Abstract
Tuberculosis (TB) takes the second place among the reasons for mortality from infectious diseases. For this reason, the problem of tuberculosis treatment requires urgent attention all over the world. Some 2-amino substituted 1,3-benzothiazin-4-ones (2-amino-1,3-BTZs) represent a promising new class of antitubercular agents. Other 1,3-benzothiazin-4-one derivatives, mostly 2-aryl and 2- (pyridin-2-yl) ones, are attractive due to their ability to suppress oxidative stress-induced cardiomyocyte apoptosis. This review covers the synthetic approaches to 2-amino- and 2-aryl(heteryl) substituted 1,3-benzothiazin-4-ones (1,3-BTZs). A brief overview of structure-activity relationships is presented.
Keywords: Antitubercular agent, 1, 3-Benzothiazin-4-one, Cyclocondensation, 2-Mercaptobenzoic acid, 2-Halogenobenzoyl isothiocyanate, apoprosis.
Graphical Abstract
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bManina, G.; Bellinzoni, M.; Pasca, M.R.; Neres, J.; Milano, A.; Ribeiro, A.L.; Buroni, S.; Skovierova, H.; Dianiskova, P.; Mikusova, K.; Marak, J.; Makarov, V.; Giganti, D.; Haouz, A.; Lucarelli, A.; Degiacomi, G.; Plazza, A.; Chiarelli, L.R.; De Rossi, E.; Salina, E.; Cole, S.T.; Alzari, P.M.; Riccardi, G. Biological and structural characterisation oft he Micobacterium smegmatis nitroreductase NfnB, and ist role in benzothiazinone resistance. Mol. Microbiol., 2010, 77, 1172-1185.
cTrefzer, C.; Skovierova, H.; Buroni, S.; Bobovska, A.; Nenci, S.; Molteni, E.; Pojer, F.; Pasca, M.R.; Makarov, V.; Cole, S.T.; Riccardi, G.; Mikusova, K.; Johnsson, K. Benzothiazinones are suicide inhibitors of mycobacterial decaprenylphosphoryl-β-D-ribofuranose 2′-oxidase DprE1. J. Am. Chem. Soc., 2012, 134, 912-915.
dTiwari, R.; Moraski, G.C.; Krchnak, V.; Miller, P.A.; Colon-Martinez, M.; Herrero, E.; Oliver, A.G.; Miller, M.J. Thiolates chemically induce redox activation of BTZ043 and related potent nitroaromatic anti-tuberculosis agents. J. Am. Chem. Soc., 2013, 135, 3539-3549.
eXu, Z.; Peng, W.; Wan, K.; Luo, C.; Zeng, H.; Zhang, P.; Liu, Z.; Zhang, Y.; Wang, X. In vitro interactions between R207910 and second-line anti-TB drugs or BTZ043 against Mycobacterium tuberculosis by microplate alamar blue assay. Int. J. Clin. Exp. Med., 2016, 9, 6336-6341.
bManina, G.; Bellinzoni, M.; Pasca, M.R.; Neres, J.; Milano, A.; Ribeiro, A.L.; Buroni, S.; Skovierova, H.; Dianiskova, P.; Mikusova, K.; Marak, J.; Makarov, V.; Giganti, D.; Haouz, A.; Lucarelli, A.; Degiacomi, G.; Plazza, A.; Chiarelli, L.R.; De Rossi, E.; Salina, E.; Cole, S.T.; Alzari, P.M.; Riccardi, G. Biological and structural characterisation oft he Micobacterium smegmatis nitroreductase NfnB, and ist role in benzothiazinone resistance. Mol. Microbiol., 2010, 77, 1172-1185.
cTrefzer, C.; Skovierova, H.; Buroni, S.; Bobovska, A.; Nenci, S.; Molteni, E.; Pojer, F.; Pasca, M.R.; Makarov, V.; Cole, S.T.; Riccardi, G.; Mikusova, K.; Johnsson, K. Benzothiazinones are suicide inhibitors of mycobacterial decaprenylphosphoryl-β-D-ribofuranose 2′-oxidase DprE1. J. Am. Chem. Soc., 2012, 134, 912-915.
dTiwari, R.; Moraski, G.C.; Krchnak, V.; Miller, P.A.; Colon-Martinez, M.; Herrero, E.; Oliver, A.G.; Miller, M.J. Thiolates chemically induce redox activation of BTZ043 and related potent nitroaromatic anti-tuberculosis agents. J. Am. Chem. Soc., 2013, 135, 3539-3549.
eXu, Z.; Peng, W.; Wan, K.; Luo, C.; Zeng, H.; Zhang, P.; Liu, Z.; Zhang, Y.; Wang, X. In vitro interactions between R207910 and second-line anti-TB drugs or BTZ043 against Mycobacterium tuberculosis by microplate alamar blue assay. Int. J. Clin. Exp. Med., 2016, 9, 6336-6341.
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