Novel 1,4-benzothiazine derivatives: synthesis, crystal structure, and anti-bacterial properties

Sebbar, Nada Kheira; Mekhzoum, Mohamed El Mehdi; Essassi, El Mokhtar; Zerzouf, Abdelfettah; Talbaoui, Ahmed; Bakri, Youssef; Saadi, Mohamed; Ammari, Lahcen El

doi:10.1007/s11164-016-2499-6

Cited by 28 publications

(21 citation statements)

References 21 publications

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“…As a continuation of our studies of N-substituted benzothiazines (Sebbar et al, 2014(Sebbar et al, , 2016Ellouz et al, 2015), we now describe the synthesis and structure of the title compound, (Fig. 1).…”

Section: Structure Descriptionmentioning

confidence: 86%

4-Methyl-3,4-dihydro-2H-1,4-benzothiazin-3-one

Ellouz¹,

Sebbar²,

Ouzidan³

et al. 2017

IUCr Data

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In the crystal of the title compound, C 9 H 9 NOS, the molecules are linked by C-HÁ Á ÁO hydrogen bonds to generate bilayers lying parallel to (001). Structure descriptionAs a continuation of our studies of N-substituted benzothiazines (Sebbar et al., 2014(Sebbar et al., , 2016 Ellouz et al., 2015), we now describe the synthesis and structure of the title compound, (Fig. 1).A puckering analysis of the heterocyclic ring gave the parameters Q = 0.668 (1) Å , = 113.2 (1) and ' = 146.9 : atoms C1, C6, S1 and N1 are roughly coplanar (r.m.s. deviation = 0.046 Å ) and atoms C7 and C8 deviate in the same sense [by 0.476 (1) and 1.111 (1) Å , respectively] from the mean plane. In the crystal, the molecules are linked by C-HÁ Á ÁO hydrogen bonds (Table 1) to form bilayers oriented parallel to (001) (Figs. 2 and 3). Synthesis and crystallizationTo a solution of 3,4-dihydro-2H-1,4-benzothiazin-3-one (2 mmol), potassium carbonate (4 mmol) and tetra n-butyl ammonium bromide (0.2 mmol) in DMF (15 ml) was added iodomethane (4 mmol). Stirring was continued at room temperature for 12 h. The mixture was filtered and the solvent removed. The residue was extracted with water. The organic compound was chromatographed on a column of silica gel with ethyl acetatehexane (9:1) as eluent. Brown crystals of the title compound were isolated when the solvent was allowed to evaporate (yield 57%; m.p. 370 K).

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Section: Structure Descriptionmentioning

confidence: 86%

4-Methyl-3,4-dihydro-2H-1,4-benzothiazin-3-one

Ellouz¹,

Sebbar²,

Ouzidan³

et al. 2017

IUCr Data

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“…With respect to biological applications, these derivatives have been found to be potent antiinflammatories (Chia et al, 2008), anti-microbials (Barazarte et al, 2008), herbicidals (Takemoto et al, 1994 and fungicidals (Yaltirik et al, 2001). The present work is a continuation of the investigation of the benzothiazine derivatives published recently by our team, including the isomer of the present compound (Sebbar et al, 2014).…”

Section: Related Literaturementioning

confidence: 77%

N-[2-(9H-Carbazol-9-yl)ethyl]-4-(methylsulfonyl)aniline

Lai

Gallucci

2014

Acta Cryst E

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“…Furthermore, imidazolones are anti-bacterial, anti-fungal, anti-viral, anti-cancer and CNSdepressant agents (Naithani et al, 1989;Harfenist et al, 1978). We have previously shown that bis(2-chloroethyl)amine hydrochloride is an interesting precursor of several heterocyclic compounds containing the oxazolidinone moiety (Sebbar et al, 2016(Sebbar et al, , 2018Ellouz et al, 2017;Hni et al, 2019). In a continuation of our research using bis(2-chloroethyl)amine hydrochloride as an intermediate in the synthesis of new heterocyclic systems, we have studied the condensation of 2-aminobenzothiazole with bis(2-chloroethyl)amine hydrochloride in the presence of tetra-n-butylammonium bromide as catalyst and potassium carbonate as base.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-(1,3-benzothiazol-2-yl)-3-(2-hydroxyethyl)imidazolidin-2-one

Srhir¹,

Sebbar

Hökelek

et al. 2020

Acta Cryst E

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In the title molecule, C12H13N3O2S, the benzothiazine moiety is slightly non-planar, with the imidazolidine portion twisted only a few degrees out of the mean plane of the former. In the crystal, a layer structure parallel to the bc plane is formed by a combination of O—HHydethy...NThz hydrogen bonds and weak C—HImdz...OImdz and C—HBnz...OImdz (Hydethy = hydroxyethyl, Thz = thiazole, Imdz = imidazolidine and Bnz = benzene) interactions, together with C—HImdz...π(ring) and head-to-tail slipped π-stacking [centroid-to-centroid distances = 3.6507 (7) and 3.6866 (7) Å] interactions between thiazole rings. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (47.0%), H...O/O...H (16.9%), H...C/C...H (8.0%) and H...S/S...H (7.6%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, C—H...N and C—H...O hydrogen-bond energies are 68.5 (for O—HHydethy...NThz), 60.1 (for C—HBnz...OImdz) and 41.8 kJ mol−1 (for C—HImdz...OImdz). Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state.

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Novel 1,4-benzothiazine derivatives: synthesis, crystal structure, and anti-bacterial properties

Cited by 28 publications

References 21 publications

4-Methyl-3,4-dihydro-2H-1,4-benzothiazin-3-one

4-Methyl-3,4-dihydro-2H-1,4-benzothiazin-3-one

N-[2-(9H-Carbazol-9-yl)ethyl]-4-(methylsulfonyl)aniline

Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-(1,3-benzothiazol-2-yl)-3-(2-hydroxyethyl)imidazolidin-2-one

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