26661-13-2

Basic information

• Product Name: N4-Benzoylcytosine
• Synonyms: Benzamide, N-(2,3-dihydro-2-oxo-4-pyrimidinyl)-;N4-Benzoylcytosine;N4-Benzoylcytosine≥ 99% (HPLC);LABOTEST-BB LT00138031;N-(2-Oxo-3H-pyrimidin-4-yl)benzamide;n-(2-oxo-1,2-dihydro-4-pyrimidinyl)benzamide;N4-BENZOYLCYTOSINE;N-Benzoylcytosine
• CAS NO: 26661-13-2
• Molecular Formula: C₁₁H₉N₃O₂
• Molecular Weight: 215.21
• EINECS: 1308068-626-2
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Pyrimidines
• Mol File: 26661-13-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: >300 °C (dec.)(lit.)
• Appearance: /
• Density: 1.33 g/cm³
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.652
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Aqueous Acid (Slightly, Heated), DMSO+DCl (Slightly, Heated)
• PKA: 7.75±0.10(Predicted)
• CAS DataBase Reference: N4-Benzoylcytosine(CAS DataBase Reference)
• NIST Chemistry Reference: N4-Benzoylcytosine(26661-13-2)
• EPA Substance Registry System: N4-Benzoylcytosine(26661-13-2)

Safety Data

• Hazard Codes: Xi
• Statements: 20/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 26661-13-2(Hazardous Substances Data)

Usage

Chemical Properties

White or almost white crystalline powder

Uses

Different sources of media describe the Uses of 26661-13-2 differently. You can refer to the following data:
1. N4-Benzoylcytosine may be employed for the following syntheses: 3′-C-ethynyl and 3′-C-(1,4-disubstituted-1,2,3-triazolo) double-headed pyranonucleosides 2′-C-methyl-4′-thiocytidine, via the Pummerer reaction2′-fluorinated L-nucleoside analogs
2. N4-Benzoylcytosine is a reactant in the synthesis of 1'',2''-cyclopentyl nucleosides as potential antiviral agents.

General Description

N4-Benzoylcytosine is an amide and its anti-microbial activity against pathogenic microorganisms has been studied using the Disk Diffusion and the Pour Plate method. It can be synthesized via the condensation of benzoyl chloride with cytosine.

InChI:InChI=1/C11H9N3O2/c15-10(8-4-2-1-3-5-8)13-9-6-7-12-11(16)14-9/h1-7H,(H2,12,13,14,15,16)

Upstream product

• 71-30-7 Cytosine 
• 98-88-4 benzoyl chloride 
• 613-90-1 benzoyl cyanide 
• 71-30-7 cytosine 
• 6020-40-2 cytosine monohydrate 
• 123413-57-0 N⁴-benzoyl-2',3'-didehydro-2',3'-dideoxycytidine 
• 93-97-0 benzoic acid anhydride 

Downstream Products

• 246039-11-2 tert-butyl 7-(N⁴-benzoylcytosin-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate 
• 495394-86-0 benzoic acid 6-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-fluoro-3,6-dihydro-2H-pyran-3-yl ester 
• 495394-84-8 benzoic acid 6-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-fluoro-3,6-dihydro-2H-pyran-3-yl ester 
• 495394-97-3 benzoic acid 6-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-fluoro-3,6-dihydro-2H-pyran-3-yl ester 
• 495394-99-5 benzoic acid 6-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-fluoro-3,6-dihydro-2H-pyran-3-yl ester 
• 441044-57-1 N⁴-benzoyl-1-[(2R,3R,4R,5R)-3-acetoxy-4-acetoxymethyl-5-(2-tertbutyldiphenylsilyloxyethyl)tetrahydrofuran-2-yl]cytosine 
• 245074-12-8 N⁴-benzoyl-1-(2',3',4'-tri-O-benzoyl-β-D-ribopyranosyl)cytosine 
• 660410-93-5 (1'S,3'R,4'R,5'R,7'R)-N⁴-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}cytosine 
• 660410-94-6 (1'S,3'R,4'R,5'R,7'S)-N⁴-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}cytosine 
• 585540-17-6 1-(5-O-benzoyl-2-chloro-2,3-dideoxy-3-fluoro-β-D-ribofuranosyl)-N⁴-benzoylcytosine 
• 585540-16-5 1-(5-O-benzoyl-2-chloro-2,3-dideoxy-3-fluoro-α-D-ribofuranosyl)-N⁴-benzoylcytosine 
• 705254-59-7 N-4-benzoyl-1-[3-benzoyloxy-2-(benzoyloxymethyl)-2-hydroxypropyl]cytosine 
• 705254-36-0 N-4-benzoyl-1-[3-benzyloxy-2-(benzyloxymethyl)-2-hydroxypropyl]cytosine 
• 740801-33-6 N-{1-[(acetyl-cyclohexyl-amino)-methyl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 

Relevant articles and documents

Dehalogenation of Halogenated Nucleobases and Nucleosides by Organoselenium Compounds

Halogenated nucleosides, such as 5-iodo-2′-deoxyuridine and 5-iodo-2′-deoxycytidine, are incorporated into the DNA of replicating cells to facilitate DNA single-strand breaks and intra- or interstrand crosslinks upon UV irradiation. In this work, it is shown that the naphthyl-based organoselenium compounds can mediate the dehalogenation of halogenated pyrimidine-based nucleosides, such as 5-X-2′-deoxyuridine and 5-X-2′-deoxycytidine (X=Br or I). The rate of deiodination was found to be significantly higher than that of the debromination for both nucleosides. Furthermore, the deiodination of iodo-cytidines was found to be faster than that of iodo-uridines. The initial rates of the deiodinations of 5-iodocytosine and 5-iodouracil indicated that the nature of the sugar moiety influences the kinetics of the deiodination. For both the nucleobases and nucleosides, the deiodination and debromination reactions follow a halogen-bond-mediated and addition/elimination pathway, respectively.

A mechanistic study of the non-oxidative decarboxylation catalyzed by the radical S-adenosyl-l-methionine enzyme BlsE involved in blasticidin S biosynthesis

Decarboxylation is a fundamentally important reaction in biology and involves highly diverse mechanisms. Here we report a mechanistic study of the non-oxidative decarboxylation catalyzed by BlsE, a radical S-adenosyl-l-methionine (SAM) enzyme involved in blasticidin S biosynthesis. Through a series of biochemical analysis with isotopically labeled reagents, we show that the BlsE-catalyzed reaction is initiated by the 5′-deoxyadenosyl (dAdo) radical-mediated hydrogen abstraction from a sugar carbon of the substrate cytosylglucuronic acid (CGA), and does not involve a carboxyl radical as has been proposed for 4-hydroxyphenylacetate decarboxylase (HPAD). Our study reveals that BlsE represents a mechanistically new type of radical-based decarboxylase.

PEPTIDE NUCLEIC ACID MONOMERS AND OLIGOMERS

Disclosed is a peptide nucleic acid monomer as well as a corresponding peptide nucleic acid molecule. The monomer comprises a terminal amino group and a terminal group A. The terminal amino group and the terminal group A are connected by an aliphatic moie