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

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

Uses

Used in Pharmaceutical Industry:
N4-Benzoylcytosine is used as a reactant in the synthesis of various nucleoside analogs for potential antiviral applications. Its role in creating 1'',2''-cyclopentyl nucleosides highlights its importance in developing new antiviral agents.
Additionally, N4-Benzoylcytosine is utilized in the synthesis of double-headed pyranonucleosides, such as 3′-C-ethynyl and 3′-C-(1,4-disubstituted-1,2,3-triazolo), which have potential applications in medicinal chemistry.
Furthermore, it serves as a reactant in the synthesis of 2′-C-methyl-4′-thiocytidine via the Pummerer reaction, a method that allows for the conversion of certain functional groups in organic compounds.
Lastly, N4-Benzoylcytosine is also used in the production of 2′-fluorinated L-nucleoside analogs, which may have potential applications in the development of new pharmaceuticals.

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

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

Downstream Products

• 64339-87-3 N₄,O-bis(trimethylsilyl)-N₄-benzoylcytosine 
• 175915-89-6 N⁴-benzoyl-1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-6'-(tert-butyldiphenylsilyl)-3',5'-dideoxy-β-allofuranosyl}cytosine 
• 159981-07-4 N⁴-benzoyl-1-(4-thio-β-D-ribo-pentofuranosyl)cytosine 
• 201853-30-7 N⁴-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-α/β-D-pentofuranosyl)cytosine 
• 402757-26-0 (2'R)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine 
• 402757-24-8 (2'R)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine 
• 402757-25-9 (2'S)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine 
• 402757-23-7 (2'S)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine 
• 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 
• 808752-78-5 (+)-(3'S,5'R,8'S)-N-[1-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-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.

Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine

Through systematical comparison of various N4-protected cytosine derivatives in the glycosylation step of gemcitabine synthesis, highly beta-stereoselective and high yielding TBAI catalyzed N-glycosylation was achieved with N4-Bz cytosine and anomeric mixture of 2,2‘-difluororibose mesylate donor. The subsequent global deprotection gave gemcitabine efficiently. Meanwhile, the anomeric chloride intermediate and fluoride-displaced side products of this N-glycosylation were identified, too. This new glycosylation method reveals the importance of N4-protection in the stereoselective preparation of pyrimidine nucleoside, also provides a potential alternative to current industrial process to gemcitabine.

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.

Preparation method for N4-benzoylcytosine

The invention discloses a preparation method for N4-benzoylcytosine. According to the invention, with benzoic acid anhydride or benzoyl chloride and cytosine as raw materials and a highly-efficient acylating reagent, i.e., 4-dimethylaminopyridine, as a ca

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

Conformer-independent ureidoimidazole motifs-tools to probe conformational and tautomeric effects on the molecular recognition of triply hydrogen-bonded heterodimers

Linear arrays of hydrogen bonds are useful for the reversible assembly of "stimuli-responsive" supramolecular materials. There is thus an ongoing requirement for easy-to-synthesise motifs that are capable of presenting hydrogen-bonding functionality in a

Microwave-assisted synthesis of amides from various amines and benzoyl chloride under solvent-free conditions: A rapid and efficient method for selective protection of diverse amines

A number of structurally diverse amides were synthesized by reaction of the corresponding amines with benzoyl chloride under microwave irradiation. The proposed procedure ensures short reaction time, high yields, and excellent selectivity and considerably broadens the series of amines as compared to the microwave-assisted synthesis of amides directly from carboxylic acids. It can also be used for selective protection of various amines, including aromatic, aliphatic, and heterocyclic.

Microwave-promoted conversion of heterocyclic amines to corresponding amides under solvent-free conditions

An array of heterocyclic amides was synthesized efficiently by combining corresponding amines and benzoyl chloride in one-pot under microwave irradiation. The reaction times were shorter, yields were higher. What is more, the regioselectivity was excellent, which made the protocol support us an entry to selective protection of diverse amino groups.

Oligomeric aminodiol-containing compounds, libraries thereof, and process of preparing the same

Oligomeric compounds comprising a plurality of aminodiol monomer subunits joined by linking groups are provided, as well as libraries of such compounds and processes for preparing the oligomeric compounds and libraries.

Labeled nucleosides and method for their preparation

The invention relates to a method for the chemical preparation of labeled nucleosides via an oxidative-ring-opening step and a reductive-ring-closure step starting from a labeled D-glucose nucleoside resulting in the corresponding D-ribose-nucleoside by removing the carbon atom 3 on the glucose and comprising the steps of:1. a protection of the sugar ring hydroxyl groups,2. a sugar-base condensation, whereby the base is a purine or a pyrimidine,3. a deprotection of the sugar ring hydroxyl groups,4. an oxidative-ring-opening and removal of the carbon atom 3, and5. a reductive-ring-closure resulting in labeled D-ribose-nucleoside.The invention further relates to a compound obtainable via the method according to the invention having the formula selected from [13C,15N] labeled 6'-O-mono- or 6'-O-bis-C1-C6-alkyloxytrityl-D-glycopyranosyl nucleosides, or [13C,15N] labeled tetra-O-acetyl-D-glycopyranosyl nucleosides or [13C,15N] labeled glycopyranosyl nucleosides.