Benzothiazole analogs as potential anti-TB agents: computational input and molecular dynamics

References

• Baell, J. B. , Forsyth, S. A. , Gable, R. W. , Norton, R. S. , & Mulder, R. J. (2001). Design and synthesis of type-III mimetics of omega-conotoxin GVIA. Journal of Computer-Aided Molecular Design , 15 , 1119–1136.10.1023/A:1015930031890
   PubMed Web of Science ®Google Scholar
• Breen, R. A. , Swaden, L. , Ballinger, J. , & Lipman, M. C. (2006). Tuberculosis and HIV co-infection: A practical therapeutic approach. Drugs , 66 , 2299–2308.10.2165/00003495-200666180-00003
   PubMed Web of Science ®Google Scholar
• Caminero, J. A. (2006). treatment of multidrug-resistant tuberculosis: Evidence and contraversies. International Journal of Tuberculosis and Lung Disease , 10 , 829–837.
   PubMed Web of Science ®Google Scholar
• Chua, M. S. , Shi, D. F. , Wrigley, S. , Bradshaw, T. D. , Hutchinson, I. , Shaw, P. N. , … Stevens, M. F. G. (1999). Antitumor benzothiazoles. 7. Synthesis of 2-(4-acylaminophenyl)benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines. Journal of Medicinal Chemistry , 42 , 381–392.10.1021/jm981076x
   PubMed Web of Science ®Google Scholar
• Corbett, E. L. , Watt, C. J. , Walker, N. , Maher, D. , Williams, B. G. , Raviglione, M. C. , & Dye, C. (2003). The growing burden of tuberculosis: Global trends and interactions with the HIV epidemic. Archives of Internal Medicine , 12 , 1009–1021.10.1001/archinte.163.9.1009
   Google Scholar
• Cox, E. , & Laessig, K. (2014). FDA approval of bedaquiline – The benefit–risk balance for drug-resistant tuberculosis. New England Journal of Medicine , 371 , 689–691.10.1056/NEJMp1314385
   PubMed Web of Science ®Google Scholar
• D’Ambrosio, L. , Centis, R. , Sotgiu, G. , Pontali, E. , Spanevello, A. , and Migliori, G. B. (2015). New anti-tuberculosis drugs and regimens: 2015 Update. ERJ Open Research , 1–15.
   Google Scholar
• Delmas, F. , Avellaneda, A. , Giorgio, C. D. , Robin, M. , Clercq, E. D. , Timon-David, P. , & Galy, J. P. (2004). Synthesis and antileishmanial activity of (1,3-benzothiazol-2-yl) amino-9-(10H)-acridinone derivatives. European Journal of Medicinal Chemistry , 39 , 685–690.10.1016/j.ejmech.2004.04.006
   PubMed Web of Science ®Google Scholar
• Delmas, F. , Giorgio, C. D. , Robin, M. , Azas, N. , Gasquet, M. , Detang, C. , … Galy, J. P. (2002). In vitro activities of position 2 substitution-bearing 6-nitro- and 6-amino-benzothiazoles and their corresponding anthranilic acid derivatives against Leishmania infantum and Trichomonas vaginalis . Antimicrobial Agents and Chemotherapy , 46 , 2588–2594.10.1128/AAC.46.8.2588-2594.2002
   PubMed Web of Science ®Google Scholar
• Dooley, K. E. , & Chaisson, R. E. (2009). Tuberculosis and diabetes mellitus: Convergence of two epidemics. The Lancet Infectious Diseases , 9 , 737–746.10.1016/S1473-3099(09)70282-8
   PubMed Web of Science ®Google Scholar
• Dorman, S. E. , & Chaisson, Richard E (2007). From magic bullets back to the Magic Mountain: The rise of extensively drug-resistant tuberculosis. Nature Medicine , 13 , 295–298.10.1038/nm0307-295
   PubMed Web of Science ®Google Scholar
• Farrugia, L. J. (1997). ORTEP-3 for windows – A version of ORTEP-III with a Graphical User Interface (GUI). Journal of Applied Crystallography , 30 , 565.10.1107/S0021889897003117
   Web of Science ®Google Scholar
• Gupta, R. , Gao, M. , Cirule, A. , Xiao, H. , Geiter, L. J. , & Wells, C. D. (2015). Delamanid for extensively drug-resistant tuberculosis. New England Journal of Medicine , 373 , 291–292.10.1056/NEJMc1415332
   PubMed Web of Science ®Google Scholar
• Haruaki, T. (2008). Development of new antituberculous agents based on new drug targets and structure–activity relationship. Expert Opinion on Drug Discovery , 3 , 21–49.
   PubMed Web of Science ®Google Scholar
• Hayashi, H. , Wada, H. , Yoshimura, T. , Esaki, N. , & Soda, K. (1990). Recent topics in pyridoxal 5′-phosphate enzyme studies. Annual Review of Biochemistry , 59 , 87–110.10.1146/annurev.bi.59.070190.000511
   PubMed Web of Science ®Google Scholar
• Jimenez-Corona, M. E. , Cruz-Hervert, L. P. , Garcia-Garcia, L. , Ferreyra-Reyes, L. , Delgado-Sanchez, G. , Bobadilla-del-Valle, M. , … Ponce-de-Leon, A. (2013). Association of diabetes and tuberculosis: Impact on treatment and post-treatment outcomes. Thorax , 68 , 214–220.10.1136/thoraxjnl-2012-201756
   PubMed Web of Science ®Google Scholar
• Khedr, M. A. , Pillay, M. , Chandrashekharappa, S. , Chopra, D. , Aldhubiab, B. E. , Attimarad, M. , … Venugopala, K. N. (2017). Molecular modeling studies and anti-TB activity of trisubstituted indolizine analogues; molecular docking and dynamic inputs. Journal of Biomolecular Structure and Dynamics , 8 , 1–16.10.1080/07391102.2017.1345325
   Google Scholar
• Kočı́, J. , Klimešová, V. , Waisser, K. , Kaustová, J. , Dahse, H. M. , & Möllmann, U. (2002). Heterocyclic benzazole derivatives with antimycobacterial In vitro activity. Bioorganic & Medicinal Chemistry Letters , 12 , 3275–3278.10.1016/S0960-894X(02)00697-2
   PubMed Web of Science ®Google Scholar
• Macrae, C. F. , Bruno, I. J. , Chisholm, J. A. , Edgington, P. R. , McCabe, P. , Pidcock, E. , … Wood, P. A. (2008). Mercury CSD 2.0 – New features for the visualization and investigation of crystal structures. Journal of Applied Crystallography , 41 , 466–470.10.1107/S0021889807067908
   Web of Science ®Google Scholar
• Mann, S. , & Ploux, O. (2006). 7,8-Diaminoperlargonic acid aminotransferase from Mycobacterium tuberculosis, a potential therapeutic target. Characterization and inhibition studies. FEBS Journal , 273 , 4778–4789.
   Google Scholar
• Marcos, A. E. (2003). The global situation of MDR-TB. Tuberculosis , 83 , 44–51.
   PubMed Web of Science ®Google Scholar
• Middlebrook, G. , Reggiards, Z. , & Tigertt, W. D. (1977). Automable radiometric detection of growth of Mycobacterium tuberculosis in selective media. The American Review of Respiratory Disease , 115 , 1067–1069.
   Google Scholar
• Nayak, S. K. , Venugopala, K. N. , Chopra, D. , & Row, T. N. G. (2011). Insights into conformational and packing features in a series of aryl substituted ethyl-6-methyl-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates. CrystEngComm , 13 , 591–605.10.1039/C0CE00045 K
   Web of Science ®Google Scholar
• Nayak, S. K. , Venugopala, K. N. , Govender, T. , Kruger, H. G. , & Maguire, G. E. M. (2013). [2-(1,3-benzothiazol-2-ylmethoxy)-5-bromophenyl](4-chlorophenyl)methanone. Acta Crystallographica Section E Structure Reports Online , 69 , o70–o70.10.1107/S1600536812049756
   PubMedGoogle Scholar
• Munshi, P. , Venugopala, K. N. , Jayashree, B. S. , & Guru Row, T. N. (2004). Concomitant polymorphism in 3-acetylcoumarin: Role of weak C−H···O and C−H···π interactions. Crystal Growth & Design , 4 , 1105–1107.10.1021/cg049948 l
   Web of Science ®Google Scholar
• O’Brien, S. E. , Browne, H. L. , Bradshaw, T. D. , Westwell, A. D. , Stevens, M. F. G. , & Laughton, C. A. (2003). Antitumor benzothiazoles. Frontier molecular orbital analysis predicts bioactivation of 2-(4-aminophenyl)benzothiazoles to reactive intermediates by cytochrome P4501A1Part 23. For part 22 see Ref. 1. Organic & Biomolecular Chemistry , 1 , 493–497.10.1039/b209067 h
   PubMed Web of Science ®Google Scholar
• Oketani, K. , Nagakura, N. , Harada, K. , & Inoue, T. (2001). In vitro effects of E3040, a dual inhibitor of 5-lipoxygenase and thromboxane A(2) synthetase, on eicosanoid production. European Journal of Pharmacology , 422 , 209–216.10.1016/S0014-2999(01)01022-6
   PubMed Web of Science ®Google Scholar
• Ormerod, L. P. (2005). Multidrug-resistant tuberculosis (MDR-TB): Epidemiology, prevention and treatment. British Medical Bulletin 73–74 , 17-24.10.1093/bmb/ldh047
   PubMed Web of Science ®Google Scholar
• Panini, P. , Venugopala, K. N. , Odhav, B. , & Chopra, D. (2014). Polymorphism in two biologically active dihydropyrimidinium hydrochloride derivatives: Quantitative inputs towards the energetics associated with crystal packing. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials , 70 , 681–696.10.1107/S2052520614006209
   PubMedGoogle Scholar
• Paramashivappa, R. , Kumar, P. P. , Rao, P. V. S. , & Rao, A. S. (2003). Design, synthesis and biological evaluation of benzimidazole/benzothiazole and benzoxazole derivatives as cyclooxygenase inhibitors. Bioorganic & Medicinal Chemistry Letters , 13 , 657–660.10.1016/S0960-894X(02)01006-5
   PubMed Web of Science ®Google Scholar
• Parida, S. K. , Axelsson-Robertson, R. , Rao, M. V. , Singh, N. , Master, I. , Lutckii, A. , … Maeurer, M. (2015). Totally drug-resistant tuberculosis and adjunct therapies. Journal of Internal Medicine , 277 , 388–405.10.1111/joim.2015.277.issue-4
   PubMed Web of Science ®Google Scholar
• Priyanka, C. , Pramod, K. S. , Anjana, S. , & Jonish, V. (2010). Recent advances in pharmacological activity of benzothiazole derivatives. International Journal of Current Pharmaceutical Research , 2 , 5–11.
   Google Scholar
• Racane, L. , Tralic-Kulenovic, V. , Fiser-Jakic, L. , Boykin, D. W. , & Karminski-Zamola, G. (2001). Synthesis of bis-substituted amidinobenzothiazoles as potential anti-HIV agents. Heterocycles , 55 , 2085–2098.
   Web of Science ®Google Scholar
• Richard, J. O. , & Paul, P. N. (2001). The need for new drugs against tuberculosis obstacles, opportunities, and next steps. The American Review of Respiratory Disease , 162 , 1055–1058.
   Google Scholar
• Sheldrick, G. M. (1997). SHELXS-97, SHELXL-97 and SADABS version 2.05 . University of Göttingen, Germany.
   Google Scholar
• Sheldrick, G. M. (2008). A short history of SHELX. Acta Crystallographica Section A , 64 , 112–122.
   PubMed Web of Science ®Google Scholar
• Shi, C. , Geders, T. W. , Park, S. W. , Wilson, D. J. , Boshoff, H. I. , Abayomi, O. , … Aldrich, C. C. (2011). Mechanism-based Inactivation by Aromatization of the Transaminase BioA involved in Biotin Biosynthesis in Mycobaterium tuberculosis . Journal of the American Chemical Society , 133 , 18194–18201.10.1021/ja204036t
   PubMed Web of Science ®Google Scholar
• Stefan, H. E. K. , & Andrew, J. M. (2005). Annulling a dangerous liaison: Vaccination strategies against AIDS and tuberculosis. Nature Medicine , 11 , 578.
   Web of Science ®Google Scholar
• Trapani, V. , Patel, V. , Leong, C. O. , Ciolino, H. P. , Yeh, G. C. , Hose, C. , … Loaiza-Perez, A. I. (2003). DNA damage and cell cycle arrest induced by 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203, NSC 703786) is attenuated in aryl hydrocarbon receptor deficient MCF-7 cells. British Journal of Cancer , 88 , 599–605.10.1038/sj.bjc.6600722
   PubMed Web of Science ®Google Scholar
• Ucar, H. , Van derpoorten, K. , Cacciaguerra, S. , Spampinato, S. , Stables, J. P. , Depovere, P. , … Poupaert, J. H. (1998). Synthesis and anticonvulsant activity of 2(3 H )-benzoxazolone and 2(3 H )-benzothiazolone derivatives. Journal of Medicinal Chemistry , 41 , 1138–1145.10.1021/jm970682+
   PubMed Web of Science ®Google Scholar
• Venugopala, K. (2017). Design, synthesis and characterization of benzothiazole analogues as promising pharmacological agents. Journal of Young Pharmacists , 9 , 158–161.10.5530/jyp
   Web of Science ®Google Scholar
• Venugopala, K. N. , Albericio, F. , Coovadia, Y. M. , Kruger, H. G. , Maguire, G. E. M. , Pillay, M. , & Govender, T. (2011). Total synthesis of a depsidomycin analogue by convergent solid-phase peptide synthesis and macrolactonization strategy for antitubercular activity. Journal of Peptide Science , 17 , 683–689.
   PubMed Web of Science ®Google Scholar
• Venugopala, K. N. , Krishnappa, M. , Nayak, S. K. , Subrahmanya, B. K. , Vaderapura, J. P. , Chalannavar, R. K. , … Odhav, B. (2013). Synthesis and antimosquito properties of 2,6-substituted benzo[d]thiazole and 2,4-substituted benzo[d]thiazole analogues against Anopheles arabiensis . European Journal of Medicinal Chemistry , 65 , 295–303.10.1016/j.ejmech.2013.04.061
   PubMed Web of Science ®Google Scholar
• Venugopala, K. N. , Nayak, S. K. , Govender, T. , Kruger, H. G. , & Maguire, G. E. M. (2012). (2-(Benzo[d]thiazol-2yl-methoxy)-5-chlorophenyl)(phenyl)methanone. Acta Crystallographica Section E Structure Reports Online , 68 , o3125–o3125.10.1107/S1600536812041888
   PubMedGoogle Scholar
• Venugopala, K. N. , Nayak, S. K. , Govender, T. , Kruger, H. G. , & Maguire, G. E. M. (2013). {2-[(1,3-Benzothiazol-2-yl)methoxy]-5-fluorophenyl}(4-chlorophenyl)methanone. Acta Crystallographica Section E Structure Reports Online , 69 , o1007–o1008.10.1107/S1600536813014621
   PubMedGoogle Scholar
• Venugopala, K. N. , Nayak, S. K. , & Odhav, B. (2013). {2-[(1,3-benzothiazol-2-yl)methoxy]-5-bromophenyl}(phenyl)methanone. Acta Crystallographica Section E Structure Reports Online , 69 , o984–o984.10.1107/S1600536813014086
   PubMedGoogle Scholar
• Venugopala, K. N. , Nayak, S. K. , & Odhav, B. (2013). {2-[(1,3-benzothiazol-2-yl)methoxy]-5-chlorophenyl}(4-chlorophenyl)methanone. Acta Crystallographica Section E Structure Reports Online , 69 , o1124–o1124.10.1107/S1600536813016243
   PubMedGoogle Scholar
• Venugopala, K. N. , Nayak, S. K. , Pillay, M. , Prasanna, R. , Coovadia, Y. M. , & Odhav, B. (2013e). Synthesis and antitubercular activity of 2-(substituted phenyl/benzyl-amino)-6-(4-chlorophenyl)-5-(methoxycarbonyl)-4-methyl-3,6-dihydropyrimidin-1-ium chlorides. Chemical Biology & Drug Design , 81 , 219–227.
   PubMed Web of Science ®Google Scholar
• Venugopala, K. N. , Rao, Dharma , Bhandary, S. , Pillay, M. , Chopra, D. , Aldhubiab, B. E. , … Mlisana, K. (2016). Design, synthesis, and characterization of (1-(4-aryl)- 1H-1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates against Mycobacterium tuberculosis. Drug Design, Development and Therapy , 10 , 2681–2690.10.2147/DDDT
   PubMed Web of Science ®Google Scholar
• Westaway, S. M. , Thompson, M. , Rami, H. K. , Stemp, G. , Trouw, L. S. , Mitchell, D. J. , … Gunthorpe, M. J. (2008). Design and synthesis of 6-phenylnicotinamide derivatives as antagonists of TRPV1. Bioorganic & Medicinal Chemistry Letters , 18 , 5609–5613.10.1016/j.bmcl.2008.08.105
   PubMedGoogle Scholar
• Yildiz-Oren, I. , Yalcin, I. , Aki-Sener, E. , & Ucarturk, N. (2004). Synthesis and structure–activity relationships of new antimicrobial active multisubstituted benzazole derivatives. European Journal of Medicinal Chemistry , 39 , 291–298.10.1016/j.ejmech.2003.11.014
   PubMed Web of Science ®Google Scholar
• Yoshida, M. , Hayakawa, C. , Hayashi, N. , Agatsuma, T. , Oda, Y. , Tanzawa, F. , … Sugano, Y. (2005). Synthesis and biological evaluation of benzothiazole derivatives as potent antitumor agents. Bioorganic & Medicinal Chemistry Letters , 15 , 3328–3332.10.1016/j.bmcl.2005.05.077
   PubMed Web of Science ®Google Scholar
• Yoshikuni, O. , Mayumi, T. , & Kenichi, S. (2001). Inhibitory activity of quinolones against DNA gyrase of Mycobacterium tuberculosis . Journal of Antimicrobial Chemotherapy , 47 , 447–450.
   PubMed Web of Science ®Google Scholar
• Zumla, A. , Nahid, P. , & Cole, S. T. (2013). Advances in the development of new tuberculosis drugs and treatment regimens. Nature Reviews Drug Discovery , 12 , 388–404.10.1038/nrd4001
   PubMed Web of Science ®Google Scholar