Synthesis and Pharmacological Use of 10<i>H</i>-Phenothiazines, Their Sulfones, and Ribofuranosides

Gautam, Naveen; Ajmera, Neha; Gupta, Shikha; Meena, Parmeshwar Lal; Kumar, Ashok; Gautam, D. C.

doi:10.1080/10426501003671452

Cited by 8 publications

(8 citation statements)

References 14 publications

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“…1,4-Benzothiazine derivatives constitute an important class of heterocyclic compounds which, even when part of a complex molecule, possess a wide spectrum of biological activities (Sebbar et al, 2016a;Gupta et al, 2009). Various 1,4-benzothiazine derivatives have been synthesized by several methods (Parai & Panda, 2009; Barange et al, 2007;Saadouni et al, 2014).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and interaction energy, DFT and antibacterial activity studies of (Z)-4-hexyl-2-(4-methylbenzylidene)-2H-benzo[b][1,4]thiazin-3(4H)-one

Sebbar

Hni²,

Hökelek

et al. 2020

Acta Cryst E

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The title compound, C22H25NOS, consists of methylbenzylidene and benzothiazine units linked to a hexyl moiety, where the thiazine ring adopts a screw-boat conformation. In the crystal, inversion dimers are formed by weak C—HMthn...OBnzthz hydrogen bonds and are linked into chains extending along the a-axis direction by weak C—HBnz...OBnzthz (Bnz = benzene, Bnzthz = benzothiazine and Mthn = methine) hydrogen bonds. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (59.2%) and H...C/C...H (27.9%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the C—HBnz...OBnzthz and C—HMthn...OBnzthz hydrogen-bond energies are 75.3 and 56.5 kJ mol−1, respectively. 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. The HOMO—LUMO behaviour was elucidated to determine the energy gap. Moreover, the antibacterial activity of the title compound was evaluated against gram-positive and gram-negative bacteria.

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and interaction energy, DFT and antibacterial activity studies of (Z)-4-hexyl-2-(4-methylbenzylidene)-2H-benzo[b][1,4]thiazin-3(4H)-one

Sebbar

Hni²,

Hökelek

et al. 2020

Acta Cryst E

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“…1,4-Benzothiazine derivatives constitute an important class of heterocyclic compounds which, even when part of a complex molecule, possess a wide spectrum of biological activities (Sebbar et al, 2016a;Gupta et al, 2009). Several sulfur-and nitrogen-containing heterocycles have been well studied and various 1,4-benzothiazine derivatives have been synthesized by several methods (Dixit et al, 2008(Dixit et al, , 2009.…”

Section: Structure Descriptionmentioning

confidence: 99%

(2Z)-2-Benzylidene-4-octadecyl-3,4-dihydro-2H-1,4-benzothiazin-3-one

Sebbar¹,

Ellouz²,

Lahmidi³

et al. 2017

IUCr Data

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The octadecyl chain in the title compound, C33H47NOS, is in the `fully extended' conformation. A puckering analysis of the thiazine ring was performed. The molecules form micellar blocks in the crystal by intercalation of the extended octadecyl chains and association of the dihydro benzothiazine units through C—H...O hydrogen bonds. These blocks are associated through intercalation of the pendant phenyl groups which reside on the outer edges of each block.

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“…A number of pharmacological tests have revealed 1,4-benzothiazine derivatives to possess a wide spectrum of biological activities, even when they are part of a complex molecule (Schiaffella et al, 2006;Gupta et al, 2009). As a result of the presence of a fold along the nitrogen-sulfur axis, the biological activities of some 1,4-benzothiazines are similar to that of phenothiazines, featuring the same structural specificity (Bansode et al, 2009;Dixit et al, 2009;Thomas et al, 2003).…”

Section: Structure Descriptionmentioning

confidence: 99%

(2Z)-2-(4-Chlorobenzylidene)-4-[2-(2-oxooxazoliden-3-yl)ethyl]-3,4-dihydro-2H-1,4-benzothiazin-3-one

Ellouz¹,

Sebbar²,

Boulhaoua³

et al. 2017

IUCr Data

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Synthesis and Pharmacological Use of 10H-Phenothiazines, Their Sulfones, and Ribofuranosides

Cited by 8 publications

References 14 publications

Crystal structure, Hirshfeld surface analysis and interaction energy, DFT and antibacterial activity studies of (Z)-4-hexyl-2-(4-methylbenzylidene)-2H-benzo[b][1,4]thiazin-3(4H)-one

Crystal structure, Hirshfeld surface analysis and interaction energy, DFT and antibacterial activity studies of (Z)-4-hexyl-2-(4-methylbenzylidene)-2H-benzo[b][1,4]thiazin-3(4H)-one

(2Z)-2-Benzylidene-4-octadecyl-3,4-dihydro-2H-1,4-benzothiazin-3-one

(2Z)-2-(4-Chlorobenzylidene)-4-[2-(2-oxooxazoliden-3-yl)ethyl]-3,4-dihydro-2H-1,4-benzothiazin-3-one

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