Synthesis, spectral characterization and biological evaluation of 4H-1,4-benzothiazines, their sulfones and ribofuranosides

Gautam, Naveen; Ajmera, Neha; Gupta, Shikha; Gautam, D. C.

doi:10.5155/eurjchem.3.1.106-111.489

Cited by 13 publications

(6 citation statements)

References 11 publications

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“…With respect to their biological applications, they have been found to have potent anti-inflammatory, (Trapani et al,1985); analgesic (Wammack et al, 2002) and anti-oxidant properties (Zia-ur-Rehman et al, 2009). Slight changes in the substitution pattern in the benzothiazine nucleus can cause a distinguishable difference in their biological properties (Niewiadomy et al, 2011;Gautam et al,2012). As a continuation of our research into the development of new 1,4-benzothiazine derivatives with potential pharmacological applications, we have studied the reaction of 1-bromobutane with (Z)-2benzylidene-2H-1,4-benzothiazin-3(4H)-one under phase-transfer catalysis conditions using tetra-n-butyl ammonium bromide as a catalyst and potassium carbonate as the base (Sebbar et al, 2016b;Ellouz et al,2017b) to give the title compound (Fig.…”

Section: Structure Descriptionmentioning

confidence: 99%

(Z)-2-Benzylidene-3-n-butoxy-2H-1,4-benzothiazine

Sebbar¹,

Ellouz²,

Ouzidan

et al. 2017

IUCr Data

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In the title compound, C19H19NOS, the thiazin-3-one ring of the 1,4-thiazin-3-one moiety adopts a screw-boat conformation. The dihedral angle between the benzene rings is 31.0 (5)°. An intramolecular C—H...S hydrogen bond forms anS(6) ring motif. In the crystal, C—H...π(ring) contacts form inversion dimers and weak π–π stacking interactions, with a centroid-to-centroid distance of 3.8766 (2) Å, also occur.

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Section: Structure Descriptionmentioning

confidence: 99%

(Z)-2-Benzylidene-3-n-butoxy-2H-1,4-benzothiazine

Sebbar¹,

Ellouz²,

Ouzidan

et al. 2017

IUCr Data

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“…To further demonstrate the potential of the chemistry, azaphenothiazine 7 , whose derivatives have antiproliferative activity toward cancer cells, was synthesized under identical conditions (Scheme ). Likewise, compound 8 derived from 2-amino-4-chlorobenzenethiol and ethyl 4,4,4-trifluoro-3-oxobutanoate (Scheme ) could be transformed into the corresponding 4 H -1,4-benzothiazine and sulfone, which are possible antibacterial and antifungal agents, through dehydration and oxidation routes, respectively …”

mentioning

confidence: 94%

Radical Route to 1,4-Benzothiazine Derivatives from 2-Aminobenzenethiols and Ketones under Transition-Metal-Free Conditions

Lin

Wang

et al. 2016

Org. Lett.

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Transition-metal-free radical access to 1,4-benzothiazine derivatives from o-aminobenzenethiols is disclosed. This procedure is available for various ketones including α,β-unsaturated, cyclic, linear, and fluoroalkyl ketones to generate a number of 1,4-benzothiazines, which exist in numerous bioactive and natural molecules, rendering this protocol attractive to both synthetic and medicinal chemistry.

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“…Synthesized 4H-1,4-benzothiazines [1][2][3][4][5][6][7][8] have widespread therapeutic uses such as vasodilator, neuroleptic, tranquilizer [9], sedative, antispasmodic, central nervous system depressant [10], dyestuff, copolymer, and flavoring agent. Distinguishable difference observed in their pharmacological activities [11][12][13][14] due to slight change in the substitution pattern in benzothiazine nucleus.…”

Section: Introductionmentioning

confidence: 99%

“…Thus knowing the immense importance of benzothiazine template, we have synthesized substituted 4H-1,4benzothiazines. To exhibit the potential of synthesized compounds as better antimicrobial agents minimum inhibitory concentration (MIC) [19][20] against selected strains of fungi, Gram-positive and Gramnegative bacteria belonging to Microbial Type Culture Collection (MTCC) were reported using broth microdilution method.…”

Section: Introductionmentioning

confidence: 99%

Spectral Evaluation and Antimicrobial Activity of Synthesized 4h-1,4-Benzothiazines

Goyal

2021

Asian J Pharm Clin Res

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Objective: 4H-1,4-Benzothiazines constitute an important class of heterocycles containing 1,4-thiazine ring fused to benzene ring. They are extensively used as tranquilizer, antispasmodic, central nervous system depressant, antiulcer, antibacterial, antifungal, antioxidant, anticancer agents, fungicides, etc. Therefore, these observations prompted us to synthesize substituted 4H-1,4-benzothiazines and investigate their antimicrobial activity against selected bacterial and fungal strains. Methods: In the present research work, 2-Amino-3,5,6-trichlorobenzenethiol condensed with β-diketones/β-ketoesters in the presence of dimethyl sulfoxide followed by oxidative cyclisation leading to the formation of 4H-1,4-benzothiazines. The spectral investigation confirmed the synthesis of these bioactive compounds. All synthesized compounds were screened for their antimicrobial activity (antibacterial and antifungal) using agar well diffusion method. Results: The minimum inhibitory concentration values of synthesized compounds gave excellent results against bacterial as well as fungal strains (Escherichia coli [Gram negative] MTCC 2939, 58–158 μg/mL, Bacillus subtilis [Gram positive] MTCC 441, 41–124 μg/mL, Streptomyces griseus [Gram negative] MTCC 1998, 85–128 μg/mL, Fusarium oxysporum MTCC 1755, 142–151 μg/mL, Aspergillus niger MTCC 281, 59–78 μg/mL, and Rhizopus stolonifer MTCC 2591, 85–118 μg/mL). Conclusion: Synthesized substituted benzothiazines have potential to be used as a new class of antibacterial and antifungal drugs. Further biomedical research is required to make 4H-1,4-benzothiazines related compounds as potential antibacterial and antifungal drugs.

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Synthesis, spectral characterization and biological evaluation of 4H-1,4-benzothiazines, their sulfones and ribofuranosides

Cited by 13 publications

References 11 publications

(Z)-2-Benzylidene-3-n-butoxy-2H-1,4-benzothiazine

(Z)-2-Benzylidene-3-n-butoxy-2H-1,4-benzothiazine

Radical Route to 1,4-Benzothiazine Derivatives from 2-Aminobenzenethiols and Ketones under Transition-Metal-Free Conditions

Spectral Evaluation and Antimicrobial Activity of Synthesized 4h-1,4-Benzothiazines

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