Enantioseparation and plant virucidal bioactivity of new quinazoline derivatives with α-aminophosphonate moiety

被引:27
作者
Zhang, Yuping [1 ]
Bai, Song [1 ]
Song, Baoan [1 ]
Bhadury, Pinaki S. [1 ]
Hu, Deyu [1 ]
Yang, Song [1 ]
Zhang, Xiaoyan [1 ]
Fan, Huitao [1 ]
Lu, Ping [1 ]
机构
[1] Guizhou Univ, Ctr Res & Dev Fine Chem, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China
来源
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES | 2010年 / 878卷 / 17-18期
基金
中国国家自然科学基金;
关键词
Quinazoline; alpha-Aminophosphonate; Enantioseparation; Bioactivities; Chiralpak IA column; Chiralpak IC column; CHIRAL STATIONARY-PHASE; PERFORMANCE-LIQUID-CHROMATOGRAPHY; ORGANIC PHOSPHONATE COMPOUNDS; TEMPERATURE-INDUCED INVERSION; DEPENDENT ELUTION ORDER; ENANTIOMERIC SEPARATION; RESOLUTION; ACID; HPLC; ENANTIOSELECTIVITY;
D O I
10.1016/j.jchromb.2009.11.024
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Enantiomers of some new quinazoline derivatives bearing alpha-aminophosphonate moiety were separated under normal-phase conditions on two immobilized polysaccharide-based chiral stationary phases (Chiralpak IA and Chiralpak IC). The role of two chiral stationary phases (CSPs), polar modifier and column temperature on retention time and separation factor was studied. Apparent thermodynamic parameters were deduced from Van't Hoff plots and plausible mechanism of chiral recognition has been discussed. The semi-preparative separation of some compounds was executed successfully in n-hexanefisopropyl alcohol (IPA) on the Chiralpak IA column. The preliminary bioassay showed that both the enantiomers of the investigated series of compounds possessed similar anti-tobacco mosaic virus (TMV) activities. (C) 2009 Elsevier B.V. All rights reserved,
引用
收藏
页码:1285 / 1289
页数:5
相关论文
共 46 条
  • [1] QUINAZOLINONES-1 - DESIGN AND SYNTHESIS OF POTENT QUINAZOLINONE-CONTAINING AT(1)-SELECTIVE ANGIOTENSIN-II RECEPTOR ANTAGONISTS
    ALLEN, EE
    DELASZLO, SE
    HUANG, SX
    QUAGLIATO, CS
    GREENLEE, WJ
    CHANG, RSL
    CHEN, TB
    FAUST, KA
    LOTTI, VJ
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (06) : 1293 - 1298
  • [2] BALMER K, 1992, J CHROMATOGR, V592, P3317
  • [3] DIRECT CHIRAL HPLC SEPARATION OF THE ENANTIOMERS OF FLUORINATED N-ARYLAMINO-1-ARYLMETHYLPHOSPHONATE ESTERS - SUBSTITUENT EFFECTS ON THE ENANTIOSELECTIVITY
    CACCAMESE, S
    PRINCIPATO, G
    GRUSS, U
    HAGELE, G
    FAILLA, S
    [J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (01) : 141 - 148
  • [4] Chen H, 1999, CHINESE J CHEM, V17, P644
  • [5] CHEN RY, 1995, SCI CHINA SER B, V25, P591
  • [6] CHEN RY, 1994, SULFUR SILICON RELAT, V89, P97
  • [7] DA IJ, 2007, J CHROMATOGR A, V1162, P97
  • [8] Chiral resolution of the enantiomers of new aromatase inhibitors by liquid chromatography on amylose stationary phases
    Danel, C
    Foulon, C
    Park, C
    Yous, S
    Bonte, JP
    Vaccher, C
    [J]. CHROMATOGRAPHIA, 2004, 59 (3-4) : 181 - 188
  • [9] Emsley J., 1976, CHEM PHOSPHORUS, P494
  • [10] Temperature-induced inversion of elution order in the enantioseparation of sotalol on a cellobiohydrolase I-based stationary phase
    Fulde, K
    Fraham, AW
    [J]. JOURNAL OF CHROMATOGRAPHY A, 1999, 858 (01) : 33 - 43