Aliphatic and alicyclic camphor imines as effective inhibitors of influenza virus H1N1

被引：44

作者：

Sokolova, Anastasiya S. ^{[1
,2
]}

Yarovaya, Olga I. ^{[1
,2
]}

Baev, Dmitry S. ^{[1
]}

Shernyukov, Andrey V. ^{[1
]}

Shtro, Anna A. ^{[3
]}

Zarubaev, Vladimir V. ^{[3
]}

Salakhutdinov, Nariman F. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Lavrentjev Ave 9, Novosibirsk 630090, Russia

[2] Novosibirsk State Univ, Pirogova St 2, Novosibirsk 630090, Russia

[3] Influenza Res Inst, Dept Chemotherapy, 15-17 Prof Popova St, St Petersburg 197376, Russia

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2017年 / 127卷

关键词：

Influenza; Camphor derivatives; Antiviral; Cage compounds; A VIRUS; ENTRY INHIBITORS; IN-VITRO; CONFORMATIONAL-CHANGE; ANTIVIRAL ACTIVITY; HEMAGGLUTININ; DERIVATIVES; DISCOVERY; AGENTS; FUSION;

D O I：

10.1016/j.ejmech.2016.10.035

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of camphor derived imines was synthesised and evaluated in vitro for antiviral activity. Theoretical evaluations of ADME properties were also carried out. Most of these compounds exhibited significant activity against the drug-resistant strains of influenza A virus. Especially, compounds 2 (SI = 632) and 3 (SI = 417) presented high inhibition against influenza subtypes A/Puerto Rico/8/34 and A/California/07/09 of H1N1pdm09. Analysis of the structure-activity relationship showed that the activity was strongly dependent on the length of the aliphatic chain: derivatives with a shorter chain possessed higher activity, while the suppressing action of compounds with long aliphatic chains was lower. (C) 2016 Elsevier Masson SAS.

引用

页码：661 / 670

页数：10

共 56 条

[1] Identification of small molecules acting against H1N1 influenza A virus [J].

Agamennone, Mariangela ;

Pietrantoni, Agostina ;

Superti, Fabiana .

VIROLOGY, 2016, 488 :249-258

[2] Designing libraries with CNS activity [J].

Ajay ;

Bemis, GW ;

Murcko, MA .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (24) :4942-4951

[3] 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

[4] Enantioselective cyanosilylation of aldehydes catalyzed by novel camphor derived Schiff bases-titanium(IV) complexes [J].

Blocka, Ewelina ;

Bosiak, Mariusz J. ;

Welniak, Mirosfaw ;

Ludwiczak, Agnieszka ;

Wojtczak, Andrzej .

TETRAHEDRON-ASYMMETRY, 2014, 25 (6-7) :554-562

[5] INHIBITION OF THE FUSION-INDUCING CONFORMATIONAL CHANGE OF INFLUENZA HEMAGGLUTININ BY BENZOQUINONES AND HYDROQUINONES [J].

BODIAN, DL ;

YAMASAKI, RB ;

BUSWELL, RL ;

STEARNS, JF ;

WHITE, JM ;

KUNTZ, ID .

BIOCHEMISTRY, 1993, 32 (12) :2967-2978

[6] Adamantane resistance among influenza A viruses isolated early during the 2005-2006 influenza season in the United States [J].

Bright, RA ;

Shay, DK ;

Shu, B ;

Cox, NJ ;

Klimov, AI .

JAMA-JOURNAL OF THE AMERICAN MEDICAL ASSOCIATION, 2006, 295 (08) :891-894

[7] Sustainable Practices in Medicinal Chemistry: Current State and Future Directions [J].

Bryan, Marian C. ;

Dillon, Barry ;

Hamann, Lawrence G. ;

Hughes, Gregory J. ;

Kopach, Michael E. ;

Peterson, Emily A. ;

Pourashraf, Mehrnaz ;

Raheem, Izzat ;

Richardson, Paul ;

Richter, Daniel ;

Sneddon, Helen F. .

JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (15) :6007-6021

[8]

Centres for Disease Control and Prevention, 2015, SEL VIR 681 SEAS INF

[9] CARBON VERSUS SULFUR ADDITION OF NUCLEOPHILES TO SULFINES - THE CASE OF AMINES [J].

CERRETA, F ;

LERIVEREND, C ;

METZNER, P .

TETRAHEDRON LETTERS, 1993, 34 (42) :6741-6742

[10] Activity of Andrographolide and Its Derivatives against Influenza Virus in Vivo and in Vitro [J].

Chen, Jian-Xin ;

Xue, Hui-Jun ;

Ye, Wen-Cai ;

Fang, Bing-Hu ;

Liu, Ya-Hong ;

Yuan, Shao-Hua ;

Yu, Pei ;

Wang, Yu-Qiang .

BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2009, 32 (08) :1385-1391

← 1 2 3 4 5 6 →