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
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 [J].
Bloom, David C. ;
Giordani, Nicole V. ;
Kwiatkowski, Dacia L. .
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 [J].
Cheng, Ran ;
Guo, Tianjian ;
Zhang-Negrerie, Daisy ;
Du, Yunfei ;
Zhao, Kang .
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 [J].
Coleman, Heather M. ;
Connor, Viv ;
Cheng, Zara S. C. ;
Grey, Finn ;
Preston, Chris M. ;
Efstathiou, Stacey .
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 [J].
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 .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (10) :2019-2030
[5]   Comparison of three cell-based drug screening platforms for HSV-1 infection [J].
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. .
ANTIVIRAL RESEARCH, 2017, 142 :136-140
[6]   A practical and versatile approach toward a one-pot synthesis of 2,3-disubstituted 4(3H)-quinazolinones [J].
Dabiri, Minoo ;
Salehi, Peyman ;
Bahramnejad, Mahboobeh ;
Alizadeh, Mohsen .
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 [J].
Dickerson, FB ;
Boronow, JJ ;
Stallings, C ;
Origoni, AE ;
Cole, S ;
Krivogorsky, B ;
Yolken, RH .
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 [J].
Du, Te ;
Zhou, Guoying ;
Roizman, Bernard .
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 [J].
Fruchter, Eyal ;
Goldberg, Shira ;
Fenchel, Daphna ;
Grotto, Itamar ;
Ginat, Keren ;
Weiser, Mark .
SCHIZOPHRENIA RESEARCH, 2015, 168 (1-2) :292-296