Synthesis and pharmacological study of new 3,4-dihydro-2H,6H-pyrimido-[2,1-b][1,3]thiazines

Bozsing, D.; Sohár, Pàl; Gigler, Gábor; Kovács, G

doi:10.1016/0223-5234(96)85874-0

Cited by 80 publications

(22 citation statements)

References 4 publications

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“…Some examples of biologically active derivatives include tetracyclic purino[8,7‐ b ][1,3]benzothiazines with antitumor activity , naphtho[2,1‐ e ][1,3]thiazine with anti‐HIV activity , perhydropyrido[2,1‐ b ][1,3]thiazine as a potent in vitro inhibitor of angiotensin‐converting enzyme and neutral endopeptidase , and 3,4‐dihydro‐2 H ,6 H ‐pyrimido[1,2‐ c ][1,3]benzothiazine as a selective inhibitor of Gram‐negative Escherichia coli strains . 2,3‐Dihydro‐4 H ,8 H ‐pyrimido[2,1‐ b ][1,3]‐thiazine‐7‐carboxylic esters and amides exhibited high activity in anti‐inflammatory and antipyretic tests , and 8‐(benzoylbenzyloxy)‐, and (benzoylbenzylthio)‐7‐methyl‐3,4‐dihydro‐2 H ,6 H ‐pyrimido[2,1‐ b ][1,3]‐thiazin‐6‐ones exhibit antitumor activity .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2,5-Disubstituted Derivatives of Pyrano[2,3-d][1,3]thiazines via the Interaction of 2-Substituted 4-Hydroxy-6H-1,3-thiazine-6-ones with Aldehydes

Shutov

Sopova

Крылов

et al. 2014

J. Heterocyclic Chem.

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A new and efficient route for the synthesis of derivatives of the poorly investigated pyrano[2,3‐d][1,3]thiazine heterocyclic system is disclosed. These compounds were prepared via annulation of 2‐aryl‐4‐hydroxy‐6H‐1,3‐thiazine‐6‐ones with aliphatic and aromatic aldehydes in the presence of pyridine. The method is general and versatile, and the interaction is independent on the nature of the aldehyde, the only exceptions being formaldehyde and salicylaldehydes.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 2,5-Disubstituted Derivatives of Pyrano[2,3-d][1,3]thiazines via the Interaction of 2-Substituted 4-Hydroxy-6H-1,3-thiazine-6-ones with Aldehydes

Shutov

Sopova

Крылов

et al. 2014

J. Heterocyclic Chem.

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“…derivatives are of considerable interest because of their anti-inflammatory, [10] antimicrobial, [11] antifungal, [12] and antibacterial [13] activities. The thiazine 3]thiazines is also an important pharmacophore for benzodiazepine receptor binding.…”

Section: Introductionmentioning

confidence: 99%

Ionic‐liquid‐promoted Four‐component One‐pot Synthesis of Highly Functionalized Benzimidazo[2,1‐b][1,3]thiazines: Facile Construction of N‐fused Heterocycles

et al. 2013

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A one‐pot, four‐component, efficient, and facile synthesis of highly functionalized benzimidazo[2,1‐b][1,3]thiazines promoted by ionic liquid ([bmim]Br)/Et3N has been developed. The protocol involves nucleophilic addition of o‐phenylenediamine to carbon disulfide to give 2‐mercaptobenzimidazole. After nucleophilic addition to the activated olefinic bond of a zwitterionic intermediate, which is generated by reaction of isocyanide with an electrophilic alkyne, subsequent cyclization gives benzimidazo[2,1‐b][1,3]thiazines with high atom economy. The ionic liquid was recovered and reused without any appreciable decrease in activity and product yield.

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“…In some cases, the pharmacological activity is increased when metal ions are present. In addition to antibiotic activity, many compounds with thiazine rings also have anti-tumour, analgesic, antiviral, antihistaminic, anti-inflammatory and sedative activities (Korolkovas & Burckhalter, 1979;Schinazi & Floyd, 1991;Bozsing et al, 1996;Shehata et al, 1996;Tozkoparan et al, 2002). This biological activity can be modified or even improved with the coordination of metal ions or atoms (Bolos et al, 2002).…”

Section: Introductionmentioning

confidence: 99%

Structure determination of nitrato-κO-bis[2-(2-pyridyl-κN)amino-5,6-dihydro-4H-1,3-thiazine-κN]copper(II) nitrateviamolecular modelling coupled with X-ray powder diffractometry

et al. 2004

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The title copper(II) coordination compound, C18H22CuN8O6S2 {[Cu(NO3)(PyTz)2]NO3}, was synthesized in the form of small crystals unsuitable for structure determination by single‐crystal X‐ray diffractometry. It was therefore characterized by molecular modelling coupled with X‐ray powder diffractometry [monoclinic, space group P21/n, a = 20.695 (7) Å, b = 8.054 (2) Å, c = 15.157 (4) Å, β = 112.09 (2)° and Rwp = 0.129]. The procedure used to resolve the structure followed direct space methods with a `Monte Carlo/parallel tempering' search algorithm, where the starting configuration was obtained by means of molecular mechanics. A final refinement was performed with the Rietveld method. Bond distances, bond angles and torsion angles were compared with those of similar compounds deposited in the Cambridge Structural Database.

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Synthesis and pharmacological study of new 3,4-dihydro-2H,6H-pyrimido-[2,1-b][1,3]thiazines

Cited by 80 publications

References 4 publications

Synthesis of 2,5-Disubstituted Derivatives of Pyrano[2,3-d][1,3]thiazines via the Interaction of 2-Substituted 4-Hydroxy-6H-1,3-thiazine-6-ones with Aldehydes

Synthesis of 2,5-Disubstituted Derivatives of Pyrano[2,3-d][1,3]thiazines via the Interaction of 2-Substituted 4-Hydroxy-6H-1,3-thiazine-6-ones with Aldehydes

Ionic‐liquid‐promoted Four‐component One‐pot Synthesis of Highly Functionalized Benzimidazo[2,1‐b][1,3]thiazines: Facile Construction of N‐fused Heterocycles

Structure determination of nitrato-κO-bis[2-(2-pyridyl-κN)amino-5,6-dihydro-4H-1,3-thiazine-κN]copper(II) nitrateviamolecular modelling coupled with X-ray powder diffractometry

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