155-15-7

Basic information

• Product Name: 5-FLUORO-1-METHYL-CYTOSINE
• Synonyms: 4-amino-5-fluoro-1-methyl-pyrimidin-2-one;4-amino-5-fluoro-1-methylpyrimidin-2-one;4-azanyl-5-fluoro-1-methyl-pyrimidin-2-one;4-AMino-5-fluoro-1-MethylpyriMidin-2(1H)-one;5-FLUORO-1-METHYL-CYTOSINE
• CAS NO: 155-15-7
• Molecular Formula: C5H6FN3O
• Molecular Weight: 143.1190432
• Mol File: 155-15-7.mol

Chemical Properties

• Boiling Point: 209 °C at 760 mmHg
• Flash Point: 80.2 °C
• Appearance: /
• Density: 1.49 g/cm³
• Vapor Pressure: 0.207mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 5-FLUORO-1-METHYL-CYTOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FLUORO-1-METHYL-CYTOSINE(155-15-7)
• EPA Substance Registry System: 5-FLUORO-1-METHYL-CYTOSINE(155-15-7)

Safety Data

• Hazardous Substances Data: 155-15-7(Hazardous Substances Data)

Usage

Uses

Used in Antiviral Applications:
5-Fluoro-1-methyl-cytosine is used as an antiviral agent for its ability to inhibit the replication of certain viruses. The presence of the fluorine and methyl groups alters the compound's interaction with viral enzymes, leading to the disruption of viral replication processes.
Used in Anticancer Applications:
5-Fluoro-1-methyl-cytosine is used as an anticancer agent due to its potential to inhibit the growth and proliferation of tumor cells. 5-FLUORO-1-METHYL-CYTOSINE may interfere with the synthesis and function of nucleic acids in cancer cells, thereby affecting their survival and division.
Used in Research Applications:
5-Fluoro-1-methyl-cytosine is used as a research tool in molecular biology and biochemistry for studying nucleic acid structure and function. Its unique chemical properties allow researchers to investigate the role of cytosine in various biological processes and to develop new strategies for manipulating nucleic acid behavior.
Used in Pharmaceutical Development:
5-Fluoro-1-methyl-cytosine is used in the development of new pharmaceuticals targeting viral and cancer-related diseases. Its potential as an antiviral and anticancer agent makes it a valuable compound for designing novel therapeutic agents with improved efficacy and selectivity.
Used in Biochemical Analysis:
5-Fluoro-1-methyl-cytosine is used in biochemical analysis to study the interactions between nucleic acids and other biomolecules. 5-FLUORO-1-METHYL-CYTOSINE's modified structure allows for the investigation of specific binding events and enzymatic activities, providing insights into the molecular mechanisms underlying various biological processes.

InChI:InChI=1/C5H6FN3O/c1-9-2-3(6)4(7)8-5(9)10/h2H,1H3,(H2,7,8,10)

Upstream product

• 66-27-3 Methyl methanesulfonate 
• 2022-85-7 4-amino-5-fluoro-pyrimidin-2-ol 
• 2022-85-7 5-fluorocytosine 
• 74-88-4 methyl iodide 
• 1122-47-0 1-methylcytosine 
• 72939-80-1 5-Fluoro-4-hydroxy-6-imino-tetrahydro-pyrimidin-2-one 
• 512-56-1 trimethyl phosphite 
• 2022-85-7 Flucytosine 

Relevant articles and documents

Flight of a cytidine deaminase complex with an imperfect transition state analogue inhibitor: Mass spectrometric evidence for the presence of a trapped water molecule

Cytidine deaminase (CDA) binds the inhibitor zebularine as its 3,4-hydrate (Kd ～ 10-12 M), capturing all but ～5.6 kcal/mol of the free energy of binding expected of an ideal transition state analogue (Ktx ～ 10-16 M). On the basis of its entropic origin, that shortfall was tentatively ascribed to the trapping of a water molecule in the enzyme-inhibitor complex, as had been observed earlier for product uridine [Snider, M. J., and Wolfenden, R. (2001) Biochemistry 40, 11364-11371]. Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS) of CDA nebularized in the presence of saturating 5-fluorozebularine reveals peaks corresponding to the masses of E2Zn2W2 (dimeric Zn-CDA with two water molecules), E2Zn2W2Fz, and E2Zn2W2Fz2, where Fz represents the 3,4-hydrate of 5-fluorozebularine. In the absence of an inhibitor, E 2Zn2 is the only dimeric species detected, with no additional water molecules. Experiments conducted in H218O indicate that the added mass W represents a trapped water molecule rather than an isobaric ammonium ion. This appears to represent the first identification of an enzyme-bound water molecule at a subunit interface (active site) using FTICR-MS. The presence of a 5-fluoro group appears to retard the decomposition of the inhibitory complex kinetically in the vapor phase, as no additional dimeric complexes (other than E2Zn2) are observed when zebularine is used in place of 5-fluorozebularine. Substrate competition assays show that in solution zebularine is released from CDA (koff > 0.14 s-1) much more rapidly than is 5-fluorozebularine (koff = 0.014 s-1), despite the greater thermodynamic stability of the zebularine complex.

Cytosine derivatives form hemiprotonated dimers in solution and the gas phase

Hemiprotonated dimers of cytosine derivatives, implicated in the formation of the i-motif of DNA, have been created in solution and the gas phase. The mechanism of dimerization has been analyzed by mass spectrometry and multidimensional NMR spectroscopy.

5-FLUOROPYRIMIDINONE DERIVATIVES

This present disclosure is related to the field of 5-fluoropyrimidinones and their derivatives and to the use of these compounds as fungicides.

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.

Glorination of Pyrimidines. Part 2. Mechanistic Aspects of the Reaction of Acetyl Hypofluorite with Uracil and Cytosine Derivatives

The reaction of acetyl hypofluorite (AcOF) with uracil, cytosine, and some N-1-substituted derivatives dissolved in either acetic acid or water has been investigated.Analysis by radio-h.p.l.c., using (18)f as a tracer, and by (1)H n.m.r. revealed that a substituent at N-1 of uracil has a remarkable effect on the stability of the intermediate 6-acetoxy-5-fluoro-5,6-dihydrouracils.In addition, it was found that these cytosine adducts rapidly deaminate in water yielding their corresponding uracil analogues.

Stereochemistry of the Formation of 4-Alkoxyimino-5,6-dihydro-6-alkoxyaminopyrimidin-2(1H)-ones from Cytosines and Hydroxylamines

High resolution 1H and 19F n.m.r. data together with deuterium labelling studies are presented which reveal that the addition of hydroxylamines across the 5,6-double bond of cytosines is predominantly trans.The 4-alkoxyimino-5,6-dihydro-6-alkoxyaminopyrimidin-2(1H)-one products show syn/anti isomerism about the 4-alkoxyimino-group dependent on the substituent at N(3) (H or Me, respectively) and conformational changes throughout the molecules which are dependent on the substituents at N(1) (H or Me) and C(5) (H or F).