Discovery of potent antiviral (HSV-1) quinazolinones and initial structure-activity relationship studies

被引：25
作者：
Brown, Carla E. [1 ]
Kong, Tiffany [1 ]
McNulty, James [1 ]
D'Aiuto, Leonardo [2 ]
Williamson, Kelly [2 ]
McClain, Lora [2 ]
Piazza, Paolo [2 ]
Nimgaonkar, Vishwajit L. [2 ]
机构：
[1] McMaster Univ, Dept Chem & Chem Biol, Hamilton, ON L8S 4M1, Canada
[2] Univ Pittsburgh, Dept Psychiat, WPIC, Sch Med, Pittsburgh, PA 15213 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2017年 / 27卷 / 20期
基金：
加拿大自然科学与工程研究理事会;
关键词：
Quinazolinone; Multi component coupling; Antiviral; HSV-1; Herpesvirus; SIMPLEX-VIRUS TYPE-1; ACID-CATALYZED CYCLOCONDENSATION; C BOND-CLEAVAGE; BIOLOGICAL EVALUATION; ANTHRANILAMIDES; INFECTIONS; INHIBITION; ALDEHYDES; OXIDANT; AGENTS;
D O I：
10.1016/j.bmcl.2017.09.026
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The discovery of antiviral activity of 2,3-disubstituted quinazolinones, prepared by a one-pot, three-component condensation of isatoic anhydride with amines and aldehydes, against Herpes Simplex Virus (HSV)-1 is reported. Sequential iterative synthesis/antiviral assessment allowed structure-activity relationship (SAR) generation revealing synergistic structural features required for potent anti-HSV-1 activity. The most potent derivatives show greater efficacy than acyclovir against acute HSV-1 infections in neurons and minimal toxicity to the host. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4601 / 4605
页数：5
相关论文
共 33 条
  • [1] Epigenetic regulation of latent HSV-1 gene expression
    Bloom, David C.
    Giordani, Nicole V.
    Kwiatkowski, Dacia L.
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA-GENE REGULATORY MECHANISMS, 2010, 1799 (3-4): : 246 - 256
  • [2] One-Pot Synthesis of Quinazolinones from Anthranilamides and Aldehydes via p-Toluenesulfonic Acid Catalyzed Cyclocondensation and Phenyliodine Diacetate Mediated Oxidative Dehydrogenation
    Cheng, Ran
    Guo, Tianjian
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    [J]. SYNTHESIS-STUTTGART, 2013, 45 (21): : 2998 - 3006
  • [3] Histone modifications associated with herpes simplex virus type 1 genomes during quiescence and following ICP0-mediated de-repression
    Coleman, Heather M.
    Connor, Viv
    Cheng, Zara S. C.
    Grey, Finn
    Preston, Chris M.
    Efstathiou, Stacey
    [J]. JOURNAL OF GENERAL VIROLOGY, 2008, 89 : 68 - 77
  • [4] Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors
    Corbett, JW
    Ko, SS
    Rodgers, JD
    Gearhart, LA
    Magnus, NA
    Bacheler, LT
    Diamond, S
    Jeffrey, S
    Klabe, RM
    Cordova, BC
    Garber, S
    Logue, K
    Trainor, GL
    Anderson, PS
    Erickson-Viitanen, SK
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (10) : 2019 - 2030
  • [5] Comparison of three cell-based drug screening platforms for HSV-1 infection
    D'Aiuto, Leonardo
    Williamson, Kelly
    Dimitrion, Peter
    McNulty, James
    Brown, Carla E.
    Dokuburra, Chanti Babu
    Nielsen, Alexander J.
    Lin, Wen Jing
    Piazza, Paolo
    Schurdak, Mark E.
    Wood, Joel
    Yolken, Robert H.
    Kinchington, Paul R.
    Bloom, David C.
    Nimgaonkar, Vishwajit L.
    [J]. ANTIVIRAL RESEARCH, 2017, 142 : 136 - 140
  • [6] A practical and versatile approach toward a one-pot synthesis of 2,3-disubstituted 4(3H)-quinazolinones
    Dabiri, Minoo
    Salehi, Peyman
    Bahramnejad, Mahboobeh
    Alizadeh, Mohsen
    [J]. MONATSHEFTE FUR CHEMIE, 2010, 141 (08): : 877 - 881
  • [7] Danaher RJ, 2009, J NEUROVIROL
  • [8] Infection with herpes simplex virus type 1 is associated with cognitive deficits in bipolar disorder
    Dickerson, FB
    Boronow, JJ
    Stallings, C
    Origoni, AE
    Cole, S
    Krivogorsky, B
    Yolken, RH
    [J]. BIOLOGICAL PSYCHIATRY, 2004, 55 (06) : 588 - 593
  • [9] Modulation of reactivation of latent herpes simplex virus 1 in ganglionic organ cultures by p300/CBP and STAT3
    Du, Te
    Zhou, Guoying
    Roizman, Bernard
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2013, 110 (28) : E2621 - E2628
  • [10] The impact of Herpes simplex virus type 1 on cognitive impairments in young, healthy individuals - A historical prospective study
    Fruchter, Eyal
    Goldberg, Shira
    Fenchel, Daphna
    Grotto, Itamar
    Ginat, Keren
    Weiser, Mark
    [J]. SCHIZOPHRENIA RESEARCH, 2015, 168 (1-2) : 292 - 296
1234