 5-LIPOXYGENASE INHIBITOR ZILEUTON IN SUBJECTS WITH VARIOUS DEGREES OF HEPATIC IMPAIRMENT
    BRAECKMAN, RA
    HUI, J
    CAVANAUGH, JH
    RUBIN, PD
    CLINICAL PHARMACOLOGY & THERAPEUTICS, 1993, 53 (02) : 181 - 181
  • [24] Antiallergic effect of ardisiaquinone A, a potent 5-lipoxygenase inhibitor
    Fukuishi, N
    Takada, T
    Fukuyama, Y
    Akagi, M
    PHYTOMEDICINE, 2001, 8 (06) : 460 - 464
  • [25] DISULFIRAM IS A POTENT INHIBITOR OF RAT 5-LIPOXYGENASE ACTIVITY
    CHOO, LY
    RIENDEAU, D
    CANADIAN JOURNAL OF PHYSIOLOGY AND PHARMACOLOGY, 1987, 65 (12) : 2503 - 2506
  • [26] GOSSYPOL, A POTENT INHIBITOR OF ARACHIDONATE 5-LIPOXYGENASE AND 12-LIPOXYGENASE
    HAMASAKI, Y
    TAI, HH
    BIOCHIMICA ET BIOPHYSICA ACTA, 1985, 834 (01) : 37 - 41
  • [27] A PILOT-STUDY OF ZILEUTON, A NOVEL SELECTIVE 5-LIPOXYGENASE INHIBITOR, IN PATIENTS WITH SYSTEMIC LUPUS-ERYTHEMATOSUS
    HACKSHAW, KV
    SHI, YH
    BRANDWEIN, SR
    JONES, K
    WESTCOTT, JY
    JOURNAL OF RHEUMATOLOGY, 1995, 22 (03) : 462 - 468
  • [28] Sinapic acid phenethyl ester as a potent selective 5-lipoxygenase inhibitor: Synthesis and structure-activity relationship
    Touaibia, Mohamed
    Hebert, Martin J. G.
    Levesque, Natalie A.
    Doiron, Jeremie A.
    Doucet, Marco S.
    Jean-Francois, Jacques
    Cormier, Marc
    Boudreau, Luc H.
    Surette, Marc E.
    CHEMICAL BIOLOGY & DRUG DESIGN, 2018, 92 (05) : 1876 - 1887
  • [29] Peroxynitrite-induced nitrotyrosination of proteins is blocked by direct 5-lipoxygenase inhibitor zileuton
    Coffey, MJ
    Phare, SM
    Peters-Golden, M
    JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2001, 299 (01): : 198 - 203
  • [30] MO ab initio study of the structural and electronic properties of the 5-lipoxygenase inhibitor zileuton
    Ramusino, MC
    THEOCHEM-JOURNAL OF MOLECULAR STRUCTURE, 1998, 427 : 237 - 242
12345