6972-82-3

Basic information

• Product Name: 5,6-Diamino-1-methyluracil
• Synonyms: 5,6-DIAMINO-1-METHYLURACIL;5,6-Diamino-1-methyl-2,4(1H,3H)-pyrimidinedione;5,6-Diamino-1-methyluracil ,97%;5,6-Diamino-1-methylpyrimidine-2,4(1H,3H)-dione;5,6-diaMino-1-Methyl-1,2,3,4-tetrahydropyriMidine-2,4-dione;1-Methyl-5,6-diaminouracil;5,6-diamino-1-methyl-pyrimidine-2,4-dione;5,6-diamino-1-methylpyrimidine-2,4-dione
• CAS NO: 6972-82-3
• Molecular Formula: C₅H₈N₄O₂
• Molecular Weight: 156.14
• Mol File: 6972-82-3.mol
• Article Data: 32

Chemical Properties

• Melting Point: 270°C(lit.)
• Appearance: /
• Density: 1.407 g/cm³
• Refractive Index: 1.582
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.18±0.40(Predicted)
• CAS DataBase Reference: 5,6-Diamino-1-methyluracil(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Diamino-1-methyluracil(6972-82-3)
• EPA Substance Registry System: 5,6-Diamino-1-methyluracil(6972-82-3)

Safety Data

• Hazard Codes: F
• Statements: 36/37/38-10
• Safety Statements: 26-36/37/39-16
• HazardClass: IRRITANT
• Hazardous Substances Data: 6972-82-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow solid

Uses

6-Diamino-1-methyluracil is used to prepare tyrosine kinase erythropoietin inhibitors producing hepatocellular carcinoma receptor B4 (EphB4).

InChI:InChI=1/C5H8N4O2/c1-9-3(7)2(6)4(10)8-5(9)11/h6-7H2,1H3,(H,8,10,11)

Upstream product

• 6972-78-7 6-amino-1-methyl-5-nitrosouracil 
• 54058-36-5 6-amino-1-methyl-5-phenylazo-1H-pyrimidine-2,4-dione 
• 2434-53-9 6-amino-1-methyluracil 
• 50996-12-8 6-amino-1-methyl-5-nitro-1H-pyrimidine-2,4-dione 
• 6972-77-6 N-cyanoacetyl-N'-methyl-urea 

Downstream Products

• 1076-22-8 3-methylxanthine 
• 14785-95-6 3-methyl-4-amino-5-formylamino-2,6-dioxypyrimidine 
• 605-99-2 3-methyluric acid 
• 55441-55-9 (6-amino-1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-carbamic acid ethyl ester 
• 50256-18-3 1-methyl-2,4-dioxo-(1H,3H)pteridine 
• 19845-24-0 1-methyl-6,7-diphenyllumazine 
• 50256-21-8 1,6,7-trimethyl-2,4-dioxo-(1H,3H)pteridine 
• 62700-61-2 4-methyl-4H-[1,2,5]thiadiazolo[3,4-d]pyrimidine-5,7-dione 
• 172751-05-2 6,7-diethyl-1-methylpteridine-2,4-dione 
• 543700-00-1 6-amino-1-methyl-5-[(2,3,5-tichlorobenzylidene)amino]-1H-pyrimidin-2,4-dione 
• 61885-33-4 6-Amino-5-{[1-(4-chloro-phenyl)-meth-(E)-ylidene]-amino}-1-methyl-1H-pyrimidine-2,4-dione 
• 61885-32-3 6-Amino-1-methyl-5-{[1-phenyl-meth-(E)-ylidene]-amino}-1H-pyrimidine-2,4-dione 
• 2083-04-7 4-methyl-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione 
• 172751-10-9 4-(4-Methyl-5,7-dioxo-4,5-dihydro-7H-[1,2,5]thiadiazolo[3,4-d]pyrimidin-6-yl)-butyric acid ethyl ester 

Relevant articles and documents

Synthesis and bio-evaluation of a novel selective butyrylcholinesterase inhibitor discovered through structure-based virtual screening

In recent years, butyrylcholinesterase (BChE) has gradually gained worldwide interests as a novel target for treating Alzheimer's disease (AD). Here, two pharmacophore models were generated using Schr?dinger suite and used to virtually screen ChemDiv database, from which three hits were obtained. Among them, 2513–4169 displayed the highest inhibitory activity and selectivity against BChE (eeAChE IC50 > 10 μM, eqBChE IC50 = 3.73 ± 1.90 μM). Molecular dynamic (MD) simulation validated the binding pattern of 2513–4169 in BChE, and it could form a various of receptor-ligand interactions with adjacent residues. In vitro cytotoxicity assay proved the safety of 2513–4169 on diverse neural cell lines. Moreover, the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) assay performed on SH-SY5Y cells proved the neuroprotective effect of 2513–4169 against toxic Aβ1–42. In vivo behavioral study further confirmed the great efficacy of 2513–4169 on reversing Aβ1–42-induced cognitive impairment of mice and clearing the toxic Aβ1–42 in brains. Moreover, 2513–4169 was proved to be able to cross blood-brain barrier (BBB) through a parallel artificial membrane permeation assay of BBB (PAMPA-BBB). Taken together, 2513–4169 is a promising lead compound for future optimization to discover anti-AD treating agents.

Novel, Dual Target-Directed Annelated Xanthine Derivatives Acting on Adenosine Receptors and Monoamine Oxidase B

Annelated purinedione derivatives have been shown to act as possible multiple-target ligands, addressing adenosine receptors and monoaminooxidases. In this study, based on our previous results, novel annelated pyrimido- and diazepino[2,1-f]purinedione derivatives were designed as dual-target-directed ligands combining A2A adenosine receptor (AR) antagonistic activity with blocking monoamine oxidase B. A library of 19 novel compounds was synthesized and biologically evaluated in radioligand binding studies at AR subtypes and for their ability to inhibit MAO-B. This allowed 9-(2-chloro-6-fluorobenzyl)-3-ethyl-1-methyl-6,7,8,9-tetrahydropyrimido[2,1-f]purine-2,4(1H,3H)-dione (13 e; Ki human A2AAR: 264 nM and IC50 human MAO-B: 243 nM) to be identified as the most potent dual-acting ligand from this series. ADMET parameters were estimated in vitro, and analysis of the structure-activity relationships was complemented by molecular-docking studies based on previously published X-ray structures of the protein targets. Such dual-acting ligands, by selectively blocking A2A AR, accompanied by the inhibition of dopamine metabolizing enzyme MAO-B, might provide symptomatic and neuroprotective effects in, among others, the treatment of Parkinson disease.

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