Synthesis of Potential Biologically Active 1,2-Benzothiazin-3-yl-quinazolin-4(3H)-ones

Zia‐ur‐Rehman, Muhammad; Choudary, Jamil Anwar; Ahmad, Saeed; Siddiqui, Hamid Latif

doi:10.1248/cpb.54.1175

Cited by 123 publications

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“…The derivatives of 1,2-benzothiazine exhibit a wide range of biological activities, e.g., anti inflammatory (Lombardino & Wiseman, 1972), analgesic (Gupta et al, 2002), anti cancer (Gupta et al, 1993) and anti bacterial (Zia-ur-Rehman et al, 2006), etc. In continuation of our research on the synthesis of biologically active benzothiazine derivatives (Siddiqui et al, 2007;Ahmad et al, 2010), we herein report the synthesis and crystal structure of the title compound.…”

Section: Methodsmentioning

confidence: 99%

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3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

et al. 2012

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Key indicators: single-crystal X-ray study; T = 173 K; mean (C-C) = 0.005 Å; R factor = 0.068; wR factor = 0.133; data-to-parameter ratio = 15.6.In the title molecule, C 24 H 19 NO 6 S, the heterocyclic thiazine ring adopts a half-chair conformation with the S and N atoms displaced by 0.180 (5) and 0.497 (5) Å , respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The benzene rings of the benzothiazine unit and the methoxyphenyl group are almost coplanar, with the dihedral angle between the mean planes of these rings being 5.9 (2) , while the benzene ring of the 2-oxo-2-phenylethyl group is inclined at 79.68 (11) and 81.01 (10) , respectively, to these rings. The molecular structure is consolidated by intramolecular O-HÁ Á ÁO and C-HÁ Á ÁN interactions, and the crystal packing is stabilized by weak C-HÁ Á ÁO hydrogen bonds. Related literature

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Section: Methodsmentioning

confidence: 99%

“…For the biological activity of 1,2-benzothiazine derivatives, see : Lombardino & Wiseman (1972); Gupta et al (1993Gupta et al ( , 2002; Zia-ur-Rehman et al (2006); Ahmad et al (2010). For a related structure, see: Siddiqui et al (2008).…”

Section: Related Literaturementioning

confidence: 99%

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

et al. 2012

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“…The proton nuclear magnetic resonance ( 1 H NMR) spectra were measured on a Brucker 300 MHz NMR spectrometer. The samples were prepared by dissolving 5 mg of each form in 600 ll of CDCl 3 . Melting points were recorded using MEL-TEMP capillary melting point apparatus and were uncorrected.…”

Section: Synthesismentioning

confidence: 99%

“…Sundry benzothiazine derivatives are known to possess a wide spectrum of biological activities like anti-inflammatory [1], analgesic and antipyretic [2], antimicrobial [3], antiviral [4], antitumor [5], antidiabetic [6] and Alzheimer's and Parkinson's disease treatment [7]. Among these, 1,2-benzothiazine 1,1-dioxide nucleus has got considerable attention after the discovery of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamides 1,1-dioxides (known as oxicams) as potent anti-inflammatory and analgesic agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and thermal behaviour of new benzo-1,2-thiazine long-chain aryl-piperazine derivatives

Krzyżak

Szczęśniak-Sięga

Malinka

2013

J Therm Anal Calorim

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A series of potential biologically active 2-[3-(4-phenyl-1-piperazinyl)propyl]-3-(4-substituted-benzoyl)-4-hydroxy-2H-1,2-benzothiazine 1,1-dioxides was synthesized in a straightforward manner by condensation of respective 3-substituted-4-hydroxy-1,2-benzothiazine 1, 1-dioxides with 1-(1-chloropropyl)-4-phenylpiperazine. The structures of all of the newly formed compounds were identified by elemental analysis, FTIR and 1 H NMR. The synthesized compounds were subjected to preliminary evaluation using differential scanning calorimetry (DSC) to determine the existence of multiple crystal forms. The DSC scans for all compounds show more than one endothermic effect, which might suggest dynamic proton transfer between two or three possible tautomeric forms: O-keto/O-enol, O-enol/O-keto and O-keto/O-keto/CH 2 in crystals 2-[3-(4-phenyl-1-piperazinyl)propyl]-3-(4-substituted-benzoyl)-4-hydroxy-2H-1,2-benzothiazine 1,1-dioxides.

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“…For the biological activity of benzothiazine derivatives, see: Turck et al (1995); Zia-ur-Rehman et al (2006); Ahmad et al (2010). For studies of benzothiazines as precursors for azodisperse dyes for polyesters, see : Rajagopal & Seshadri (1990).…”

Section: Related Literaturementioning

confidence: 99%

1-(4-Chlorophenyl)-2-[4-hydroxy-3-(3-methoxybenzoyl)-1,1-dioxo-2H-1λ⁶,2-benzothiazin-2-yl]ethanone

et al. 2012

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Key indicators: single-crystal X-ray study; T = 123 K; mean (C-C) = 0.004 Å; R factor = 0.054; wR factor = 0.111; data-to-parameter ratio = 15.8.In the title molecule, C 24 H 18 ClNO 6 S, the heterocyclic thiazine ring adopts a half-chair conformation with the S and N atoms displaced by 0.406 (5) and 0.444 (5) Å , respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The methoxybenzoyl and the chlorophenyl rings lie roughly parallel to each other, with a dihedral angle between the mean planes of these rings of 8.86 (10) . The molecular structure is consolidated by intramolecular O-HÁ Á ÁO and C-HÁ Á ÁO interactions and the crystal packing is stabilized by intermolecular O-HÁ Á ÁO and C-HÁ Á ÁCl hydrogen bonds. Table 1 Hydrogen-bond geometry (Å , ). etc. A few benzothiazines have also been studied as precursors for azodisperse dyes for polyesters (Rajagopal & Seshadri 1990). In continuation of our research on the synthesis of biologically active benzothiazine derivatives (Siddiqui et al., 2007;Ahmad et al., 2010), we herein report the synthesis and crystal structure of the title compound. Related literatureThe bond distances and angles in the title compound ( Fig. 1) agree very well with the corresponding bond distances and angles reported in closely related compounds (Siddiqui et al., 2008). The heterocyclic thiazine ring adopts a half chair conformation with the S1 and N1 atoms displaced by 0.406 (5) and 0.444 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The methoxybenzoyl and the chlorophenyl rings lie roughly parallel to each other with a dihedral angle between the mean planes of these rings of 8.86 (10)°; the distance between the centroids of these rings is 3.828 (14) Å. The molecular structure of the title compound is consolidated by intramolecular interactions O3-H3O···O4 and C24-H24···O2 and the crystal packing is stabilized by intermolecular O3-H3O···O4 and C3-H3···Cl1 hydrogen bonds ( Fig. 2 and Table 1). S2. ExperimentalA mixture of (4-hydroxy-1,1-dioxido-2H-1,2-benzothiazin-3-yl)(3-methoxyphenyl) methanone (5.0 g, 0.015 mol), K 2 CO 3 (2.07 g, 0.015 mol) and 4-chlorophenacyl bromide (3.50 g, 0.015 mol) in acetonitrile (30 ml) was refluxed for 3 h. The contents of the flask were poured on ice cold HCl (5%, 30 ml). The precipitate of the title compound thus formed was

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Synthesis of Potential Biologically Active 1,2-Benzothiazin-3-yl-quinazolin-4(3H)-ones

Cited by 123 publications

References 16 publications

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

Synthesis and thermal behaviour of new benzo-1,2-thiazine long-chain aryl-piperazine derivatives

1-(4-Chlorophenyl)-2-[4-hydroxy-3-(3-methoxybenzoyl)-1,1-dioxo-2H-1λ⁶,2-benzothiazin-2-yl]ethanone

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Synthesis of Potential Biologically Active 1,2-Benzothiazin-3-yl-quinazolin-4(3H)-ones

Cited by 123 publications

References 16 publications

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ6,2-benzothiazine-1,1,4-trione

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ6,2-benzothiazine-1,1,4-trione

Synthesis and thermal behaviour of new benzo-1,2-thiazine long-chain aryl-piperazine derivatives

1-(4-Chlorophenyl)-2-[4-hydroxy-3-(3-methoxybenzoyl)-1,1-dioxo-2H-1λ6,2-benzothiazin-2-yl]ethanone

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3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

1-(4-Chlorophenyl)-2-[4-hydroxy-3-(3-methoxybenzoyl)-1,1-dioxo-2H-1λ⁶,2-benzothiazin-2-yl]ethanone