Synthesis of novel benzo[ b ]pyrimido[4′,5′:5,4]thieno[2,3-e][1,6]naphthyridine-8-ones via Pictet–Spengler cyclization

Traditional methods of chemical synthesis of alkaloids exhibit various problems such as lack of enantioselectivity, the use of toxic chemical and intermediates, and multiple numbers of synthetic steps. Consequently, various enzymatic methods for the formation of CÀC bonds in the alkaloid skeleton have been developed. Herein, we report advances achieved in the enzymatic or chemo-enzymatic synthesis of pharmaceutically important alkaloids that employ three CÀC bond forming enzymes: two Pictet-Spenglerases and the oxidative CÀC bond forming flavoenzyme Berberine Bridge Enzyme. Protein engi-neering studies, improving the substrate scope of these enzymes, and thereby leading to the synthesis of non-natural alkaloids possessing higher or newer pharmacological activities, are also discussed. Furthermore, the integration of these biocatalysts with other enzymes, in multi-enzymatic cascades for the enantioselective synthesis of alkaloids, is also reviewed. Current results suggest that these enzymes hold great promise for the generation of CÀC bonds in the selective synthesis of alkaloid compounds possessing diverse pharmacological properties.

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Biocatalyzed C−C Bond Formation for the Production of Alkaloids

Patil

Grogan

Yun

2018

ChemCatChem

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ChemInform Abstract: Synthesis of Novel Benzo[b]pyrimido[4′,5′:5,4]thieno[2,3‐e][1,6]naphthyridine‐8‐ones via Pictet—Spengler Cyclization.

et al. 2016

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Synthesis and Anticancer Properties of Functionalized 1,6-Naphthyridines

et al. 2021

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Synthesis of novel benzo[ b ]pyrimido[4′,5′:5,4]thieno[2,3-e][1,6]naphthyridine-8-ones via Pictet–Spengler cyclization

Cited by 5 publications

References 27 publications

Biocatalyzed C−C Bond Formation for the Production of Alkaloids

Biocatalyzed C−C Bond Formation for the Production of Alkaloids

ChemInform Abstract: Synthesis of Novel Benzo[b]pyrimido[4′,5′:5,4]thieno[2,3‐e][1,6]naphthyridine‐8‐ones via Pictet—Spengler Cyclization.

Synthesis and Anticancer Properties of Functionalized 1,6-Naphthyridines

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