Design and synthesis of benzofuran- and naphthalene-fused thiazinones as antimycobacterial agents.
BTZ-043
DprE1
antimycobacterial
benzothiazinones
tuberculosis
Journal
Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167
Informations de publication
Date de publication:
Nov 2023
Nov 2023
Historique:
revised:
16
08
2023
received:
05
07
2023
accepted:
17
08
2023
medline:
3
11
2023
pubmed:
5
9
2023
entrez:
5
9
2023
Statut:
ppublish
Résumé
Benzothiazinones (BTZs) have widely inspired medicinal chemistry and translational research due to their remarkable antitubercular potency and clinical potential. While most structure-activity relationship campaigns have largely focused on lateral chain modifications and substituents on the BTZ core, scaffold hopping strategies have been rarely investigated previously. In this work, we report the first example of ring expansion of the BTZ core toward benzofuran- and naphthalene-fused thiazinones. In vitro testing showed micromolar activity for both compounds, and molecular docking simulations provided insights into their reduced inhibitory capacity toward the enzymatic target (DprE1). Calculated electrochemical potentials revealed a lower susceptibility to reduction as opposed to BTZ drug candidates, in line with the mechanistic requirement for covalent binding.
Identifiants
pubmed: 37667452
doi: 10.1002/ardp.202300356
doi:
Substances chimiques
Antitubercular Agents
0
Benzofurans
0
Naphthalenes
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2300356Subventions
Organisme : Free State of Thuringi
ID : 2017 FGR 0072
Organisme : German Ministry for Education and Research
ID : 03TTA01
Organisme : InfectControl
ID : 03ZZ0835
Informations de copyright
© 2023 The Authors. Archiv der Pharmazie published by Wiley-VCH GmbH on behalf of Deutsche Pharmazeutische Gesellschaft.
Références
World Health Organization, in Global Tuberculosis Report 2022 (Ed:), World Health Organization, 2022.
World Health Organization, in WHO Consolidated Guidelines on Tuberculosis Module 4: Treatment Drug-Susceptible Tuberculosis Treatment. (Ed: World Health Organization), World Health Organization, Geneva, 2022.
J. Furin, H. Cox, M. Pai, Lancet 2019, 393, 1642.
World Health Organization, in WHO Operational Handbook on Tuberculosis Module 4 Treatment Drug-Resistant Tuberculosis Treatment (Ed: World Health Organization), World Health Organization, Geneva, 2020.
G. Fekadu, T. Tolossa, E. Turi, F. Bekele, G. Fetensa, J. Glob. Antimicrob. Resist. 2022, 31, 175.
M. Hoelscher, “BTZ-043 - Multiple Ascending Dose (MAD) to Evaluate Safety, Tolerability and Early Bactericidal Activity (EBA),” can be found under https://clinicaltrials.gov/ct2/show/NCT04044001 (accessed: July, 2023) n.d.
V. Makarov, G. Manina, K. Mikusova, U. Möllmann, O. Ryabova, B. Saint-Joanis, N. Dhar, M. R. Pasca, S. Buroni, A. P. Lucarelli, A. Milano, E. De Rossi, M. Belanova, A. Bobovska, P. Dianiskova, J. Kordulakova, C. Sala, E. Fullam, P. Schneider, J. D. McKinney, P. Brodin, T. Christophe, S. Waddell, P. Butcher, J. Albrethsen, I. Rosenkrands, R. Brosch, V. Nandi, S. Bharath, S. Gaonkar, R. K. Shandil, V. Balasubramanian, T. Balganesh, S. Tyagi, J. Grosset, G. Riccardi, S. T. Cole, Science 2009, 324(80), 801.
C. Trefzer, M. Rengifo-Gonzalez, M. J. Hinner, P. Schneider, V. Makarov, S. T. Cole, K. Johnsson, J. Am. Chem. Soc. 2010, 132, 13663.
J. Neres, F. Pojer, E. Molteni, L. R. Chiarelli, N. Dhar, S. Boy-Röttger, S. Buroni, E. Fullam, G. Degiacomi, A. P. Lucarelli, R. J. Read, G. Zanoni, D. E. Edmondson, E. De Rossi, M. R. Pasca, J. D. McKinney, P. J. Dyson, G. Riccardi, A. Mattevi, S. T. Cole, C. Binda, Sci. Transl. Med. 2012, 4, 150ra121.
T. Karoli, B. Becker, J. Zuegg, U. Möllmann, S. Ramu, J. X. Huang, M. A. Cooper, J. Med. Chem. 2012, 55, 7940.
R. Zhang, K. Lv, B. Wang, L. Li, B. Wang, M. Liu, H. Guo, A. Wang, Y. Lu, RSC Adv. 2017, 7, 1480.
K. Lv, X. You, B. Wang, Z. Wei, Y. Chai, B. Wang, A. Wang, G. Huang, M. Liu, Y. Lu, ACS Med. Chem. Lett. 2017, 8, 636.
L. Xiong, C. Gao, Y. J. Shi, X. Tao, J. Rong, K. L. Liu, C. T. Peng, N. Y. Wang, Q. Lei, Y. W. Zhang, L. T. Yu, Y. Q. Wei, RSC Adv. 2018, 8, 11163.
A. Richter, G. Narula, I. Rudolph, R. W. Seidel, C. Wagner, Y. Av-Gay, P. Imming, ChemMedChem 2022, 17, 17. https://doi.org/10.1002/cmdc.202100733
S. Schieferdecker, F. A. Bernal, K. P. Wojtas, F. Keiff, Y. Li, H.-M. Dahse, F. Kloss, J. Med. Chem. 2022, 65, 6748.
S. K. Sahoo, S. N. R. Gajula, M. N. Ahmad, G. Kaul, S. Nanduri, R. Sonti, A. Dasgupta, S. Chopra, V. M. Yaddanapudi, Arch. Pharm. 2022, 355, 2200168.
V. A. Makarov, S. T. Cole, U. Möllmann, EP 2020406, 2009.
C. Gao, T. H. Ye, N. Y. Wang, X. X. Zeng, L. D. Zhang, Y. Xiong, X. Y. You, Y. Xia, Y. Xu, C. T. Peng, W. Q. Zuo, Y. Wei, L. T. Yu, Bioorg. Med. Chem. Lett. 2013, 23, 4919.
D. Fan, B. Wang, G. Stelitano, K. Savková, R. Shi, S. Huszár, Q. Han, K. Mikušová, L. R. Chiarelli, Y. Lu, C. Qiao, J. Med. Chem. 2021, 64, 14526.
V. A. Makarov, S. T. Cole, WO 2012066518 2012.
V. A. Makarov, S. T. Cole, U. Möllmann, WO 2007134625, 2007.
F. Kloss, V. Krchnak, A. Krchnakova, S. Schieferdecker, J. Dreisbach, V. Krone, U. Möllmann, M. Hoelscher, M. J. Miller, Angew. Chem. Int. Ed. 2017, 56, 2187.
R. Tiwari, P. A. Miller, S. Cho, S. G. Franzblau, M. J. Miller, ACS Med. Chem. Lett. 2015, 6, 128.
A. Richter, R. W. Seidel, R. Goddard, T. Eckhardt, C. Lehmann, J. Dörner, F. Siersleben, T. Sondermann, L. Mann, M. Patzer, C. Jäger, N. Reiling, P. Imming, ACS Med. Chem. Lett. 2022, 13, 1302.
V. A. Makarov, WO 2011132070, 2011.
C. Qian, X. Cai, H. Zhai, WO 2009036055, 2008.
M. K. Anwer, A. F. Spatola, Tetrahedron Lett. 1985, 26, 1381.
K. Hilpert, F. Hubler, D. Renneberg, S. Stamm, WO 2014097140, 2014.
W. T. Wei, W. M. Zhu, W. Liang, Y. Wu, H. Y. Huang, Y. L. Huang, J. Luo, H. Liang, Synlett 2017, 28, 2153.
A. Daina, O. Michielin, V. Zoete, Sci. Rep. 2017, 7, 42717.
A. J. Clark, P. Tiwary, K. Borrelli, S. Feng, E. B. Miller, R. Abel, R. A. Friesner, B. J. Berne, J. Chem. Theory Comput. 2016, 12, 2990.
H. L. Van De Wouw, J. Y. Lee, M. A. Siegler, R. S. Klausen, Org. Biomol. Chem. 2016, 14, 3256.
M. P. Jacobson, R. A. Friesner, Z. Xiang, B. Honig, J. Mol. Biol. 2002, 320, 597.
M. P. Jacobson, D. L. Pincus, C. S. Rapp, T. J. F. Day, B. Honig, D. E. Shaw, R. A. Friesner, Proteins: Struct. Funct. Bioinf. 2004, 55, 351.
M. H. M. Olsson, C. R. Søndergaard, M. Rostkowski, J. H. Jensen, J. Chem. Theory Comput. 2011, 7, 525.
C. Lu, C. Wu, D. Ghoreishi, W. Chen, L. Wang, W. Damm, G. A. Ross, M. K. Dahlgren, E. Russell, C. D. Von Bargen, R. Abel, R. A. Friesner, E. D. Harder, J. Chem. Theory Comput. 2021, 17, 4291.
K. Zhu, K. W. Borrelli, J. R. Greenwood, T. Day, R. Abel, R. S. Farid, E. Harder, J. Chem. Inf. Model. 2014, 54, 1932.
D. Bashford, D. A. Case, Annu. Rev. Phys. Chem. 2000, 51, 129.
E. Wang, H. Sun, J. Wang, Z. Wang, H. Liu, J. Z. H. Zhang, T. Hou, Chem. Rev. 2019, 119, 9478.
R. A. Friesner, J. L. Banks, R. B. Murphy, T. A. Halgren, J. J. Klicic, D. T. Mainz, M. P. Repasky, E. H. Knoll, M. Shelley, J. K. Perry, D. E. Shaw, P. Francis, P. S. Shenkin, J. Med. Chem. 2004, 47, 1739.
T. A. Halgren, R. B. Murphy, R. A. Friesner, H. S. Beard, L. L. Frye, W. T. Pollard, J. L. Banks, J. Med. Chem. 2004, 47, 1750.
J. C. Shelley, A. Cholleti, L. L. Frye, J. R. Greenwood, M. R. Timlin, M. Uchimaya, J. Comput.-Aided Mol. Des. 2007, 21, 681.
F. Neese, WIREs Comput. Mol. Sci. 2012, 2, 73.
F. Neese, WIREs Comput. Mol. Sci. 2022, 12, 1.
T. A. Young, J. J. Silcock, A. J. Sterling, F. Duarte, Angew. Chem. Int. Ed. 2021, 60, 4266.
C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158.
J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865.
S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys. 2010, 132, 154104.
S. Grimme, S. Ehrlich, L. Goerigk, J. Comput. Chem. 2011, 32, 1456.
F. Neese, F. Wennmohs, A. Hansen, U. Becker, Chem. Phys. 2009, 356, 98.
J. Zheng, X. Xu, D. G. Truhlar, Theor. Chem. Acc. 2011, 128, 295.
V. Barone, M. Cossi, J. Phys. Chem. A 1998, 102, 1995.
V. Gold, Ed., The IUPAC Compendium of Chemical Terminology, International Union Of Pure And Applied Chemistry (IUPAC), Research Triangle Park, NC, 2019.