Functionally substituted 2-aminothiazoles as antimicrobial agents: in vitro and in silico evaluation

References

• S. Andrei, L. Valeanu, R. Chirvasuta, and M.-G. Stefan, New FDA approved antibacterial drugs: 2015-2017, Discoveries 6 (2018), pp. e81. doi:10.15190/d.2018.1.
   Google Scholar
• A.H. Holmes, L.S. Moore, A. Sundsfjord, M. Steinbakk, S. Regmi, A. Karkey, P. Guerin, and L. Piddock, Understanding the mechanisms and drivers of antimicrobial resistance, Lancet 387 (2016), pp. 176–187. doi:10.1016/S0140-6736(15)00473-0.
   PubMed Web of Science ®Google Scholar
• S.E. Winter, C.A. Lopez, and A. Bäumler, The dynamics of gut-associated microbial communities during inflammation, EMBO Rep. 14 (2013), pp. 319–327. doi:10.1038/embor.2013.27.
   PubMed Web of Science ®Google Scholar
• Available at https://europa.eu/european-union/about-eu/agencies/ecdc_en (accessed February 10, 2023).
   Google Scholar
• Available at http://ecdc.europa.eu/en/publications/Publications/antimicrobial-resistance-annual-epidemiological-report.pdf (accessed February 10, 2023).
   Google Scholar
• Available at http://ecdc.europa.eu/en/publications/Publications/antimicrobial-resistance-europe-2014.pdf (accessed February 10, 2023).
   Google Scholar
• M.A. Pfaller, Antifungal drug resistance: Mechanisms, epidemiology, and consequences for treatment, Am. J. Med. 125 (2012), pp. S3–S13. doi:10.1016/j.amjmed.2011.11.001.
   PubMed Web of Science ®Google Scholar
• B.P. Mathew and M. Nath, Recent approaches to antifungal therapy for invasive mycoses, Chem. Med. Chem. 4 (2009), pp. 310–323. doi:10.1002/cmdc.200800353.
   Web of Science ®Google Scholar
• C.A. Munro, Echinocandin resistance in human pathogenic fungi, Expert Rev. Anti-Infect. 10 (2012), pp. 115–116. doi:10.1586/eri.11.171.
   PubMed Web of Science ®Google Scholar
• D.S. Perlin, Resistance to echinocandin-class antifungal drugs, Drug Resist. Updat. 10 (2007), pp. 121–130. doi:10.1016/j.drup.2007.04.002.
   PubMed Web of Science ®Google Scholar
• S. Shabnam Thakur, R. Sharma, and S. Sardana, The potential of thiazole derivatives as antimicrobial agents, Chem. Proc. 12 (2022), pp. 36–46.
   Google Scholar
• I. Althagafi, N. El-Metwaly, and T. Farghaly, New series of thiazole derivatives: Synthesis, structural elucidation, antimicrobial activity, molecular modeling and MOE docking, Molecules 24 (2019), pp. 1741. doi:10.3390/molecules24091741.
   PubMed Web of Science ®Google Scholar
• A. Biernasiuk, M. Kawczyńska, and A. Berecka-Rycerz, Synthesis, antimicrobial activity, and determination of the lipophilicity of ((cyclohex-3-enylmethylene)hydrazinyl)thiazole derivatives, Med. Chem. Res. 28 (2019), pp. 2023–2036. doi:10.1007/s00044-019-02433-2.
   Web of Science ®Google Scholar
• R.D. Kamble, R.J. Meshram, S.V. Hese, R.A. More, S.S. Kamble, R.N. Gacche, and B.S. Dawane, Synthesis and in silico investigation of thiazoles bearing pyrazoles derivatives as anti-inflammatory agents, Comput. Biol. Chem. 61 (2016), pp. 86–96. doi:10.1016/j.compbiolchem.2016.01.007.
   PubMed Web of Science ®Google Scholar
• Z.A. Muhammad, G.S. Masaret, M.M. Amin, M.A. Abdallah, and T.A. Farghaly, Anti-inflammatory, analgesic and anti-ulcerogenic activities of novel bis-thiadiazoles, bis-thiazoles and bis-formazanes, Med. Chem. 13 (2017), pp. 226–238. doi:10.2174/1573406412666160920091146.
   PubMed Web of Science ®Google Scholar
• S. Di Franco, B. Parrino, M. Gaggianesi, V.D. Pantina, P. Bianca, A. Nicotra, L.R. Mangiapane, M. Lo Iacono, G. Ganduscio, V. Veschi, O.R. Brancato, A. Glaviano, A. Turdo, I. Pillitteri, L. Colarossi, S. Cascioferro, D. Carbone, C. Pecoraro, M.E. Fiori, R. De Maria, M. Todaro, I. Screpanti, G. Cirrincione, P. Diana, and G. Stassi, CHK1 inhibitor sensitizes resistant colorectal cancer stem cells to nortopsentin, Science 24 (2021), pp. 102664.
   Google Scholar
• Z. Xu, M. Ba, H. Zhou, Y. Cao, C. Tang, Y. Yang, R. He, Y. Liang, X. Zhang, Z. Li, L. Zhu, Y. Guo, and C. Guo, 2,4,5-Trisubstituted thiazole derivatives: A novel and potent class of non-nucleoside inhibitors of wild type and mutant HIV-1 reverse transcriptase, Eur. J. Med. Chem. 85 (2014), pp. 27–42. doi:10.1016/j.ejmech.2014.07.072.
   PubMed Web of Science ®Google Scholar
• K. Liaras, M. Fesatidou, and A. Geronikaki, Thiazoles and thiazolidinones as COX/LOX inhibitors, Molecules 18 (2018), pp. 685. doi:10.3390/molecules23030685.
   Google Scholar
• C.H. Sowjanya, S.S. Swamy, S. Gomathi, and A.K. Babu, Synthesis, chemistry and anti-hypertensive activity of some new thiazole-thiadiazole derivatives, Ijarmps 1 (2016), pp. 6–10.
   Google Scholar
• U. Salar, K.M. Khan, S. Chigurupati, M. Taha, A. Wadood, S. Vijayabalan, M. Ghufran, and S. Perveen, New hybrid hydrazinyl thiazole substituted chromones: As potential α-amylase inhibitors and radical (DPPH & ABTS) scavengers, Sci. Rep. 7 (2017), pp. 16980. doi:10.1038/s41598-017-17261-w.
   PubMed Web of Science ®Google Scholar
• R.E. Khidre and I.A.M. Radini, Design, synthesis and docking studies of novel thiazole derivatives incorporating pyridine moiety and assessment as antimicrobial agents, Sci. Rep. 11 (2021), pp. 7846. doi:10.1038/s41598-021-86424-7.
   PubMed Web of Science ®Google Scholar
• V. Kartsev, A. Geronikaki, A. Zubenko, A. Petrou, M. Ivanov, J. Glamoˇclija, M. Sokovic, L. Divaeva, A. Morkovnik, and A. Klimenko, Synthesis and antimicrobial activity of new heteroaryl(aryl) thiazole derivatives molecular docking studies, Antibiotics 11 (2022), pp. 133–1357. doi:10.3390/antibiotics11101337.
   Google Scholar
• U. Acar Çevik, A. Işık, A.E. Evren, Ö. Kapusız, Ü.D. Gül, Y. Özkay, and Z.A. Kaplancıklı, Synthesis of new benzimidazole derivatives containing 1,3,4-thiadiazole: Their in vitro antimicrobial, in silico molecular docking and molecular dynamic simulations studies, SAR QSAR Environ. Res. 33 (2022), pp. 899–914. doi:10.1080/1062936X.2022.2149620.
   PubMed Web of Science ®Google Scholar
• C. Tratrat, M. Haroun, E. Tsolaki, A. Petrou, A. Gavalas, and A. Geronikaki, Thiazole-based chalcone derivatives as potential anti-inflammatory agents: Biological evaluation and molecular modelling, Curr. Top. Med. Chem. 21 (2021), pp. 257–268. doi:10.2174/1568026621999201214232458.
   PubMed Web of Science ®Google Scholar
• M. Modri, M. Božiˇcevi, and I. Faraho, Design, synthesis and biological evaluation of new 1,3-thiazole derivatives as potential anti-inflammatory agents, J. Mol. Struct. 1239 (2021), pp. 130526. doi:10.1016/j.molstruc.2021.130526.
   Web of Science ®Google Scholar
• Α. Kryshchyshyn, Ο. Roman, Α. Lozynskyi, and R. Lesyk, Thiopyrano[2,3-d]thiazoles as new efficient scaffolds in medicinal chemistry, Sci. Pharm. 86 (2018), pp. 26–50. doi:10.3390/scipharm86020026.
   PubMed Web of Science ®Google Scholar
• A. Ayati, S. Emami, S. Moghimi, and A. Foroumadi, Thiazole in the targeted anticancer drug discovery, Future Med. Chem. 11 (2019), pp. 1929–1952. doi:10.4155/fmc-2018-0416.
   PubMed Web of Science ®Google Scholar
• D. Carbone, V. Vestuto, M.R. Ferraro, T. Ciaglia, C. Pecoraro, E. Sommella, S. Cascioferro, E. Salviati, S. Novi, M.F. Tecce, M.F. Amodio, N. Iraci, G. Cirrincione, P.D. Campiglia, A. Bertamino, B. Parrino, and C. Ostacolo, Metabolomics-assisted discovery of a new anticancer GLS-1 inhibitor chemotype from a nortopsentin-inspired library: From phenotype screening to target identification, Eur. J. Med. Chem. 234 (2022), pp. 114233. doi:10.1016/j.ejmech.2022.114233.
   PubMed Web of Science ®Google Scholar
• S. Patchipala, V. Pasupuleti, A. Audipudi, and H. Bollikoll, Synthesis, in-vivo anti-diabetic & anticancer activities and molecular modelling studies of tetrahydrobenzo[d]thiazole tethered nicotinohydrazide derivatives, Arab. J. Chem. 15 (2022), pp. 103546. doi:10.1016/j.arabjc.2021.103546.
   Web of Science ®Google Scholar
• A. Petrou, P. Eleftheriou, A. Geronikaki, M.G. Akrivou, and I. Vizirianakis, Novel thiazolidin-4-ones as potential non-nucleoside inhibitors of HIV-1 reverse transcriptase, Molecules 24 (2019), pp. 3821. doi:10.3390/molecules24213821.
   PubMed Web of Science ®Google Scholar
• T.A. Farghaly, A.M.R. Alsaedi, N.A. Alenazi, and M.F. Harras, Anti-viral activity of thiazole derivatives: An updated patent review, Expert Opin. Ther. Pat. 32 (2022), pp. 791–815.
   PubMed Web of Science ®Google Scholar
• R. Meleddu, S. Distinto, A. Corona, E. Tramontano, G. Bianco, C. Melis, F. Cottiglia, and E. Maccioni, Isatin thiazoline hybrids as dual inhibitors of HIV-1 reverse transcriptase, J. Enz. Inhib. Med. Chem. 32 (2017), pp. 130–136. doi:10.1080/14756366.2016.1238366.
   PubMed Web of Science ®Google Scholar
• M. Djukic, M. Fesatidou, I. Xenikakis, A. Geronikaki, V.T. Angelova, V. Savic, M. Pasic, B. Krilovic, D. Djukic, B. Gobeljic, M. Pavlica, A. Djuric, I. Stanojevic, D. Vojvodic, and L. Saso, In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole, Chem. Biol. Interact 286 (2018), pp. 119–131. doi:10.1016/j.cbi.2018.03.013.
   PubMed Web of Science ®Google Scholar
• C.C.B. Brito, H.V.C.D. Silva, D.J. Brondani, A.R. Faria, R.M. Ximenes, I.M.D. Silva, J.F.C. Albuquerque, and M.S. Castilho, Synthesis and biological evaluation of thiazole derivatives as LbSOD inhibitors, J. Enz. Inhib. Med. Chem. 34 (2019), pp. 333–342. doi:10.1080/14756366.2018.1550752.
   PubMed Web of Science ®Google Scholar
• C.A. Rodrigues, P.F. Dos Santos, M.O.L. da Costa, T.F.A. Pavani, P. Xander, M.M. Geraldo, A. Mengarda, J. de Moraes, and D.G.G. Rando, 4-Phenyl-1,3-thiazole-2-amines as scaffolds for new antileishmanial agents, J. Venom. Anim. Toxins Incl. Trop. Dis. 24 (2018), pp. 26. doi:10.1186/s40409-018-0163-x.
   PubMed Web of Science ®Google Scholar
• M.K. Kumawat, Thiazole containing heterocycles with antimalarial activity, Curr. Drug Discov. Technol. 15 (2018), pp. 196–200. doi:10.2174/1570163814666170725114159.
   PubMedGoogle Scholar
• R. Kenchappa, Y.D. Bodke, S. Telkar, and M. Aruna Sindhe, Antifungal and anthelmintic activity of novel benzofuran derivatives containing thiazolo benzimidazole nucleus: An in vitro evaluation, J. Chem. Biol. 10 (2017), pp. 11–23. doi:10.1007/s12154-016-0160-x.
   PubMedGoogle Scholar
• M.F. Abo-Ashour, W.M. Eldehna, A. Nocentini, H.S. Ibrahim, S. Bua, H.A. Abdel-Aziz, S.M. Abou-Seri, and C.T. Supuran, Novel synthesized SLC-0111 thiazole and thiadiazole analogues: Determination of their carbonic anhydrase inhibitory activity and molecular modeling studies, Bioorg. Chem. 87 (2019), pp. 794–802. doi:10.1016/j.bioorg.2019.04.002.
   PubMed Web of Science ®Google Scholar
• A. Rouf and C. Tanyeli, Bioactive thiazole and benzothiazole derivatives, Eur. J. Med. Chem. 97 (2015), pp. 911–927. doi:10.1016/j.ejmech.2014.10.058.
   PubMed Web of Science ®Google Scholar
• N. Kardos and A.L. Demain, Penicillin: The medicine with the greatest impact on therapeutic outcomes, Appl. Microbiol. Biotechnol. 92 (2011), pp. 677–687. doi:10.1007/s00253-011-3587-6.
   PubMed Web of Science ®Google Scholar
• A.C. Pasqualotto, K.O. Thiele, and L.Z. Goldani, Novel triazole antifungal drugs: Focus on isavuconazole, ravuconazole and albaconazole, Curr. Opin. Investig. Drugs 11 (2010), pp. 165–174.
   PubMed Web of Science ®Google Scholar
• G. Thierbach and H. Reichenbach, Myxothiazol, a new antibiotic interfering with respiration, Antimicrob. Agents Chemother. 19 (1981), pp. 504–507. doi:10.1128/AAC.19.4.504.
   PubMed Web of Science ®Google Scholar
• X.H. Li, X.L. Yang, Y. Ling, Z.J. Fan, X.M. Liang, D.Q. Wang, F.H. Chen, and Z.M. Li, Synthesis and fungicidal activity of novel 2-oxocycloalkylsulfonylureas, J. Agric. Food Chem. 53 (2005), pp. 2202–2206. doi:10.1021/jf0403944.
   PubMed Web of Science ®Google Scholar
• Y.V. Burov, V.V. Poroikov, and L.V. Korolchenko, National system for registration and biological testing of chemical compounds: Facilities for new drugs search, Bull. Natl. Centr. Biol. Act. Compnds. (Rus.) 1 (1990), pp. 4–25.
   Google Scholar
• V.V. Poroikov, D.A. Filimonov, T.A. Gloriozova, A.A. Lagunin, D.S. Druzhilovskiy, A.V. Rudik, L.A. Stolbov, A.V. Dmitriev, O.A. Tarasova, S.M. Ivanov, and P.V. Pogodin, Computer-aided prediction of biological activity spectra for organic compounds: The possibilities and limitations, Russ. Chem. Bull. 68 (2019), pp. 2143–2154. doi:10.1007/s11172-019-2683-0.
   Web of Science ®Google Scholar
• V.V. Poroikov, D.A. Filimonov, and A.P. Boudunova, Comparison of the results of prediction of the spectra of biological activity of chemical compounds by experts and the PASS system, Aut. Doc. Math. Ling. 27 (1993), pp. 40–43.
   Google Scholar
• A. Lagunin, A. Stepanchikova, D. Filimonov, and V. Poroikov, PASS: Prediction of activity spectra for biologically active substances, Bioinformatics 16 (2000), pp. 747–748. doi:10.1093/bioinformatics/16.8.747.
   PubMed Web of Science ®Google Scholar
• PASS Online. Available at http://www.way2drug.com/passonline (accessed March 20, 2022).
   Google Scholar
• K.A. Murtazalieva, D.S. Druzhilovskiy, R.K. Goel, G.N. Sastry, and V.V. Poroikov, How good are publicly available web services that predict bioactivity profiles for drug repurposing? SAR QSAR Environ. Res. 28 (2017), pp. 843–862. doi:10.1080/1062936X.2017.1399448.
   PubMed Web of Science ®Google Scholar
• D.A. Filimonov, A.A. Lagunin, T.A. Gloriozova, A.V. Rudik, D.S. Druzhilovskiy, P.V. Pogodin, and V.V. Poroikov, Prediction of the biological activity spectra of organic compounds using the PASS online web resource, Chem. Heterocycl. Compnds. 50 (2014), pp. 444–457. doi:10.1007/s10593-014-1496-1.
   Web of Science ®Google Scholar
• V. Kartsev, B. Lichitsky, A. Geronikaki, A. Petrou, M. Smiljkovic, M. Kostic, O. Radanovic, and M. Soković, Design, synthesis and antimicrobial activity of usnic acid derivatives, Med. Chem. Comm. 9 (2018), pp. 870–882. doi:10.1039/C8MD00076J.
   Google Scholar
• S. Simakov, V. Kartsev, A. Petrou, I. Nicolaou, A. Geronikaki, M. Ivanov, M. Kostic, J. Glamočlija, M. Soković, D. Talea, and I. Vizirianakis, 4-(Indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole acylamines as novel antimicrobial agents: Synthesis, in silico and in vitro evaluation, Pharmaceuticals 14 (2021), pp. 1096. doi:10.3390/ph14111096.
   Web of Science ®Google Scholar
• E. Kritsi, M.T. Matsoukas, C. Potamitis, A. Detsi, M. Ivanov, M. Sokovic, and P. Zoumpoulakis, Novel hit compounds as putative antifungals: The case of Aspergillus fumigatus, Molecules 24 (2019), pp. 3853. doi:10.3390/molecules24213853.
   PubMed Web of Science ®Google Scholar
• M. Aleksić, D. Stanisavljević, M. Smiljković, P. Vasiljević, M. Stevanović, M. Soković, and D. Stojković, Pyrimethanil: Between efficient fungicide against Aspergillus rot on cherry tomato and cytotoxic agent on human cell lines, Ann. Appl. Biol. 175 (2019), pp. 228–235. doi:10.1111/aab.12532.
   Web of Science ®Google Scholar
• M. Fesatidou, P. Zagaliotis, C. Camoutsis, A. Petrou, P. Eleftheriou, C. Tratrtat, M. Haroun, A. Geronikaki, A. Ciric, and M. Sokovic, 5-Adamantan thiadiazole-based thiazolidinones as antimicrobial agents. Design, synthesis, molecular docking and evaluation, Bioorg. Med. Chem. 26 (2018), pp. 4664–4676. doi:10.1016/j.bmc.2018.08.004.
   PubMed Web of Science ®Google Scholar
• T.K. Karami, S. Hailu, S. Feng, R. Graham, and H.J. Gukasyan, Eyes on Lipinski’s rule of five: A new “rule of thumb” for physicochemical design space of ophthalmic drugs, J. Ocul. Pharmacol. Ther. 38 (2022), pp. 43–55. doi:10.1089/jop.2021.0069.
   PubMed Web of Science ®Google Scholar
• T.E. Benson, C.T. Walsh, and V. Massey, Kinetic characterization of wild-type and S229A mutant MurB: Evidence for the role of Ser 229 as a general acid, Biochemistry 36 (1997), pp. 796–805. doi:10.1021/bi962220o.
   PubMed Web of Science ®Google Scholar