136199-02-5

Usage

Uses

Used in Neurodegenerative Disease Treatment:
KW 3902 is used as a therapeutic agent for the treatment of Tau-induced neurodegenerative diseases. It functions as an adenosine A1-receptor antagonist, which has been shown to alleviate axonopathy caused by human Tau ΔK280. This makes KW 3902 a potential candidate for the development of treatments aimed at hypometabolism and neuronal dysfunction associated with such diseases.
Used in Renal Protection:
In the medical industry, KW 3902 is used as a renal protective agent during hypoxemic conditions in rabbits. Its ability to exhibit renal protective effects makes it a valuable compound for the development of treatments aimed at preserving kidney function under conditions of low oxygen supply.
Used in Pharmaceutical Research:
KW 3902 is also used as a research tool in the pharmaceutical industry for studying the role of adenosine A1 receptors in various physiological and pathological processes. Its high selectivity for A1 receptors over A2A receptors and its inhibitory activity on human organic anion transporter 1 (OAT1) make it a valuable compound for investigating the mechanisms of action and potential therapeutic applications in different disease states.

InChI:InChI=1/C20H28N4O2/c1-3-5-23-16-15(17(25)24(6-4-2)19(23)26)21-18(22-16)20-10-12-7-13(11-20)9-14(20)8-12/h12-14H,3-11H2,1-2H3,(H,21,22)

Upstream product

• 81250-34-2 1,3-dipropyl-5,6-diaminouracil 
• 16200-53-6 3-noradamantanecarboxylic acid 
• 67064-09-9 3-noradamantanecarboxylic acid chloride 
• 81250-33-1 1,3-di-n-propyl-5-nitroso-6-aminouracil 
• 136199-22-9 Hexahydro-2,5-methano-pentalene-3a-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide 

Relevant academic research and scientific papers

Convenient one-pot synthesis of 8-substituted xanthines from 6-amino-5- nitrosouracils

C-8 substituted 1,3-dipropylxanthines are typically prepared by reduction of the aminonitrosouracil 2 to the corresponding diamine, which is acylated and then treated with strongly basic or dehydrating reagents to afford the xanthine 1. Working to discover a milder, more efficient, reaction sequence it was found that the C-6 amino group of 2 can be acylated, and that treatment of the resulting compounds with Sn(OAc)2 gave 8-substituted xanthines. Overall, a one-pot conversion of the aminonitrosouracil 2 to dipropylxanthines 1a-i was achieved involving in situ acylation, reduction, and cyclodehydration. These conditions can be used to generate the imidazole substructure in the presence of acid and base sensitive groups on the C-8 position that may be problematic the conventional three-step xanthine syntheses.

XANTHINE DERIVATIVES

Novel xanthine compounds represented by the following formula: STR1 wherein each of X 1 and X 2 independently represents oxygen or sulfur; and Q represents; STR2 where-----represents a single bond or a double bond; Y represents a single bond or alkylene, n represents 0 or 1, each of W 1 and W 2 independently represents hydrogen, lower alkyl or amino, Z represents--CH 2-,--O--,--S--or--NH--; represents STR3 each of R 1 and R 2 independently represents hydrogen, lower alkyl, allyl or propargyl; and R 3 represents hydrogen or lower alkyl, and when Q represents the groups other than STR4 each of R 1, R 2 and R. sup.3 independently represents hydrogen or lower alkyl; provided that when Q is STR5 then R 1 R 2 and R 3 are not simultaneously methyl; and pharmaceutically acceptable salts thereof have a diuretic effect, a renal-protecting effect and a bronchodilatory effect.

8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for A1-adenosine receptors

With the aim of characterizing the hydrophobic interactions between xanthines and the A1 receptor site, 1,3-dipropyl-8-substituted xanthines were synthesized. Introduction of a quaternary carbon and the conformationally restricted cyclopentyl moiety into the 8-position of xanthines enhanced the adenosine A1 antagonism. 1,3-Dipropyl-8-(3- noradamantyl)xanthine (42) was identified to be a selective and the most potent A1 receptor antagonist reported to date. Under our structure-activity relationship, the 8-substituent of xanthine antagonists and the N6- substituent of adenosine agonists appears to bind to the same region of the A1 receptor.