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Research Article

Synthesis of 1,3,4-Oxadiazoles with 4-Methoxynaphthalene Ring: Discovering New Compounds with Antimicrobial Activity

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Pages 2239-2255 | Received 25 May 2023, Accepted 31 Oct 2023, Published online: 28 Nov 2023

References

  • Martinez R . New trends in paracoccidioidomycosis epidemiology. J. Fungi3(1), 1–13 (2017).
  • Ramos DA , AlzateJA , MontoyaÁMG , TrujiloYA , RamosYA. Thinking in paracoccidioidomycosis: a delayed diagnosis of a neglected tropical disease, case report and review of clinical reports and eco-epidemiologic data from Colombia since the 2000. BMC Infect. Dis.20(119), 4–9 (2020).
  • Nel J , LachiewiczA , van DuinD. Emerging epidemics in transplant: histoplasmosis, blastomycosis and paracoccidioidomycosis. In: Emerging Transplant Infections.MorrisMI, KottonCN, WolfeCR ( Eds). Springer, Cham, Switzerland, 1–26 (2021).
  • Martinez R . Epidemiology of paracoccidioidomycosis. Rev. Inst. Med. Trop.57(19), 11–20 (2015).
  • Santos AL , GrisoliaJSC , BurgerE , PaulaFBDA , DiasALT , MalaquiasLCC. Virulence factors of Paracoccidioides brasiliensis as therapeutic targets: a review. Antonie Van Leeuwenhoek113, 593–604 (2020).
  • Shikanai-yasuda MA , MendesRP , ColomboALet al. Brazilian guidelines for the clinical management of paracoccidioidomycosis. Rev. Soc. Bras. Med. Trop.50(5), 715–740 (2017).
  • Hahn RC , RodriguesAM , PortellaPet al. Clinical and epidemiological features of paracoccidioidomycosis due to Paracoccidioides lutzii. PLOS Negl. Trop. Dis.13(6), 1–13 (2019).
  • Messina F , RomeroM , BenchetritAet al. Clinical and microbiological characteristics of paracoccidioidomycosis in patients with AIDS in Buenos Aires, Argentina. Med. Mycol.58(1), 22–29 (2019).
  • Godoy H , ReichartPA. Oral manifestations of paracoccidioidomycosis. Report of 21 cases from Argentina. Mycoses46, 412–417 (2003).
  • Blatzer M , LanternierF , LatgéJP , BeauvaisA , BretagneS. Fungal infections of the CNS. In: Infections of the Central Nervous System: Pathology and Genetics. 1st Edition.ChrétienF, WongKT, SharerLR, KeohaneC, GrayF ( Eds). John Wiley & Sons Ltd., Oxford, UK, 419–436 (2020).
  • Colombo AL , TobónA , RestrepoA , Queiroz-tellesF , NucciM. Epidemiology of endemic systemic fungal infections in Latin America. Med. Mycol.49(8), 785–798 (2011).
  • Queiroz-Telles F , FahalAH , FalciDR , CaceresDH , ChillerT , PasqualottoAC. Neglected endemic mycoses. Lancet Infect. Dis.17(11), e367–e377 (2017).
  • de Queiroz-Telles F , PietrobomPMP , JúniorMR , deMelo Baptista R , PeçanhaPM. New insights on pulmonary paracoccidioidomycosis. Semin. Respir. Crit. Care Med.41(1), 53–68 (2020).
  • Santos R da S , LimaP de S , DePaula LB , ReisAA da S , BarbosaMS. The human pathogen Paracoccidioides brasiliensis and paracoccidioidomycosis: a medical and molecular approach. Rev. Univ. Val. Rio Verde9(2), 281–295 (2011).
  • Mendes RP , deSouza Cavalcante R , MarquesSAet al. Paracoccidioidomycosis: current perspectives from Brazil. Open Microbiol. J.11(1), 224–282 (2017).
  • Ambrósio AVA , CameloCCS , BarbosaCVet al. Paracoccidioidomicose tratamento, duração do tratamento, recidiva, reação paradoxal, prognóstico, profilaxia. Rev. Med. Minas Gerais24(1), 74–80 (2014).
  • World Health Organization . Global Tuberculosis Report 2022.World Health Organization, Geneva, Switzerland (2022).
  • Nunura J , SalazarD , VásquezT , EndoS , RodríguezA , ZerpaR. Paracoccidioidomicosis and multidrug-resistant tuberculosis (TBC-MDR) in patient coinfected with HIV and hepatitis C. Ver. Chil. Infect.27(6), 551–555 (2010).
  • Domingues-Ferreira M , LevyA , BarrosNC , BertoliniDL , deMoraes Vasconcelos D. Case report of myeloperoxidase deficiency associated with disseminated paracoccidioidomycosis and peritoneal tuberculosis. Rev. Soc. Bras. Med. Trop.50(4), 568–570 (2017).
  • Torres-Pereira C , GiovaniniAF , StramandinoliRT , AmenabarJM , PiazzettaCM. Oral paracoccidioidomycosis and pulmonary tuberculosis co-infection: relevance of oral biopsy in establishing the diagnosis and therapeutic approach. Int. J. Infect. Dis.13(1), 114–116 (2009).
  • Bellissimo-Rodrigues F , MachadoAA , MartinezR. Paracoccidioidomycosis epidemiological features of a 1000-cases series from a hyperendemic area on the southeast of Brazil. Am. J. Trop. Med. Hyg.85(3), 546–550 (2011).
  • Quagliato R , deAraújo Guerra Grangeia T , deCarvalho Massucio RA , DeCapitani EM , deMoraes Rezende S , BalthazarAB. Associação entre paracoccidioidomicose e tuberculose: realidade e erro diagnóstico. J. Bras. Pneumol.33(3), 295–300 (2007).
  • Pellicioli ACA , Neves-SilvaR , Santos-SilvaAR , VargasPA , LopesMA. Synchronous oral paracoccidioidomycosis and pulmonary tuberculosis in an immunocompetent patient. Mycopathologia179( 5-6), 459–464 (2015).
  • Massi LS , BelloAD , d’AzevedoPA , SeveroLC. Diagnóstico molecular de paracoccidioidomicose associada à tuberculose em amostras de escarro. Clin. Biomed. Res.36(3), 142–147 (2016).
  • Rozada AMF , RodriguesFAV , SampironEGet al. Novel 4-methoxynaphthalene-N-acylhydrazones as potential agents for the treatment of paracoccidioidomycosis and tuberculosis co-infection. Future Microbiol.14(7), 587–598 (2019).
  • Gomtsyan A . Heterocycles in drugs and drugs discovery. Chem. Heterocycl. Compd.48(1), 7–10 (2012).
  • Patel KD , PrajapatiSM , PanchalSN , HiteshD. Review of synthesis of 1,3,4-oxadiazole derivatives. Synth. Commun.44(13), 1859–1875 (2014).
  • Rodrigues-Vendramini FAV , FariaDR , AritaGSet al. Antifungal activity of two oxadiazole compounds for the paracoccidioidomycosis treatment. PLOS Negl. Trop. Dis.13(6), 1–16 (2019).
  • Makane VB , KrishnaVS , KrishnaEVet al. Novel 1,3,4-oxadiazoles as antitubercular agents with limited activity against drug-resistant tuberculosis. Future Med. Chem.11(6), 499–510 (2019).
  • Yu W , HuangG , ZhangYet al. I2-Mediated oxidative C-O bond formation for the synthesis of 1,3,4-oxadiazoles from aldehydes and hydrazides. J. Org. Chem.78(20), 10337–10343 (2013).
  • Garg S , RaghavN. 2,5-Diaryloxadiazoles and their precursors as novel inhibitors of cathepsins B, H and L. Bioorg. Chem.67, 64–74 (2016).
  • Bagatin MC , RozadaAMF , RodriguesFAVet al. New 4-methoxy-naphthalene derivatives as promisor antifungal agents for paracoccidioidomycosis treatment. Future Microbiol.14(1), 235–245 (2019).
  • Zdyrko B , BanderaY , TsyalkovskyVet al. Rational design of methacrylate monomers containing oxadiazole moieties for single-layer organic light emitting devices. J. Polym. Sci. B Polym. Phys.53(23), 1663–1673 (2015).
  • Netto CF , VegasVS , SciannaméaIM , GuarnieriDB. Antígeno polissacarídico do Paracoccidioides brasiliensis estudo do tempo de cultivo do P. brasiliensis, necessário ao preparo do antígeno. Rev. Inst. Med. Trop. São Paulo11(3), 177–181 (1969).
  • Clinical and Laboratory Standards Institute . Reference method for broth dilution antifungal susceptibility testing of yeasts; approved standard, third edition (2008). https://clsi.org/media/1461/m27a3_sample.pdf
  • Palomino J , MartinA , CamachoM , GuerraH , SwingsJ. Resazurin microtiter assay plate: simple and inexpensive method for detection of drug resistance in Mycobacterium tuberculosis. Antimicrob. Agents Chemother.46(8), 2720–2722 (2002).
  • Pires CTA , BrenzanMA , ScodroRBet al. Anti-Mycobacterium tuberculosis activity and cytotoxicity of Calophyllum brasiliense Cambess (Clusiaceae). Mem. Inst. Oswaldo Cruz109(3), 324–329 (2014).
  • Cong Z-Q , WangC , ChenT , YinB-Z. Efficient and rapid method for the oxidation of electron-rich aromatic aldehydes to carboxylic acids using improved basic hydrogen peroxide. Synth. Commun.36(5), 679–683 (2006).
  • Rocha OB , doCarmo Silva L , deCarvalho Júnior MAB , de OliveiraAA , deAlmeida Soares CM , PereiraM. In vitro and in silico analysis reveals antifungal activity and potential targets of curcumin on Paracoccidioides spp. Braz. J. Microbiol.52(4), 1897–1911 (2021).
  • Bueno PSA , RodriguesFAV , SantosJLet al. New inhibitors of homoserine dehydrogenase from Paracoccidioides brasiliensis presenting antifungal activity. J. Mol. Model.25(11), 325 (2019).
  • Lima RM , Freitase Silva KS , doCarmo Silva Let al. A structure-based approach for the discovery of inhibitors against methylcitrate synthase of Paracoccidioides lutzii. J. Biomol. Struct. Dyn.40(19), 9361–9373 (2021).
  • Karabanovich G , DušekJ , SavkováKet al. Development of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues as highly efficient antitubercular agents inhibiting decaprenylphosphoryl-β-D-ribofuranose 2′-oxidase. J. Med. Chem.62(17), 8115–8139 (2019).
  • Karabanovich G , NěmečekJ , ValáškováLet al. S-substituted 3,5-dinitrophenyl 1,3,4-oxadiazole-2-thiols and tetrazole-5-thiols as highly efficient antitubercular agents. Eur. J. Med. Chem.126, 369–383 (2017).
  • Wang A , XuS , ChaiYet al. Design, synthesis and biological evaluation of nitrofuran-1,3,4-oxadiazole hybrids as new antitubercular agents. Bioorganic Med. Chem.53(1), 116529 (2022).

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