A hit expansion of 3-benzamidopyrazine-2-carboxamide: Toward inhibitors of prolyl-tRNA synthetase with antimycobacterial activity
Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články
Grantová podpora
NU21-05-00482 (grant to J. Z.)
Supported by Ministry of Health of the Czech Republic
The publication was supported by the research project 2200/04/2024-2026 as part of the "Competition for 2024-2026 Postdoctoral Job Positions at the University of Hradec Králové", at the Faculty of Science, University of Hradec Králové (grant to M. J.)
Grant Agency of Charles University with Project GA UK No. 349 721 and Charles University with project SVV 260 666
PubMed
38710636
DOI
10.1002/ardp.202400171
Knihovny.cz E-zdroje
- Klíčová slova
- 3‐aminopyrazinamide, antimycobacterial, hit expansion, multidrug‐resistant, prolyl‐tRNA synthetase,
- MeSH
- aminoacyl-tRNA-synthetasy antagonisté a inhibitory metabolismus MeSH
- antituberkulotika * farmakologie chemie chemická syntéza MeSH
- inhibitory enzymů farmakologie chemie chemická syntéza MeSH
- mikrobiální testy citlivosti * MeSH
- molekulární struktura MeSH
- Mycobacterium tuberculosis * účinky léků enzymologie MeSH
- pyraziny farmakologie chemie chemická syntéza MeSH
- vztah mezi dávkou a účinkem léčiva MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- aminoacyl-tRNA-synthetasy MeSH
- antituberkulotika * MeSH
- inhibitory enzymů MeSH
- prolyl T RNA synthetase MeSH Prohlížeč
- pyraziny MeSH
This study presents an exploration of the chemical space around derivatives of 3-benzamidopyrazine-2-carboxamides, previously identified as potent antimycobacterial compounds with predicted binding to mycobacterial prolyl-transfer RNA synthetase. New urea derivatives (Series-1) were generally inactive, probably due to their preference for cis-trans conformation (confirmed by density functional theory calculations and experimentally by nuclear overhauser effect spectroscopy NMR). Series-2 (3-benzamidopyrazine-2-carboxamides with disubstituted benzene ring) demonstrated that substituents larger than fluorine are not tolerated in the ortho position of the benzene ring. This series brought two new compounds (21: R = 2-F, 4-Cl and 22: R = 2-F, 4-Br) with in vitro activity against Mycobacterium tuberculosis H37Rv as well as multidrug-resistant clinical isolates, with minimum inhibitory concentration ranging from 6.25 to 25 μg/mL. The lactone-type derivatives 4H-pyrazino[2,3-d][1,3]oxazin-4-ones (Series-3) were inactive, but solvent stability studies of compound 29 indicated that they might be developed to usable lactone prodrugs of inhibitors of mycobacterial aspartate decarboxylase (PanD).
Biomedical Research Centre University Hospital Hradec Králové Hradec Králové Czech Republic
Department of Chemistry University of Milan Milan Italy
Department of Clinical Microbiology University Hospital Hradec Králové Hradec Králové Czech Republic
Department of Pharmaceutical Sciences University of Milan Milan Italy
Faculty of Pharmacy in Hradec Králové Charles University Hradec Králové Czech Republic
Faculty of Science University of Hradec Králové Hradec Králové Czech Republic
Zobrazit více v PubMed
B. Cheng, Z. Cai, Z. Luo, S. Luo, Z. Luo, Y. Cheng, Y. Yu, J. Guo, Y. Ju, Q. Gu, J. Xu, X. Jiang, G. Li, H. Zhou, J. Med. Chem. 2022, 65, 15840.
S. Jiang, Q. Zeng, M. Gettayacamin, A. Tungtaeng, S. Wannaying, A. Lim, P. Hansukjariya, C. O. Okunji, S. Zhu, D. Fang, Antimicrob. Agents Chemother. 2005, 49, 1169.
N. P. McLaughlin, P. Evans, M. Pines, Bioorg. Med. Chem. 2014, 22, 1993.
Y. Luo, X. Xie, D. Luo, Y. Wang, Y. Gao, J. Leukoc. Biol. 2017, 102, 1333.
A. Demiroglu‐Zergeroglu, G. Turhal, H. Topal, H. Ceylan, F. Donbaloglu, K. Karadeniz Cerit, R. R. Odongo, Cell Biol. Int. 2020, 44, 1934.
I. Yoon, S. Kim, M. Cho, K. A. You, J. Son, C. Lee, J. H. Suh, D. J. Bae, J. M. Kim, S. Oh, EMBO Mol. Med. 2023, 15, e16940.
R. Adachi, K. Okada, R. Skene, K. Ogawa, M. Miwa, K. Tsuchinaga, S. Ohkubo, T. Henta, T. Kawamoto, Biochem. Biophys. Res. Commun. 2017, 488, 393.
K. Kurata, A. James‐Bott, M. A. Tye, L. Yamamoto, M. K. Samur, Y.‐T. Tai, J. Dunford, C. Johansson, F. Senbabaoglu, M. Philpott, C. Palmer, K. Ramasamy, S. Gooding, M. Smilova, G. Gaeta, M. Guo, J. C. Christianson, N. C. Payne, K. Singh, K. Karagoz, M. E. Stokes, M. Ortiz, P. Hagner, A. Thakurta, A. Cribbs, R. Mazitschek, T. Hideshima, K. C. Anderson, U. Oppermann, Blood Cancer J. 2023, 13, 12.
L. Pang, S. D. Weeks, M. Juhás, S. V. Strelkov, J. Zitko, A. Van Aerschot, Int. J. Mol. Sci. 2021, 22, 7793.
V. S. K. Pallabothula, M. Kerda, M. Juhás, O. Janďourek, K. Konečná, P. Bárta, P. Paterová, J. Zitko, Biomolecules 2022, 12, 1561.
A. K. Ghosh, M. Brindisi, J. Med. Chem. 2019, 63, 2751.
G. Bouz, M. Juhás, P. Niklová, O. Janďourek, P. Paterová, J. Janoušek, L. Tůmová, Z. Kovalíková, P. Kastner, M. Doležal, J. Zitko, Molecules 2017, 22, 1797.
L. Semelková, O. Janďourek, K. Konečná, P. Paterová, L. Navrátilová, F. Trejtnar, V. Kubíček, J. Kuneš, M. Doležal, J. Zitko, Molecules 2017, 22, 495.
H. Wamhoff, E. Kroth, Synthesis 1994, 1994, 405.
P. Jakobsen, A. M. Horneman, E. Persson, Bioorg. Med. Chem. 2000, 8, 2803.
P. Gopal, W. Nartey, P. Ragunathan, J. Sarathy, F. Kaya, M. Yee, C. Setzer, M. S. S. Manimekalai, V. Dartois, G. Grüber, T. Dick, ACS Infect. Dis. 2017, 3, 807.
H. L. Stewart, M. Bon, C. Wills, M. P. Martin, L. Z. Wang, E. S. Mackenzie, P. G. Waddell, M. J. Waring, Bioorg. Med. Chem. 2023, 19, 117387.
V. S. Bryantsev, T. K. Firman, B. P. Hay, J. Phys. Chem. A 2005, 109, 832.
G. Luchini, D. M. H. Ascough, J. V. Alegre‐Requena, V. Gouverneur, R. S. Paton, Tetrahedron 2019, 75, 697.
A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2009, 113, 6378.
I. J. Bruno, J. C. Cole, M. Kessler, J. Luo, W. D. S. Motherwell, L. H. Purkis, B. R. Smith, R. Taylor, R. I. Cooper, S. E. Harris, A. G. Orpen, J. Chem. Inf. Comput. Sci. 2004, 44, 2133.
S. J. Cottrell, T. S. G. Olsson, R. Taylor, J. C. Cole, J. W. Liebeschuetz, J. Chem. Inf. Model. 2012, 52, 956.
M. A. Spackman, D. Jayatilaka, CrystEngComm. 2009, 11, 19.
O. Jandourek, M. Tauchman, P. Paterova, K. Konecna, L. Navratilova, V. Kubicek, O. Holas, J. Zitko, M. Dolezal, Molecules 2017, 22, 223.
J. Lin, Z. Zhang, X. Lin, Z. Chen, T. Luc, D. Zha, J. Wang, X. Xu, Z. Li, Med. Chem. 2022, 18, 353.
M. C. Burla, R. Caliandro, B. Carrozzini, G. L. Cascarano, C. Cuocci, C. Giacovazzo, M. Mallamo, A. Mazzone, G. Polidori, J. Appl. Crystallogr. 2015, 48, 306.
G. M. Sheldrick, Acta Crystallogr., Sect. C: Struct, Chem, 2015, 71, 3.
L. J. Farrugia, J. Appl. Crystallogr. 2012, 45, 849.
M. Nardelli, J. Appl. Crystallogr. 1995, 28, 659.
C. F. Macrae, I. Sovago, S. J. Cottrell, P. T. A. Galek, P. McCabe, E. Pidcock, M. Platings, G. P. Shields, J. S. Stevens, M. Towler, P. A. Wood, J. Appl. Crystallogr. 2020, 53, 226.
P. R. Spackman, M. J. Turner, J. J. McKinnon, S. K. Wolff, D. J. Grimwood, D. Jayatilaka, M. A. Spackman, J. Appl. Crystallogr. 2021, 54, 1006.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams‐Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D. J. Fox, Gaussian, Inc., Wallingford, CT, 2016.
I. J. Bruno, J. C. Cole, P. R. Edgington, M. Kessler, C. F. Macrae, P. McCabe, J. Pearson, R. Taylor, Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 389.
