Synthesis and antitubercular activities of bis-glycosylated diamino alcohols.
Conjugate addition of diamines to glycosyl olefinic esters 1a and 1b followed by reduction of resulting bis-glycosyl beta-amino esters (2-7 and 14-19) with lithium aluminium hydride led to the respective glycosyl amino alcohols (8-13 and 20-25) in moderate to good yields. All the compounds were evaluated for antitubercular activity against Mycobacterium tuberculosis H(37)Ra and H(37)Rv. Few of the compounds exhibited antitubercular activity with MIC as low as 6.25-3.12microg/mL in virulent and avirulent strains. Compound 13 was found to be active against MDR strain and showed mild protection in mice.
Tripathi
R P
RP
Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow 226001, India. rpt_56@yahoo.com
Tiwari
V K
VK
Tewari
N
N
Katiyar
D
D
Saxena
N
N
Sinha
S
S
Gaikwad
A
A
Srivastava
A
A
Chaturvedi
V
V
Manju
Y K
YK
Srivastava
R
R
Srivastava
B S
BS
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000494:pharmacology*; D000818:Animals; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D004195:Disease Models, Animal; D006031:Glycosylation; D051379:Mice; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D009161:Mycobacterium / Q000187:drug effects; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013329:Structure-Activity Relationship
D000605:Amino Alcohols; D000995:Antitubercular Agents