Synthesis and Decomposition of Parabanic Acid Derivatives

Abstract

INTRODUCTION Parabanic acid(imidazolidine-2,4,5-trione, oxalylurea) resulting from the oxidation of biological fundamental compounds such as uric acid, guanine, uracil and alloxanic acid has attracted the attention of agricultural and medicinal chemists for many decades 1,2. Parabanic acid derivatives are useful phamaceuticals for the treatment of diabetic complications such as diabetic neuropathy, diabetic cataracts and diabetic dermotopathy 3-6. Further, parabanic acid derivatives are known for their herbicidal, plant growth regulating and fungicidal properties 7. Polymers containing imidazolidine-2,4,5-trione (parabanic) rings are known as highly thermally stable polymers with improved chemical resistance in organic solvents 8-13. Recently, many marine imidazol alkaloids have been isolated from sponges and their antitumor and antibacterial activities have also been identified 14,15. In our previous works to obtain new agrochemicals, we reported the synthesis of new saccharin derivatives containing the 2,4,5-imidazolidinetrione group 16. As a part of research program related to the synthetic study of pharmacologically and agrochemically important imidazolidines 16 , we chose to identify imidazolidine-2,4,5-trione and imidazolidine-2,4,5-trione,2-thioxo-imidazolidine-4,5-dione, benzimidazole, orsaccharin rings as active components for the desired property, the synthesis of (imidazolidine-2,4,5-trionyl) imidazolidine-2,4,5-triones (1), 2,4,5-imidazolidinetrionyl-1,2-benzisothiazol-3-one-1,1-dioxide 2, 4,5-dioxo-2-thioxoimidazolidin-1-ylmethyl-imidazolidine-2,4,5-triones (2) and 1-benzoimidazole-1-yl-3-imidazolidine-2,4,5-trione (3) are already reported.

Synthesis of Novel 8‐cyclo‐1,5,3,7‐Diazadiphosphocine Derivatives Via [4 + 2] Cycloaddition

“…Currently, polyamino polycarboxylic acid and polyamino polyphosphonic/phosphinic acid scaffolds are in use as efficient chelating ligands of trivalent gadolinium (Gd 3+ ) in magnetic resonance imaging (MRI) contrast agents 1,2 . Extensive efforts have been devoted to reducing toxicity arising from demetallation of Gd 3+ complexes in vivo .…”