Synthesis and pharmacological activity of benzothiazine derivatives

Lopatina, K. I.; Artemenko, G. N.; Sokolova, T. V.; Avdulov, N. A.; Zagorevskii, V. A.

doi:10.1007/bf00762029

Cited by 8 publications

(6 citation statements)

References 2 publications

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“…Derivatives of benzothiazine have, depending upon the substituents present, shown biological activities that range from antipsychotic to anti-inflammatory [6,7,8]. The 1,2-benzothiazines have shown various biological activities such as anti-inflammatory [9], CNS depressant [10,11], anti-depressants [12], anticancer [13] and antimicrobial [14]. They also act as potent calpain I inhibitors [15] and vasodilators [16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives

et al. 2016

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A number of 1,2-benzothiazines have been synthesized in a three-step process. Nine chalcones 1-9 bearing methyl, fluoro, chloro and bromo substituents were chlorosulfonated with chlorosulfonic acid to generate the chalcone sulfonyl chlorides 10-18. These were converted to the dibromo compounds 19-27 through reaction with bromine in glacial acetic acid. Compounds 19-27 were reacted with ammonia, methylamine, ethylamine, aniline and benzylamine to generate a library of 45 1,2-benzothiazines 28-72. Compounds 28-72 were evaluated for their antimicrobial activity using broth microdilution techniques against two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and two Gram-negative bacteria (Proteus vulgaris and Salmonella typhimurium). The results demonstrated that none of the compounds showed any activity against Gram-negative bacteria P. vulgaris and S. typhimurium; however, compounds 31, 33, 38, 43, 45, 50, 53, 55, 58, 60, 63 and 68 showed activity against Gram-positive bacteria Bacillus subtilis and Staphylococcous aureus. The range of minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) was 25-600 µg/mL, though some of the MIC and MBC concentrations were high, indicating weak activity. Structure activity relationship studies revealed that the compounds with a hydrogen atom or an ethyl group on the nitrogen of the thiazine ring exerted antibacterial activity against Gram-positive bacteria. The results also showed that the compounds where the benzene ring of the benzoyl moiety contained a methyl group or a chlorine or bromine atom in the para position showed higher antimicrobial activity. Similar influences were identified where either a bromine or chlorine atom was in the meta position.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives

et al. 2016

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“…Several derivatives of benzothiazines form an important class of bioactive molecules in the field of drugs and pharmaceuticals. Applications in various therapeutic areas, include their use as anti-depressants (Lopatina et al, 1982); anti-fungals (Fringuelli et al, 1998) and anti-microbials (Rathore & Kumar, 2006). The present work is a continuation of the investigation of the benzothiazine derivatives published recently by our team (Keita et al, 2000;Zerzouf et al, 2001;Barryala et al, 2011).…”

Section: S2 Results and Discussionmentioning

confidence: 60%

“…For the pharmacological activity of benzothiazine derivatives, see: Fringuelli et al (1998); Lopatina et al (1982); Rathore & Kumar (2006). For related structures, see: Keita et al (2000); Zerzouf et al (2001); Barryala et al (2011).…”

Section: Related Literaturementioning

confidence: 99%

Ethyl 2-{5-[(3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl)methyl]-1H-1,2,3-triazol-1-yl}acetate

Sebbar¹,

Zerzouf²,

Essassi³

et al. 2014

Acta Cryst E

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In the title compound, C15H16N4O3S, the six-membered heterocycle of the benzothiazine fragment exhibits a screw boat conformation. The dihedral angle between the planes through the triazole ring and the benzene ring fused to the 1,4-thiazine ring is 62.98 (11)°. The mean plane formed by the atoms belonging to the acetate group is nearly perpendicular to the triazole ring [dihedral angle = 74.65 (12)°]. In the crystal, molecules are linked by pairs of C—H...O interactions, forming dimeric aggregates.

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“…For general background to the synthesis of benzothiazines, see: Harmata et al (2005). For the pharmacological activity of benzothiazine derivatives, see: Lopatina et al (1982). For related structures, see: Saeed et al (2010); Aouine et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

“…Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010 [Lopatina et al 1982].…”

Section: Data Collectionmentioning

confidence: 99%