Synthesis, characterization, in-vitro biological evaluation and theoretical studies of 1,2,3-triazoles derived from triclosan as difenoconazole analogues
Tài liệu tham khảo
Lass-Flörl, 2011, Triazole antifungal agents in invasive fungal infections: a comparative review, Drugs, 71, 2405, 10.2165/11596540-000000000-00000
Jefreys, 2019, Novel insights into P450 BM3 interactions with FDA-approved antifungal azole drugs, Sci. Rep.-UK, 9, 1577, 10.1038/s41598-018-37330-y
Ruegg, 1990, Biology and control of Entyloma eryngii (Cda.) de by., the cause of a leaf spot disease on the blue thistle (Eryngium alpinum L.), J. Phytopathol., 130, 9, 10.1111/j.1439-0434.1990.tb01148.x
Roberts, 1999, 1036
Dong, 2013, Chiral triazole fungicide difenoconazole: absolute stereochemistry, stereoselective bioactivity, aquatic toxicity, and environmental behavior in vegetables and soil, Environ. Sci. Technol., 47, 3386, 10.1021/es304982m
Wang, 2016, Activities of azoxystrobin and difenoconazole against Alternaria alternata and their control efficacy, Crop Prot, 90, 54, 10.1016/j.cropro.2016.08.022
Reuveni, 2002, Sensitivity of Red Delicious apple fruit at various phenologic stages to infection by Alternaria alternata and moldy-core control, Eur. J. Plant Pathol., 108, 421, 10.1023/A:1016063626633
Shtienberg, 1991, Suppression of Alternaria leaf spot in Pima cotton by systemic fungicides, Crop Prot, 10, 381, 10.1016/S0261-2194(06)80028-1
Munkvold, 2002, Laboratory and growth chamber evaluation of fungicidal seed treatments for maize seedling blight caused by fusarium species, Plant Dis, 86, 143, 10.1094/PDIS.2002.86.2.143
Jayasena, 2002, Evaluation of fungicides in control of spot-type net blotchon barley, Crop Prot., 21, 63, 10.1016/S0261-2194(01)00118-1
Cook, 2002, Yield responses of direct-seeded wheat to rhizobacteria and fungicide seed treatments, Plant Dis., 86, 780, 10.1094/PDIS.2002.86.7.780
Dahmen, 1992, Protective, curative, and eradicant activity of difenoconazole against Venturia inaequalis, Cercospora arachidicola and Alternaria solani, Plant Dis., 76, 774, 10.1094/PD-76-0774
Bowyer, 2014, Environmental fungicides and triazole resistance in Aspergillus, Pestic. Manag. Sci., 70, 173, 10.1002/ps.3567
Snelders, 2012, Triazole Fungicides Can Induce Cross-Resistance to Medical Triazoles in Aspergillus fumigatus, PLoS ONE, 7, e31801, 10.1371/journal.pone.0031801
Howard, 2009, Frequency and evolution of azole resistance in aspergillus fumigatus associated with treatment failure, Emerg. Infect. Dis., 15, 1068, 10.3201/eid1507.090043
Kunz, 1997, Acquisition of resistance to sterol demethylation inhibitors by populations of Venturia inaequalis, Phytopathology, 87, 1272, 10.1094/PHYTO.1997.87.12.1272
D'Mello, 1998, Pesticide use and mycotoxin production in Fusarium and Aspergillus phytopathogens, Eur. J. Plant Pathol., 104, 741, 10.1023/A:1008621505708
Suárez-García, 2021, Synthesis and antifungal activity evaluation of 1-(2-benzyloxy-2-phenylethyl)-1,2,3-triazole miconazole analogs, Pharm. Chem. J., 55, 436, 10.1007/s11094-021-02440-x
Zambrano-Huerta, 2019, Synthesis and in vitro biological evaluation of 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives as antifungal compounds fluconazole analogues, Med. Chem. Res., 28, 571, 10.1007/s00044-019-02317-5
Haroun, 2021, Recent advances in the development of 1,2,3-triazole-containing derivatives as potential antifungal agents and inhibitors of lanosterol 14α-demethylase, Curr. Top. Med. Chem., 21, 462, 10.2174/1568026621999201214232018
Estrada-Valdés, 2019, Design and synthesis of antifungal compounds from 1,2,3-triazoles through the click chemistry approach, Org. Med. Chem. Int. J., 8
Bozorova, 2019, 1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: a recent overview, Bioorg. Med. Chem., 27, 3511, 10.1016/j.bmc.2019.07.005
Bonandi, 2017, The 1,2,3-triazole ring as a bioisostere in medicinal chemistry, Drug Discov. Today, 22, 1572, 10.1016/j.drudis.2017.05.014
Thirumurugan, 2013, Click chemistry for drug development and diverse chemical-biology applications, Chem. Rev., 113, 4905, 10.1021/cr200409f
Zhou, 2012, Recent researches in triazole compounds as medicinal drugs, Curr. Med. Chem., 19, 239, 10.2174/092986712803414213
Agalave, 2011, Click Chemistry: 1,2,3-Triazoles as Pharmacophores, Chem. Asian J., 6, 2696, 10.1002/asia.201100432
Jones, 2000, Triclosan: a review of effectiveness and safety in health care settings, Am. J. Infect. Control, 28, 184, 10.1067/mic.2000.102378
Levy, 1999, Molecular basis of triclosan activity, Nature, 398, 383, 10.1038/18803
Ali, 2021, Design, synthesis, molecular modeling, anticancer studies, and density functional theory calculations of 4‑(1,2,4-triazol-3-ylsulfanylmethyl)-1,2,3-triazole derivatives, ACS Omega, 6, 301, 10.1021/acsomega.0c04595
Fizer, 2021, Identifying and explaining the regioselectivity of alkylation of 1,2,4-triazole-3-thiones using NMR, GIAO and DFT methods, J. Mol. Struct., 1223, 10.1016/j.molstruc.2020.128973
Zamora, 2021, Theoretical determination of a reaction intermediate: Fukui function analysis, dual reactivity descriptor and activation energy, J. Mol. Struct., 1227, 10.1016/j.molstruc.2020.129369
2011
Stephens, 1994, Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields, J. Phys. Chem., 98, 11623, 10.1021/j100096a001
Becke, 1993, Density-functional thermochemistry. III. The role of exact exchange, J. Chem. Phys., 98, 5648, 10.1063/1.464913
Lee, 1988, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B, 37, 785, 10.1103/PhysRevB.37.785
Schaefer, 1992, Fully optimized contracted Gaussian-basis sets for atoms Li to Kr, J. Chem. Phys., 97, 2571, 10.1063/1.463096
Schaefer, 1994, Fully optimized contracted Gaussian-basis sets of triple zeta valence quality for atoms Li to Kr, J. Chem. Phys., 100, 5829, 10.1063/1.467146
Neese, 2020, The ORCA quantum chemistry program package, J. Chem. Phys., 152, 10.1063/5.0004608
te Velde, 2001, Chemistry with ADF, J. Comput. Chem., 22, 931, 10.1002/jcc.1056
Fuentealba, 2000, On the condensed Fukui function, J. Chem. Phys., 113, 2544, 10.1063/1.1305879
Weigend, 2005, Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy, Phys. Chem. Chem. Phys., 7, 3297, 10.1039/b508541a
Laplaza, 2021, Visualizing non-covalent interactions with NCIPLOT, 353
Ríos-Malváez, 2021, Synthesis, characterization and cytotoxic activity evaluation of 4-(1,2,3-triazol-1-yl) salicylic acid derivatives, J. Mol. Struct., 1225, 10.1016/j.molstruc.2020.129149
Bodrumlu, 2006, Evaluation of antimicrobial and antifungal effects of iodoform-integrating Gutta-Percha, J. Can. Dent. Assoc., 72, 733
Mahdally, 2021, Staquorsin: a novel staphylococcus aureus Agr-mediated quorum sensing inhibitor impairing virulence in vivo without notable resistance development, Front. Microbiol., 12, 10.3389/fmicb.2021.700494
Kesici, 2020, Antimicrobial effects of fentanyl and bupivacaine: an in vitro study, Rev. Bras. Anestesiol., 70, 357, 10.1016/j.bjan.2020.04.010
Schöneberg, 2018, Can plant phenolic compounds reduce Fusarium growth and mycotoxin production in cereals?, Food Addit. Contam. A, 35, 2455, 10.1080/19440049.2018.1538570
Gnonlonfoun, 2022, Inhibition of the growth of fusarium tricinctum and reduction of its enniatin production by erwinia gerundensis isolated from Barley Kernels, J. Am. Soc. Brew. Chem.