Design and synthesis of vandetanib derivatives containing nitroimidazole groups as tyrosine kinase inhibitors in normoxia and hypoxia was written by Wei, Huiqiang;Li, Deguan;Yang, Xiangbo;Shang, Haihua;Fan, Saijun;Li, Yiliang;Song, Dan. And the article was included in Molecules in 2016.Quality Control of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid This article mentions the following:
Sixteen novel epidermal growth factor receptor (EGFR)/vascular endothelial growth factor (VEGF)-2 inhibitors (nitroimidazole-substituted 4-anilinoquinazoline derivatives) I (R1 = H, CH3, NO2; R2 = H, NO2; X1 = H, F, Cl; X2 = H, F, Br, Cl; X3 = H, Br, F, Me, Cl; n = 1, 2, 3) were designed and prepared via the introduction of a nitroimidazole group in the piperidine side chain and modification on the aniline moiety of vandetanib. Preliminary biol. tests showed that comparing with vandetanib, some target compounds exhibited excellent EGFR inhibitory activities and anti-proliferative over A549/H446 cells in hypoxia. Meanwhile, several of the above compounds demonstrated better bioactivity than vandetanib in VEGF gene expression inhibition. Owing to the excellent IC50 value (1.64 μmol/L), the inhibition ratios of compound I (R1 = H; R2 = NO2; X1 = F; X2 = H; X3 = Br; n = 1) over A549 and H446 cells were 62.01% and 59.86% at the concentration of 0.5 μM in hypoxia, resp. All of these results indicated that compound I (R1 = H; R2 = NO2; X1 = F; X2 = H; X3 = Br; n = 1) was a potential cancer therapeutic agent in hypoxia and was worthy of further development. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Quality Control of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid).
2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Quality Control of 2-(2-Nitro-1H-imidazol-1-yl)acetic acid
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem