2347-43-5

Basic information

• Product Name: 5-CHLOROCYTOSINE
• Synonyms: 5-CHLOROCYTOSINE;2(1H)-Pyrimidinone, 4-amino-5-chloro- (9CI);4-AMINO-5-CHLORO-2(1H)-PYRIMIDINONE;4-aMino-5-chloropyriMidin-2-ol;6-amino-5-chloropyrimidin-2(1H)-one
• CAS NO: 2347-43-5
• Molecular Formula: C₄H₄ClN₃O
• Molecular Weight: 145.54706
• Product Categories: PYRIMIDINE
• Mol File: 2347-43-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: >288 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.79g/cm³
• Refractive Index: 1.717
• Storage Temp.: 2-8°C(protect from light)
• PKA: 7.34±0.10(Predicted)
• CAS DataBase Reference: 5-CHLOROCYTOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLOROCYTOSINE(2347-43-5)
• EPA Substance Registry System: 5-CHLOROCYTOSINE(2347-43-5)

Safety Data

• Hazardous Substances Data: 2347-43-5(Hazardous Substances Data)

Usage

General Description

5-Chlorocytosine is a nucleobase analog of cytosine that contains a chlorine atom at the 5 position of the pyrimidine ring. It is used as a chemical intermediate in the synthesis of pharmaceutical compounds and in research studies as a potential antiviral and antitumor agent. 5-Chlorocytosine has been investigated for its ability to inhibit viral replication and cell proliferation by interfering with nucleic acid synthesis. Its structural similarity to cytosine makes it a potential candidate for targeted drug design and further exploration in the development of novel therapeutic agents.

InChI:InChI=1/C4H4ClN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)

Upstream product

• 128-09-6 N-chloro-succinimide 
• 71-30-7 Cytosine 

Downstream Products

• 178687-97-3 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-chlorocytosine 
• 197452-33-8 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-L-erythro-pentofuranos-1-yl)-5-chlorocytosine 
• 197452-34-9 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-L-erythro-pentofuranos-1-yl)-5-chlorocytosine 
• 2280037-51-4 1-([1,1'-biphenyl]-3-yl)-4-amino-5-chloropyrimidin-2(1H)-one 
• 69124-00-1 1-(O³-acetyl-O⁵-benzoyl-2-fluoro-β-D-2-deoxy-arabinofuranosyl)-4-amino-5-chloro-1H-pyrimidin-2-one 
• 255818-58-7 5-chloro-1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-L-threo-pentofuranosyl)cytosine 

Relevant articles and documents

CYTOSINE-BASED TET ENZYME INHIBITORS

Provided herein, in some embodiments, are cytosine analogs, compositions comprising cytosine analogs, and methods of use for inhibiting a Ten-eleven translocation (TET) enzyme.

Cytosine-Based TET Enzyme Inhibitors

DNA methylation is known as the prima donna epigenetic mark for its critical role in regulating local gene transcription. Changes in the landscape of DNA methylation across the genome occur during cellular transition, such as differentiation and altered neuronal plasticity, and become dysregulated in disease states such as cancer. The TET family of enzymes is known to be responsible for catalyzing the reverse process that is DNA demethylation by recognizing 5-methylcytosine and oxidizing the methyl group via an Fe(II)/alpha-ketoglutarate-dependent mechanism. Here, we describe the design, synthesis, and evaluation of novel cytosine-based TET enzyme inhibitors, a class of small molecule probes previously underdeveloped but broadly desired in the field of epigenetics. We identify a promising cytosine-based lead compound, Bobcat339, that has mid-μM inhibitor activity against TET1 and TET2, but does not inhibit the DNA methyltransferase, DNMT3a. In silico modeling of the TET enzyme active site is used to rationalize the activity of Bobcat339 and other cytosine-based inhibitors. These new molecular tools will be useful to the field of epigenetics and serve as a starting point for new therapeutics that target DNA methylation and gene transcription.

A fluorescein-containing, small-molecule, water-soluble receptor for cytosine free bases

In this study, we synthesized small-molecule, water-soluble, fluorescein-containing ureido compounds 6 and 8 as target receptors for cytosine free bases and then investigated the binding of cytosine free bases with the receptors using 15N NMR spectroscopy and partially labeled cytosine-2,4-13C-1,3,4-15N-cytosine. Binding with the receptor 6a (the disodium form of 6) caused the chemical shift of the nitrogen atom of the amino group of cytosine to move downfield; binding of the receptor 8a (the disodium form of 8), which is possessing no corresponding aryl nitrogen atom, had no effect on this signal. Fluorescence spectroscopy revealed that binding of cytosine and its derivatives led to quenching of the fluorescence of receptor 6a; in contrast, the quenching of receptor 8a was only slightly affected by cytosine. Because the fluorescence of 6a was not quenched by either deoxycytidine or uracil, it appears that this receptor is a specific for cytosine among the DNA bases. We used the fluorescence of 6a to measure the apparent binding constants for various cytosine derivatives, including the anticancer prodrug 5-fluorocytosine. Receptor 6a is the first small-molecule, water-soluble fluorescent receptor for the specific binding of cytosine free bases in aqueous solution.