1122-47-0

Usage

Uses

Used in Pharmaceutical Industry:
1-METHYLCYTOSIN is used as a therapeutic agent for its potential role in the treatment of certain diseases. The methylation at the nitrogen position 1 may provide distinct advantages over the parent compound, cytosine, in terms of stability, bioavailability, and interaction with biological targets.
Used in Research and Development:
1-METHYLCYTOSIN serves as a valuable compound in the field of research and development, particularly in the study of nucleic acid structure, function, and interactions. Its unique chemical properties allow for the investigation of various biological processes and the development of novel therapeutic strategies.
Used in Chemical Synthesis:
As a modified nucleoside, 1-METHYLCYTOSIN can be utilized as a key building block or intermediate in the synthesis of more complex molecules, such as nucleic acid analogs, modified oligonucleotides, and other bioactive compounds. Its unique structure may offer advantages in the development of new drugs and therapeutic agents.
Used in Diagnostic Applications:
The distinct chemical and biological properties of 1-METHYLCYTOSIN may also find applications in the development of diagnostic tools and assays. Its ability to interact with specific biological targets could be harnessed for the detection and monitoring of various diseases and conditions.

InChI:InChI=1/C5H7N3O/c1-8-3-2-4(6)7-5(8)9/h2-3H,1H3,(H2,6,7,9)

Upstream product

• 35455-86-8 1-methyl-4-thiouracil 
• 71-30-7 Cytosine 
• 74-88-4 methyl iodide 
• 7152-66-1 1-methyl-4-methoxy-2-oxo-1,2-dihydropyrimidine 
• 512-56-1 trimethyl phosphite 
• 10504-60-6 diphenylmethylsulfonium tetrafluoroborate 
• 616-38-6 carbonic acid dimethyl ester 
• 77738-01-3 N⁴-<(Dimethylamino)methylene>-1-methylcytosine 
• 6749-83-3 1-methylcytosine hemihydroiodide 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 615-77-0 1-methyluracil 
• 77738-01-3 4-N-(N,N-dimethyl-aminomethylene)-1-methylcytosine 

Downstream Products

• 108850-47-1 3,4,5-trimethoxy-benzoic acid-(1-methyl-2-oxo-1,2-dihydro-pyrimidin-4-ylamide) 
• 71937-96-7 4-benzoylamino-1-methyl-1H-pyrimidin-2-one 
• 111664-87-0 3-benzoyl-4-benzoylimino-1-methyl-3,4-dihydro-1H-pyrimidin-2-one 
• 100115-28-4 1-methyl-N₄-( p-toluenesulfonyl)cytosine 
• 64966-90-1 1-methyl-4-phenylhydrazino-2-pyrimidone 
• 185846-28-0 2-[(1-Methyl-2-oxo-1,2-dihydro-pyrimidin-4-ylamino)-methylene]-malonaldehyde 

Relevant academic research and scientific papers

One-Electron Redox Potentials of Purines and Pyrimidines

One-electron redox potentials of some purine and pyrimidine derivatives were determined by pulse radiolysis from electron transfer equilibria involving their and other free radicals.The redox potentials were determined at pH 13 by using p-methoxyphenol (E=0.4 V), Trolox C (E=0.19 V), and tryptophan (E=0.56 V) as references.The lowest oxidation potential measured for DNA bases was guanosine (E=0.72 V vs.NHE), and the highest was for 1-methylpyrimidines (E ca. 1.6 V) Uric acid (E=0.26 V) and isobarbituric acid (E=0.13 V) were found to have the lowest potentials.

Cytosine modules in quadruple hydrogen bonded arrays

Cytosine modules have been investigated for applications in supramolecular quadruple hydrogen bonded arrays. Notably, the importance of the C-5-H in the formation of unfolded and folded arrays by substitution to C-5-F was established. In addition, the incorporation of different alkyl chain lengths at N-1 and N-9 indicated that longer alkyl chains give rise to more of the unfolded rotamer, with the chain length and degree of unsaturation at N-1 having the major effect. Methyl cytosine modules were also able to readily form hetero-associated Upy-UCyt dimers as efficiently as the hexyl cytosine modules and a polyadipate telechelic polymer was used to prepare cytosine polymers.

Gas-phase tautomers of protonated 1-methylcytosine. Preparation, energetics, and dissociation mechanisms

Tautomers of 1-methylcytosine that are protonated at N-3 (1+) and C-5 (2+) have been specifically synthesized in the gas phase and characterized by tandem mass spectrometry and quantum chemical calculations. Ion 1+ is the most stable tautomer in aqueous and methanol solution and is likely to be formed by electrospray ionization of 1-methylcytosine and transferred in the gas phase. Gas-phase protonation of 1-methylcytosine produces a mixture of 1+ and the O-2-protonated tautomer (3+), which are nearly isoenergetic. Dissociative ionization of 6-ethyl-5,6-dihydro-1- methylcytosine selectively forms isomer 2+. Upon collisional activation, ions 1+ and 3+ dissociate by loss of ammonia and [C,H,N,O], whose mechanisms have been established by deuterium labeling and ab initio calculations. The main dissociations of 2+ following collisional activation are losses of CH2=C=NH and HN=C=O. The mechanisms of these dissociations have been elucidated by deuterium labeling and theoretical calculations. Copyright

SUBSTITUTED IMIDAZOPYRIMIDIN-5(6H)-ONES AS ALLOSTERIC MODULATORS OF MGLUR5 RECEPTORS

In one aspect, the invention relates to imidazopyrimidin-5(6H)-one analogs, derivatives thereof, and related compounds, which are useful as positive allosteric modulators of the metabotropic glutamate receptor subtype 5 (mGluR5); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with glutamate dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

SUBSTITUTED IMADAZAPYRINIDIN-5(6H)-ONES AS ALLOSTERIC MODULATORS OF MGLUR5 RECEPTORS

In one aspect, the invention relates to imidazopyrimidin-5(6H)-one analogs, derivatives thereof, and related compounds, which are useful as positive allosteric modulators of the metabotropic glutamate receptor subtype 5 (mGluR5); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with glutamate dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Universal Base

The present invention provides artificial universal base capable of base pairing nonspecifically with any of four kinds of natural nucleic acid bases (A, T, G, and C) without the function to specifically recognize pairing natural nucleic acid bases for base pair formation. Universal base capable of base paring nonspecifically with four kinds of natural nucleic acid bases, wherein the universal base has a structure represented by the following chemical formula: wherein R represents a monovalent group other than a hydrogen atom.

Synthesis of modified pyrimidine bases and positive impact of chemically reactive substituents on their in vitro antiproliferative activity

The antiproliferative activity screening on human tumor cell lines of a series of modified uracil and cytosine bases as well as some corresponding acyclonucleosides, and comparison of structure-activity relationship revealed the importance of chemical rea

Novel synthetic route to 1-substituted cytosines

1-Alkylcytosines, cytidine and 2'-deoxy-5-methylcytidine were synthesized in good yields from appropriate 1-alkyluracils, uridine or thymidine derivatives by hydrogenation of 6-substituted tetrazolo[1,5-c]pyrimidin-5(6H)-ones 2 over 10% palladium on charcoal in methanol. Compounds 2 were obtained by the reaction of 1-substituted uracils 1 with sodium azide and phosphorus oxychloride in acetonitrile.

Reactions with Dimethyl Carbonate, 5 Methylation of the Pyrimidine Bases of Nucleic Acids

The methylation of the pyrimidine bases of nucleic acids by dimethyl carbonate is described compared to dimethyl sulphate.The reaction needs higher temperature, a base and the help of 18-crown-6 and DMF as cosolvent. - Keywords: Dimethyl Carbonate, Methylations, Pyrimidine Bases of Nucleic Acids

The efficiency of diphenylalkylsulfonium salts as alkylating agents

A series of the title reagents have been used for the alkylation of a number of nucleophiles including iodide, cyanide, thiocyanate and fluoride ions as well as ethyl acetoacetate, phenylacetonitrile and a variety of nitrogen heterocyclic compounds.The results compared favorably with literature methods.