Synthesis of arabinose glycosyl sulfamides as potential inhibitors of mycobacterial cell wall biosynthesis

European Journal of Medicinal Chemistry
2015.0

Abstract

A series of arabinose glycosyl sulfamides with varying alkyl chain types and lengths were synthesised as mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Unprecedented conversion of the desired furanose to the thermodynamically more stable pyranose form occurred during final de-protection. Biological testing against Mycobacterium smegmatis revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which in the case of mono-substituted sulfamides was maximal for a C-10 chain.

Knowledge Graph

Similar Paper

Synthesis of arabinose glycosyl sulfamides as potential inhibitors of mycobacterial cell wall biosynthesis
European Journal of Medicinal Chemistry 2015.0
Synthesis of Arabino glycosyl triazoles as potential inhibitors of mycobacterial cell wall biosynthesis
Bioorganic & Medicinal Chemistry Letters 2008.0
Synthesis of methyl 5-S-alkyl-5-thio-d-arabinofuranosides and evaluation of their antimycobacterial activity
Bioorganic & Medicinal Chemistry 2008.0
Synthesis of symmetrical C- and pseudo-symmetrical O-linked disaccharide analogs for arabinosyltransferase inhibitory activity in Mycobacterium tuberculosis
Bioorganic & Medicinal Chemistry Letters 2007.0
Anti-mycobacterial activity of a bis-sulfonamide
Bioorganic & Medicinal Chemistry Letters 2007.0
Demonstration that the galactosyl and arabinosyl residues in the cell-wall arabinogalactan of Mycobacterium leprae and Myobacterium tuberculosis are furanoid
Carbohydrate Research 1987.0
1,3-Diarylpyrazolyl-acylsulfonamides as Potent Anti-tuberculosis Agents Targeting Cell Wall Biosynthesis in Mycobacterium tuberculosis
Journal of Medicinal Chemistry 2021.0
Synthesis and in vitro antitubercular activity of 4-aryl/alkylsulfonylmethylcoumarins as inhibitors of Mycobacterium tuberculosis
Bioorganic & Medicinal Chemistry Letters 2012.0
A New Class of Antituberculosis Agents
Journal of Medicinal Chemistry 2000.0
Synthesis and evaluation of in vitro anti-tuberculosis activity of N-substituted glycolamides
European Journal of Medicinal Chemistry 2009.0