{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T00:00:10Z","timestamp":1792454410069,"version":"4.5.0"},"reference-count":44,"publisher":"Elsevier BV","issue":"19","license":[{"start":{"date-parts":[[2017,10,1]],"date-time":"2017-10-01T00:00:00Z","timestamp":1506816000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2017,10,1]],"date-time":"2017-10-01T00:00:00Z","timestamp":1506816000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"}],"funder":[{"name":"Russian Scientific Foundation","award":["15-13-00017"],"award-info":[{"award-number":["15-13-00017"]}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic & Medicinal Chemistry Letters"],"published-print":{"date-parts":[[2017,10]]},"DOI":"10.1016\/j.bmcl.2017.08.062","type":"journal-article","created":{"date-parts":[[2017,9,1]],"date-time":"2017-09-01T12:46:33Z","timestamp":1504269993000},"page":"4531-4535","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":23,"title":["Anti-influenza activity of diazaadamantanes combined with monoterpene moieties"],"prefix":"10.1016","volume":"27","author":[{"given":"Evgeniy","family":"Suslov","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vladimir V.","family":"Zarubaev","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander V.","family":"Slita","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Konstantin","family":"Ponomarev","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dina","family":"Korchagina","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel M.","family":"Ayine-Tora","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J\u00f3hannes","family":"Reynisson","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Konstantin","family":"Volcho","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nariman","family":"Salakhutdinov","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.bmcl.2017.08.062_b0005","doi-asserted-by":"crossref","first-page":"77","DOI":"10.3851\/IMP2235","article-title":"Influenza nucleoprotein: promising target for antiviral chemotherapy","volume":"23","author":"Cianci","year":"2013","journal-title":"Antiviral Chem Chemother"},{"key":"10.1016\/j.bmcl.2017.08.062_b0010","first-page":"1","article-title":"Antiviral agents for the treatment and chemoprophylaxis of influenza","volume":"60","author":"Fiore","year":"2011","journal-title":"MMWR Recomm Rep"},{"key":"10.1016\/j.bmcl.2017.08.062_b0015","doi-asserted-by":"crossref","first-page":"3516","DOI":"10.1021\/cr100264t","article-title":"The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives","volume":"113","author":"Wanka","year":"2013","journal-title":"Chem Rev"},{"key":"10.1016\/j.bmcl.2017.08.062_b0020","doi-asserted-by":"crossref","first-page":"591","DOI":"10.1038\/nature06531","article-title":"Structure and mechanism of the M2 proton channel of influenza A virus","volume":"451","author":"Schnell","year":"2008","journal-title":"Nature"},{"key":"10.1016\/j.bmcl.2017.08.062_b0025","doi-asserted-by":"crossref","first-page":"e0119115","DOI":"10.1371\/journal.pone.0119115","article-title":"Adamantane-resistant influenza a viruses in the world (1902\u20132013): frequency and distribution of M2 gene mutations","volume":"10","author":"Dong","year":"2015","journal-title":"PLoS One"},{"key":"10.1016\/j.bmcl.2017.08.062_b0030","doi-asserted-by":"crossref","first-page":"419","DOI":"10.1016\/j.apsb.2015.07.006","article-title":"New small-molecule drug design strategies for fighting resistant influenza A","volume":"5","author":"Shen","year":"2015","journal-title":"Acta Pharmaceut Sin B"},{"key":"10.1016\/j.bmcl.2017.08.062_b0035","doi-asserted-by":"crossref","first-page":"2804","DOI":"10.1021\/jm301538e","article-title":"Discovery of novel dual inhibitors of the wild-type and the most prevalent drug-resistant mutant, S31N, of the M2 proton channel from influenza A virus","volume":"56","author":"Wang","year":"2013","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmcl.2017.08.062_b0040","doi-asserted-by":"crossref","first-page":"1580","DOI":"10.1021\/acs.jmedchem.6b01852","article-title":"Expeditious lead optimization of isoxazole-containing influenza A virus M2\u2013S31N inhibitors using the Suzuki\u2013Miyaura cross-coupling reaction","volume":"60","author":"Li","year":"2017","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmcl.2017.08.062_b0045","doi-asserted-by":"crossref","first-page":"1207","DOI":"10.1021\/acs.jmedchem.5b01910","article-title":"Discovery of highly potent inhibitors targeting the predominant drug-resistant S31N mutant of the influenza A virus M2 proton channel","volume":"59","author":"Li","year":"2016","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmcl.2017.08.062_b0050","doi-asserted-by":"crossref","first-page":"477","DOI":"10.2174\/1570180811310060002","article-title":"Synthesis of new compounds combining adamantanamine and monoterpene fragments and their antiviral activity against influenza virus A(H1N1)pdm09","volume":"10","author":"Teplov","year":"2013","journal-title":"Lett Drug Des Discovery"},{"key":"10.1016\/j.bmcl.2017.08.062_b0055","doi-asserted-by":"crossref","first-page":"1033","DOI":"10.1070\/RC1989v058n11ABEH003495","article-title":"Azaadamantanes with nitrogen atoms in the bridgehead positions","volume":"58","author":"Kuznetsov","year":"1989","journal-title":"Russ Chem Rev"},{"key":"10.1016\/j.bmcl.2017.08.062_b0060","series-title":"Structural analysis of cyclic systems","first-page":"101","article-title":"Molecular structure of 1-azaadamantanes and 1,3-diazaadamantanes","author":"Jimenez-Cruz","year":"2005"},{"key":"10.1016\/j.bmcl.2017.08.062_b0065","doi-asserted-by":"crossref","first-page":"4146","DOI":"10.1007\/s00044-015-1464-z","article-title":"Synthesis and analgesic activity of new compounds combining azaadamantane and monoterpene moieties","volume":"24","author":"Ponomarev","year":"2015","journal-title":"Med Chem Res"},{"key":"10.1016\/j.bmcl.2017.08.062_b0070","doi-asserted-by":"crossref","first-page":"657","DOI":"10.1134\/S1068162015060199","article-title":"Inhibitory properties of nitrogen-containing adamantane derivatives with monoterpenoid fragments against tyrosyl-DNA phosphodiesterase 1","volume":"41","author":"Zakharenko","year":"2015","journal-title":"Russ J Bioorg Chem"},{"key":"10.1016\/j.bmcl.2017.08.062_b0075","doi-asserted-by":"crossref","DOI":"10.2174\/1573406413666170525124316","article-title":"Synthesis and analgesic activity of amines combining azaadamantane and monoterpene fragments","author":"Ponomarev","year":"2017","journal-title":"Med Chem"},{"key":"10.1016\/j.bmcl.2017.08.062_b0085","doi-asserted-by":"crossref","first-page":"1442","DOI":"10.1002\/hlca.201500125","article-title":"The first synthesis of (4S,5R,6R)-5,6-dihydroxy-4-(prop-1-en-2-yl)cyclohex-1-enecarboxylic acid","volume":"98","author":"Ardashov","year":"2015","journal-title":"Helv Chim Acta"},{"key":"10.1016\/j.bmcl.2017.08.062_b0090","doi-asserted-by":"crossref","first-page":"1953","DOI":"10.1080\/00397919608003550","article-title":"Radical chemistry based on (+)-cis-pinononic and (+)-pinonic acids","volume":"26","author":"Barton","year":"1996","journal-title":"Synth Commun"},{"key":"10.1016\/j.bmcl.2017.08.062_b0095","doi-asserted-by":"crossref","first-page":"9097","DOI":"10.1016\/S0040-4020(01)85375-8","article-title":"Aminium salts catalyzed rearrangement of \u03b1-pinene and \u03b2-ionone oxides","volume":"50","author":"Lopez","year":"1994","journal-title":"Tetrahedron"},{"key":"10.1016\/j.bmcl.2017.08.062_b0110","doi-asserted-by":"crossref","first-page":"7060","DOI":"10.1016\/j.bmcl.2012.09.084","article-title":"Anti-viral activity of (\u2212)- and (+)-usnic acids and their derivatives against influenza virus A(H1N1)2009","volume":"22","author":"Sokolov","year":"2012","journal-title":"Bioorg Med Chem Lett"},{"key":"10.1016\/j.bmcl.2017.08.062_b0120","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0022-1759(83)90303-4","article-title":"Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays","volume":"65","author":"Mosmann","year":"1983","journal-title":"J Immunol Methods"},{"key":"10.1016\/j.bmcl.2017.08.062_b0125","doi-asserted-by":"crossref","first-page":"596","DOI":"10.1038\/nature06528","article-title":"Structural basis for the function and inhibition of an influenza virus proton channel","volume":"451","author":"Stouffer","year":"2008","journal-title":"Nature"},{"key":"10.1016\/j.bmcl.2017.08.062_b0130","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1093\/nar\/28.1.235","article-title":"The protein data bank","volume":"28","author":"Berman","year":"2000","journal-title":"Nucleic Acids Res"},{"key":"10.1016\/j.bmcl.2017.08.062_b0135","doi-asserted-by":"crossref","DOI":"10.1038\/nsb1203-980","article-title":"Announcing the worldwide protein data bank","volume":"10","author":"Berman","year":"2003","journal-title":"Nat Struct Mol Biol"},{"key":"10.1016\/j.bmcl.2017.08.062_b0140","unstructured":"Scigress: Version FJ 2.6 (EU 3.1.7), Fijitsu Limited, 2008\u20132016."},{"key":"10.1016\/j.bmcl.2017.08.062_b0145","doi-asserted-by":"crossref","first-page":"1551","DOI":"10.1002\/pro.2937","article-title":"Crystal structure of the drug-resistant S31N influenza M2 proton channel","volume":"25","author":"Thomaston","year":"2016","journal-title":"Protein Sci"},{"key":"10.1016\/j.bmcl.2017.08.062_b0150","doi-asserted-by":"crossref","first-page":"727","DOI":"10.1006\/jmbi.1996.0897","article-title":"Development and validation of a genetic algorithm for flexible docking","volume":"267","author":"Jones","year":"1997","journal-title":"J Mol Biol"},{"key":"10.1016\/j.bmcl.2017.08.062_b0155","doi-asserted-by":"crossref","first-page":"425","DOI":"10.1023\/A:1007996124545","article-title":"Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes","volume":"11","author":"Eldridge","year":"1997","journal-title":"J Comput-Aided Mol Des"},{"key":"10.1016\/j.bmcl.2017.08.062_b0160","doi-asserted-by":"crossref","first-page":"609","DOI":"10.1002\/prot.10465","article-title":"Improved protein-ligand docking using GOLD","volume":"52","author":"Verdonk","year":"2003","journal-title":"Proteins"},{"key":"10.1016\/j.bmcl.2017.08.062_b0165","doi-asserted-by":"crossref","first-page":"84","DOI":"10.1021\/ci800298z","article-title":"Empirical scoring functions for advanced protein-ligand docking with PLANTS","volume":"49","author":"Korb","year":"2009","journal-title":"J Chem Inf Model"},{"key":"10.1016\/j.bmcl.2017.08.062_b0170","doi-asserted-by":"crossref","first-page":"272","DOI":"10.1002\/prot.20588","article-title":"General and targeted statistical potentials for protein\u2013ligand interactions","volume":"61","author":"Mooij","year":"2005","journal-title":"Proteins"},{"key":"10.1016\/j.bmcl.2017.08.062_b0175","doi-asserted-by":"crossref","first-page":"31038","DOI":"10.1074\/jbc.M003663200","article-title":"Permeation and activation of the M2 ion channel of influenza A virus","volume":"275","author":"Mould","year":"2000","journal-title":"J Biol Chem"},{"key":"10.1016\/j.bmcl.2017.08.062_b0180","doi-asserted-by":"crossref","first-page":"5000","DOI":"10.1073\/pnas.94.10.5000","article-title":"The active oligomeric state of the minimalistic influenza virus M2 ion channel is a tetramer","volume":"94","author":"Sakaguchi","year":"1997","journal-title":"Proc Natl Acad Sci"},{"key":"10.1016\/j.bmcl.2017.08.062_b0185","doi-asserted-by":"crossref","first-page":"2511","DOI":"10.1016\/S0006-3495(97)78279-1","article-title":"Transmembrane four-helix bundle of influenza A M2 protein channel: structural implications from helix tilt and orientation","volume":"73","author":"Kovacs","year":"1997","journal-title":"Biophys J"},{"key":"10.1016\/j.bmcl.2017.08.062_b0190","doi-asserted-by":"crossref","first-page":"4457","DOI":"10.1128\/AAC.00650-09","article-title":"Large-scale sequence analysis of M gene of influenza A viruses from different species: mechanisms for emergence and spread of amantadine resistance","volume":"53","author":"Furuse","year":"2009","journal-title":"Antimicrob Agents Chemother"},{"key":"10.1016\/j.bmcl.2017.08.062_b0195","doi-asserted-by":"crossref","first-page":"556","DOI":"10.1128\/AAC.49.2.556-559.2005","article-title":"Generation and characterization of recombinant influenza A (H1N1) viruses harboring amantadine resistance mutations","volume":"49","author":"Abed","year":"2005","journal-title":"Antimicrob Agents Chemother"},{"key":"10.1016\/j.bmcl.2017.08.062_b0200","doi-asserted-by":"crossref","first-page":"17987","DOI":"10.1021\/ja508461m","article-title":"Flipping in the pore: discovery of Inhibitors that bind in different orientations to the Wild-Type versus the Amantadine-Resistant S31N Mutant of Influenza A Virus M2 Proton Channel","volume":"136","author":"Wu","year":"2014","journal-title":"J Am Chem Soc"},{"key":"10.1016\/j.bmcl.2017.08.062_b0205","doi-asserted-by":"crossref","first-page":"737","DOI":"10.1007\/s10822-012-9551-4","article-title":"Pose prediction and virtual screening performance of GOLD scoring functions in a standardized test","volume":"26","author":"Liebeschuetz","year":"2012","journal-title":"J Comput Aided Mol Des"},{"key":"10.1016\/j.bmcl.2017.08.062_b0210","doi-asserted-by":"crossref","first-page":"1717","DOI":"10.1021\/ci500081m","article-title":"Comparative assessment of scoring functions on an updated benchmark: 2. Evaluation methods and general results","volume":"54","author":"Li","year":"2014","journal-title":"J Chem Inf Mod"},{"key":"10.1016\/j.bmcl.2017.08.062_b0215","doi-asserted-by":"crossref","first-page":"5646","DOI":"10.1016\/j.ejmech.2010.09.018","article-title":"Characteristics of known drug space. natural products, their derivatives and synthetic drugs","volume":"45","author":"Bade","year":"2010","journal-title":"Eur J Med Chem"},{"key":"10.1016\/j.bmcl.2017.08.062_b0220","doi-asserted-by":"crossref","first-page":"1250","DOI":"10.1021\/jm021053p","article-title":"A comparison of physiochemical property profiles of development and marketed oral drugs","volume":"46","author":"Wenlock","year":"2003","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmcl.2017.08.062_b0225","doi-asserted-by":"crossref","first-page":"4872","DOI":"10.1016\/j.bmcl.2008.07.071","article-title":"Physochemical drug properties associated with in vivo toxicological outcomes","volume":"18","author":"Hughes","year":"2008","journal-title":"Bioorg Med Chem Lett"},{"key":"10.1016\/j.bmcl.2017.08.062_b0230","doi-asserted-by":"crossref","first-page":"847","DOI":"10.1002\/minf.201200103","article-title":"Wine compounds as a source for HTS screening collections. A feasibility study","volume":"31","author":"Zhu","year":"2012","journal-title":"Mol Inf"},{"key":"10.1016\/j.bmcl.2017.08.062_b0235","unstructured":"QikProp, v3.2; Schr\u00f6dinger: New York; 2009."},{"key":"10.1016\/j.bmcl.2017.08.062_b0240","doi-asserted-by":"crossref","first-page":"445","DOI":"10.1002\/qsar.200730051","article-title":"Benchmarking the reliability of QikProp. Correlation between experimental and predicted values","volume":"27","author":"Ioakimidis","year":"2008","journal-title":"QSAR Comb Sci"}],"container-title":["Bioorganic & Medicinal Chemistry Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X17308661?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X17308661?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T07:17:32Z","timestamp":1760771852000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0960894X17308661"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,10]]},"references-count":44,"journal-issue":{"issue":"19","published-print":{"date-parts":[[2017,10]]}},"alternative-id":["S0960894X17308661"],"URL":"https:\/\/doi.org\/10.1016\/j.bmcl.2017.08.062","relation":{},"ISSN":["0960-894X"],"issn-type":[{"value":"0960-894X","type":"print"}],"subject":[],"published":{"date-parts":[[2017,10]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Anti-influenza activity of diazaadamantanes combined with monoterpene moieties","name":"articletitle","label":"Article Title"},{"value":"Bioorganic & Medicinal Chemistry Letters","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bmcl.2017.08.062","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2017 Elsevier Ltd. All rights reserved.","name":"copyright","label":"Copyright"}]}}