Synthesis of 4-phenoxybenzamide adenine dinucleotide as NAD analogue with inhibitory activity against enoyl-ACP reductase (InhA) of Mycobacterium tuberculosis |
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Authors: | Bonnac Laurent Gao Guang-Yao Chen Liqiang Felczak Krzysztof Bennett Eric M Xu Hua Kim TaeSoo Liu Nina Oh HyeWon Tonge Peter J Pankiewicz Krzysztof W |
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Affiliation: | Center for Drug Design, University of Minnesota, Minneapolis, MN 55455, USA. |
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Abstract: | The chemical synthesis of 4-phenoxybenzamide adenine dinucleotide (3), a NAD analogue which mimics isoniazid-NAD adduct and inhibits Mycobacterium tuberculosis NAD-dependent enoyl-ACP reductase (InhA), is reported. The 4-phenoxy benzamide riboside (1) has been prepared as a key intermediate, converted into its 5'-mononucleotide (2), and coupled with AMP imidazolide to give the desired NAD analogue 3. It inhibits InhA with IC50 = 27 microM. |
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