ChemInform Abstract: A Novel System: 2H‐Pyrido(3,2‐e)‐1,2‐thiazine‐1,1‐dioxide. Synthesis and Properties of Some Derivatives.

Zawisza, T; Malinka, Wiesław

doi:10.1002/chin.198719208

Cited by 4 publications

(4 citation statements)

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“…The new derivatives were obtained as a result of multistage synthesis, as shown in Figure 2. The key intermediate ethyl ester of 3-benzoyl-4-hydroxy-5,7-dimethyl-2H-pyrido[3,2-e]-1,2-thiazine-1,1-dioxide-2-acetic acid (1) was obtained by a few reactions, which have been described in the literature [50,51]. Ester (1) was easily converted into pyridothiazine-1,1-dioxide-2-acetic acid hydrazide (2) in a reaction with hydrazine hydrate.…”

Section: Synthesis Of New 134-oxadiazole Derivatives Of Pyridothiazmentioning

confidence: 99%

New 1,3,4-Oxadiazole Derivatives of Pyridothiazine-1,1-Dioxide with Anti-Inflammatory Activity

Glomb

Wiatrak

Gębczak

et al. 2020

IJMS

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Numerous studies have confirmed the coexistence of oxidative stress and inflammatory processes. Long-term inflammation and oxidative stress may significantly affect the initiation of the neoplastic transformation process. Here, we describe the synthesis of a new series of Mannich base-type hybrid compounds containing an arylpiperazine residue, 1,3,4-oxadiazole ring, and pyridothiazine-1,1-dioxide core. The synthesis was carried out with the hope that the hybridization of different pharmacophoric molecules would result in a synergistic effect on their anti-inflammatory activity, especially the ability to inhibit cyclooxygenase. The obtained compounds were investigated in terms of their potencies to inhibit cyclooxygenase COX-1 and COX-2 enzymes with the use of the colorimetric inhibitor screening assay. Their antioxidant and cytotoxic effect on normal human dermal fibroblasts (NHDF) was also studied. Strong COX-2 inhibitory activity was observed after the use of TG6 and, especially, TG4. The TG11 compound, as well as reference meloxicam, turned out to be a preferential COX-2 inhibitor. TG12 was, in turn, a non-selective COX inhibitor. A molecular docking study was performed to understand the binding interaction of compounds at the active site of cyclooxygenases.

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Section: Synthesis Of New 134-oxadiazole Derivatives Of Pyridothiazmentioning

confidence: 99%

New 1,3,4-Oxadiazole Derivatives of Pyridothiazine-1,1-Dioxide with Anti-Inflammatory Activity

Glomb

Wiatrak

Gębczak

et al. 2020

IJMS

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“…In continuation of our research groups’ work in the field of synthetic organic chemistry [ 1 , 2 , 3 , 4 , 5 ]; we would like to report here on the annulation of isothiazole, 1,3-thiazine and 1,4-thiazepine ring systems to pyridine. Promising biological activities are reported in the literature concerning the targeted ring systems: Isothiazolo[5,4-b]pyridines could be used as analgesics [ 6 , 7 ] and as CNS and antimicrobial agents [ 8 ], pyrido[3,2-e][1,3]thiazines could be used as CNS and antioxidant agents [ 9 ] and as analgesic agents [ 10 ] and pyrido[3,2-f]-[1,4]-thiazepines were used as calcium antagonists in both cardiac and smooth muscles [ 11 ] and as channel blockers for treatment of cardiovascular diseases [ 12 ]. Microwave-assisted technique offer several advantages over conventional methods of synthesis.…”

Section: Introductionmentioning

confidence: 99%

Bromination and Diazo-Coupling of Pyridinethiones; Microwave Assisted Synthesis of Isothiazolopyridine, Pyridothiazine and Pyridothiazepines

2012

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Isothiazolopyridines, pyridothiazines and pyridothiazepines are important compounds that possess valuable biological activities. This paper reports on the synthesis of these compounds using both conventional chemical methods and modern microwave techniques. 3-Bromo-6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-carboxamide, 5-arylazo-6-hydroxy-4-methyl-2-thioxo-1,2-dihydropyridine-3-carboxamides, 3,5-bis-arylazo-6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-caboxamide, 4-methyl-2,3,6,7-tetra-hydroisothiazolo[5,4-b]-pyridine-3,6-dione, 2,2'-(methylene-bis-(sulfanediyl))bis(4-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide), 2-hydroxy-5-methyl-4H-pyrido[3,2-e][1,3]-thiazine-4,7(8H)-dione and 2-arylmethylene-8-hydroxy-6-methyl-2,3,4,5-tetrahydropyrido-[3,2-f][1,4]thiazepine-3,5-diones have been prepared from 6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-carboxamide. Some of these compounds were prepared using microwave-assisted reaction conditions, that provided higher yields in shorter times than the conventional methods.

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confidence: 99%

“…On the other hand, the transformation of the nitrile group as a substituent in the pyridine ring into an amide [4], ester [5], or acid group [6] requires relatively rigorous conditions, similar to most reactions of nitriles [7].We have found that cyclopentylidenecyanoacetamide 1a and cyclohexylidenecyanoacetamide 1b react under conditions of the Michael reaction with acetoacetanilide 2a or ethyl acetoacetate 2b to give functionalized spiro-substituted 1,2,3,4-tetrahydronicotinamides 3a,b in good yields.The mechanism for the transformation of the nitrile group into an amide group, the scope of this reaction, and the chemical and biological properties of products 3a,b are under investigation. O NH 2 NC O R O Me NH O NH 2 N H Me O O R ( ) n + ( ) n 1a,b 2a,b 3a,b EtOH, 20 o C 1, 3 а n = 1, b n = 2; 2, 3 a R = PhNH, b R = EtO…”

mentioning

confidence: 99%

Unusually mild and efficient synthesis of functionalized spiro-substituted 1,2,3,4-tetrahydro- nicotinamides by the michael reaction

Dyachenko

2011

Chem Heterocycl Comp

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The use of chalcogen amides of cyanoacetic acid in the synthesis of nicotinic acid nitriles by means of the Michael reaction is well known [1][2][3]. On the other hand, the transformation of the nitrile group as a substituent in the pyridine ring into an amide [4], ester [5], or acid group [6] requires relatively rigorous conditions, similar to most reactions of nitriles [7].We have found that cyclopentylidenecyanoacetamide 1a and cyclohexylidenecyanoacetamide 1b react under conditions of the Michael reaction with acetoacetanilide 2a or ethyl acetoacetate 2b to give functionalized spiro-substituted 1,2,3,4-tetrahydronicotinamides 3a,b in good yields.The mechanism for the transformation of the nitrile group into an amide group, the scope of this reaction, and the chemical and biological properties of products 3a,b are under investigation. O NH 2 NC O R O Me NH O NH 2 N H Me O O R ( ) n + ( ) n 1a,b 2a,b 3a,b EtOH, 20 o C 1, 3 а n = 1, b n = 2; 2, 3 a R = PhNH, b R = EtOThe IR spectra were taken on a Perkin-Elmer FIR Spectrum One for KBr pellets. The 1 H NMR spectra were taken on a Bruker DR-500 spectrometer at 500 MHz in DMSO-d 6 solution with TMS as internal standard. The 13 C NMR spectrum for product 3a was taken on a Varian VXR-300 spectrometer at 75 MHz in DMSO-d 6 with TMS as internal standard. The mass spectrum of product 3b was obtained on a Kratos MS-890 mass

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ChemInform Abstract: A Novel System: 2H‐Pyrido(3,2‐e)‐1,2‐thiazine‐1,1‐dioxide. Synthesis and Properties of Some Derivatives.

Abstract: The pyridoisothiazoline (Ia) reacts with sodium ethoxide to give the nicotinic acid (II).

Cited by 4 publications

References 0 publications

New 1,3,4-Oxadiazole Derivatives of Pyridothiazine-1,1-Dioxide with Anti-Inflammatory Activity

New 1,3,4-Oxadiazole Derivatives of Pyridothiazine-1,1-Dioxide with Anti-Inflammatory Activity

Bromination and Diazo-Coupling of Pyridinethiones; Microwave Assisted Synthesis of Isothiazolopyridine, Pyridothiazine and Pyridothiazepines

Unusually mild and efficient synthesis of functionalized spiro-substituted 1,2,3,4-tetrahydro- nicotinamides by the michael reaction

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