5614-56-2

Usage

Central nervous system stimulant

It serves as a central nervous system stimulant.

Diuretic effects

Theophylline has diuretic effects, helping the body eliminate excess fluid.

InChI:InChI=1/C9H10N4O4/c1-11-4-10-7-6(11)8(16)13(3-5(14)15)9(17)12(7)2/h4H,3H2,1-2H3,(H,14,15)/p-1

Upstream product

• 83-67-0 theobromine / 
• 79-11-8 chloroacetic acid 
• 75449-03-5 (3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-purine-1-yl) acetic acid ethyl ester 

Downstream Products

• 169563-63-7 1,2,3,6-Tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purine-7-acetic acid 2-(1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purin-7-yl)ethyl ester 
• 169563-66-0 N-(1-Acetyl-2,3,6,7-tetrahydro-3,7-dimethyl-2,6-dioxo-1H-purine)-N,N'-dicyclohexylurea 
• 169563-64-8 2,3,6,7-Tetrahydro-3,7-dimethyl-2,6-dioxo-1H-purine-1-acetic acid 2-(1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purin-7-yl)ethyl ester 

Relevant academic research and scientific papers

N-(4-Arylpiperazinoalkyl)acetamide derivatives of 1,3- and 3,7-dimethyl-1H-purine-2,6(3H,7H)-diones and their 5-HT6, 5-HT7, and D2 receptors affinity

A series of N-(arylpiperazinyl)acetamide derivatives of 1,3- and 3,7-dimethyl-1H-purine-2,6(3H,7H)-dione was synthesized and biologically evaluated in in vitro competition binding experiments for serotonin 5-HT6, 5-HT7, and dopamine D2 receptors. The structure-affinity relationships for this group of compounds allowed for determination of structural features responsible for receptor affinity. Among the investigated derivatives, compounds 5 and 12 with (2,3-dichlorophenyl)piperazine moiety were classified as potent dual 5-HT6/D2 receptors ligands, whereas compound 4, with 4-(benzo[d]isothiazol-3-yl)piperazine moiety, and compounds 8 and 15, with (2,3-dichlorophenyl)piperazine moiety, were classified as potent D2 receptor ligands.

Discovery of the theobromine derivative MQS-14 that induces death of MGC-803 cells mainly through ROS-mediated mechanisms

Reactive oxygen species (ROS) play crucial roles in maintaining redox balance and regulating physiological processes, ROS levels in cancer cells are relatively higher than those in normal cells. Therefore, elevating cellular ROS levels may be a viable strategy for selective killing of cancer cells. In this work, we synthesized a series of new theobromine derivatives and evaluated their cytotoxicity against gastric cancer cells MGC-803, SGC-7901 and HGC-27. Particularly, MQS-14 potently inhibited cell growth of MGC-803, SGC-7901 and HGC-27 cells at low micromolar levels. Mechanistic studies showed that compound MQS-14 decreased cell viability of MGC-803 cells and inhibited cell division revealed by the CFDA and EdU staining assays. MQS-14 increased cellular ROS levels and activated the MAPK pathway accompanied by the decreased p-ERK and increased p-JNK expression. MQS-14 also induced DNA damage and apoptosis in MGC-803 cells. To conclude, MQS-14 induced cell death of MGC-803 cells partly through elevating cellular ROS levels.

Xanthine LSD1 inhibitor and preparation method and application thereof

The invention belongs to the field of medicinal chemistry, and discloses a xanthine structure containing LSD1 inhibitor, a synthesizing method and related application. The xanthine LSD1 inhibitor is characterized in that the structure formula is shown in the description, wherein R1 is benzyl; R2 is 1-3 alkyl and carboxylic acid derivates; R3 is heteroatom substituted hexatomic ring. The LSD1 enzymatic activity detection result shows that the xanthine compound of such series is good in effect on inhibiting LSD1 and can be used as a lead compound, and on that basis, a novel LSD inhibitor is further designed (refer to Specification).

Synthesis and analgesic activity of 3,7-dimethylpurine-2,6-dion-1-yl derivatives of acetic and butanoic acid

Hydrazones are a group of compounds possessing diversified biological activity, anti-inflammatory and analgesic activities. There are also known xanthine derivatives possessing such activity. The aim of our study was to investigate if introduction of hydrazone moiety to 3,7-dimethylpurine-2,6-dion-1-yl acetic and butanoic acid derivatives would enhance the analgesic activity. The designed series of compounds were synthesized in a multi-step procedure. Their pharmacological activity was investigated in the writhing syndrome test. Based on the results the structure-activity relationship was discussed. From the synthesized group of twenty compounds, nineteen were tested in vivo. The analgesic activity of most compounds, except for compound 4, was higher than for acetylsalicylic acid in the writhing syndrome test. Our study showed that the introduction of hydrazone moiety generally enhances analgesic activity of xanthine derivatives, compared to derivatives with free carboxylic group, ester, benzylamide and hydrazide moieties. The presence of hydroxyl moiety or substituent with high electron density does not seem to be necessary for the activity of hydrazone derivatives