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About This Item
Empirical Formula (Hill Notation):
C11H9N3O2
CAS Number:
Molecular Weight:
215.21
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
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
Related Categories
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
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
Antimicrobial activity of amide, N4-benzoylcytosine.
Jagessar RC and Gomathinayagam S.
Journal of Pharmacy and Clinical Sciences, 1, 12-19 (2011)
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
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