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Fig 1.

Structures of selected marketed antitubercular drugs containing pyridine and tetrahydropyran scaffolds.

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Fig 2.

Fluorinated chalcones, pyridine and pyran derivatives with significant antitubercular activity.

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Fig 3.

Scheme 1, Synthesis of fluorinated chalcones (1–20) and their 2-amino-pyridine-3-carbonitrile (21–40) and 2-amino-4H-pyran-3-carbonitrile (41–60) derivatives.

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Fig 4.

Summary of the antitubercular activities of fluorinated chalcones (1–20), 2-amino-pyridine-3-carbonitrile (21–40) and 2-amino-4H-pyran-3-carbonitrile (41–60) derivatives.

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Fig 4 Expand

Fig 5.

Structure activity relationships of fluorinated chalcones (1–20), 2-amino-pyridine-3-carbonitrile (21–40) and 2-amino-4H-pyran-3-carbonitrile (41–60) derivatives.

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Fig 5 Expand

Fig 6.

2D and 3D interactions of 40 with PZA active site of 1G3U, which shown hydrogen bond and other interactions.

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Fig 6 Expand