Concise and Efficient Synthesis of Highly Potent and Selective Dipeptidyl Peptidase II Inhibitors

Peptides U 0400 Concise and Efficient Synthesis of Highly Potent and Selective Dipeptidyl Peptidase II Inhibitors. -A more practical, shorter, high yielding route for the synthesis of the highly potent and selective DPP II inhibitors (IX) and (XII) starts from L-glutamine. -(RASHEED*, M. A.; NAMALA, R.; MANNE, N.; VANJIVAKA, S.; DHAMJEWAR, R.; BALASUBRAMANIAN, G.; Synth. Commun. 38 (2008) 2, 162-169; GVK Biosci., IDA, Hyderabad 500 076, India; Eng.) -H. Toeppel 26-192

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ChemInform Abstract: Concise and Efficient Synthesis of Highly Potent and Selective Dipeptidyl Peptidase II Inhibitors.

Rasheed

Rambabu

Manne

et al. 2008

ChemInform

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Synthesis of γ,δ‐Aziridino α‐Amino Acid Derivatives and their Stereoselective Ring Transformation to 2‐(Aminomethyl)‐1‐aminocyclopropanecarboxylic Acid Derivatives

et al. 2013

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1‐Benzyl‐2‐(bromomethyl)aziridine was successfully substituted with protected glycine esters to afford alkyl 3‐(N‐benzylaziridin‐2‐yl)‐2‐aminopropanoates, as constrained heterocyclic diamino acid derivatives, in good isolated yields. These new aziridines proved to be excellent building blocks for ring transformation to the corresponding stereochemically defined 2‐(aminomethyl)‐1‐aminocyclopropanecarboxylic acid derivatives, including methyl esters, piperidyl amides, and free carboxylic acids.

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Discovery of N-(4-sulfamoylphenyl)thioureas as Trypanosoma brucei leucyl-tRNA synthetase inhibitors

Zhang

Wang

et al. 2013

Org. Biomol. Chem.

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Human African trypanosomiasis (HAT) is one of the most neglected diseases in the tropic regions, which is fatal if not treated in time. There is an urgent need for new therapeutics, especially those in new chemical classes. Leucyl-tRNA synthetase (LeuRS) has been paid much attention as a recently clinically validated antimicrobial target. Our group has previously reported T. brucei LeuRS (TbLeuRS) inhibitors, including benzoxaboroles targeting the editing site and pyrrolinones targeting the synthetic site. Here we report the discovery of N-(4-sulfamoylphenyl)thioureas as a new class of TbLeuRS inhibitors. The R(1) and R(2) groups, reminiscent of the leucyl and adenyl regions of aa-AMP and aa-AMS, were optimized to result in a significant 13-fold increase of inhibitory activity (compound 19, IC50 = 13.7 μM). Aided by ligand-protein docking, the 1,3-substitution at the central phenyl ring was predicted and proved to give significantly improved activity (59, IC50 = 1.1 μM). This work provided a new scaffold for the exploration of novel inhibitors against TbLeuRS, which may become potential therapeutics for the treatment of HAT.

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Concise and Efficient Synthesis of Highly Potent and Selective Dipeptidyl Peptidase II Inhibitors

Cited by 4 publications

References 7 publications

ChemInform Abstract: Concise and Efficient Synthesis of Highly Potent and Selective Dipeptidyl Peptidase II Inhibitors.

ChemInform Abstract: Concise and Efficient Synthesis of Highly Potent and Selective Dipeptidyl Peptidase II Inhibitors.

Synthesis of γ,δ‐Aziridino α‐Amino Acid Derivatives and their Stereoselective Ring Transformation to 2‐(Aminomethyl)‐1‐aminocyclopropanecarboxylic Acid Derivatives

Discovery of N-(4-sulfamoylphenyl)thioureas as Trypanosoma brucei leucyl-tRNA synthetase inhibitors

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