118024-67-2

Usage

InChI:InChI=1/C9H12N4O2/c1-3-4-13-7-6(10-5-11-7)8(14)12(2)9(13)15/h5H,3-4H2,1-2H3,(H,10,11)

Upstream product

• 64-18-6 formic acid 
• 116545-97-2 5,6-Diamino-3-methyl-1-n-propyluracil 
• 141357-40-6 1-methyl-3-propyl-9-aminoxanthine 
• 125292-26-4 N-(6-Amino-3-methyl-2,4-dioxo-1-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-formamide 
• 141357-44-0 1-methyl-3-propyl-9-benzylideneaminoxanthine 
• 141357-42-8 potassium salt of 1-methyl-9-benzylideneaminoxanthine 
• 53681-48-4 6-amino-3-methyl-1-propyl-1H-pyrimidine-2,4-dione 
• 38014-52-7 N-methyl-N'-propylurea 
• 116545-96-1 6-amino-3-methyl-5-nitroso-1-n-propyluracil 

Relevant academic research and scientific papers

Effects of Alkyl Substitutions of Xanthine Skeleton on Bronchodilation

Structure-activity relationships in a series of 1,3,7-trialkyl-xanthine were studied with guinea pigs.Relaxant actions in the tracheal muscle were increased with alkyl chain length at the 1- and 3-positions of the xanthine skeleton, but decreased by alkylation at the 7-position.Positive chronotropic actions in the right atrium were potentiated with 3-alkyl chain length but tended to decrease with 1-alkylation and diminish by 7-substitution.Consequently, while the 1- and 3-substitutions were equally important for the tracheal smooth muscle relaxation, the substitution at the 1-position was more important than the 3-substitution for bronchoselectivity.The 7-alkylation may be significant to cancel heart stimulation.There were good correlations between the smooth muscle relexant action and the cyclic AMP-PDE inhibitory activity in 3-substituents and the affinity for adenosine (A1)receptors in 1-,3-, and 7-substituents.This suggests that not only the cyclic AMP-PDE inhibitory activity but also the adenosine antagonistic activity is important in the bronchodilatory effects of alkylxanthines.Among these xanthine derivatives, 1-butyl-3-propylxanthine and its 7-methylated derivative showed high bronchoselectivity in the in vitro and in vivo experiments compared to theophylline and enprofylline and may be new candidates for bronchodilator.

PURINES, PYRIMIDINES AND CONDENSED SYSTEMS BASED ON THEM. VIII. A NEW METHOD OF SYNTHESIS OF 1-METHYL-3-R-XANTHINES

A method of synthesis of difficult to obtain 1-methyl-3-R-xanthines has been developed, starting from the recently synthesized 1-methyl-9-benzylideneaminoxanthine.A potassium salt of the latter is readily alkylated in an absolute DMFA medium with the form

Structure-activity relationships in a series of xanthine derivatives with antibronchoconstrictory and bronchodilatory activities

Thirty-one 1,3,7,8-substituted xanthine derivatives have been synthesized and evaluated for bronchodilator and anti-bronchoconstrictory activities in in vitro tracheal relaxation and in vivo bronchospasm inhibition models. Activity tests have been complemented with phosphodiesterase inhibition and toxicological data. Structure-activity relationships are discussed. Compound 21 (1,3-diisobutyl-8-methylxanthine) has been selected for further pharmacological development because of its good activity profile and favourable therapeutic index, which is 14- and 38-fold greater than that of theophylline and IBMX, respectively.