71579-95-8Relevant academic research and scientific papers
Spectroscopic and theoretical study of the o-vanillin hydrazone of the mycobactericidal drug isoniazid
González-Baró, Ana C.,Pis-Diez, Reinaldo,Parajón-Costa, Beatriz S.,Rey, Nicolás A.
, p. 95 - 101 (2012)
A complete and detailed study of the hydrazone obtained from condensation of antituberculous isoniazid (hydrazide of the isonicotinic acid, INH) and o-vanillin (2-hydroxy-3-methoxybenzaldehyde, o-HVa) is performed. It includes structural and spectroscopic
An integrated approach (synthetic, structural and biological) to the study of aroylhydrazone salts
Vrdoljak, Vi?nja,Prugove?ki, Biserka,Primo?i?, Ines,Hrenar, Tomica,Cvijanovi?, Danijela,Parlov Vukovi?, Jelena,Od?ak, Renata,Sko?ibu?i?, Mirjana,Prugove?ki, Stjepan,Lovri?, Jasna,Matkovi?-?alogovi?, Dubravka,Cindri?, Marina
, p. 11697 - 11707 (2018/07/25)
The reaction of two methoxy substituted salinazid-based hydrazones, 4-methoxysalicylaldehyde isonicotinoyl hydrazone (L1) and 3-methoxysalicylaldehyde isonicotinoyl hydrazone (L2), with HCl, HBr, HNO3 and H2SO4 in methanol yielded salts of different stoichiometries (1:1 or 2:1) and/or polymorphic forms. In such a way, (HL1)+X- and (HL2)+X- salts, where X = Cl, Br, NO3, HSO4, as well as [H(L1)2]+Br- and (HL1)2+SO42- were obtained. The solid state properties and the propensity for transformation between different forms in solution were also investigated. The crystal structures of compounds (HL1)+Cl-, (HL1)+Br- (α and β), [H(L1)2]+Br-, (HL1)2+SO42-, (HL2)+Br-·MeOH and (HL2)+NO3- were solved by the single-crystal X-ray diffraction method while the structures of (HL1)+NO3- and (HL1)+HSO4- (α and β) were solved by the powder diffraction method. The details of anion binding with the isoniazid functionality are discussed. The aroylhydrazone salts were evaluated for cytotoxic activity in vitro. All compounds exhibited weak cytotoxicity against THP-1 and no cytotoxicity against HepG2 cells. In a preliminary antimicrobial screening assay, these compounds were not only active against antibiotic susceptible Gram-positive bacteria, but also exhibited antibacterial effects on a wide range of multidrug-resistant Gram-positive as well as multidrug resistant Gram-negative bacterial pathogens.
