6306-73-6

Basic information

• Product Name: 1-benzyl-5-methyl-pyrimidine-2,4-dione
• Synonyms: 1-benzyl-5-methyl-pyrimidine-2,4-dione;1-benzyl-5-methyl-2,4-pyrimidinedione
• CAS NO: 6306-73-6
• Molecular Formula: C₁₂H₁₂N₂O₂
• Molecular Weight: 216.24
• Mol File: 6306-73-6.mol

Chemical Properties

• Appearance: /
• Density: 1.227g/cm³
• Refractive Index: 1.585
• CAS DataBase Reference: 1-benzyl-5-methyl-pyrimidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-5-methyl-pyrimidine-2,4-dione(6306-73-6)
• EPA Substance Registry System: 1-benzyl-5-methyl-pyrimidine-2,4-dione(6306-73-6)

Safety Data

• Hazardous Substances Data: 6306-73-6(Hazardous Substances Data)

Usage

Molecular structure

Pyrimidine derivative with a benzyl group on position 1 and a methyl group on position 5

Potential biological activities

May be used in pharmaceutical research and drug development

Pharmacokinetic properties

Benzyl group imparts lipophilicity, affecting the compound's pharmacokinetic properties

Biological activity

Influenced by the presence of the benzyl and methyl groups, which can affect interactions with biological targets

Therapeutic applications

Of interest for potential pharmacological properties and may have applications in the development of new therapeutic agents

InChI:InChI=1/C12H12N2O2/c1-9-7-14(12(16)13-11(9)15)8-10-5-3-2-4-6-10/h2-7H,8H2,1H3,(H,13,15,16)

Upstream product

• 254887-27-9 (cis)-1-benzoyloxy-4-benzyloxy-2-butene 
• 128741-83-3 (cis)-1-benzyloxy-4-(tert-butyldimethyl)silyloxy-2-butene 
• 100-51-6 benzyl alcohol 
• 4330-20-5 N-3-benzoylthymine 
• 100-39-0 benzyl bromide 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 65-71-4 thymin 
• 25902-91-4 2-methoxy-5-methylpyrimidin-4(3H)-one 
• 4010-63-3 1-benzyl-5-methyl-dihydro-pyrimidine-2,4-dione 

Downstream Products

• 186387-21-3 1-benzyl-3-(3-chloropropyl)-5-methyl-2,4(1H,3H)-pyrimidinedione 
• 186387-77-9 1-benzyl-3-(1-cyanocycloprop-1-ylmethyl)-5-methyl-2,4(1H,3H)-pyrimidinedione 
• 1418746-20-9 2-(3-benzyl-5-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-1-yl)-N-phenylacetamide 
• 190069-78-4 4-(3-Benzyl-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl)-5-pyrrolidin-1-yl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester 
• 190069-80-8 4-(3-Benzyl-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl)-isoxazole-3-carboxylic acid ethyl ester 
• 190069-71-7 3-(3-Benzyl-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-propionaldehyde 
• 186385-55-7 1-benzyl-5-methyl-3-(1-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperazin-1-ylmethyl}-cyclopropylmethyl)-1H-pyrimidine-2,4-dione 
• 592527-10-1 1-benzyl-5-methyl-3-(3-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperazin-1-yl}-propyl)-1H-pyrimidine-2,4-dione 
• 232953-52-5 RS-100329 
• 186387-75-7 1-(1-benzyl-5-methyl-2,4-dioxo-(1H,3H)-pyrimidin-3-ylmethyl)cycloprop-1-ylmethyl methanesulfonate 
• 186387-78-0 1-(1-benzyl-5-methyl-2,4-dioxo-(1H,3H)-pyrimidin-3-ylmethyl)-1-cyclopropanecarboxylic acid 
• 186387-79-1 1-(1-benzyl-5-methyl-2,4-dioxo-(1H,3H)-pyrimidin-3-ylmethyl)cycloprop-1-ylmethanol 
• 190069-68-2 1-Benzyl-3-(3-hydroxy-propyl)-5-methyl-1H-pyrimidine-2,4-dione 
• 190069-65-9 1-Benzyl-3-(2-[1,3]dioxolan-2-yl-ethyl)-5-methyl-1H-pyrimidine-2,4-dione 

Relevant articles and documents

Molecular recognition in structured matrixes: Control of guest localization in block copolymer films

We demonstrate the use of molecular recognition to control the spatial distribution of guest molecules within block copolymer films. Block copolymers bearing recognition units were combined with complementary and noncomplementary molecules, and the extent

3-Hydroxypyrimidine-2,4-diones as an Inhibitor Scaffold of HIV Integrase

Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). Inhibitors with a novel structure core are essential for combating resistance associated with known IN inhibitors (INIs). We have previously disclosed a novel dual inhibitor scaffold of HIV IN and reverse transcriptase (RT). Here we report the complete structure-activity relationship (SAR), molecular modeling, and resistance profile of this inhibitor type on IN inhibition. These studies support an antiviral mechanism of dual inhibition against both IN and RT and validate 3-hydroxypyrimidine-2,4-diones as an IN inhibitor scaffold.

DNA-protein cross-linking: Model systems for pyrimidine-aromatic amino acid cross-linking

We have synthesized simple model systems to explore the possibility of photo-cross-linking between the pyrimidine bases and the side chains of the aromatic amino acids. Thymine/phenylalanine and thymine/tyrosine models gave cross-links, and thymine/tryptophan models gave complex mixtures; the cytosine/phenylalanine model was unreactive. The quantum yields for the model cross-linking reactions were 18-46 times smaller than those for thymine dimer formation. Biphotonic excitation contributes little to the yield of these reactions.

Synthesis of carbocyclic pyrimidine nucleosides using the Mitsunobu reaction - Part I: Influence of the alcohol on N1- versus O2- alkylation

The Mitsunobu reaction is an important tool in carbocyclic nucleoside chemistry for the direct coupling of alcohols with heterocyclic bases under mild conditions. Here, we report on the influence of the alcohol on the N1- vs. O2-alkylation of N

Synthesis, pharmacology and pharmacokinetics of 3-(4-Arylpiperazin-1-ylalkyl)-uracils as uroselective α1A-antagonists

Predominance in the urethra and prostate of the α1A-adrenoceptor subtype, which is believed to be the receptor mediating noradrenaline induced smooth muscle contraction in these tissues, led to the preparation of α1A-selective antagonists to be tested as uroselective compounds for the treatment of benign prostatic hyperplasia. Thus, a number of selective α1A-adrenoceptor antagonists were synthesized and assayed in vitro for potency and selectivity. Dog pharmacokinetic parameters of 12 (RO700004) and its metabolite 40 (RO1104253) were established. The relative selectivity of intravenously administered 12, 40 and standard prazosin to inhibit hypogastric nerve stimulation-induced increases in intraurethral prostatic pressure versus phenylephrine-induced increases in diastolic blood pressure in anesthetized dogs was 76, 71 and 0.6, respectively.

Synthesis of new nucleoside analogues comprising a geminal difluorocyclopropane moiety as potential antiviral/antitumor agents

Geminal difluorocyclopropane analogues of nucleosides 7a - 7e were synthesized. Compounds 7a and 7c - 7e were obtained by alkylation of nucleic acid bases or their appropriate precursors with (cis)-1- benzyloxymethyl-2-bromomethyl-3,3-difluorocyclopropane (8). Analogue 7b was prepared by hydrolysis of 2-amino-6-chloropurine derivative 7e. Compounds 7a - 7d did not exhibit any antiviral activity against HCMV, HSV-1, HSV-2, EBV, VZV, HBV and HIV-1 or antitumor effects against murine leukemia L1210, mouse tumors PO3 or C38 and human tumor H15.

HSAB driven chemoselectivity in alkylation of uracil derivatives. A high yielding preparation of 3-alkylated and unsymmetrically 1,3-dialkylated uracils

A qualitative hardness scale (N134) has been found for the conjugated bases of 2-methoxy-4(3H)-pyrimidinones 1-3 and applied to high yielding chemoselective N3 methylation, ethylation and benzylation reactions. Removal of the 2-methoxy group followed by a second alkylation affords unsymmetrically 1,3-disubstituted uracils.