Regioselective Synthesis of 1,2-Benzothiazine 1,1-Dioxide Derivatives by Intramolecular Heck Cyclization

Debnath, Sudarshan; Malakar, Suniti

doi:10.1055/s-0035-1562440

Cited by 9 publications

References 6 publications

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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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Sultams: Recent Syntheses and Applications

Debnath¹,

Mondal²

2018

Eur J Org Chem

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Synthesis of Indole-2-methylsulfonamides by Domino Sonogashira Coupling and Hydroamination Reaction

Debnath

Malakar

2017

ChemistrySelect

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A domino Sonogashira coupling and hydroamination reaction between o-iodo-N,N-dimethylaniline derivatives and propargyl sulfonamides are described. This protocol allows access to a variety of indole-2-methylsulfonamides in good to excellent yields. The structures of the synthesized compounds are confirmed by XRD studies. Results and DiscussionThe required precursors of our present study, o-iodoaniline derivatives (20a-c) [15] and propargyl sulfonamide derivatives [a] S.

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Novel 1,2,3‐Triazole‐Functionalized 1,2‐Benzothiazine 1,1‐Dioxide Derivatives: Regioselective Synthesis, Biological Evaluation and Docking Studies

et al. 2018

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A series of novel 1,2‐benzothiazine‐1,1‐dioxide derivatives (Z)‐3‐hydroxy‐1‐(4‐hydroxy‐2‐methyl‐1,1‐dioxido‐2H‐benzo[e][1, 2]thiazin‐3‐yl)‐3‐phenyl substituted prop‐2‐en‐1‐one (6 a‐d) were synthesized starting from sodium salt of saccharin 1 in series of steps via 3‐acetyl‐2‐methyl‐1,1‐dioxido‐2H‐benzo[e][1, 2]thiazin‐4‐yl substituted benzoates (5 a‐d). Compound 6 e was obtained alternately from 1‐(4‐Hydroxy‐2‐methyl‐1,1‐dioxo‐1,2‐dihydro‐1λ6‐benzo[e][1, 2]thiazin‐3‐yl)‐ethanone (4). Compounds 6 a‐e were further reacted with aromatic azides to form (4‐hydroxy‐2‐methyl‐1,1‐dioxido‐2H‐benzo[e][1, 2]thiazin‐3‐yl)(1‐substitutedphenyl)‐5‐ substituted pheny or methyl‐1H‐1,2,3‐triazol‐4‐yl)methanone derivatives (7 a‐o) by regioselective cyclization. All the compounds were evaluated for anti‐inflammatory and anti‐cancer activities. Compounds 5 a‐b, 6 a‐b, 7 a, 7 c‐d, 7 i and 7 k‐l which showed significant anti‐inflammatory activity at micro molar concentration have been identified. Also screened for cytotoxic activity against four human cancer cells and one normal cell such as prostate cancer (PC‐3), breast adenocarcinoma (MDA‐MB‐231), liver hepatocellular carcinoma (Hep G2), cervical cancer (HeLa) and normal umbilical vein endothelial cell (HUVEC). Compounds 6 a, 7 g, 7 h and 7 k have been identified as promising candidates. Further, anti‐inflammatory activity is also validated by docking studies and compounds 5 a, 5 b and 7 d found to show good interactions when docked with IL‐1β signaling complex.

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Regioselective Synthesis of 1,2-Benzothiazine 1,1-Dioxide Derivatives by Intramolecular Heck Cyclization

Cited by 9 publications

References 6 publications

Sultams: Recent Syntheses and Applications

Sultams: Recent Syntheses and Applications

Synthesis of Indole-2-methylsulfonamides by Domino Sonogashira Coupling and Hydroamination Reaction

Novel 1,2,3‐Triazole‐Functionalized 1,2‐Benzothiazine 1,1‐Dioxide Derivatives: Regioselective Synthesis, Biological Evaluation and Docking Studies

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