Synthesis and antitubercular activity of novel Schiff bases derived from d-mannitol.
Six Schiff base derivatives of d-mannitol, 1,6-dideoxy-1,6-bis-{[(E)-arylmethylidene]amino}-d-mannitol (6: aryl=XC(6)H(4): X=o-, m- and p- Cl or NO(2)), have been synthesized and evaluated for their in vitro antibacterial activity against Mycobacterium tuberculosis H(37)Rv using the Alamar Blue susceptibility test and the activity expressed as the minimum inhibitory concentration (MIC) in microg/mL. All three nitro derivatives exhibit significant activities: activities of (6d: X=o-NO(2)), (6e: X=m-NO(2)) and (6f: X=p-NO(2)) are 12.5, 25.0 and 25.0microg/mL, respectively. When compared with first line drugs, such as ethambutol, they can be considered as a good starting point to develop new lead compounds for the treatment of multidrug-resistant tuberculosis. Characterization of the new compounds 6 is generally achieved spectroscopically. The structure of compound 3 has been confirmed by X-ray crystallography.
Ferreira
Marcelle de L
Mde L
Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Far Manguinhos, Rio de Janeiro, RJ, Brazil.
Vasconcelos
Thatyana R A
TR
de Carvalho
Erika M
EM
Lourenço
Maria C S
MC
Wardell
Solange M S V
SM
Wardell
James L
JL
Ferreira
Vitor F
VF
de Souza
Marcus V N
MV
D000818:Animals; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D008264:Macrophages / Q000166:cytology / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008353:Mannitol / Q000737:chemistry*; D051379:Mice; D050296:Microbial Viability / Q000187:drug effects; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D012545:Schiff Bases / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000995:Antitubercular Agents; D012545:Schiff Bases; D008353:Mannitol