Synthesis and antimycobacterial activities of glycosylated amino alcohols and amines.
Reduction of glycosyl beta-amino esters (6-14 and 25-30) with lithium aluminum hydride resulted in glycosyl amino alcohols (15-23 and 31-36) in good yields. However, reductive amination of glycosyl aldehydes (1-3) with different amines in presence of sodium borohydride resulted in good to moderate yields of glycosyl amines (37-41). All the compounds were evaluated for antitubercular activity against Mycobacterium tuberculosis H37Ra and H37Rv. Compounds 18, 21, 35 and 36 exhibited antitubercular activities with MIC ranging from 6.25 to 3.12 microg ml(-1).
Katiyar
D
D
Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow 226001, India.
Tiwari
V K
VK
Tewari
N
N
Verma
S S
SS
Sinha
S
S
Gaikwad
A
A
Srivastava
A
A
Chaturvedi
V
V
Srivastava
R
R
Srivastava
B S
BS
Tripathi
R P
RP
D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006031:Glycosylation; D015394:Molecular Structure; D009161:Mycobacterium / Q000187:drug effects* / Q000502:physiology
D000588:Amines; D000605:Amino Alcohols; D000900:Anti-Bacterial Agents