1. 2-Aminonicotinic acid
A J Dobson, R E Gerkin Acta Crystallogr C. 1997 Oct 15;53 ( Pt 10):1427-9. doi: 10.1107/s0108270197008226.
2-Aminonicotinic acid, C6H6N2O2, crystallized in the centrosymmetric space group P2(1)/c in the zwitterionic form. Intermolecular N--H...O hydrogen bonds with N...O distances of 2.652 (2) and 2.807 (2) A link molecules into two sets of zigzag chains propagating along the b axis. The two sets of chains are crosslinked by C--H...O interactions. The dihedral angle between the planes of adjacent molecules in a chain is 9.77 (7) degrees. An intramolecular N--H...O hydrogen bond is also present.
2. Synthesis, spectral studies and biological evaluation of 2-aminonicotinic acid metal complexes
Muhammad Nawaz, Muhammad Waseem Abbasi, Soleiman Hisaindee, Muhammad Javed Zaki, Hira Fatima Abbas, Hu Mengting, M Arif Ahmed Spectrochim Acta A Mol Biomol Spectrosc. 2016 May 15;161:39-43. doi: 10.1016/j.saa.2016.02.022. Epub 2016 Feb 26.
We synthesized 2-aminonicotinic acid (2-ANA) complexes with metals such as Co(II), Fe(III), Ni(II), Mn(II), Zn(II), Ag(I),Cr(III), Cd(II) and Cu(II) in aqueous media. The complexes were characterized and elucidated using FT-IR, UV-Vis, a fluorescence spectrophotometer and thermo gravimetric analysis (TGA). TGA data showed that the stoichiometry of complexes was 1:2 metal/ligand except for Ag(I) and Mn(II) where the ratio was 1:1. The metal complexes showed varied antibacterial, fungicidal and nematicidal activities. The silver and zinc complexes showed highest activity against Bacillus subtilis and Bacillus licheniformis respectively. Fusarium oxysporum was highly susceptible to nickel and copper complexes whereas Macrophomina phaseolina was completely inert to the complexes. The silver and cadmium complexes were effective against the root-knot nematode Meloidogyne javanica.
3. 2-Aminonicotinic acid 1-oxides are chemically stable inhibitors of quinolinic acid synthesis in the mammalian brain: a step toward new antiexcitotoxic agents
Gian Paolo Vallerini, Laura Amori, Claudia Beato, Margarita Tararina, Xiao-Dan Wang, Robert Schwarcz, Gabriele Costantino J Med Chem. 2013 Dec 12;56(23):9482-95. doi: 10.1021/jm401249c. Epub 2013 Dec 3.
3-Hydroxyanthranilic acid 3,4-dioxygenase (3-HAO) is the enzyme responsible for the production of the neurotoxic tryptophan metabolite quinolinic acid (QUIN). Elevated brain levels of QUIN are observed in several neurodegenerative diseases, but pharmacological investigation on its role in the pathogenesis of these conditions is difficult because only one class of substrate-analogue 3-HAO inhibitors, with poor chemical stability, has been reported so far. Here we describe the design, synthesis, and biological evaluation of a novel class of chemically stable inhibitors based on the 2-aminonicotinic acid 1-oxide nucleus. After the preliminary in vitro evaluation of newly synthesized compounds using brain tissue homogenate, we selected the most active inhibitor and showed its ability to acutely reduce the production of QUIN in the rat brain in vivo. These findings provide a novel pharmacological tool for the study of the mechanisms underlying the onset and propagation of neurodegenerative diseases.
