58850-86-5

Usage

InChI:InChI=1/C6H12N2O2/c1-6(2,3)4(9)8-5(7)10/h1-3H3,(H3,7,8,9,10)

Upstream product

• 3282-30-2 pivaloyl chloride 
• 57-13-6 urea 
• 854643-13-3 N-acetyl-N'-pivaloyl-urea 
• 137524-55-1 2,2-dimethyl β-keto S-phenyl thiobutanoate 
• 75-98-9 Trimethylacetic acid 
• 102618-89-3 3-Pivaloyl-2H-1,3,5-oxadiazine-2,4,6(3H,5H)-trione 
• 102618-91-7 6-tert-Butyl-2H-1,3,5-oxadiazine-2,4(3H)-dione 

Downstream Products

• 854643-13-3 N-acetyl-N'-pivaloyl-urea 
• 754-10-9 2,2-dimethylpropionamide 

Relevant academic research and scientific papers

Copper(II)-Catalyzed Reactions of α-Keto Thioesters with Azides via C-C and C-S Bond Cleavages: Synthesis of N-Acylureas and Amides

Cu(II)-catalyzed reaction of α-keto thioesters with trimethylsilyl azide (TMSN3) proceeds with the transformation of the thioester group into urea through C-C and C-S bond cleavages, constituting a practical and straightforward synthesis of N-acylureas. When diphenyl phosphoryl azide (DPPA) is used instead as the azide source in an aqueous environment, primary amides are formed via substitution of the thioester group. The reactions are proposed to proceed through Curtius rearrangement of the initially formed α-keto acyl azide to generate an acyl isocyanate intermediate, which reacts further with an additional amount of azide or water and rearranges to afford the corresponding products. To demonstrate the potentiality of the method, one-step syntheses of pivaloylurea and isovaleroylurea, displaying anticonvulsant activities, have been carried out.

Synthesis and evaluation of antiallodynic and anticonvulsant activity of novel amide and urea derivatives of valproic acid analogues

Valproic acid (VPA, 1) is a major broad spectrum antiepileptic and central nervous system drug widely used to treat epilepsy, bipolar disorder, and migraine. VPA's clinical use is limited by two severe and lifethreatening side effects, teratogenicity and hepatotoxicity. A number of VPA analogues and their amide, N-methylamide and urea derivatives, were synthesized and evaluated in animal models of neuropathic pain and epilepsy. Among these, two amide and two urea derivatives of 1 showed the highest potency as antineuropathic pain compounds, with ED50 values of 49 and 51 mg/kg for the amides (19 and 20) and 49 and 74 mg/kg for the urea derivatives (29 and 33), respectively. 19, 20, and 29 were equipotent to gabapentin, a leading drug for the treatment of neuropathic pain. These data indicate strong potential for the above-mentioned novel compounds as candidates for future drug development for the treatment of neuropathic pain. 2009 American Chemical Society.

ACYL-UREA DERIVATIVES AND USES THEREOF

Novel acyl-urea containing compounds, processes of preparing same, compositions containing same and uses thereof in the treatment of neurological diseases and disorders such as epilepsy, neuropathic pain, bipolar disorder, status epilepticus, chemically-induced convulsions and/or seizure disorders, febrile convulsions conditions, metabolic disturbances and a sustenance withdrawal conditions, are provided. Also provided are uses of these and other acyl-urea containing compounds in the treatment of neurological diseases and disorders.

Reactions of Carbonyl Diisocyanate with Amides and Acids

Carbonyl diisocyanate (1) reacts with primary amides to give 1-acylated isocyanuric acids (5, 6).With secondary amides, 1 affords the rather instable oxadiazinediones 4, which for certain substituents rearrange to give triazines (5, 10).With nucleophiles, compounds 4 give oligourets, e.g. with ureas pentaurets (11, 12) were obtained.Carbonyl diisocyanate reacts with hydrogen halides to afford the crystalline urea-1,3-dicarbonyl halides 13a-c.Diverse products (16, 17, 24, 26) were obtained with carboxylic acids.In most cases oxadiazinediones (26) were isolated, which can be transformed with nucleophiles into acyl ureas 30, 31, biurets 32, and triurets 33.Acetylation of 26 leads to the reactive heterocycles 34.