116
Views
0
CrossRef citations to date
0
Altmetric
Original Research

(2Z)-3-Hydroxy-3-(4-R-Phenyl)-Prop-2-Enedithioic Acids as New Antituberculosis Compounds

, , , , , , & ORCID Icon show all
Pages 4323-4332 | Published online: 20 Oct 2021

References

  • World Health Organization [homepage on the internet]. Geneva; 1948. Available from: https://www.who.int/en/news-room/fact-sheets/detail/tuberculosis. Accessed October 6, 2021.
  • Teague SJ. Learning lessons from drugs that have recently entered the market. Drug Discov Today. 2011;16(9,10):398–411. doi:10.1016/j.drudis.2011.03.00321414418
  • Flick AC, Ding HX, Leverett CA, et al. Synthetic approaches to the 2014 new drugs. Bioorg Med Chem. 2016;24(9):1937–1980. doi:10.1016/j.bmc.2016.03.00427020685
  • Mueck W, Schwers S, Stampfuss J. Rivaroxaban and other novel oral anticoagulants: pharmacokinetics in healthy subjects, specific patient populations and relevance of coagulation monitoring. Thromb J. 2013;11(10):1–17. doi:10.1186/1477-9560-11-1023311309
  • Bassetto M, Ferla S, Pertusati F, et al. Design and synthesis of novel bicalutamide and enzalutamide derivatives as antiproliferative agents for the treatment of prostate cancer. Eur J Med Chem. 2016;118:230–243. doi:10.1016/j.ejmech.2016.04.05227131065
  • Pal A, Pattanayak RD, Sagar R. Tracing the journey of disulfiram: from an unintended discovery to a treatment option for alcoholism. J Mental Health Hum Behav. 2015;20(1):41–43. doi:10.4103/0971-8990.164826
  • Laborde J, Deraeve C, Bernardes-Génisson V. Update of antitubercular prodrugs from a molecular perspective: mechanisms of action, bioactivation pathways, and associated resistance. ChemMedChem. 2017;12(20):1657–1676. doi:10.1002/cmdc.20170042428921911
  • Konreddy AK, Toyama M, Ito W, Bal C, Baba M, Sharon A. Synthesis and anti-HCV activity of 4-hydroxyamino α-pyranone carboxamide analogues. ACS Med Chem Lett. 2014;5(3):259–263. doi:10.1021/ml400432f24900815
  • Garcia-Orozco I, Lopez-Cortes JG, Ortega-Alfaro MC, Toscano RA, Penieres-Carrillo G, Alvarez-Toledano C. Synthesis, characterization, and tautomerism of four novel copper(I) complexes from 3-hydroxy-3-(p-R-phenyl)-2-propenedithioic acids. Inorg Chem. 2004;43(26):8572–8576. doi:10.1021/ic048813215606208
  • Larsson FCV, Lawesson SO. Preparation and alkylation of substituted β-hydroxydithiocinnamic acids. Tetrahedron. 1972;28(21):5341–5347. doi:10.1016/S0040-4020(01)93857-8
  • Mossman T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983;65(1–2):55–63. doi:10.1016/0022-1759(83)90303-46606682
  • Collins LA, Franzblau SG. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob Agents Chemother. 1997;41(5):1004–1009. doi:10.1128/AAC.41.5.10049145860
  • Molina SGM, Ramos GMC, Vargas VJ, Mata CBD, Becerril MP, Said FS. Activity of organic extracts from Flourensia cernua DC against strains of Mycobacterium tuberculosis. Arch Med Res. 2006;37(1):45–49. doi:10.1016/j.arcmed.2005.04.01016314185
  • Lagorce D, Bouslama L, Becot J, Miteva MA, Villoutreix BO. FAF-Drugs4: free ADME-tox filtering computations for chemical biology and early stages drug discovery. Bioinformatics. 2017;33(22):3658–3660. doi:10.1093/bioinformatics/btx49128961788
  • Schyman P, Liu R, Desai V, Wallqvist A. vNN web server for ADMET predictions. Front Pharmacol. 2017;8:889. doi:10.3389/fphar.2017.0088929255418
  • Yang H, Lou C, Sun L, et al. admetSAR 2.0: web-service for prediction and optimization of chemical ADMET properties. Bioinformatics. 2019;35(6):1067–1069. doi:10.1093/bioinformatics/bty70730165565
  • Pires DEV, Blundell TL, Ascher DB. pkCSM: predicting small-molecule pharmacokinetic and toxicity properties using graph-based signatures. J Med Chem. 2015;58(9):4066–4072. doi:10.1021/acs.jmedchem.5b0010425860834
  • Cousins KR. Computer review of ChemDraw Ultra 12.0. J Am Chem Soc. 2011;133(21):8388. doi:10.1021/ja204075s21561109
  • Swain M. Chemicalize.org. J Chem Inf Mod. 2012;52(2):613–615. doi:10.1021/ci300046g
  • Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 16, Revision C.01. Wallingford CT: Gaussian, Inc.; 2016.
  • Sanner MF. Python: a programming language for software integration and development. J Mol Graph Model. 1999;17(1):57–61. doi:10.1016/S1093-3263(99)99999-010660911
  • Rose PW, Prlić A, Bi C, et al. The RCSB protein data bank: views of structural biology for basic and applied research and education. Nucleic Acids Res. 2015;43(D1):D345–D356. doi:10.1093/nar/gku121425428375
  • Pettersen EF, Goddard TD, Huang CC, et al. UCSF Chimera—A visualization system for exploratory research and analysis. J Comput Chem. 2004;25(13):1605–1612. doi:10.1002/jcc.2008415264254
  • Morris GM, Goodsell DS, Halliday RS, et al. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comp Chem. 1998;19(14):1639–1662. doi:10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B
  • BIOVIA, Dassault Systèmes, Discovery Studio 2019. San Diego: Dassault Systèmes; 2019. Available from: https://www.3ds.com/products-services/biovia/. Accessed October 6, 2021.
  • Chung MC, Bosquesi PL, dos Santos JL. A prodrug approach to improve the physico-chemical properties and decrease the genotoxicity of nitro compounds. Curr Pharm Des. 2011;17(32):3515–3526. doi:10.2174/13816121179819451222074424
  • Cambridge MedChem Consulting. Available from: https://www.cambridgemedchemconsulting.com/resources/bioisoteres/. Accessed December 18, 2019.
  • Szatylowicz H, Stasyuk OA, Fonseca Guerra C, Krygowski TM. Effect of intra- and intermolecular interactions on the properties of para-substituted nitrobenzene derivatives. Crystals. 2016;6(3):29–45. doi:10.3390/cryst6030029
  • Katsuno K, Burrows JN, Duncan K, et al. Hit and lead criteria in drug discovery for infectious diseases of the developing world. Nat Rev Drug Discov. 2015;14(11):751–758. doi:10.1038/nrd468326435527
  • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 1997;23(1–3):3–25. doi:10.1016/S0169-409X(96)00423-1
  • Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kopple KD. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem. 2002;45(12):2615–2623. doi:10.1021/jm020017n12036371
  • Egan WJ, Merz KM, Baldwin JJ. Prediction of drug absorption using multivariate statistics. J Med Chem. 2000;43(21):3867–3877. doi:10.1021/jm000292e11052792
  • Dong Y, Qui X, Shaw N, et al. Molecular basis for the inhibition of β-hydroxyacyl-ACP dehydratase HadAB complex from Mycobacterium tuberculosis by flavonoid inhibitors. Prot Cell. 2015;6(7):504–517. doi:10.1007/s13238-015-0181-1