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Synthesis of novel 8-nitro-substituted 1,3-benzothiazin-4-ones

Emiliya Vladimirovna Nosova 1, 2
Emiliya Vladimirovna Nosova
, 
Olga Aleksandrovna Batanova 2
Olga Aleksandrovna Batanova
, 
Galina Nikolaevna Lipunova 1, 2
Galina Nikolaevna Lipunova
, 
Valery Nikolaevich Charushin 1, 2
Valery Nikolaevich Charushin
10.1016/j.mencom.2020.07.007
Published 2020-06-26
Communication , Volume 30, Issue 4, 427-429
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Nosova E. V. et al. Synthesis of novel 8-nitro-substituted 1,3-benzothiazin-4-ones // Mendeleev Communications. 2020. Vol. 30. No. 4. pp. 427-429.
GOST all authors (up to 50) Copy
Nosova E. V., Batanova O. A., Lipunova G. N., Charushin V. N. Synthesis of novel 8-nitro-substituted 1,3-benzothiazin-4-ones // Mendeleev Communications. 2020. Vol. 30. No. 4. pp. 427-429.
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TY - JOUR
DO - 10.1016/j.mencom.2020.07.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.007
TI - Synthesis of novel 8-nitro-substituted 1,3-benzothiazin-4-ones
T2 - Mendeleev Communications
AU - Nosova, Emiliya Vladimirovna
AU - Batanova, Olga Aleksandrovna
AU - Lipunova, Galina Nikolaevna
AU - Charushin, Valery Nikolaevich
PY - 2020
DA - 2020/06/26
PB - Mendeleev Communications
SP - 427-429
IS - 4
VL - 30
ER -
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@article{2020_Nosova,
author = {Emiliya Vladimirovna Nosova and Olga Aleksandrovna Batanova and Galina Nikolaevna Lipunova and Valery Nikolaevich Charushin},
title = {Synthesis of novel 8-nitro-substituted 1,3-benzothiazin-4-ones},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.007},
number = {4},
pages = {427--429},
doi = {10.1016/j.mencom.2020.07.007}
}
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Nosova, Emiliya Vladimirovna, et al. “Synthesis of novel 8-nitro-substituted 1,3-benzothiazin-4-ones.” Mendeleev Communications, vol. 30, no. 4, Jun. 2020, pp. 427-429. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.007.

Keywords

1,3-benzothiazin-4-ones
amino defluorination
benzoyl isothiocyanates
heterocyclization
nitro compounds
organofluorine compounds
tuberculostatic activity

Abstract

New 2,5-bis(azacyclohex-1-yl)-8-nitro-1,3-benzothiazin-4-ones were synthesized from 2,6-difluorobenzoic acid in two preparative stages. The ethoxycarbonylpiperazino derivative surpasses in tuberculostatic activity (MIC 4μgml−1) its 5-fluoro-8-H-counterpart. The first representative of 5-fluoro-8-nitro-1,3-benzothiazin-4-ones was obtained through the condensation of 2,6-difluoro-3-nitrobenzoyl isothiocyanate and N-methylindole.

References

1.
New structural classes of antituberculosis agents
Kumar V., Patel S., Jain R.
Medicinal Research Reviews, 2017
2.
Synthesis and biological activity of 2-amino- and 2-aryl (heteryl) substituted 1,3-benzothiazin-4-ones.
Nosova E.V., Lipunova G.N., Charushin V.N., Chupakhin O.N.
Mini-Reviews in Medicinal Chemistry, 2018
3.
Recent advancements in the development of anti-tuberculosis drugs
Chetty S., Ramesh M., Singh-Pillay A., Soliman M.E.
Bioorganic and Medicinal Chemistry Letters, 2017
5.
An Update on the Chemistry and Medicinal Chemistry of Novel Antimycobacterial Compounds
Branco F., Pinto A., Boechat N.
Current Topics in Medicinal Chemistry, 2013
6.
Towards a new combination therapy for tuberculosis with next generation benzothiazinones
Makarov V., Lechartier B., Zhang M., Neres J., Sar A.M., Raadsen S.A., Hartkoorn R.C., Ryabova O.B., Vocat A., Decosterd L.A., Widmer N., Buclin T., Bitter W., Andries K., Pojer F., et. al.
EMBO Molecular Medicine, 2014
7.
Whole Cell Target Engagement Identifies Novel Inhibitors of Mycobacterium tuberculosis Decaprenylphosphoryl-β-d-ribose Oxidase
Batt S.M., Cacho Izquierdo M., Castro Pichel J., Stubbs C.J., Vela-Glez Del Peral L., Pérez-Herrán E., Dhar N., Mouzon B., Rees M., Hutchinson J.P., Young R.J., McKinney J.D., Barros Aguirre D., Ballell L., Besra G.S., et. al.
ACS Infectious Diseases, 2015
8.
Benzothiazinones: Prodrugs That Covalently Modify the Decaprenylphosphoryl-β-d-ribose 2′-epimerase DprE1 of Mycobacterium tuberculosis
Trefzer C., Rengifo-Gonzalez M., Hinner M.J., Schneider P., Makarov V., Cole S.T., Johnsson K.
Journal of the American Chemical Society, 2010
9.
SYNTHESIS AND ANTITUBERCULAR EVALUATION OF FLUORINATED 2-CYCLOALKYLIMINO SUBSTITUTED 1,3-BENZOTHIAZIN-4-ONES
Nosova E.V., Batanova O.A., Lipunova G.N., Kotovskaya S.K., Slepukhin P.A., Kravchenko M.A., Charushin V.N.
Journal of Fluorine Chemistry, 2019
10.
Synthesis of Fluorine-Containing 2-Pyrrolyl- and 2-Indolyl-Substituted 1,3-Benzothiazin-4-ones
Nosova E.V., Poteeva A.D., Lipunova G.N., Slepukhin P.A., Charushin V.N.
Russian Journal of Organic Chemistry, 2019
11.
Studies on Anti-Helicobacter pylori Agents. Part 1: Benzyloxyisoquinoline Derivatives
Yoshida Y., Barrett D., Azami H., Morinaga C., Matsumoto S., Matsumoto Y., Takasugi H.
Bioorganic and Medicinal Chemistry, 1999