1186016-52-3Relevant academic research and scientific papers
Design, synthesis and activity of thio-linked arabinofuranosyl disaccharides against mycobacterial tuberculosis (MTB) and Mycobacterium avium complex (MAC)
Khare, Naveen K.,Duarte, Franco J.,Reynolds, Robert C.,Maddry, Joseph A.
, p. 290 - 315 (2013/02/26)
We report the chemical synthesis of a series of disaccharides of arabinofuranose with a glycosidic sulfur linker as mimics of the acceptor for arabinofuranosyltransferases with and without using any activator to avoid any complex reactions. These analogs were tested for in vitro activity against MTB strain H37Ra and 3 MAC clinical isolates. MICs were determined using a colorimetric microdilution broth assay. Bactericidal activity was studied with kill curves over a period of seven days. Intracellular activity against MTB H37Ra was determined in the Mono Mac 6 (MM6) human monocytic cell line. ARKAT-USA, Inc.
Synthesis of 4-deoxy-4-thioarabinofuranosyl disaccharides, analogs of Mycobacterial arabinogalactan
Khare, Naveen K.,Reynolds, Robert C.,Maddry, Joseph A.
experimental part, p. 1748 - 1752 (2009/06/28)
The first chemical synthesis of disaccharides, octyl 5-O-(4-deoxy-4-thio- α-D-arabinofuranosyl)-α-D-arabinofuranoside 1 and octyl 5-O-(4-deoxy-4-thio-β-D-arabinofuranosyl)-α-D-arabinofuranoside 2 incorporating 4-deoxy-4-thioarabinose is described. Designed to mimic components of mycobacterial arabinogalactan, a major and essential constituent of the cell wall of tuberculosis and related bacteria, the compounds may disrupt cell wall biogenesis. A variety of coupling methods have been investigated before finding satisfactory techniques useful for thiofuranoses. Reductive deprotection of the sulfur-containing species is problematic, though lithium naphthalenide has proved to be an effective technique.
