{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T23:27:31Z","timestamp":1790724451202,"version":"4.1.0"},"reference-count":78,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2022,9,5]],"date-time":"2022-09-05T00:00:00Z","timestamp":1662336000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Russian Science Foundation","award":["21\u201371\u201320031"],"award-info":[{"award-number":["21\u201371\u201320031"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Candidates to being inhibitors of the main protease (Mpro) of SARS-CoV-2 were selected from the database of Voronezh State University using molecular modeling. The database contained approximately 19,000 compounds represented by more than 41,000 ligand conformers. These ligands were docked into Mpro using the SOL docking program. For one thousand ligands with best values of the SOL score, the protein\u2013ligand binding enthalpy was calculated by the PM7 quantum-chemical method with the COSMO solvent model. Using the SOL score and the calculated protein\u2013ligand binding enthalpies, eighteen compounds were selected for the experiments. Several of these inhibitors suppressed the replication of the coronavirus in cell culture, and we used the best three among them in the search for chemical analogs. Selection among analogs using the same procedure followed by experiments led to identification of seven inhibitors of the SARS-CoV-2 replication in cell culture with EC50 values at the micromolar level. The identified inhibitors belong to three chemical classes. The three inhibitors, 4,4-dimethyldithioquinoline derivatives, inhibit SARS-CoV-2 replication in Vero E6 cell culture just as effectively as the best published non-covalent inhibitors, and show low cytotoxicity. These results open up a possibility to develop antiviral drugs against the SARS-CoV-2 coronavirus.<\/jats:p>","DOI":"10.3390\/molecules27175732","type":"journal-article","created":{"date-parts":[[2022,9,7]],"date-time":"2022-09-07T01:51:57Z","timestamp":1662515517000},"page":"5732","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["New Chemicals Suppressing SARS-CoV-2 Replication in Cell Culture"],"prefix":"10.3390","volume":"27","author":[{"given":"Alexey","family":"Sulimov","sequence":"first","affiliation":[{"name":"Dimonta Ltd., 15 Nagornaya Str., Bldg 8, 117186 Moscow, Russia"},{"name":"Research Computing Center, Lomonosov Moscow State University, Leninskie Gory, 1, Building 4, 119234 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ivan","family":"Ilin","sequence":"additional","affiliation":[{"name":"Dimonta Ltd., 15 Nagornaya Str., Bldg 8, 117186 Moscow, Russia"},{"name":"Research Computing Center, Lomonosov Moscow State University, Leninskie Gory, 1, Building 4, 119234 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4777-6522","authenticated-orcid":false,"given":"Danil","family":"Kutov","sequence":"additional","affiliation":[{"name":"Dimonta Ltd., 15 Nagornaya Str., Bldg 8, 117186 Moscow, Russia"},{"name":"Research Computing Center, Lomonosov Moscow State University, Leninskie Gory, 1, Building 4, 119234 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Khidmet","family":"Shikhaliev","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Chemistry, Voronezh State University, 1 Universitetskaya Sq., 394018 Voronezh, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8023-4453","authenticated-orcid":false,"given":"Dmitriy","family":"Shcherbakov","sequence":"additional","affiliation":[{"name":"State Research Centre of Virology and Biotechnology \u201cVector\u201d, 630559 Koltsovo, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oleg","family":"Pyankov","sequence":"additional","affiliation":[{"name":"State Research Centre of Virology and Biotechnology \u201cVector\u201d, 630559 Koltsovo, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1819-6414","authenticated-orcid":false,"given":"Nadezhda","family":"Stolpovskaya","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Chemistry, Voronezh State University, 1 Universitetskaya Sq., 394018 Voronezh, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0073-1084","authenticated-orcid":false,"given":"Svetlana","family":"Medvedeva","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Chemistry, Voronezh State University, 1 Universitetskaya Sq., 394018 Voronezh, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vladimir","family":"Sulimov","sequence":"additional","affiliation":[{"name":"Dimonta Ltd., 15 Nagornaya Str., Bldg 8, 117186 Moscow, Russia"},{"name":"Research Computing Center, Lomonosov Moscow State University, Leninskie Gory, 1, Building 4, 119234 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,9,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"8853056","DOI":"10.1155\/2021\/8853056","article-title":"An Updated Review of Computer-Aided Drug Design and Its Application to COVID-19","volume":"2021","author":"Gurung","year":"2021","journal-title":"Biomed Res. Int."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Chang, L.J., and Chen, T.H. (2021). NSP16 2\u2019-O-MTase in Coronavirus Pathogenesis: Possible Prevention and Treatments Strategies. Viruses, 13.","DOI":"10.3390\/v13040538"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"12359","DOI":"10.1021\/acs.jmedchem.0c00606","article-title":"COVID-19: Drug Targets and Potential Treatments","volume":"63","author":"Gil","year":"2020","journal-title":"J. Med. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"115745","DOI":"10.1016\/j.bmc.2020.115745","article-title":"Druggable targets from coronaviruses for designing new antiviral drugs","volume":"28","author":"Silva","year":"2020","journal-title":"Bioorganic Med. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"409","DOI":"10.1126\/science.abb3405","article-title":"Crystal structure of SARS-CoV-2 main protease provides a basis for design of improved \u03b1-ketoamide inhibitors","volume":"368","author":"Zhang","year":"2020","journal-title":"Science"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"259","DOI":"10.18596\/jotcsa.634130","article-title":"Development of docking programs for Lomonosov supercomputer","volume":"7","author":"Sulimov","year":"2019","journal-title":"J. Turk. Chem. Soc. Sect. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"7555","DOI":"10.2174\/0929867325666180904115000","article-title":"Advances in Docking","volume":"26","author":"Sulimov","year":"2019","journal-title":"Curr. Med. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"507","DOI":"10.2174\/1568026620666201207095626","article-title":"Docking paradigm in Drug Design","volume":"21","author":"Sulimov","year":"2021","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1913","DOI":"10.1007\/s11172-017-1966-6","article-title":"Search for approaches to improving the calculation accuracy of the protein-ligand binding energy by docking","volume":"66","author":"Sulimov","year":"2017","journal-title":"Russ. Chem. Bull."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"581","DOI":"10.1002\/jmr.2471","article-title":"Improvements, trends, and new ideas in molecular docking: 2012\u20132013 in review","volume":"28","author":"Yuriev","year":"2015","journal-title":"J. Mol. Recognit."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2324","DOI":"10.1021\/acs.jcim.5b00559","article-title":"ZINC 15 \u2013 Ligand Discovery for Everyone","volume":"55","author":"Sterling","year":"2015","journal-title":"J. Chem. Inf. Model."},{"key":"ref_12","unstructured":"(2022, August 16). ZINC Catalog DrugBank-Approved. Available online: https:\/\/zinc.docking.org\/catalogs\/dbap\/."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"D1091","DOI":"10.1093\/nar\/gkt1068","article-title":"DrugBank 4.0: Shedding new light on drug metabolism","volume":"42","author":"Law","year":"2013","journal-title":"Nucleic Acids Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2526","DOI":"10.1021\/acsmedchemlett.0c00521","article-title":"Identification of 14 Known Drugs as Inhibitors of the Main Protease of SARS-CoV-2","volume":"11","author":"Ghahremanpour","year":"2020","journal-title":"ACS Med. Chem. Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"467","DOI":"10.1021\/acscentsci.1c00039","article-title":"Potent Noncovalent Inhibitors of the Main Protease of SARS-CoV-2 from Molecular Sculpting of the Drug Perampanel Guided by Free Energy Perturbation Calculations","volume":"7","author":"Zhang","year":"2021","journal-title":"ACS Cent. Sci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"5308","DOI":"10.1021\/acs.jcim.0c00547","article-title":"Evolution of Alchemical Free Energy Methods in Drug Discovery","volume":"60","author":"Song","year":"2020","journal-title":"J. Chem. Inf. Model."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"140","DOI":"10.1021\/acsmedchemlett.1c00299","article-title":"Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors","volume":"13","author":"Shcherbakov","year":"2022","journal-title":"ACS Med. Chem. Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1008","DOI":"10.1021\/acsptsci.0c00108","article-title":"Identification of SARS-CoV-2 3CL Protease Inhibitors by a Quantitative High-Throughput Screening","volume":"3","author":"Zhu","year":"2020","journal-title":"ACS Pharmacol. Transl. Sci."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1096","DOI":"10.1021\/acsptsci.0c00216","article-title":"Identification of Inhibitors of SARS-CoV-2 3CL-Pro Enzymatic Activity Using a Small Molecule in Vitro Repurposing Screen","volume":"4","author":"Kuzikov","year":"2021","journal-title":"ACS Pharmacol. Transl. Sci."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1586","DOI":"10.1126\/science.abl4784","article-title":"An oral SARS-CoV-2 M<sup>pro<\/sup> inhibitor clinical candidate for the treatment of COVID-19","volume":"374","author":"Owen","year":"2021","journal-title":"Science"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1038\/s41467-022-28354-0","article-title":"The oral protease inhibitor (PF-07321332) protects Syrian hamsters against infection with SARS-CoV-2 variants of concern","volume":"13","author":"Abdelnabi","year":"2022","journal-title":"Nat. Commun."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"6055","DOI":"10.1038\/s41467-021-26239-2","article-title":"Preclinical characterization of an intravenous coronavirus 3CL protease inhibitor for the potential treatment of COVID19","volume":"12","author":"Boras","year":"2021","journal-title":"Nat. Commun."},{"key":"ref_23","first-page":"1","article-title":"Identification of Chymotrypsin-like Protease Inhibitors of SARS-CoV-2 Via Integrated Computational Approach","volume":"39","author":"Zia","year":"2020","journal-title":"J. Biomol. Struct. Dyn."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"672","DOI":"10.1021\/acscentsci.0c00489","article-title":"Remdesivir: A Review of Its Discovery and Development Leading to Emergency Use Authorization for Treatment of COVID-19","volume":"6","author":"Eastman","year":"2020","journal-title":"ACS Cent. Sci."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"995","DOI":"10.1002\/2211-5463.12875","article-title":"Potential anti-SARS-CoV-2 drug candidates identified through virtual screening of the ChEMBL database for compounds that target the main coronavirus protease","volume":"10","author":"Tsuji","year":"2020","journal-title":"FEBS Open Bio"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Ruiz-Carmona, S., Alvarez-Garcia, D., Foloppe, N., Garmendia-Doval, A.B., Juhos, S., Schmidtke, P., Barril, X., Hubbard, R.E., and Morley, S.D. (2014). rDock: A Fast, Versatile and Open Source Program for Docking Ligands to Proteins and Nucleic Acids. PLoS Comput. Biol., 10.","DOI":"10.1371\/journal.pcbi.1003571"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1038\/s41586-020-2223-y","article-title":"Structure of Mpro from SARS-CoV-2 and discovery of its inhibitors","volume":"582","author":"Jin","year":"2020","journal-title":"Nature"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1265","DOI":"10.1021\/acsptsci.0c00130","article-title":"Ebselen, Disulfiram, Carmofur, PX-12, Tideglusib, and Shikonin Are Nonspecific Promiscuous SARS-CoV-2 Main Protease Inhibitors","volume":"3","author":"Ma","year":"2020","journal-title":"ACS Pharmacol. Transl. Sci."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"113157","DOI":"10.1016\/j.ejmech.2021.113157","article-title":"The race to treat COVID-19: Potential therapeutic agents for the prevention and treatment of SARS-CoV-2","volume":"213","author":"Shagufta","year":"2021","journal-title":"Eur. J. Med. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"113789","DOI":"10.1016\/j.ejmech.2021.113789","article-title":"Discovery of juglone and its derivatives as potent SARS-CoV-2 main proteinase inhibitors","volume":"225","author":"Cui","year":"2021","journal-title":"Eur. J. Med. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"113863","DOI":"10.1016\/j.ejmech.2021.113863","article-title":"Identification of a dual acting SARS-CoV-2 proteases inhibitor through in silico design and step-by-step biological characterization","volume":"226","author":"Lauro","year":"2021","journal-title":"Eur. J. Med. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"113584","DOI":"10.1016\/j.ejmech.2021.113584","article-title":"Improved SARS-CoV-2 Mpro inhibitors based on feline antiviral drug GC376: Structural enhancements, increased solubility, and micellar studies","volume":"222","author":"Vuong","year":"2021","journal-title":"Eur. J. Med. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/j.ymeth.2021.01.003","article-title":"Bisindolylmaleimide IX: A novel anti-SARS-CoV2 agent targeting viral main protease 3CLpro demonstrated by virtual screening pipeline and in vitro validation assays","volume":"195","author":"Gupta","year":"2021","journal-title":"Methods"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"595097","DOI":"10.3389\/fchem.2020.595097","article-title":"In Silico Study of Coumarins and Quinolines Derivatives as Potent Inhibitors of SARS-CoV-2 Main Protease","volume":"8","author":"Osorio","year":"2021","journal-title":"Front. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1796","DOI":"10.3389\/fmicb.2020.01796","article-title":"Quinolines-Based SARS-CoV-2 3CLpro and RdRp Inhibitors and Spike-RBD-ACE2 Inhibitor for Drug-Repurposing Against COVID-19: An in silico Analysis","volume":"11","author":"Alexpandi","year":"2020","journal-title":"Front. Microbiol."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"6499","DOI":"10.1021\/acs.jmedchem.2c00117","article-title":"Discovery of S-217622, a Noncovalent Oral SARS-CoV-2 3CL Protease Inhibitor Clinical Candidate for Treating COVID-19","volume":"65","author":"Unoh","year":"2022","journal-title":"J. Med. Chem."},{"key":"ref_37","first-page":"4","article-title":"Supercomputer Lomonosov-2: Large Scale, Deep Monitoring and Fine Analytics for the User Community","volume":"6","author":"Voevodin","year":"2019","journal-title":"Supercomput. Front. Innov."},{"key":"ref_38","first-page":"41","article-title":"In Search of Non-covalent Inhibitors of SARS-CoV-2 Main Protease: Computer Aided Drug Design Using Docking and Quantum Chemistry","volume":"7","author":"Sulimov","year":"2020","journal-title":"Supercomput. Front. Innov."},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Brown, J.P. (1968). Reactions of 2,2-dialkyl-1,2-dihydroquinolines. Part IV. 4,5-Dihydro-4,4-dimethyl-1H-1,2-dithiolo[3,4-c]quinoline-1-thiones. J. Chem. Soc. C, 1074\u20131075.","DOI":"10.1039\/j39680001074"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1016\/j.ejmech.2019.04.046","article-title":"Appendix A. dithioloquinolinethiones as new potential multitargeted antibacterial and antifungal agents: Synthesis, biological evaluation and molecular docking studies","volume":"175","author":"Kartsev","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"2252","DOI":"10.1021\/ja01105a504","article-title":"2,2,4-Trimethyl-1,2-dihydroquinoline","volume":"75","author":"Craig","year":"1953","journal-title":"J. Am. Chem. Soc."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"5901","DOI":"10.1007\/s00044-013-0582-8","article-title":"Design, synthesis and evaluation of aminobenzophenone derivatives containing nitrogen mustard moiety as potential central nervous system antitumor agent","volume":"22","author":"Singh","year":"2013","journal-title":"Med. Chem. Res."},{"key":"ref_43","unstructured":"Kubota, H., Suzuki, T., Miura, M., Nakai, E., Yahiro, K., Miyake, A., Mochizuki, S., and Nakato, K. (2009). 2,4,6-Triamino-1,3,5-triazine Derivative. (No. EP1479397A4)."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"700","DOI":"10.1248\/cpb.c14-00218","article-title":"Synthesis and Structure\u2013Activity Relationship Study of Triazine-Based Inhibitors of the DNA Binding of NF-kB","volume":"62","author":"Fujii","year":"2014","journal-title":"Chem. Pharm. Bull."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1016\/j.dyepig.2016.04.016","article-title":"Bistriazine-based streptocyanines. Preparation, structural determination and optoelectronic properties","volume":"131","author":"Elizalde","year":"2016","journal-title":"Dye. Pigment."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"510","DOI":"10.1016\/j.ejmech.2009.10.037","article-title":"Synthesis of some new S-triazine based chalcones and their derivatives as potent antimicrobial agents","volume":"45","author":"Solankee","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1038\/s41422-020-0282-0","article-title":"Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro","volume":"30","author":"Wang","year":"2020","journal-title":"Cell Res."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1499","DOI":"10.1126\/science.abc1560","article-title":"Structural basis for inhibition of the RNA-dependent RNA polymerase from SARS-CoV-2 by remdesivir","volume":"368","author":"Yin","year":"2020","journal-title":"Science"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"5673","DOI":"10.1021\/acs.jmedchem.8b01153","article-title":"Emerging and Re-Emerging Warheads for Targeted Covalent Inhibitors: Applications in Medicinal Chemistry and Chemical Biology","volume":"62","author":"Gehringer","year":"2019","journal-title":"J. Med. Chem."},{"key":"ref_50","unstructured":"Delano, W.L. (2021, January 14). The PyMOL Molecular Graphics System. Available online: http:\/\/www.pymol.org."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"W443","DOI":"10.1093\/nar\/gkv315","article-title":"PLIP: Fully automated protein\u2013ligand interaction profiler","volume":"43","author":"Salentin","year":"2015","journal-title":"Nucleic Acids Res."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"104767","DOI":"10.1016\/j.bioorg.2021.104767","article-title":"Discovery of novel inhibitors against main protease (Mpro) of SARS-CoV-2 via virtual screening and biochemical evaluation","volume":"110","author":"Guo","year":"2021","journal-title":"Bioorganic Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"4282","DOI":"10.1038\/s41467-020-18096-2","article-title":"Feline coronavirus drug inhibits the main protease of SARS-CoV-2 and blocks virus replication","volume":"11","author":"Vuong","year":"2020","journal-title":"Nat. Commun."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"2848","DOI":"10.1021\/acs.jmedchem.1c00509","article-title":"Expedited Approach toward the Rational Design of Noncovalent SARS-CoV-2 Main Protease Inhibitors","volume":"65","author":"Kitamura","year":"2022","journal-title":"J. Med. Chem."},{"key":"ref_55","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":"ref_56","doi-asserted-by":"crossref","first-page":"1946","DOI":"10.1021\/ci400094h","article-title":"Application of the Docking Program SOL for CSAR Benchmark","volume":"53","author":"Sulimov","year":"2013","journal-title":"J. Chem. Inf. Model."},{"key":"ref_57","unstructured":"(2022, August 16). The Department of Organic Chemistry of Voronezh State University. Available online: http:\/\/www.vsu.ru\/english\/depts\/chem.html."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1016\/j.jmgm.2019.03.017","article-title":"New factor Xa inhibitors based on 1,2,3,4-tetrahydroquinoline developed by molecular modelling","volume":"89","author":"Ilin","year":"2019","journal-title":"J. Mol. Graph. Model."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"975","DOI":"10.1007\/s11094-018-1726-4","article-title":"Synthesis, Docking, and Anticoagulant Activity of New Factor-Xa Inhibitors in a Series of Pyrrolo[3,2,1-ij]Quinoline-1,2-Diones","volume":"51","author":"Medvedeva","year":"2018","journal-title":"Pharm. Chem. J."},{"key":"ref_60","doi-asserted-by":"crossref","unstructured":"Novichikhina, N., Ilin, I., Tashchilova, A., Sulimov, A., Kutov, D., Ledenyova, I., Krysin, M., Shikhaliev, K., Gantseva, A., and Gantseva, E. (2020). Synthesis, Docking, and In Vitro Anticoagulant Activity Assay of Hybrid Derivatives of Pyrrolo[3,2,1-ij]Quinolin-2(1H)-one as New Inhibitors of Factor Xa and Factor XIa. Molecules, 25.","DOI":"10.3390\/molecules25081889"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"787","DOI":"10.1007\/s11172-020-2834-3","article-title":"Synthesis of 4H-pyrrolo[3,2,1-ij]quinoline-1,2-diones containing a piperazine fragment and study of their inhibitory properties against protein kinases","volume":"69","author":"Novichikhina","year":"2020","journal-title":"Russ. Chem. Bull."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"1322","DOI":"10.1134\/S1070428019090094","article-title":"Synthesis of Substituted Aminopyrimidines as Novel Promising Tyrosine Kinase Inhibitors","volume":"55","author":"Stolpovskaya","year":"2019","journal-title":"Russ. J. Org. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"120802","DOI":"10.1155\/2015\/120802","article-title":"Application of Molecular Modeling to Development of New Factor Xa Inhibitors","volume":"2015","author":"Sulimov","year":"2015","journal-title":"Biomed Res. Int."},{"key":"ref_64","first-page":"327","article-title":"Synthesized organic compounds as growth stimulators for woody plants","volume":"17","author":"Vostrikova","year":"2020","journal-title":"Period. Tche Quim."},{"key":"ref_65","first-page":"781","article-title":"Use of new compounds of the quinoline series as effective stimulants of growth processes","volume":"17","author":"Kalaev","year":"2020","journal-title":"Period. Tche Quim."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1186\/1758-2946-3-33","article-title":"Open Babel: An Open Chemical Toolbox","volume":"3","author":"Banck","year":"2011","journal-title":"J. Cheminformatics"},{"key":"ref_67","unstructured":"(2022, August 16). Marvin Was Used for Drawing, Displaying and Characterizing Chemical Structures, Substructures and Reactions, Marvin 21.3.0, 2021, ChemAxon. Available online: https:\/\/chemaxon.com\/products\/marvin."},{"key":"ref_68","first-page":"213","article-title":"The SOL docking package for computer-aided drug design","volume":"9","author":"Romanov","year":"2008","journal-title":"Numer. Methods Program. (Vychislitel\u2019Nye Metod. Program.)"},{"key":"ref_69","unstructured":"Sulimov, A.V., Sulimov, V.B., Romanov, A.N., Grigoriev, F.V., Kondakova, O.A., Bryzgalov, P.A., and Ostapenko, D.A. (2007, January 1\u20135). Web-oriented system Keenbase for new drugs design. Proceedings of the 4th International Symposium on Computational Methods in Toxicology and Pharmacology Integrating Internet Resourses, Moscow, Russia."},{"key":"ref_70","doi-asserted-by":"crossref","unstructured":"Sinauridze, E.I., Romanov, A.N., Gribkova, I.V., Kondakova, O.A., Surov, S.S., Gorbatenko, A.S., Butylin, A.A., Monakov, M.Y., Bogolyubov, A.A., and Kuznetsov, Y.V. (2011). New Synthetic Thrombin Inhibitors: Molecular Design and Experimental Verification. PLoS ONE, 6.","DOI":"10.1371\/journal.pone.0019969"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"700","DOI":"10.1007\/s10517-015-2839-3","article-title":"Molecular Modeling as a New Approach to the Development of Urokinase Inhibitors","volume":"158","author":"Beloglazova","year":"2015","journal-title":"Bull. Exp. Biol. Med."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"625176","DOI":"10.1155\/2014\/625176","article-title":"Application of Molecular Modeling to Urokinase Inhibitors Development","volume":"2014","author":"Sulimov","year":"2014","journal-title":"Biomed Res. Int."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"9323","DOI":"10.1021\/jp046721s","article-title":"Surface Generalized Born Method: A Simple, Fast, and Precise Implicit Solvent Model beyond the Coulomb Approximation","volume":"108","author":"Romanov","year":"2004","journal-title":"J. Phys. Chem."},{"key":"ref_74","unstructured":"Stewart, J. (2022, August 16). MOPAC2016. Available online: http:\/\/openmopac.net\/MOPAC2016.html."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s00894-012-1667-x","article-title":"Optimization of parameters for semiempirical methods VI: More modifications to the NDDO approximations and re-optimization of parameters","volume":"19","author":"Stewart","year":"2013","journal-title":"J. Mol. Model."},{"key":"ref_76","doi-asserted-by":"crossref","unstructured":"Klamt, A., and Schuurmann, G. (1993). COSMO: A new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J. Chem. Soc. Perkin Trans. 2, 799\u2013805.","DOI":"10.1039\/P29930000799"},{"key":"ref_77","first-page":"363","article-title":"Search for Approaches to Supercomputer Quantum-Chemical Docking","volume":"Volume 1129","author":"Voevodin","year":"2019","journal-title":"Supercomputing. RuSCDays 2019"},{"key":"ref_78","doi-asserted-by":"crossref","unstructured":"Sulimov, A., Kutov, D., Ilin, I., and Sulimov, V. (2022). Quantum-Chemical Quasi-Docking for Molecular Dynamics Calculations. Nanomaterials, 12.","DOI":"10.3390\/nano12020274"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/17\/5732\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T00:23:48Z","timestamp":1760142228000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/17\/5732"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,9,5]]},"references-count":78,"journal-issue":{"issue":"17","published-online":{"date-parts":[[2022,9]]}},"alternative-id":["molecules27175732"],"URL":"https:\/\/doi.org\/10.3390\/molecules27175732","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,9,5]]}}}