Discovery of a new class of antiviral compounds: Camphor imine derivatives

被引:86
作者
Sokolova, Anastasiya S. [1 ,2 ]
Yarovaya, Olga I. [1 ,2 ]
Shernyukov, Andrey V. [1 ]
Gatilov, Yuriy V. [1 ,2 ]
Razumova, Yuliya V. [2 ]
Zarubaev, Vladimir V. [3 ]
Tretiak, Tatiana S. [3 ]
Pokrovsky, Andrey G. [2 ]
Kiselev, Oleg I. [3 ]
Salakhutdinov, Nariman F. [1 ,2 ]
机构
[1] Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
[2] Novosibirsk State Univ, Novosibirsk 630090, Russia
[3] Influenza Res Ctr, Dept Chemotherapy, St Petersburg 197376, Russia
基金
俄罗斯基础研究基金会; 俄罗斯科学基金会;
关键词
Influenza; Camphor derivatives; Antiviral; Cage compounds; IN-VITRO; INFLUENZA; VIRUS; AGENTS; ANTIINFLUENZA; RESISTANCE; INHIBITORS; MEMBRANE; DESIGN;
D O I
10.1016/j.ejmech.2015.10.010
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new class of compounds featuring a camphor moiety has been discovered that exhibits potent inhibitory activity against influenza A(H1N1)pdm09 and A(H5N1) viruses. The synthesized compounds were characterized by spectroscopic analysis; in addition the structures of compound 2 and 14 were elucidated by the X-ray diffraction technique. Structure activity relationship studies have been conducted to identify the 1,7,7-trimethylbicyclo[2.2.1]heptanes2-ylidene group as the key functional group responsible for the observed antiviral activity. The most potent antiviral compound is imine 2 with therapeutic index more than 500. (C) 2015 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:263 / 273
页数:11
相关论文
共 56 条
[1]   Inhibition of Influenza H7 Hemagglutinin-Mediated Entry [J].
Antanasijevic, Aleksandar ;
Cheng, Han ;
Wardrop, Duncan J. ;
Rong, Lijun ;
Caffrey, Michael .
PLOS ONE, 2013, 8 (10)
[2]  
Ardashov OV, 2011, LETT DRUG DES DISCOV, V8, P375
[3]   Comparative Study on the Antiviral Activity of Selected Monoterpenes Derived from Essential Oils [J].
Astani, Akram ;
Reichling, Juergen ;
Schnitzler, Paul .
PHYTOTHERAPY RESEARCH, 2010, 24 (05) :673-679
[4]   Emergence of Oseltamivir-Resistant Pandemic H1N1 Virus during Prophylaxis [J].
Baz, Mariana ;
Abed, Yacine ;
Papenburg, Jesse ;
Bouhy, Xavier ;
Hamelin, Marie-Eve ;
Boivin, Guy .
NEW ENGLAND JOURNAL OF MEDICINE, 2009, 361 (23) :2296-2297
[5]   Carvone Schiff base of isoniazid as a novel antitumor agent: Nanoemulsion development and pharmacokinetic evaluation [J].
Bhat, Mashooq A. ;
Lqbal, Muzaffar ;
Al-Dhfyan, Abdullah ;
Shakeel, Faiyaz .
JOURNAL OF MOLECULAR LIQUIDS, 2015, 203 :111-119
[6]   Synthesis, characterization, and in vitro anti-Mycobacterium tuberculosis activity of terpene Schiff bases [J].
Bhat, Mashooq A. ;
Al-Omar, Mohamed A. .
MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (09) :4522-4528
[7]   Biotransformation of monoterpenoids and their antimicrobial activities [J].
Bhattia, Haq Nawaz ;
Khan, Saleha Suleman ;
Khan, Ajmal ;
Rani, Mubeen ;
Ahmad, Viqar Uddin ;
Choudhary, Muhammad Iqbal .
PHYTOMEDICINE, 2014, 21 (12) :1597-1626
[8]   PREPARATION AND REDUCTION OF SOME CAMPHOR IMINES [J].
BOLTON, R ;
DANKS, TN ;
PAUL, JM .
TETRAHEDRON LETTERS, 1994, 35 (20) :3411-3412
[9]  
Borkenhagen F, 1998, Z ANORG ALLG CHEM, V624, P650
[10]   Synthesis, Coordination Properties and Application of New N,N-Ligands Based on Bornyl and Binaphthylazepine Chiral Backbones in Palladium-Catalyzed Allylic Substitution Reactions [J].
Bottari, Giovanni ;
Meduri, Angelo ;
Drommi, Dario ;
Brancatelli, Giovanna ;
Faraone, Felice .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2011, (17) :2738-2745