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436798

Sigma-Aldrich

N4-Benzoylcytosine

98%

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About This Item

Empirical Formula (Hill Notation):
C11H9N3O2
CAS Number:
26661-13-2
Molecular Weight:
215.21
MDL number:
MFCD00239434
UNSPSC Code:
12352100
PubChem Substance ID:
24867302
NACRES:
NA.22

Quality Level

100

assay

98%

mp

>300 °C (dec.) (lit.)

SMILES string

O=C1NC=CC(NC(=O)c2ccccc2)=N1

InChI

1S/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)

InChI key

XBDUZBHKKUFFRH-UHFFFAOYSA-N

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.

Application

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 reaction
  • 2′-fluorinated L-nucleoside analogs

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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K Lee et al.
Journal of medicinal chemistry, 42(7), 1320-1328 (1999-04-10)
The synthesis of L-nucleoside analogues containing 2'-vinylic fluoride was accomplished by direct condensation method, and their anti-HIV and anti-HBV activities were evaluated in vitro. The key intermediate 8, the sugar moiety of our target compounds, was prepared from 1,2-O-isopropylidene-L-glyceraldehyde via
Antimicrobial activity of amide, N4-benzoylcytosine.
Jagessar RC and Gomathinayagam S.
Journal of Pharmacy and Clinical Sciences, 1, 12-19 (2011)
Christos Kiritsis et al.
Medicinal chemistry (Shariqah (United Arab Emirates)), 8(3), 320-329 (2012-04-26)
A novel series of 3'-C-ethynyl and 3'-C-(1,4-disubstituted-1,2,3-triazolo) double-headed pyranonucleosides has been designed and synthesized. Reaction of 3-keto glucoside 1 with ethynyl magnesium bromide gave the desired precursor 3-C-ethynyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (2). Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-ethynyl-β-D-allopyranose (3). Compound 3
Daisuke Kaga et al.
Nucleosides, nucleotides & nucleic acids, 24(10-12), 1789-1800 (2006-01-28)
The synthesis of 2'-C-methyl-4'-thiocytidine (16) is described. Since the 2'-keto-4'-thiocytidine derivative 2beta unexpectedly isomerized to 2alpha and the methylation of 2beta proceeded predominantly from the less hindered alpha-face to give 7, the desired product 16 was synthesized via the Pummerer

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