Login Register Cart 0
Generic placeholder image

Current Topics in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1568-0266
ISSN (Online): 1873-4294

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Current Frontiers

5-Membered Heterocyclic Compounds as Antiviral Agents

Author(s): Christophe Tratrat, Anthi Petrou, Maria Fesatidou, Michelyne Haroun, Geronikaki Athina*, Katharigatta Venugopala, Nagaraja Sreeharsha and Jad Chemali

Volume 23, Issue 7, 2023

Published on: 05 May, 2023

Page: [520 - 538] Pages: 19

DOI: 10.2174/1568026623666230325153927

Price: $65

Abstract

Viral infections range from self-limiting to more serious and fatal infections; therefore, some viral infections are of great public health concern worldwide, e.g., Hepatitis B virus, Hepatitis C virus, and HIV. Recently, the world faced a new infection due to the coronavirus, COVID-19, which was announced as a pandemic in early 2020. This virus infected more than 500 million people, killing around 6 million people worldwide. On the other hand, the increase in drug-resistant strains is also creating serious health problems. Thus, developing new selective antiviral agents with a different mode of action to fight against mutated and novel viruses is a primary goal of many researchers. Taking into account the role of heterocyclic compounds in drug discovery as a key structural component of most of the bioactive molecules; herein, we report an extensive review of the antiviral activity of five-membered heterocyclic compounds reported from 2015 to date. In this review, the antiviral activities of the agents containing the specified ring systems thiadiazoles, triazoles, oxadiazoles, and thiazoles are discussed.

« Previous Next »
Graphical Abstract

[1]
Krishnan, N.; Devadasan, V.; Raman, P. Plant-derived alkaloids as anti-viral agents. Int. J. Pharm. Sci. Res., 2020, 11(4), 6174-6182.
[http://dx.doi.org/10.26452/ijrps.v11i4.3291]
[2]
Martinez, J.P.; Sasse, F.; Brönstrup, M.; Diez, J.; Meyerhans, A. Antiviral drug discovery: Broad-spectrum drugs from nature. Nat. Prod. Rep., 2015, 32(1), 29-48.
[http://dx.doi.org/10.1039/C4NP00085D] [PMID: 25315648]
[3]
Worldometers. COVID-19 Coronavirus Outbreak. Worldometers. 2020 2020. Available from: https://www.worldometers.info/coronavirus/#countries
[4]
De Clercq, E. Fifty years in search of selective antiviral drugs. J. Med. Chem., 2019, 62(16), 7322-7339.
[http://dx.doi.org/10.1021/acs.jmedchem.9b00175] [PMID: 30939009]
[5]
Zhan, P.; Pannecouque, C.; De Clercq, E.; Liu, X. Anti-HIV drug discovery and development: Current innovations and future trends. J. Med. Chem., 2016, 59(7), 2849-2878.
[http://dx.doi.org/10.1021/acs.jmedchem.5b00497] [PMID: 26509831]
[6]
Wang, Q.Y.; Bushell, S.; Qing, M.; Xu, H.Y.; Bonavia, A.; Nunes, S.; Zhou, J.; Poh, M.K.; Florez de Sessions, P.; Niyomrattanakit, P.; Dong, H.; Hoffmaster, K.; Goh, A.; Nilar, S.; Schul, W.; Jones, S.; Kramer, L.; Compton, T.; Shi, P.Y. Inhibition of dengue virus through suppression of host pyrimidine biosynthesis. J. Virol., 2011, 85(13), 6548-6556.
[http://dx.doi.org/10.1128/JVI.02510-10] [PMID: 21507975]
[7]
Sarafianos, S.G.; Marchand, B.; Das, K.; Himmel, D.M.; Parniak, M.A.; Hughes, S.H.; Arnold, E. Structure and function of HIV-1 reverse transcriptase: Molecular mechanisms of polymerization and inhibition. J. Mol. Biol., 2009, 385(3), 693-713.
[http://dx.doi.org/10.1016/j.jmb.2008.10.071] [PMID: 19022262]
[8]
Ma, Y.; Frutos-Beltrán, E.; Kang, D.; Pannecouque, C.; De Clercq, E.; Menéndez-Arias, L.; Liu, X.; Zhan, P. Medicinal chemistry strategies for discovering antivirals effective against drug-resistant viruses. Chem. Soc. Rev., 2021, 50(7), 4514-4540.
[http://dx.doi.org/10.1039/D0CS01084G] [PMID: 33595031]
[9]
Kerru, N.; Gummidi, L.; Maddila, S.; Gangu, K.K.; Jonnalagadda, S.B. A review on recent advances in nitrogen-containing molecules and their biological applications. Molecules, 2020, 25(8), 1909.
[http://dx.doi.org/10.3390/molecules25081909] [PMID: 32326131]
[10]
Guo, Z.; Song, X.; Zhao, L.M.; Piao, M.G.; Quan, J.; Piao, H.R.; Jin, C.H. Synthesis and biological evaluation of novel benzo[c][1,2,5]thiadiazol-5-yl and thieno[3,2-c]- pyridin-2-yl imidazole derivatives as ALK5 inhibitors. Bioorg. Med. Chem. Lett., 2019, 29(16), 2070-2075.
[http://dx.doi.org/10.1016/j.bmcl.2019.07.015] [PMID: 31303386]
[11]
Takate, S.J.; Shinde, A.D.; Karale, B.K.; Akolkar, H.; Nawale, L.; Sarkar, D.; Mhaske, P.C. Thiazolyl-pyrazole derivatives as potential antimycobacterial agents. Bioorg. Med. Chem. Lett., 2019, 29(10), 1199-1202.
[http://dx.doi.org/10.1016/j.bmcl.2019.03.020] [PMID: 30910461]
[12]
Bhagdev, K.; Sarkar, B. Benzothiazole: As an antidiabetic agent. Ann. Rom. Soc. Cell Biol., 2021, 25, 20269-20285.
[13]
Ullah, S.; Mirza, S.; Salar, U.; Hussain, S.; Javaid, K.; Khan, K.M.; Khalil, R.; Atia-tul-Wahab; Ul-Haq, Z.; Perveen, S.; Choudhary, M.I. 2-mercapto benzothiazole derivatives: As potential leads for the diabetic management. Med. Chem., 2020, 16(6), 826-840.
[http://dx.doi.org/10.2174/1573406415666190612153150] [PMID: 31195949]
[14]
Evaluation of some novel benzothiazole derivatives as anti tubercular agents targeting glutamine synthetase-I. J. Pharm Chem. Biol. Sci, 2018, 5, 312-319.
[15]
Haroun, M.; Tratrat, C.; Kositsi, K.; Tsolaki, E.; Petrou, A.; AlDhubiab, B.; Attimarad, M.; Harsha, S.; Elsewedy, H.; Gavalas, A. New benzothiazole-based thiazolidinones as potent dual anti-inflammatory/antimicrobial agents. Design, synthesis and biological evaluation. Curr. Top. Med. Chem., 2018, 18, 75-87.
[http://dx.doi.org/10.2174/1568026618666180206101814] [PMID: 29412109]
[16]
Glomb, T.; Świątek, P. Antimicrobial activity of 1,3,4-oxadiazole derivatives. Int. J. Mol. Sci., 2021, 22(13), 6979.
[http://dx.doi.org/10.3390/ijms22136979] [PMID: 34209520]
[17]
Nagaraju, B.; Kovvuri, J.; Kumar, C.G.; Routhu, S.R.; Shareef, M.A.; Kadagathur, M.; Adiyala, P.R.; Alavala, S.; Nagesh, N.; Kamal, A. Synthesis and biological evaluation of pyrazole linked benzothiazole-β-naphthol derivatives as topoisomerase I inhibitors with DNA binding ability. Bioorg. Med. Chem., 2019, 27(5), 708-720.
[http://dx.doi.org/10.1016/j.bmc.2019.01.011] [PMID: 30679134]
[18]
Chaudhry, F.; Naureen, S.; Ashraf, M.; Al-Rashida, M.; Jahan, B.; Munawar, M.A.; Khan, M.A. Imidazole-pyrazole hybrids: Synthesis, characterization and in vitro bioevaluation against α-glucosidase enzyme with molecular docking studies. Bioorg. Chem., 2019, 82, 267-273.
[http://dx.doi.org/10.1016/j.bioorg.2018.10.047] [PMID: 30396060]
[19]
Zhu, W.J.; Cui, B.W.; Wang, H.M.; Nan, J.X.; Piao, H.R.; Lian, L.H.; Jin, C.H. Design, synthesis, and antifibrosis evaluation of 4-(benzo-[c][1,2,5]thiadiazol-5-yl)-3(5)-(6-methyl- pyridin-2-yl)pyrazole and 3(5)-(6-methylpyridin- 2-yl)-4-(thieno-[3,2,-c]pyridin-2-yl)pyrazole derivatives. Eur. J. Med. Chem., 2019, 180, 15-27.
[http://dx.doi.org/10.1016/j.ejmech.2019.07.013] [PMID: 31299584]
[20]
Gedawy, E.M.; Kassab, A.E.; El Kerdawy, A.M. Design, synthesis and biological evaluation of novel pyrazole sulfonamide derivatives as dual COX-2/5-LOX inhibitors. Eur. J. Med. Chem., 2020, 189, 112066.
[http://dx.doi.org/10.1016/j.ejmech.2020.112066] [PMID: 31982653]
[21]
Saeedi, M.; Mohammadi-Khanaposhtani, M.; Pourrabia, P.; Razzaghi, N.; Ghadimi, R.; Imanparast, S.; Faramarzi, M.A.; Bandarian, F.; Esfahani, E.N.; Safavi, M.; Rastegar, H.; Larijani, B.; Mahdavi, M.; Akbarzadeh, T. Design and synthesis of novel quinazolinone-1,2,3-triazole hybrids as new anti-diabetic agents: In vitro α-glucosidase inhibition, kinetic, and docking study. Bioorg. Chem., 2019, 83, 161-169.
[http://dx.doi.org/10.1016/j.bioorg.2018.10.023] [PMID: 30366316]
[22]
Sun, L.; Huang, T.; Dick, A.; Meuser, M.E.; Zalloum, W.A.; Chen, C.H.; Ding, X.; Gao, P.; Cocklin, S.; Lee, K.H.; Zhan, P.; Liu, X. Design, synthesis and structure-activity relationships of 4-phenyl-1H-1,2,3-triazole phenylalanine derivatives as novel HIV-1 capsid inhibitors with promising antiviral activities. Eur. J. Med. Chem., 2020, 190, 112085.
[http://dx.doi.org/10.1016/j.ejmech.2020.112085] [PMID: 32066010]
[23]
Tageldin, G.N.; Ibrahim, T.M.; Fahmy, S.M.; Ashour, H.M.; Khalil, M.A.; Nassra, R.A.; Labouta, I.M. Synthesis, modeling and biological evaluation of some pyrazolo[3,4-d]pyrimidinones and pyrazolo[4,3-e][1,2,4]triazolo[4,3-a]pyrimidinones as anti-inflamma-tory agents. Bioorg. Chem., 2019, 90, 102844.
[http://dx.doi.org/10.1016/j.bioorg.2019.03.018] [PMID: 31229797]
[24]
Fan, C.; Zhong, T.; Yang, H.; Yang, Y.; Wang, D.; Yang, X.; Xu, Y.; Fan, Y. Design, synthesis, biological evaluation of 6-(2-amino-1H-benzo[d]imidazole-6-yl)quinazolin-4(3H)-one derivatives as novel anticancer agents with Aurora kinase inhibition. Eur. J. Med. Chem., 2020, 190, 112108.
[http://dx.doi.org/10.1016/j.ejmech.2020.112108] [PMID: 32058239]
[25]
Ding, H.W.; Yu, L.; Bai, M.; Qin, X.C.; Song, M.; Zhao, Q.C. Design, synthesis and evaluation of some 1,6-disubstituted-1H-benzo[d]imidazoles derivatives targeted PI3K as anticancer agents. Bioorg. Chem., 2019, 93, 103283.
[http://dx.doi.org/10.1016/j.bioorg.2019.103283] [PMID: 31585260]
[26]
Dincel, E.D.; Ulusoy-Güzeldemirci, N.; Şatana, D.; Küçükbasmacı, Ö. Design, synthesis, characterization and antimicrobial evaluation of some novel hydrazinecarbothioamide, 4‐thiazolidinone and 1,2,4‐triazole‐3‐thione derivatives. J. Heterocycl. Chem., 2021, 58(1), 195-205.
[http://dx.doi.org/10.1002/jhet.4159]
[27]
Sunil Kumar, A.; Kudva, J.; Bharath, B.R.; Ananda, K.; Sadashiva, R.; Madan Kumar, S.; Revanasiddappa, B.C.; Kumar, V.; Rekha, P.D.; Naral, D. Synthesis, structural, biological and in silico studies of new 5-arylidene-4-thiazolidinone derivatives as possible anticancer, antimicrobial and antitubercular agents. New J. Chem., 2019, 43(3), 1597-1610.
[http://dx.doi.org/10.1039/C8NJ03671C]
[28]
Karaburun, A.; Acar Çevik, U.; Osmaniye, D.; Sağlık, B.; Kaya Çavuşoğlu, B.; Levent, S.; Özkay, Y.; Koparal, A.; Behçet, M.; Kaplancıklı, Z. Synthesis and evaluation of new 1,3,4-thiadiazole derivatives as potent antifungal agents. Molecules, 2018, 23(12), 3129-3147.
[http://dx.doi.org/10.3390/molecules23123129] [PMID: 30501053]
[29]
Biernasiuk, A. Berecka-Rycerz, A.; Gumieniczek, A.; Malm, M.; Łączkowski, K.Z.; Szymańska, J.; Malm, A. The newly synthesized thiazole derivatives as potential antifungal compounds against Candida albicans. Appl. Microbiol. Biotechnol., 2021, 105(16-17), 6355-6367.
[http://dx.doi.org/10.1007/s00253-021-11477-7] [PMID: 34410437]
[30]
Martins, P.; Jesus, J.; Santos, S.; Raposo, L.; Roma-Rodrigues, C.; Baptista, P.; Fernandes, A. Heterocyclic anticancer compounds: Recent advances and the paradigm shift towards the use of nanomedicine’s toolbox. Molecules, 2015, 20(9), 16852-16891.
[http://dx.doi.org/10.3390/molecules200916852] [PMID: 26389876]
[31]
Saeedi, M.; Mohammadi-Khanaposhtani, M.; Asgari, M.S.; Eghbalnejad, N.; Imanparast, S.; Faramarzi, M.A.; Larijani, B.; Mahdavi, M.; Akbarzadeh, T. Design, synthesis, in vitro, and in silico studies of novel diarylimidazole-1,2,3-triazole hybrids as potent α-glucosidase inhibitors. Bioorg. Med. Chem., 2019, 27(23), 115148.
[http://dx.doi.org/10.1016/j.bmc.2019.115148] [PMID: 31679980]
[32]
Wu, J.; Tang, H.; Xu, J. Rapid synthesis of curcuminoid pyrazoles with antiviral effects through one-pot combinatorial modification of total curcuminoids. Res. Rep. Med. Chem., 2015, 5, 41-47.
[33]
Bhadoriya, K.S.; Sharma, M.C.; Jain, S.V. 2,4-Dihydropyrano[2,3-c]pyrazole: Discovery of new lead as through pharmacophore modelling, atom-based 3D-QSAR, virtual screening and docking strategies for improved anti-HIV-1 chemotherapy. J. Taibah Univ. Sci., 2015, 9(4), 521-530.
[http://dx.doi.org/10.1016/j.jtusci.2014.12.005]
[34]
Fioravanti, R.; Desideri, N.; Biava, M.; Droghini, P.; Atzori, E.M.; Ibba, C.; Collu, G.; Sanna, G.; Delogu, I.; Loddo, R.N. -((1,3-Diphenyl-1H-pyrazol-4-yl)methyl)anilines: A novel class of anti-RSV agents. Bioorg. Med. Chem. Lett., 2015, 25(11), 2401-2404.
[http://dx.doi.org/10.1016/j.bmcl.2015.04.006] [PMID: 25913116]
[35]
Han, C.; Guo, Y.C.; Wang, D.D.; Dai, X.J.; Wu, F.J.; Liu, H.F.; Dai, G.F.; Tao, J.C. Novel pyrazole fused heterocyclic ligands: Synthesis, characterization, DNA binding/cleavage activity and anti-BVDV activity. Chin. Chem. Lett., 2015, 26(5), 534-538.
[http://dx.doi.org/10.1016/j.cclet.2015.01.006]
[36]
Manvar, D.; Pelliccia, S.; La Regina, G.; Famiglini, V.; Coluccia, A.; Ruggieri, A.; Anticoli, S.; Lee, J.C.; Basu, A.; Cevik, O.; Nencioni, L.; Palamara, A.T.; Zamperini, C.; Botta, M.; Neyts, J.; Leyssen, P.; Kaushik-Basu, N.; Silvestri, R. New 1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides inhibit hepatitis C virus replication via suppression of cyclooxygenase-2. Eur. J. Med. Chem., 2015, 90, 497-506.
[http://dx.doi.org/10.1016/j.ejmech.2014.11.042] [PMID: 25483263]
[37]
Chuang, H.; Huang, L.C.S.; Kapoor, M.; Liao, Y.J.; Yang, C.L.; Chang, C.C.; Wu, C.Y.; Hwu, J.R.; Huang, T.J.; Hsu, M.H. Design and synthesis of pyridine-pyrazole-sulfonate derivatives as potential anti-HBV agents. MedChemComm, 2016, 7(5), 832-836.
[http://dx.doi.org/10.1039/C6MD00008H]
[38]
Jia, H.; Bai, F.; Liu, N.; Liang, X.; Zhan, P.; Ma, C.; Jiang, X.; Liu, X. Design, synthesis and evaluation of pyrazole derivatives as non-nucleoside hepatitis B virus inhibitors. Eur. J. Med. Chem., 2016, 123, 202-210.
[http://dx.doi.org/10.1016/j.ejmech.2016.07.048] [PMID: 27484509]
[39]
Liu, G.N.; Luo, R.H.; Zhou, Y.; Zhang, X.J.; Li, J.; Yang, L.M.; Zheng, Y.T.; Liu, H. Synthesis and anti-HIV-1 activity evaluation for novel 3a,6a-Dihydro-1H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives. Molecules, 2016, 21(9), 1198-1209.
[http://dx.doi.org/10.3390/molecules21091198] [PMID: 27617994]
[40]
Corona, A.; Onnis, V.; Deplano, A.; Bianco, G.; Demurtas, M.; Distinto, S.; Cheng, Y.C.; Alcaro, S.; Esposito, F.; Tramontano, E. Design, synthesis and antiviral evaluation of novel heteroarylcarbothioamide derivatives as dual inhibitors of HIV-1 reverse transcriptase-associated RNase H and RDDP functions. Pathog. Dis., 2017, 75(6), ftx078.
[http://dx.doi.org/10.1093/femspd/ftx078] [PMID: 28859311]
[41]
Cocco, M.T.; Congiu, C.; Onnis, V. Synthesis and in vitro antitumoral activity of new N-phenyl-3-pyrrolecarbothioamides. Bioorg. Med. Chem., 2003, 11(4), 495-503.
[http://dx.doi.org/10.1016/S0968-0896(02)00465-0] [PMID: 12538014]
[42]
Cocco, M.T.; Congiu, C.; Lilliu, V.; Onnis, V. Amidrazones as precursors of biologically active compounds--synthesis of diaminopyrazoles for evaluation of anticancer activity. Arch. Pharm. (Weinheim), 2006, 339(1), 7-13.
[http://dx.doi.org/10.1002/ardp.200500179] [PMID: 16411176]
[43]
Mosaad, S.; Yasser, M.; Waleed, M. Synthesis and biological screening of novel pyrazoles and their precursors as potential antiviral agents. Pharmacophore, 2018, 9(1), 126-139.
[44]
Walum, E.; Strenberg, K.J.D. Understanding Cell Toxicology: Principles and Pratice; Ellis Howood: New York, 1990, pp. 97-111.
[45]
Vlietinck, A.J.; Vanden Berghe, D.A. Can ethnopharmacology contribute to the development of antiviral drugs? J. Ethnopharmacol., 1991, 32(1-3), 141-153.
[46]
Yang, Z.; Li, P.; Gan, X. Novel pyrazole-hydrazone derivatives containing an isoxazole moiety: Design, synthesis, and antiviral activity. Molecules, 2018, 23(7), 1798-1810.
[http://dx.doi.org/10.3390/molecules23071798] [PMID: 30037021]
[47]
Da Costa, L.; Scheers, E.; Coluccia, A.; Casulli, A.; Roche, M.; Di Giorgio, C.; Neyts, J.; Terme, T.; Cirilli, R.; La Regina, G.; Silvestri, R.; Mirabelli, C.; Vanelle, P. Structure-based drug design of potent pyrazole derivatives against rhinovirus replication. J. Med. Chem., 2018, 61(18), 8402-8416.
[http://dx.doi.org/10.1021/acs.jmedchem.8b00931] [PMID: 30153009]
[48]
Desideri, N.; Fioravanti, R.; Proietti Monaco, L.; Atzori, E.M.; Carta, A.; Delogu, I.; Collu, G.; Loddo, R. Design, synthesis, antiviral evaluation, and SAR studies of new 1-(Phenylsulfonyl)-1H-pyrazol−4-yl-methylaniline derivatives. Front Chem., 2019, 7, 214.
[http://dx.doi.org/10.3389/fchem.2019.00214] [PMID: 31024899]
[49]
Wassel, M.; El-Din, W.; Raga, A. Antiviral activity of adamantane-pyrazole derivatives against foot and mouth disease virus infection in vivo and in vitro with molecular docking study. J. App Vet Sci., 2020, 5(4), 37-46.
[50]
Wassel, M.M.S.; Ragab, A.; Elhag Ali, G.A.M.; Mehany, A.B.M.; Ammar, Y.A. Novel adamantane-pyrazole and hydrazone hybridized: Design, synthesis, cytotoxic evaluation, SAR study and molecular docking simulation as carbonic anhydrase inhibitors. J. Mol. Struct., 2021, 1223, 128966.
[http://dx.doi.org/10.1016/j.molstruc.2020.128966]
[51]
Youssif, B.G.M.; Mohamed, Y.A.M.; Salim, M.T.A.; Inagaki, F.; Mukai, C.; Abdu-Allah, H.H.M. Synthesis of some benzimidazole derivatives endowed with 1,2,3-triazole as potential inhibitors of hepatitis C virus. Acta Pharm., 2016, 66(2), 219-231.
[http://dx.doi.org/10.1515/acph-2016-0014] [PMID: 27279065]
[52]
Shaker, Y.M.; Omar, M.A.; Mahmoud, K.; Elhallouty, S.M.; El-Senousy, W.M.; Ali, M.M.; Mahmoud, A.E.; Abdel-Halim, A.H.; Soliman, S.M.; El Diwani, H.I. Synthesis, in vitro and in vivo antitumor and antiviral activity of novel 1-substituted benzimidazole derivatives. J. Enzyme Inhib. Med. Chem., 2015, 30(5), 826-845.
[http://dx.doi.org/10.3109/14756366.2014.979344] [PMID: 25567722]
[53]
Kharitonova, M.; Аntonov, K.; Fateev, I.; Berzina, М.; Kaushin, A.; Paramonov, A.; Kotovskaya, S.; Аndronova, V.; Konstantinova, I.; Galegov, G.; Charushin, V.; Miroshnikov, A. Chemoenzymatic Synthesis of Modified 2′-Deoxy-2′-fluoro-β-darabinofuranosyl Benzimidazoles and Evaluation of Their Activity Against Herpes Simplex Virus Type 1. Synthesis, 2016, 49(5), 1043-1052.
[http://dx.doi.org/10.1055/s-0036-1588625]
[54]
Tsay, S.C.; Lin, S.Y.; Huang, W.C.; Hsu, M.H.; Hwang, K.; Lin, C.C.; Horng, J.C.; Chen, I.C.; Hwu, J.; Shieh, F.K.; Leyssen, P.; Neyts, J. Synthesis and structure-activity relationships of imidazole-coumarin conjugates against Hepatitis C virus. Molecules, 2016, 21(2), 228.
[http://dx.doi.org/10.3390/molecules21020228] [PMID: 26901180]
[55]
Paeshuyse, J.; Kaul, A.; De Clercq, E.; Rosenwirth, B.; Dumont, J.M.; Scalfaro, P.; Bartenschlager, R.; Neyts, J. The non-immunosuppressive cyclosporin DEBIO-025 is a potent inhibitor of hepatitis C virus replication in vitro. Hepatology, 2006, 43(4), 761-770.
[http://dx.doi.org/10.1002/hep.21102] [PMID: 16557546]
[56]
Güzeldemirci, N.U. Küçükbasmacı Ö. Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety. Eur. J. Med. Chem., 2010, 45(1), 63-68.
[http://dx.doi.org/10.1016/j.ejmech.2009.09.024] [PMID: 19939519]
[57]
Ulusoy, N. Synthesis and antituberculosis activity of cycloalkylidenehydrazide and 4-aza-1-thiaspiro[4.5]decan-3-one derivatives of imidazo[2,1-b]thiazole. Arzneimittelforschung, 2002, 52(7), 565-571.
[PMID: 12189781]
[58]
Ulusoy, G.N.; Karaman, B.; Küçükbasmaci, Ö. Antibacterial, antitubercular and antiviral activity evaluations of some arylidenehydrazide derivatives bearing imidazo[2,1-b]thiazole moiety. Turk. J. Pharm. Sci., 2017, 14(2), 157-163.
[http://dx.doi.org/10.4274/tjps.25743] [PMID: 32454607]
[59]
Ferro, S.; Buemi, M.R.; De Luca, L.; Agharbaoui, F.E.; Pannecouque, C.; Monforte, A.M. Searching for novel N 1 -substituted benzimidazol-2-ones as non-nucleoside HIV-1 RT inhibitors. Bioorg. Med. Chem., 2017, 25(14), 3861-3870.
[http://dx.doi.org/10.1016/j.bmc.2017.05.040] [PMID: 28559060]
[60]
Monforte, A.M.; Logoteta, P.; Luca, L.D.; Iraci, N.; Ferro, S.; Maga, G.; De Clercq, E.; Pannecouque, C.; Chimirri, A. Novel 1,3-dihydro-benzimidazol-2-ones and their analogues as potent non-nucleoside HIV-1 reverse transcriptase inhibitors. Bioorg. Med. Chem., 2010, 18(4), 1702-1710.
[http://dx.doi.org/10.1016/j.bmc.2009.12.059] [PMID: 20097079]
[61]
Monforte, A.M.; Logoteta, P.; Ferro, S.; Luca, L.D.; Iraci, N.; Maga, G.; Clercq, E.D.; Pannecouque, C.; Chimirri, A. Design, synthesis, and structure-activity relationships of 1,3-dihydro-benzimidazol-2-one analogues as anti-HIV agents. Bioorg. Med. Chem., 2009, 17(16), 5962-5967.
[http://dx.doi.org/10.1016/j.bmc.2009.06.068] [PMID: 19616956]
[62]
Monforte, A.M.; Logoteta, P.; Ferro, S.; De Luca, L. Novel N1-substituted 1,3-dihydro-2H-benzimidazol-2-ones as potent non-nucleoside reverse transcriptase inhibitors. Bioorg. Med. Chem., 2008, 16, 7429-7502.
[http://dx.doi.org/10.1016/j.bmc.2008.06.012] [PMID: 18585918]
[63]
Monforte, A.M.; De Luca, L.; Buemi, M.R.; Agharbaoui, F.E.; Pannecouque, C.; Ferro, S. Structural optimization of N1-aryl-benzimidazoles for the discovery of new non-nucleoside reverse transcriptase inhibitors active against wild-type and mutant HIV-1 strains. Bioorg. Med. Chem., 2018, 26(3), 661-674.
[http://dx.doi.org/10.1016/j.bmc.2017.12.033] [PMID: 29291935]
[64]
Ibba, R.; Piras, S.; Delogu, I.; Loddo, R.; Carta, A. Anti-BVDV activity evaluation of naphthoimidazole derivatives compared with parental imidazoquinoline compounds. Open Med. Chem. J., 2020, 14(1), 65-70.
[http://dx.doi.org/10.2174/1874104502014010065]
[65]
Briguglio, I.; Loddo, R.; Laurini, E.; Fermeglia, M.; Piras, S.; Corona, P.; Giunchedi, P.; Gavini, E.; Sanna, G.; Giliberti, G.; Ibba, C.; Farci, P.; La Colla, P.; Pricl, S.; Carta, A. Synthesis, cytotoxicity and antiviral evaluation of new series of imidazo[4,5-g]quinoline and pyrido[2,3-g]quinoxalinone derivatives. Eur. J. Med. Chem., 2015, 105, 63-79.
[http://dx.doi.org/10.1016/j.ejmech.2015.10.002] [PMID: 26479028]
[66]
Srivastava, R.; Gupta, S.K.; Naaz, F.; Sen Gupta, P.S.; Yadav, M.; Singh, V.K.; Singh, A.; Rana, M.K.; Gupta, S.K.; Schols, D.; Singh, R.K. Alkylated benzimidazoles: Design, synthesis, docking, DFT analysis, ADMET property, molecular dynamics and activity against HIV and YFV. Comput. Biol. Chem., 2020, 89, 107400.
[http://dx.doi.org/10.1016/j.compbiolchem.2020.107400] [PMID: 33068917]
[67]
Srivastava, R.; Gupta, S.K.; Naaz, F.; Singh, A.; Singh, V.K.; Verma, R.; Singh, N.; Singh, R.K. Synthesis, antibacterial activity, synergistic effect, cytotoxicity, docking and molecular dynamics of benzimidazole analogues. Comput. Biol. Chem., 2018, 76, 1-16.
[http://dx.doi.org/10.1016/j.compbiolchem.2018.05.021] [PMID: 29857255]
[68]
Kachaeva, M.V.; Pilyo, S.G.; Hartline, C.B.; Harden, E.A.; Prichard, M.N.; Zhirnov, V.V.; Brovarets, V.S. In vitro activity of novel derivatives of 1,3-oxazole-4-carboxylate and1,3-oxazole-4-carbonitrile against human cytomegalovirus. Med. Chem. Res., 2019, 28, 1205-1211.
[http://dx.doi.org/10.1007/s00044-019-02365-x]
[69]
Rawle, D.J.; Li, D.; Wu, Z.; Wang, L.; Choong, M.; Lor, M.; Reid, R.C.; Fairlie, D.P.; Harris, J.; Tachedjian, G.; Poulsen, S.A.; Harrich, D. Oxazole-benzenesulfonamide derivatives inhibit HIV-1 reverse transcriptase interaction with cellular eEF1A and reduce viral replication. J. Virol., 2019, 93(12), e00239-e19.
[http://dx.doi.org/10.1128/JVI.00239-19] [PMID: 30918071]
[70]
Warren, K.; Wei, T.; Li, D.; Qin, F.; Warrilow, D.; Lin, M.H.; Sivakumaran, H.; Apolloni, A.; Abbott, C.M.; Jones, A.; Anderson, J.L.; Harrich, D. Eukaryotic elongation factor 1 complex subunits are critical HIV-1 reverse transcription cofactors. Proc. Natl. Acad. Sci. USA, 2012, 109(24), 9587-9592.
[http://dx.doi.org/10.1073/pnas.1204673109] [PMID: 22628567]
[71]
Li, D.; Wei, T.; Rawle, D.J.; Qin, F.; Wang, R.; Soares, D.C.; Jin, H.; Sivakumaran, H.; Lin, M.H.; Spann, K.; Abbott, C.M.; Harrich, D. Specific interactionbetween eEF1A and HIV RT is critical for HIV-1 reverse transcription anda potential anti-HIV target. PLoS Pathog., 2015, 11(12), e1005289.
[http://dx.doi.org/10.1371/journal.ppat.1005289] [PMID: 26624286]
[72]
García-Ramírez, V.G.; Suarez-Castro, A.; Villa-Lopez, M.G.; Díaz-Cervantes, E.; Chacón-García, L.; Cortes-García, C.J. Synthesis of novel acylhydrazone-oxazole hybrids and docking studies of SARS-CoV-2 main protease. Chem. Proc., 2020, 3, 1.
[http://dx.doi.org/10.3390/ecsoc-24-08329]
[73]
Creager, A.N.H.; Scholthof, K.B.G.; Citovsky, V.; Scholthof, H.B. Tobacco mosaic virus. Pioneering research for a century. Plant Cell, 1999, 11(3), 301-308.
[http://dx.doi.org/10.1105/tpc.11.3.301] [PMID: 10072391]
[74]
Chen, M.H.; Chen, Z.; Song, B.A.; Bhadury, P.S.; Yang, S.; Cai, X.J.; Hu, D.Y.; Xue, W.; Zeng, S. Synthesis and antiviral activities of chiral thiourea derivatives containing an alpha-aminophos-phonate moiety. J. Agric. Food Chem., 2009, 57(4), 1383-1388.
[http://dx.doi.org/10.1021/jf803215t] [PMID: 19199594]
[75]
Yang, Z.B.; Li, P.; He, Y.J. Design, synthesis, and bioactivity evaluation of novel isoxazole-amide derivatives containing an acylhydrazone moiety as new active antiviral agents. Molecules, 2019, 24(20), 3766.
[http://dx.doi.org/10.3390/molecules24203766] [PMID: 31635044]
[76]
Egorova, A.; Kazakova, E.; Jahn, B.; Ekins, S.; Makarov, V.; Schmidtke, M. Novel pleconaril derivatives: Influence of substituents in the isoxazole and phenyl rings on the antiviral activity against enteroviruses. Eur. J. Med. Chem., 2020, 188, 112007.
[http://dx.doi.org/10.1016/j.ejmech.2019.112007] [PMID: 31881489]
[77]
Makarov, V.A.; Riabova, O.B.; Granik, V.G.; Wutzler, P.; Schmidtke, M. Novel [(biphenyloxy)propyl]isoxazole derivatives for inhibition of human rhinovirus 2 and coxsackievirus B3 replication. J. Antimicrob. Chemother., 2005, 55(4), 483-488.
[http://dx.doi.org/10.1093/jac/dki055] [PMID: 15743897]
[78]
Schmidtke, M.; Wutzler, P.; Zieger, R.; Riabova, O.B.; Makarov, V.A. New pleconaril and [(biphenyloxy)propyl]isoxazole derivatives with substitutions in the central ring exhibit antiviral activity against pleconaril-resistant coxsackievirus B3. Antiviral Res., 2009, 81(1), 56-63.
[http://dx.doi.org/10.1016/j.antiviral.2008.09.002] [PMID: 18840470]
[79]
Cascella, M.; Rajnik, M.; Cuomo, A.; Dulebohn, S.C.; Di Napoli, R. Features, Evaluation and Treatment Coronavirus (COVID-19); Stat Pearls Publishing: Treasure Island, FL, USA, 2020.
[80]
Sohrabi, C.; Alsafi, Z.; O’Neill, N.; Khan, M.; Kerwan, A.; Al-Jabir, A.; Iosifidis, C.; Agha, R. World Health Organization declares global emergency: A review of the 2019 novel coronavirus (COVID-19). Int. J. Surg., 2020, 76, 71-76.
[http://dx.doi.org/10.1016/j.ijsu.2020.02.034] [PMID: 32112977]
[81]
Algethami, F.K.; Cherif, M.; Jlizi, S.; Ben Hamadi, N.; Romdhane, A.; Elamin, M.R.; Alghamdi, M.A.; Ben Jannet, H. Design, microwave-assisted synthesis and in silico prediction study of novel isoxazole linked pyranopyrimidinone conjugates as new targets for searching potential Anti-SARS-CoV-2 agents. Molecules, 2021, 26(20), 6103-6121.
[http://dx.doi.org/10.3390/molecules26206103] [PMID: 34684683]
[82]
Sokolova, A.S.; Yarovaya, O.I.; Bormotov, N.I.; Shishkina, L.N.; Salakhutdinov, N.F. Synthesis and antiviral activity of camphor-based 1,3-thiazolidin-4-one and thiazole derivatives as Orthopoxvirus -reproduction inhibitors. MedChemComm, 2018, 9(10), 1746-1753.
[http://dx.doi.org/10.1039/C8MD00347E] [PMID: 30429979]
[83]
Kasralikar, H.M.; Jadhavar, S.C.; Goswami, S.V.; Kaminwar, N.S.; Bhusare, S.R. Design, synthesis and molecular docking of pyrazolo [3,4d] thiazole hybrids as potential anti-HIV-1 NNRT inhibitors. Bioorg. Chem., 2019, 86, 437-444.
[http://dx.doi.org/10.1016/j.bioorg.2019.02.006] [PMID: 30771690]
[84]
Gürsoy, E.; Dincel, E.D.; Naesens, L.; Ulusoy Güzeldemirci, N. Design and synthesis of novel Imidazo[2,1-b]thiazole derivatives as potent antiviral and antimycobacterial agents. Bioorg. Chem., 2020, 95, 103496.
[http://dx.doi.org/10.1016/j.bioorg.2019.103496] [PMID: 31862455]
[85]
Kumar, M.; Chung, S.M.; Enkhtaivan, G.; Patel, R.V.; Shin, H.S.; Mistry, B.M. Molecular docking studies and biological evaluation of berberine-benzothiazole derivatives as an anti-influenza agent via blocking of neuraminidase. Int. J. Mol. Sci., 2021, 22(5), 2368.
[http://dx.doi.org/10.3390/ijms22052368] [PMID: 33673431]
[86]
Petrou, A.; Zagaliotis, P.; Theodoroula, N.F.; Mystridis, G.A.; Vizirianakis, I.S.; Walsh, T.J.; Geronikaki, A. Thiazole/thiadiazole/benzothiazole based thiazolidin-4-one derivatives as potential inhibitors of main protease of SARS-CoV-2. Molecules, 2022, 27(7), 2180.
[http://dx.doi.org/10.3390/molecules27072180] [PMID: 35408577]
[87]
Manvar, D. Küçükgüzel, İ.; Erensoy, G.; Tatar, E.; Deryabaşoğulları G.; Reddy, H.; Talele, T.T.; Cevik, O.; Kaushik-Basu, N. Discovery of conjugated thiazolidinone-thiadiazole scaffold as anti-dengue virus polymerase inhibitors. Biochem. Biophys. Res. Commun., 2016, 469(3), 743-747.
[http://dx.doi.org/10.1016/j.bbrc.2015.12.042] [PMID: 26697747]
[88]
Gan, X.; Hu, D.; Chen, Z.; Wang, Y.; Song, B. Synthesis and antiviral evaluation of novel 1,3,4-oxadiazole/thiadiazole-chalcone conjugates. Bioorg. Med. Chem. Lett., 2017, 27(18), 4298-4301.
[http://dx.doi.org/10.1016/j.bmcl.2017.08.038] [PMID: 28838690]
[89]
Zhang, J.P.; Li, X-Y.; Dong, Y-W.; Qin, Y-G.; Li, X-L.; Song, B-A.; Yang, X-L. Synthesis and biological evaluation of 4-methyl-1,2,3-thiadiazole-5-carboxaldehyde benzoyl hydrazone derivatives. Chin. Chem. Lett., 2017, 28(6), 1238-1242.
[http://dx.doi.org/10.1016/j.cclet.2017.02.002]
[90]
Fascio, M.L.; Sepúlveda, C.S.; Damonte, E.B.; D’Accorso, N.B. Synthesis and antiviral activity of some imidazo[1,2-b][1,3,4]thiadiazole carbohydrate derivatives. Carbohydr. Res., 2019, 480, 61-66.
[http://dx.doi.org/10.1016/j.carres.2019.05.003] [PMID: 31176191]
[91]
Buemi, M.R.; Gitto, R.; Ielo, L.; Pannecouque, C.; De Luca, L. Inhibition of HIV-1 RT activity by a new series of 3-(1,3,4-thiadiazol-2-yl)thiazolidin-4-one derivatives. Bioorg. Med. Chem., 2020, 28(8), 115431.
[http://dx.doi.org/10.1016/j.bmc.2020.115431] [PMID: 32197813]
[92]
Tatar, E. Yaldız, S.; Kulabaş N.; Vanderlinden, E.; Naesens, L.; Küçükgüzel, İ. Synthesis and structure-activity relationship of L ‐methionine‐coupled 1,3,4‐thiadiazole derivatives with activity against influenza virus. Chem. Biol. Drug Des., 2022, 99(3), 398-415.
[http://dx.doi.org/10.1111/cbdd.13995] [PMID: 34873848]
[93]
Tatar, E. Kόηόkgόzel, G.; Karakuş S.; de Clercq, E.; Andrei, G.; Snoeck, R.; Pannecouque, C. Synthesis and biological evaluation of some new 1,3,4-thiadiazole and 1,2,4-triazole derivatives from L-methionine as antituberculosis and antiviral agents. Marmara Pharm. J., 2015, 19(2), 88-102.
[http://dx.doi.org/10.12991/mpj.2015199639]
[94]
Dong, J.; Xiao, M.; Ma, Q.; Zhang, G.; Zhao, W.; Kong, M.; Zhang, Y.; Qiu, L.; Hu, W. Design and synthesis of pinane oxime derivatives as novel anti-influenza agents. Bioorg. Chem., 2020, 102, 104106.
[http://dx.doi.org/10.1016/j.bioorg.2020.104106] [PMID: 32739481]
[95]
Dong, J.; Yan, F.; Li, S.; Li, Z.; Qin, Y. Multigram scale synthesis and anti-influenza activity of 3-indoleacetonitrile glucosides. Nat. Prod. Commun., 2020, 15(10), 1934578X2095328.
[http://dx.doi.org/10.1177/1934578X20953289]
[96]
Zhao, X.; Li, R.; Zhou, Y.; Xiao, M.; Ma, C.; Yang, Z.; Zeng, S.; Du, Q.; Yang, C.; Jiang, H.; Hu, Y.; Wang, K.; Mok, C.K.P.; Sun, P.; Dong, J.; Cui, W.; Wang, J.; Tu, Y.; Yang, Z.; Hu, W. Discovery of highly potent pinanamine-based inhibitors against amantadine- and oseltamivir-resistant influenza A viruses. J. Med. Chem., 2018, 61(12), 5187-5198.
[http://dx.doi.org/10.1021/acs.jmedchem.8b00042] [PMID: 29799746]
[97]
Dong, J.; Chen, S.; Li, R.; Cui, W.; Jiang, H.; Ling, Y.; Yang, Z.; Hu, W. Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus. Eur. J. Med. Chem., 2016, 108, 605-615.
[http://dx.doi.org/10.1016/j.ejmech.2015.12.013] [PMID: 26722757]
[98]
Dong, J.; Pei, Q.; Wang, P.; Ma, Q.; Hu, W. Optimized POCl3-assisted synthesis of 2-amino-1,3,4-thiadiazole/1,3,4-oxadiazole derivatives as anti-influenza agents. Arab. J. Chem., 2022, 15(4), 103712.
[http://dx.doi.org/10.1016/j.arabjc.2022.103712]
[99]
Benmansour, F.; Eydoux, C.; Querat, G.; de Lamballerie, X.; Canard, B.; Alvarez, K.; Guillemot, J.C.; Barral, K. Novel 2-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,3,4-oxadiazole and 3-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,2,4-oxadiazole derivatives as dengue virus inhibitors targeting NS5 polymerase. Eur. J. Med. Chem., 2016, 109, 146-156.
[http://dx.doi.org/10.1016/j.ejmech.2015.12.046] [PMID: 26774922]
[100]
Wang, P.Y.; Shao, W.B.; Xue, H.T.; Fang, H.S.; Zhou, J.; Wu, Z.B.; Song, B.A.; Yang, S. Synthesis of novel 1,3,4-oxadiazole derivatives containing diamides as promising antibacterial and antiviral agents. Res. Chem. Intermed., 2017, 43(11), 6115-6130.
[http://dx.doi.org/10.1007/s11164-017-2980-x]
[101]
Kim, J.; Shin, J.S.; Ahn, S.; Han, S.B.; Jung, Y.S. 3-Aryl-1,2,4-oxadiazole derivatives active against human rhinovirus. ACS Med. Chem. Lett., 2018, 9(7), 667-672.
[http://dx.doi.org/10.1021/acsmedchemlett.8b00134] [PMID: 30034598]
[102]
Hamdani, S.S.; Khan, B.A.; Hameed, S.; Batool, F.; Saleem, H.N.; Mughal, E.U.; Saeed, M. Synthesis and evaluation of novel S-benzyl- and S-alkylphthalimide- oxadiazole -benzenesulfonamide hybrids as inhibitors of dengue virus protease. Bioorg. Chem., 2020, 96, 103567.
[http://dx.doi.org/10.1016/j.bioorg.2020.103567] [PMID: 32062063]
[103]
Vernekar, S.K.V.; Qiu, L.; Zhang, J.; Kankanala, J.; Li, H.; Geraghty, R.J.; Wang, Z. 5′ - silylated 3′ -1,2,3-triazolyl thymidine analogues as inhibitors of West Nile Virus and Dengue virus. J. Med. Chem., 2015, 58(9), 4016-4028.
[http://dx.doi.org/10.1021/acs.jmedchem.5b00327] [PMID: 25909386]
[104]
Chudinov, M.V.; Matveev, A.V.; Prutkov, A.N.; Konstantinova, I.D.; Fateev, I.V.; Prasolov, V.S.; Smirnova, O.A.; Ivanov, A.V.; Galegov, G.A.; Deryabin, P.G. Novel 5-alkyl(aryl)-substituted ribavirine analogues: Synthesis and antiviral evaluation. Mendeleev Commun., 2016, 26(3), 214-216.
[http://dx.doi.org/10.1016/j.mencom.2016.04.012]
[105]
Artyushin, O.I.; Sharova, E.V.; Vinogradova, N.M.; Genkina, G.K.; Moiseeva, A.A.; Klemenkova, Z.S.; Orshanskaya, I.R.; Shtro, A.A.; Kadyrova, R.A.; Zarubaev, V.V.; Yarovaya, O.I.; Salakhutdinov, N.F.; Brel, V.K. Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity. Bioorg. Med. Chem. Lett., 2017, 27(10), 2181-2184.
[http://dx.doi.org/10.1016/j.bmcl.2017.03.051] [PMID: 28366530]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy