5440-00-6

Usage

Uses

5,6-DIAMINO-1,3-DIMETHYL URACIL is used as a reactant in the synthesis of biologically active molecules for various applications in the pharmaceutical and chemical industries. 5,6-DIAMINO-1,3-DIMETHYL URACIL is involved in the creation of several types of molecules, each serving a specific purpose:
1. Used in Pharmaceutical Industry:
5,6-DIAMINO-1,3-DIMETHYL URACIL is used as a reactant for synthesizing 1H-Imidazol-1-yl substituted 8-phenylxanthines, which serve as adenosine receptor ligands. These ligands are crucial in the development of drugs targeting adenosine receptors, which are involved in various physiological processes, including cardiovascular function and neuroprotection.
2. Used in Organic Synthesis:
5,6-DIAMINO-1,3-DIMETHYL URACIL is used as a reactant for the synthesis of pyrimidinyl purinediones via cyclocondensation. These molecules have potential applications in the development of new drugs and pharmaceutical agents.
3. Used in Adenosine Receptor Antagonists:
5,6-DIAMINO-1,3-DIMETHYL URACIL is used as a reactant for the synthesis of theophylline derivatives, which act as adenosine receptor antagonists. These antagonists have potential applications in the treatment of various conditions, such as asthma, chronic obstructive pulmonary disease (COPD), and certain neurological disorders.
4. Used in Enzyme Inhibitors:
5,6-DIAMINO-1,3-DIMETHYL URACIL is used as a reactant for the synthesis of pteridine analogs, which serve as inhibitors for monoamine oxidase B (MAO-B) and nitric oxide synthase (NOS). These inhibitors are essential in the development of drugs targeting these enzymes, which are involved in various neurological and psychiatric disorders.
5. Used in Anticancer Applications:
5,6-DIAMINO-1,3-DIMETHYL URACIL is used as a reactant for the synthesis of fused tricyclic xanthines and cadmium uraciliminoethylpyridine complexes. These compounds have potential applications as antiproliferatives against C6 glioma cells, which are involved in the development of brain tumors.

Purification Methods

It recrystallises from EtOH. The hydrochloride has m 310o (from MeOH), and the perchlorate has m 246-248o. [UV: Bredereck et al. Chem Ber 92 583 1959, Taylor et al. J Am Chem Soc 77 2243 1955, Beilstein 25 III/IV 4133.]

InChI:InChI=1/C6H10N4O2/c1-9-4(8)3(7)5(11)10(2)6(9)12/h7-8H2,1-2H3

Upstream product

• 6632-68-4 6-amino-1,3-dimethyl-5-nitroso-1H-pyrimidine-2,4-dione 
• 7597-60-6 1,3-dimethyl-4-amino-5-(formylamino)uracil 
• 10184-41-5 5-acetylamino-6-amino-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 122707-25-9 6-amino-1,3-dimethyl-5-phenylazouracilate 
• 906428-70-4 1,3-dimethyl-5-nitro-6-hydrazinouracil 
• 3346-61-0 6-amino-1,3-dimethyl-5-nitro-1H-pyrimidine-2,4-dione 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 17743-04-3 1,3-dimethyl-6-iminouracil 
• 769-42-6 1,3-dimethylbarbituric acid 
• 6972-27-6 1,3-Dimethyl-6-chlorouracil 
• 1203-25-4 6-chloro-1,3-dimethyl-5-nitrouracil 
• 10184-42-6 5-acetylamino-6-amino-1-methyl-1H-pyrimidine-2,4-dione 
• 39615-79-7 1-(2-cyanoacetyl)-1,3-dimethyl-urea 
• 58537-55-6 1,3-dimethyl-6-imino-5-isonitrosouracil 

Downstream Products

• 7145-52-0 1,3-dimethyl-8-[2]thienylmethyl-3,7-dihydro-purine-2,6-dione 
• 109286-41-1 8-(4-chloro-benzyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 5770-30-9 8-Isobutyltheophyllin 
• 5429-31-2 8-(1-ethyl-propyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 2879-15-4 8-benzyltheophylline 
• 2879-16-5 8-hydroxymethyltheophylline 
• 5429-48-1 1,3-dimethyl-8-[1]naphthylmethyl-3,7-dihydro-purine-2,6-dione 
• 91130-03-9 1.3-Dimethyl-2.4.6-trioxo-hexahydropteridin-carbonsaeure-(7)-methylamid 
• 5429-45-8 acetic acid-[4-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-anilide] 
• 74039-62-6 8-allyltheophylline 
• 100144-13-6 N-(6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-lactamide 
• 964-45-4 1,3-dimethyl-7-phenyllumazine 
• 147699-92-1 1,3-dimethyl-8-(E)-styryl-3,7-dihydro-1H-purine-2,6-dione 
• 101092-80-2 4-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-benzoic acid 

Relevant academic research and scientific papers

5,6-amino -1,3-dihydrocarbyl substituted uracil and preparation method thereof (by machine translation)

The invention belongs to the technical field of fine chemical engineering, and particularly relates to 5,6 -amino - 1111,dihydrocarbyl substituted uracil and a preparation method, of the dihydrocarbyl-substituted uracil 5,6 - diamino - 1111, 3-dihydrocarbyl- R substituted uracil, 5,6 - as shown in Formula (I). 1 And R2 Hydrochloride gas 1 - 10, each independently selected from hydrogen or carbon chain lengths of, carbon atoms according to the present invention 5,6 - of the present invention PVC diamino - 1111, 3-dihydrocarbyl-substituted uracil capable of absorbing, degradation processes, can also produce synergistic effect PVC by substituting labile chlorine atoms, with zinc stearate and calcium stearate PVC in combination with zinc stearate and calcium stearate for PVC to have better stabilization effect, The process performance, is improved PVC DEG, with good, stabilization effect PVC in combination. Heat stability 5,6 - can also be produced by the method, of the PVC present invention, for PVC, % of the stable effect of the present invention. (by machine translation)

Synthesis method of theophylline

The invention discloses a synthesis method of theophylline, and relates to the technical field of preparation of heterocyclic compounds containing purine ring systems. The preparation method comprisesthe following steps: mixing cyanoacetic acid and acetic anhydride at 30-80 DEG C for reaction, adding a solvent and dimethylurea, cooling to room temperature after reflux reaction is finished, filtering, concentrating filtrate, combining solids to obtain dimethylacetamide, adding liquid caustic soda to adjust the pH to 8-11, and reacting at 80-100 DEG C to generate dimethyl 4AU; completely dissolving dimethyl 4AU in formic acid, adding sodium nitrite, reacting at room temperature, adding a catalyst and water, keeping the temperature at 30-70 DEG C, recovering the catalyst after the reaction is finished, and concentrating mother liquor to recover formic acid, thereby obtaining dimethyl FAU; adding dilute sulfuric acid into the dimethyl FAU to adjust the pH value to 36, heating to 90-100 DEG C, allowing the feed liquid to pass through an ozone reactor and a decolorizer, crystallizing by a crystallizer, and carrying out cold filtration to obtain theophylline. The method has the advantages of few reaction steps, mild reaction conditions, simple operation, high yield, stable product quality, small discharge capacity, reduction of the environmental protection treatment difficulty, and easy industrialization.

Method for synthesizing caffeine

The invention discloses a method for synthesizing caffeine, and relates to the technical field of preparation of heterocyclic compounds containing purine ring systems. The preparation method comprisesthe following steps: mixing cyanoacetic acid and acetic anhydride at 30-80 DEG C for reaction, adding a solvent and dimethylurea, cooling to room temperature after reflux reaction is finished, filtering, concentrating filtrate, combining solids to obtain dimethylacetamide, adding liquid caustic soda to adjust the pH to 8-11, and reacting at 80-100 DEG C to generate dimethyl 4AU; the method comprises the following steps: completely dissolving dimethyl 4AU in formic acid, adding sodium nitrite, reacting at room temperature, adding a catalyst, keeping the temperature at 30-70 DEG C, recovering the catalyst after the reaction is finished, and concentrating mother liquor to recover formic acid, thereby obtaining dimethyl FAU; adding water and liquid caustic soda into dimethyl FAU, and carryingout a ring-closure reaction to obtain theophylline sodium salt; the theophylline sodium salt is subjected to methylation reaction and refining to obtain caffeine. The method has the advantages of accessible raw materials, mild and controllable reaction conditions, fewer steps, high yield and greatly higher product quality, is simple to operate, and can easily implement industrial production.

Preparation method of theophylline sodium salt

The invention relates to the technical field of pharmaceutical chemicals, and particularly discloses a preparation method of theophylline sodium salt. The preparation method of theophylline sodium salt comprises the following process steps: mixing cyanoacetic acid and acetic anhydride for reaction to obtain mixed anhydride, and performing a condensation reaction on the mixed anhydride and 1,3-dimethylurea to obtain 1,3-dimethyl cyanoacetylurea; sequentially carrying out cyclization, nitrosation, hydrogenation and acylation on the 1,3-dimethyl cyanoacetylurea to obtain 1,3-dimethyl-4-amino-5-formylamino uracil; subjecting the 1,3-dimethyl-4-amino-5-formylamino uracil to ring closing to obtain the theophylline sodium salt. According to the preparation method, the reaction conditions are mildand easy to control, the product yield is high, byproducts are few, strong ammonia gas smell is avoided, the cost is low, and generated pollution wastes are few.

Synthesis and biological evaluation of novel xanthine derivatives as potential apoptotic antitumor agents

A series of novel xanthine/NO donor hybrids containing 1,3,8-trisubstituted or 1,8-disubstituted xanthine derivatives were designed and synthesized. The synthesized compounds were tested in a cell viability assay using human mammary gland epithelial cell line (MCF-10A) where all the compounds exhibited no cytotoxic effects and more than 90% cell viability at a concentration of 50 μM. The oxime containing compounds 7a-b and 17-24 were more active as antiproliferative agents than their non-oxime congeners 6a-b and 9-16. Hydroxyimino-phenethyl scaffold compounds 17-24 were more active than the hydroxyimino-ethyl phenyl acetamide 7a-b derivatives. Compounds 18–20 and 22-24 exhibited inhibition of EGFR with IC50 ranging from 0.32 to 2.88 μM. Compounds 18-20 and 22-24 increased the level of active caspase 3 by 4–8 folds, compared to the control cells in Panc-1 cell lines compared to doxorubicin as a reference drug. Compounds 18, 22 and 23 were the most caspase-3 inducers. Compounds 22 and 23 increased the levels of caspase-8 and 9 indicating activation of both intrinsic and extrinsic pathways and showed potent induction of Bax, down-regulation of Bcl-2 protein levels and over-expression of cytochrome c levels in Panc-1 human pancreas cancer cells. Compound 23 exhibited mainly cell cycle arrest at the Pre-G1 and G2/M phases in the cell cycle analysis of Panc-1 cell line. The drug likeness profiles of compounds 18-20 and 22-24 were predicted to have good to excellent drug likeness profiles specially compounds 18-20 and 23. Finally molecular docking study was performed at the EGFR active site to suggest thier possible binding mode. The hydroxyimino-phenethyl scaffold compounds 17-24 represent an interesting starting point to optimize their pharmacokinetics and pharmacodynamics profiles.

EGFR inhibitors and apoptotic inducers: Design, synthesis, anticancer activity and docking studies of novel xanthine derivatives carrying chalcone moiety as hybrid molecules

One of the helpful ways to improve the effectiveness of anticancer agents and weaken drug resistance is to use hybrid molecules. therefore, the current study intended to introduce 20 novel xanthine/chalcone hybrids 9–28 of promising anticancer activity. Compounds 10, 11, 13, 14, 16, 20 and 23 exhibited potent inhibition of cancer cells growth with IC50 ranging from 1.0 ± 0.1 to 3.5 ± 0.4 μM compared to doxorubicin with IC50 ranging from 0.90 ± 0.62 to 1.41 ± 0.58 μM and that compounds 11 and 16 were the best. To verify the mechanism of their anticancer activity, compounds 10, 11, 13, 14, 16, 20 and 23 were evaluated for their EGFR inhibitory effect. The study results revealed that compound 11 showed IC50 = 0.3 μM on the target enzyme which is more potent than staurosporine reference drug (IC50 = 0.4 μM). Accordingly, the apoptotic effect of the most potent compounds 11 was extensively investigated and showed a marked increase in Bax level up to 29 folds, and down-regulation in Bcl2 to 0.28 fold, in comparison to the control. Furthermore, the effect of compound 11 on Caspases 3 and 8 was evaluated and was found to increase their levels by 8 and 14 folds, respectively. Also, the effect of compound 11 on the cell cycle and its cytotoxic effect were examined. Moreover, a molecular docking study was adopted to confirm mechanism of action.

Structural and conformational studies on carboxamides of 5,6-diaminouracils-precursors of biologically active xanthine derivatives

8-Arylethynylxanthine derivatives are potent, selective adenosine A2A receptor antagonists, which represent (potential) therapeutics for Parkinson's disease, Alzheimer's dementia, and the immunotherapy of cancer. 6-Amino-5-amidouracil derivatives are important precursors for the synthesis of such xanthines. We noticed an unexpected duplication of NMR signals in many of these uracil derivatives. Here, we present a detailed analytical study of structurally diverse 6-amino-5-carboxamidouracils employing dynamic and two-dimensional NMR spectroscopy, density functional theory calculations, and X-ray analysis to explain the unexpected properties of these valuable drug intermediates.

For the treatment of diabetes type II a pharmaceutical intermediates preparation method (by machine translation)

The invention belongs to the technical field of chemical industry, and in particular relates to a medicament for the treatment of diabetes type II intermediate preparation method. The invention to PdCl2 . 2 H2 O and ammonium metatungstate as precursor, the silicon nitride film as the catalyst carrier, depositing a - precipitation method to prepare a new kind of ammonium metatungstate modified palladium metal catalyst; said catalyst can be used for catalytic 6 - amino - 5 - nitroso - 1 - methyl uracil reduction preparation of 5, 6 - diamino - 1 - methyl uracil, high selectivity and conversion, green is pollution-free; at the same time the materials can be added one time, avoiding the traditional sodium dithionite reduction system batch add to the shortcoming of the operating requirement is high. (by machine translation)

N a caffeinum intermediate, N-1,3-dimethyl -4,5-b [...] method for the preparation of

The invention relates to a preparation method of the caffeine intermediate N,N-1,3-dimethyl-4,5-diamido urazine and belongs to the technical field of synthesis and preparation of organic compounds. According to the preparation method, a hydrogen addition reaction is carried out under heated and pressurized conditions with N,N-1,3-dimethyl-4-imido-5-isonitroso urazine as the starting material and raney nickel as the catalyst, an aqueous solution containing metal halide and alkaline substances is used as the reaction medium, the preparation method has the advantages of being smooth and controllable in reaction, high in catalytic activity and stable in quality of dimethyl-DAU, and the yield and the quality of the dimethyl-DAU are improved.

Synthesis and Evaluation of a New Series of 8-(2-Nitroaryl)Xanthines as Adenosine Receptor Ligands

(Table presented.). A new series of 1,3-dimethylxanthine derivatives bearing 8-(2-nitroaryl) residue was synthesized and evaluated for affinity for recombinant human adenosine receptors subtypes. Nitrate esters of 7-substituted-1,3-dimethyl-8-phenylxanthines were also synthesized and tested. Introducing a nitro substituent at the 2-position of the 8-substituted phenyl ring resulted in generally low affinity for adenosine receptors (ARs), selectivity toward the A2A subtype was enhanced in some of the compounds. 8-(4-Cyclopentyloxy-5-methoxy-2-nitrophenyl)-1,3-dimethylxanthine (9e) proved to be a potent compound among the 2-nitrophenyl substituted xanthines exhibiting a Ki = 1 μM at human A2A ARs with at least 30 fold selectivity versus human A1 and A2B ARs. Replacement of 8-chloropropoxy phenyl with 8-nitrooxypropoxy phenyl resulted in a negligible change in binding affinity of the 8-substituted xanthines for various AR subtypes. Drug Dev Res 77 : 241–250, 2016.