A review of synthesis, biological activity, & docking studies of anti-tubercular agents
Abstract
The World Health Organization suggests treating tuberculosis with a 6-month course of isoniazid (INH), rifampicin (RMP), ethambutol, and pyrazinamide. The anti-TB activity of a number of novel styryl-1,2,4-oxadiazoles against the MTB H37Ra strain was assessed. These compounds were motivated by the molecular structure of cinnamic acid. There is a substantial correlation between the antibacterial activity and the location of the pyridine substituent on the thiosemicarbazide skeleton. A total of thirty-three ligands were docked against the two proteins AftaA and EmbA during the primary protein-ligand docking process, which was carried out using iGemDock. The following study included eight anti-tuberculosis medications as a control group: rifampicin, isoniazid, bed aquiline, delamanid, ethionamide, ethambutol, Gemifloxacin, and thioacetazone.
Keywords:
Isoniazid (INH), rifampicin (RMP), Bedaquiline, ligand docking, lapazine, Building Evidence to Advance Treatment of TB (BEAT)
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References
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3. Silveira N, Longuinho MM, Leitão SG, Silva RS, Lourenço MC, Silva PE, Maria do Carmo FR, Abraçado LG, Finotelli PV. Synthesis and characterization of the antitubercular phenazine lapazine and development of PLGA and PCL nanoparticles for its entrapment. Materials Science and Engineering: C. 2016 Jan 1;58:458-66.
4. Dos Santos Fernandes GF, De Souza PC, Moreno-Viguri E, Santivañez-Veliz M, Paucar R, Pérez-Silanes S, Chegaev K, Guglielmo S, Lazzarato L, Fruttero R, Man Chin C. Design, synthesis, and characterization of N-oxide-containing heterocycles with in vivo sterilizing antitubercular activity. Journal of Medicinal Chemistry. 2017 Oct 26;60(20):8647-60.
5. Munnaluri RK, Manga V. in silico Quest Guided by Physico-Chemical Descriptors of Bedaquiline for New Scaffolds with Potential Inhibitory Capacity against Homology Model of Mycobacterium F 1 F 0 ATP Synthase. Asian Journal of Chemistry. 2018 Apr 1;30(4).Gawad J, Bonde C. Synthesis, biological evaluation and molecular docking studies of 6-(4-nitrophenoxy)-1H-imidazo [4, 5-b] pyridine derivatives as novel antitubercular agents: future DprE1 inhibitors. Chemistry Central Journal. 2018 Dec;12(1):1-1.
6. Deb PK, Al-Shar’i NA, Venugopala KN, Pillay M, Borah P. In vitro anti-TB properties, in silico target validation, molecular docking and dynamics studies of substituted 1, 2, 4-oxadiazole analogues against Mycobacterium tuberculosis. Journal of enzyme inhibition and medicinal chemistry. 2021 Jan 1;36(1):869-84.
7. PANT K, Thapliyal A, Tufchi N. In Silico Docking analysis of Mycobacterium tuberculosis potential targets AftB and EmbAwithselected phytochemicals. International Journal of Pharmacy Research & Technology (IJPRT). 2017;7(2):15-22.
8. Padmapriyadarsini C, Vohra V, Bhatnagar A, Solanki R, Sridhar R, Anande L, Muthuvijaylakshmi M, Rana MB, Jeyadeepa B, Taneja G, Balaji S. Bedaquiline, delamanid, linezolid, and clofazimine for treatment of pre-extensively drug-resistant tuberculosis. Clinical Infectious Diseases. 2023 Feb 1;76(3):e938-46.
9. Da Costa CF, Pinheiro AC, De Almeida MV, Lourenço MC, De Souza MV. Synthesis and antitubercular activity of novel amino acid derivatives. Chemical biology & drug design. 2012 Feb;79(2):216-22.
10. Obakiro SB, K'Owino I, Kigondu E, Andima M, Owor RO, Kiprop A. Molecular Docking Interactions with Mycobacterial ATP and Polyketide-13 Synthase Enzymes of Phytoconstituents Isolated from Entada abyssinica Stem Bark.
11. Jordão AK, Sathler PC, Ferreira VF, Campos VR, de Souza MC, Castro HC, Lannes A, Lourenco A, Rodrigues CR, Bello ML, Lourenco MC. Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1, 2, 3-triazole-4-carbohydrazides. Bioorganic & medicinal chemistry. 2011 Sep 15;19(18):5605-11.
12. Guruvelli PV, Wagmare P, Harinath BC, Jamullamudi RN, Kurre PN, Muthyala MK. Synthesis, Screening and Docking Analysis of Novel Benzimidazolium and Benzotriazolium Compounds as Potent Anti Tubercular Agents. Anti-Infective Agents. 2019 Apr 1;17(1):20-7.
13. Doria Jorge S, Palace-Berl F, Masunari A, Cechinel Ca, Ishii M, Mesquita Pasqualoto Kf. Novel benzofuroxan derivatives against multidrug-resistant Staphylococcus aureus strains: Design using Topliss' decision tree, synthesis and biological assay. Bioorganic & medicinal chemistry. 2011;19(16):5031-8.
14. Jones G, Willett P, Glen RC, Leach AR, Taylor R. Development and validation of a genetic algorithm for flexible docking. Journal of molecular biology. 1997 Apr 4;267(3):727-48.
15. Hooker SC. On the Oxidation of 2-Hydroxy-1, 4-naphthoquinone Derivatives with Alkaline Potassium Permanganate1, 2. Journal of the American Chemical Society. 1936 Jul;58(7):1174-9.
16. Ettlinger MG. Hydroxynaphthoquinones. II. Cyclization and the basicity and interconversion of ortho and para quinones. Journal of the American Chemical Society. 1950 Jul;72(7):3090-5.
17. Krajewski, W.W.; Jones, T.A.; Mowbray, S.L. Structure of Mycobacterium tuberculosis glutamine synthetase in complex with a transition-state mimic provides functional insights. Proc. Natl. Acad. Sci. USA 2005, 102, 10499–10504
18. Hu, G.Q.; Li, S.; Huang, W.L.; Wang, H. Synthesis and bioactivity of arecoline derivatives containing 1,2,4-triazone. Youji Huaxue 2002, 22, 667–671.
Published
07/12/2023
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Chukka, A. K., K, V. G., Ch, S., M, L. S., M, D. C., M, H. S., SK, I., & J. N, S. K. (2023). A review of synthesis, biological activity, & docking studies of anti-tubercular agents. Journal of Innovations in Applied Pharmaceutical Science (JIAPS), 8(3), 45-50. https://doi.org/10.37022/jiaps.v8i3.542
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