An Efficient Route to N-Monosubstituted Guanidino-Lactams

被引:2
|
作者
Tommasi, Sara [1 ]
Zanato, Chiara [1 ]
Carabeo, Rey [2 ]
Mangoni, Arduino A. [3 ,4 ]
Dall'Angelo, Sergio [1 ]
Zanda, Matteo [1 ,5 ]
机构
[1] Univ Aberdeen, Inst Med Sci, Kosterlitz Ctr Therapeut, Foresterhill AB25 2ZD, Scotland
[2] Univ Aberdeen, Inst Med Sci, Bacteriol Sect, Programme Microbiol, Foresterhill AB25 2ZD, Scotland
[3] Flinders Univ S Australia, Sch Med, Dept Clin Pharmacol, Bedford Pk, SA 5042, Australia
[4] Flinders Med Ctr, Bedford Pk, SA 5042, Australia
[5] CNR ICRM, I-20131 Milan, Italy
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 19期
关键词
guanidines; guanylation; lactams; cyclization; antimicrobials; PRO-ARG-H; THROMBIN INHIBITORS; ARGININE; DESIGN;
D O I
10.1055/s-0034-1378845
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A small library of guanidino-lactams were synthesized in four steps and good overall yields by following the routes: preparation of guanylating agents, synthesis of protected guanidino-acids, cyclization to fully protected guanidino-lactams, and deprotection to the target compounds. The guanidino-lactams were assayed as antimicrobials on E. coli showing no significant antibiotic activity.
引用
收藏
页码:3067 / 3078
页数:12
相关论文
共 50 条
  • [41] PREDICTION OF TAUTOMERIC EQUILIBRIA FOR N,N',N''-TRISUBSTITUTED, N,N'-DISUBSTITUTED AND N-MONOSUBSTITUTED GUANIDINES
    RACZYNSKA, ED
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (11): : 1789 - 1793
  • [42] CONVERSIONS OF N-MONOSUBSTITUTED ALPHA-AMINOCARBOXYLIC ACID-ESTERS
    GOLOLOBOV, YG
    NESTEROVA, LI
    ZHURNAL ORGANICHESKOI KHIMII, 1978, 14 (04): : 739 - 745
  • [43] STUDIES OF THE SYNTHESES OF PIPERAZINES .1. SYNTHESES OF N-MONOSUBSTITUTED PIPERAZINES
    FUJII, K
    TOMINO, K
    WATANABE, H
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1954, 74 (10): : 1049 - 1052
  • [44] DIBORANE REDUCTION OF NITRO SALTS . A NEW SYNTHESIS OF N-MONOSUBSTITUTED HYDROXYLAMINES
    FEUER, H
    BARTLETT, RS
    VINCENT, BF
    ANDERSON, RS
    JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (09): : 2880 - &
  • [45] New Synthesis Method of N-Monosubstituted Ammonium-closo-Decaborates
    A. P. Zhdanov
    V. V. Voinova
    I. N. Klyukin
    A. S. Kubasov
    K. Yu. Zhizhin
    N. T. Kuznetsov
    Journal of Cluster Science, 2019, 30 : 1327 - 1333
  • [46] PHOTO-CHEMICAL REACTION OF N-MONOSUBSTITUTED ALPHA-OXOAMIDES
    SHIOZAKI, M
    HIRAOKA, T
    SYNTHETIC COMMUNICATIONS, 1979, 9 (03) : 179 - 183
  • [47] New Synthesis Method of N-Monosubstituted Ammonium-closo-Decaborates
    Zhdanov, A. P.
    Voinova, V. V.
    Klyukin, I. N.
    Kubasov, A. S.
    Zhizhin, K. Yu.
    Kuznetsov, N. T.
    JOURNAL OF CLUSTER SCIENCE, 2019, 30 (05) : 1327 - 1333
  • [48] RING-CHAIN ISOMERISM OF N-MONOSUBSTITUTED 2-CYANOBENZENESULPHONAMIDES
    BALODE, DE
    VALTER, RE
    VALTER, SP
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1978, (12): : 1632 - 1635
  • [49] Reaction of N-monosubstituted hydrazones with nitroolefins:: A novel regioselective pyrazole synthesis
    Deng, Xiaohu
    Mani, Neelakandha S.
    ORGANIC LETTERS, 2006, 8 (16) : 3505 - 3508
  • [50] THERMAL ANALYSIS OF NICKEL(II) COMPLEXES WITH SOME N-MONOSUBSTITUTED ETHYLENEDIAMINES
    BASSETT, J
    GRZESKOW.R
    OLEARY, BL
    JOURNAL OF THERMAL ANALYSIS, 1971, 3 (02): : 143 - &