6046-63-5

Usage

Uses

Used in Pharmaceutical Compositions:
5-Chloro-35di-O-acetyl-2'-deoxyuridine is used as an active pharmaceutical ingredient for the development of medications targeting specific diseases. Its unique structure allows it to interact with cellular processes, potentially leading to therapeutic effects.
Used in Antiviral Applications:
In the field of antiviral drug development, 5-Chloro-35di-O-acetyl-2'-deoxyuridine is used as an antiviral agent. Its mechanism of action may involve the inhibition of viral replication by interfering with the synthesis of viral nucleic acids, thus helping to control the spread of the virus within the host.
Used in Anticancer Applications:
5-Chloro-35di-O-acetyl-2'-deoxyuridine is also utilized as an anticancer agent. It may work by disrupting the nucleic acid synthesis in cancer cells, leading to the inhibition of their proliferation and potentially contributing to the treatment of various types of cancer.
Used in Research and Development:
In the research and development sector, 5-Chloro-35di-O-acetyl-2'-deoxyuridine serves as a valuable compound for studying the mechanisms of nucleic acid synthesis and the development of new therapeutic strategies against diseases involving abnormal cell proliferation, such as cancer and viral infections.
Used in Drug Delivery Systems:
To enhance the bioavailability and delivery of 5-Chloro-35di-O-acetyl-2'-deoxyuridine, it can be incorporated into various drug delivery systems, such as nanoparticles or liposomes. These systems aim to improve the compound's stability, solubility, and targeted delivery to specific cells or tissues, thereby increasing its therapeutic efficacy and reducing potential side effects.

InChI:InChI=1/C13H15ClN2O7/c1-6(17)21-5-10-9(22-7(2)18)3-11(23-10)16-4-8(14)12(19)15-13(16)20/h4,9-11H,3,5H2,1-2H3,(H,15,19,20)/t9-,10-,11-/m1/s1

Upstream product

• 13030-62-1 3',5'-di-O-acetyl-2'-deoxyuridine 
• 108-24-7 acetic anhydride 
• 50-90-8 5-chloro-2'-deoxyuridine 

Downstream Products

• 58349-26-1 5-Chloro-5'-O-p-tolylsulphonyl-2'-deoxyuridine 
• 50-90-8 5-chloro-2'-deoxyuridine 

Relevant academic research and scientific papers

Systematic assignment of NMR spectra of 5-substituted-4-thiopyrimidine nucleosides

Unambiguous characterization of 5-substituted-4-thiopyrimidine nucleosides (ribonucleosides and 2'-deoxynucleosides) was performed using NMR spectroscopy. Assignments of all proton and carbon signals of 5-bromo-4-thiouridine and related nucleosides were systematically carried out and firmly established by COSY and HMQC techniques. The NMR data of various 4-thiopyrimidine nucleosides are compared, and the key contributing factors discussed. The approach presented here is applicable to other modified nucleosides and nucleotides, as well as nucleobases. Copyright

Synthesis and properties of DNA containing cyclonucleosides

Here, we present efficient syntheses of the R and S diastereomers of 8,5′-cyclo-2′-deoxyadenosine and 6,5′-cyclo-2′- deoxyuridine. We incorporated these interesting nucleosides into DNA to study how the cyclo linkage affects the stability of duplex formation.

Ionic liquid mediated synthesis of 5-halouracil nucleosides: Key precursors for potential antiviral drugs

Synthesis of antiviral 5-halouracil nucleosides, also used as key precursors for the synthesis of other potential antiviral drugs, has been demonstrated using ionic liquids as convenient and efficient reaction medium.

A mild and efficient methodology for the synthesis of 5-halogeno uracil nucleosides that occurs via a 5-halogeno-6-azido-5,6-dihydro intermediate

A mild and efficient methodology for the synthesis of 5-halogeno (iodo, bromo, or chloro) uracil nucleosides has been developed. 5-Halo-2'-deoxyuridines 4a-c (84-95%), 5-halouridines 7a-c (45-95%), and 5-haloarabinouridines 8a-c (65-95%) were synthesized in good to excellent yields by the reaction of 2'-deoxyuridine (2), uridine (5) and arabinouridine (6), respectively with iodine monochloride, or N-bromo (or chloro)succinimide, and sodium azide at 25-45°C. These C-5 halogenation reactions proceed via a 5-halo-6-azido-5,6-dihydro intermediate (3), from which HN3 is eliminated, to yield the 5-halogeno uracil nucleoside. The 5-halo-6-azido-5,6-dihydro intermediate products (10a, 10b) could be isolated from the reaction of 3',5'-di-O-acetyl-2'-deoxyuridine (9) with iodine monochloride or N-bromosuccinimide and sodium azide at 0°C. The isolation of 10a, 10b indicates that the C-5 halogenation reaction proceeds via a 5-halo-6-azido-5,6-dihydro intermediate.

In-cell Indirect Electrochemical Halogenation of Pyrimidine Bases and their Nucleosides to 5-Haloderivatives

Reaction of anodically generated "halonium" species (LiX or Bu4NX, LiClO4, MeCN, Pt/Pt; I2, LiClO4, MeCN) with pyrimidine bases and their nucleosides leads to 5-halo compounds in good yields.

Cerium(IV)-Mediated Halogenation at C-5 of Uracil Derivatives

Treatment of protected uracil nucleosides 1 or 2 with elemental iodine or metal halogenides and ceric ammonium nitrate (CAN) at 80 deg C gave the corresponding protected 5-halouracil nucleosides 3a-f in excellent yields.Treatment of the resulting crude 3a-f with 0.1 M NaOMe/MeOH at ambient temperature gave the corresponding 5-halouridines 4a-f in high overall yields from 1 or 2.Further, 5-halouraciles 9a-f were prepared in good yields by treatment of 1,3-dimethyluracil (7) or uracil (8) with elemental iodine, metal halogenides, or hydrochloric acid and CAN.Halouridines 4a-e also were obtained in good yields by treatment of unprotected uracil nucleosides 5 or 6 with halogen sources as above and CAN.

SYNTHESIS OF 6,5'-cyclo-2',5'-DIDEOXYPYRIMIDINE NUCLEOSIDES ( NUCLEOSIDES AND NUCLEOTIDES. LXXII )

6,5'-cyclo-2',5'-dideoxyuridine and 6,5'-cyclo-5'-deoxythymidine, pyrimidine deoxynucleosides fixed in the anti conformation were synthesized.The key intermediate, 3'-O-acetyl-5-chloro-2',5'-dideoxy-5'-iodouridine ( 12 ), prepared from 2'-deoxyuridine, was cyclized by treatment with tributyltin hydride to the 6,5'-cyclo derivative ( 13 ), then dehydrochlorinated to furnish, after de-O-acetylation, 6,5'-cyclo-2',5'dideoxyuridine ( 14 ).For the synthesis of 6,5'-cyclothymidine, 3'-O-acetyl-2',5'-dideoxy-5'-iodo-5-phenylthiomethyluridine ( 22 ) was prepared from 2'-deoxyuridine and this compound was cyclized by treatment with tributyltin hydride to yield, after de-O-acetylation 6,5'-cyclo-5'-deoxythymidine ( 24 ).Keywords - cyclonucleoside; C-cyclouridine; 6,5'-cyclo-2',5'-dideoxyuridine; 6,5'-cyclo-5'deoxythymidine; 5-bromo-6,5'-cyclo-2',5'-dideoxyuridine; radical cyclization; tributyltin hydride; NMR; CD