• SENTHIL KUMAR NATARAJAN

      Articles written in Journal of Chemical Sciences

    • Synthesis of metabolites of dapagliflozin: an SGLT2 inhibitor

      KISHORE KARUMANCHI SENTHIL KUMAR NATARAJAN RAMADAS CHAVAKULA RAGHU BABU KORUPOLU KISHORE BABU BONIGE BADARINADH GUPTA PERURI

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      Dapagliflozin is one of the gliflozin class drugs, useful for the treatment of type-2 diabetes. Dapagliflozin undergoes extensive metabolism and transforms to metabolites in humans. The contribution of pharmacologically active metabolites in drug discovery and development is significant. A streamlined synthetic approach is devised to access three metabolites of dapagliflozin namely, benzylic hydroxy dapagliflozin, oxo dapagliflozin and desethyl dapagliflozin.Two synthetic protocols have been proposed for the synthesis of benzylic hydroxy dapagliflozin and oxo dapagliflozin. An enantioselective deethylation of dapagliflozin is also reported

    • A new synthesis of tafamidis via zinc-MsOH mediated reductive cyclisation strategy

      KISHORE KARUMANCHI SENTHIL KUMAR NATARAJAN SUNIL GADDE KRISHNA VANCHANAGIRI KRISHNAMURTHY V R MOTURU

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      A practical zinc-MsOH mediated intra-molecular reductive cyclisation and its application in thesynthesis of tafamidis is presented starting from the readily available 3-hydroxy-4-nitrobenzoic acid as aprecursor. The key reductive cyclization step involves the use of a combination of the readily available zincand MsOH as the catalyst system. This methodology provides an attractive route to 2-aryl benzoxazoles from

      ortho-nitro phenols under mild reaction conditions. This methodology is developed on a multi-gram scale andwithout the need for column chromatography.

      A new and alternative zinc-MsOH mediated intra-molecular reductive cyclisation and its application in the synthesis of tafamidis is reported starting from the readily available 3-hydroxy-4-nitrobenzoic acid as precursor. This method provides an attractive route to 2-aryl benzoxazoles from ortho-nitro phenols under mild reaction conditions.

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