Synthesis and antitubercular activity of N-(2-naphthyl)glycine hydrazide analogues.
N-(2-Naphthyl)glycine hydrazide analogues were synthesized and tested for possible in vitro antitubercular activity. N-(2-Naphthyl)alanine hydrazide (3), N-methyl-N-(2-naphthyl)glycine hydrazide (5), N-(6-methoxy-2-naphthyl)glycine hydrazide (7), and 3-(2-naphthylamino)butyric acid hydrazide (23) showed potent inhibitory action against Mycobacterium tuberculosis H37Rv in Youman's medium at concentrations ranging from 0.5 to 10.0 micrograms/mL. These compounds showed significant inhibitory action against isonicotinic acid hydrazide and streptomycin-resistant strains of M. tuberculosis. N-(6-Quinolyl)glycine hydrazide (18) and 3-(2-quinolylamino)butyric acid hydrazide (24), which are bioisosteres of compounds 1 and 23, showed loss of antitubercular activity at low concentrations.
Ramamurthy
B
B
Department of Organic Chemistry, Indian Institute of Science, Bangalore, India.
Bhatt
M V
MV
D000995:Antitubercular Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D005998:Glycine / Q000031:analogs & derivatives*; D006834:Hydrazines / Q000138:chemical synthesis / Q000494:pharmacology*; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D009281:Naphthalenes / Q000138:chemical synthesis / Q000494:pharmacology*
D000995:Antitubercular Agents; D006834:Hydrazines; D009281:Naphthalenes; D005998:Glycine