Evaluation of an enantioselective synthesis of 6-chloro-3,4-dihydro-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide and its derivatives

Bluķe, Zanda; Sladek, Meik; Abel, Ulrich; Kauss, Valerjans

doi:10.1007/s10593-015-1679-4

Cited by 5 publications

(2 citation statements)

References 13 publications

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“…In recent years there has been a rapid growth in the literature pertaining to the benzothiazine ring system; much of this literature relates to the discovery that 3-carboxamides of 2-alkyl-4-hydroxy-2 H -1,2-benzothiazine-1,1-dioxides are anti-inflammatory agents, which includes the drugs piroxicam, ampiroxicam and meloxicam (Figure 1) [21,22,23,24,25,26,27,28]. The common route to these types of compounds is via the alkoxide rearrangement of saccharin derivatives (Scheme 1) [29,30,31,32,33,34,35].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives

et al. 2016

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A number of 1,2-benzothiazines have been synthesized in a three-step process. Nine chalcones 1-9 bearing methyl, fluoro, chloro and bromo substituents were chlorosulfonated with chlorosulfonic acid to generate the chalcone sulfonyl chlorides 10-18. These were converted to the dibromo compounds 19-27 through reaction with bromine in glacial acetic acid. Compounds 19-27 were reacted with ammonia, methylamine, ethylamine, aniline and benzylamine to generate a library of 45 1,2-benzothiazines 28-72. Compounds 28-72 were evaluated for their antimicrobial activity using broth microdilution techniques against two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and two Gram-negative bacteria (Proteus vulgaris and Salmonella typhimurium). The results demonstrated that none of the compounds showed any activity against Gram-negative bacteria P. vulgaris and S. typhimurium; however, compounds 31, 33, 38, 43, 45, 50, 53, 55, 58, 60, 63 and 68 showed activity against Gram-positive bacteria Bacillus subtilis and Staphylococcous aureus. The range of minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) was 25-600 µg/mL, though some of the MIC and MBC concentrations were high, indicating weak activity. Structure activity relationship studies revealed that the compounds with a hydrogen atom or an ethyl group on the nitrogen of the thiazine ring exerted antibacterial activity against Gram-positive bacteria. The results also showed that the compounds where the benzene ring of the benzoyl moiety contained a methyl group or a chlorine or bromine atom in the para position showed higher antimicrobial activity. Similar influences were identified where either a bromine or chlorine atom was in the meta position.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives

et al. 2016

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“…In 2015, Kauss and co‐workers demonstrated a fruitful procedure for the synthesis of chiral six‐membered sultams in moderate enantiomeric excess (Scheme ) . In the presence of base, sultams 73.2 were formed from arylsulfonyl chloride derivatives 73.1 .…”

Section: Metal‐free Synthesis Of Sultamsmentioning

confidence: 99%

Sultams: Recent Syntheses and Applications

Debnath¹,

Mondal²

2018

Eur J Org Chem

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Sultams are very important scaffolds both in medicinal chemistry and in synthetic organic chemistry. Very important methodologies for the asymmetric and non‐asymmetric synthesis of sultams, including asymmetric synthesis with memory of chirality (MOC), have recently been developed. Nowadays sultams are tremendously widely applied both in the medicinal field and in the synthetic field for the synthesis of different natural and non‐natural heterocycles. This review covers the recent development (2011–June 2017) of powerful methodologies for the synthesis of sultams and their applications in various fields during this period. A critical view of the mechanisms of the developed methodologies together with the scope and limitations of these methods add an extra dimension to the text.

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1,2-Thiazines and Their Benzo Derivatives

Evans

Geoghegan

2022

Comprehensive Heterocyclic Chemistry IV

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Evaluation of an enantioselective synthesis of 6-chloro-3,4-dihydro-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide and its derivatives

Cited by 5 publications

References 13 publications

Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives

Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives

Sultams: Recent Syntheses and Applications

1,2-Thiazines and Their Benzo Derivatives

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