7481-90-5

Usage

Uses

Used in Medicinal Chemistry:
1-(3,5-ANHYDRO-2-DEOXY-BETA-D-THREO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE is used as a key intermediate in the synthesis of various nucleoside and nucleotide analogs for medicinal chemistry applications. Its unique structure allows for the development of compounds with enhanced biological activity and selectivity.
Used in Drug Development:
In the pharmaceutical industry, 1-(3,5-ANHYDRO-2-DEOXY-BETA-D-THREO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE is used as a starting material for the development of new drugs, particularly those targeting viral infections and cancer. Its potential as an antiviral or anticancer agent is attributed to its ability to interfere with nucleic acid synthesis and disrupt the replication of viruses and cancer cells.
Used in Biological Research:
1-(3,5-ANHYDRO-2-DEOXY-BETA-D-THREO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE is employed as a research tool in biological studies to investigate the interactions and mechanisms of action of nucleoside analogs in biological systems. This helps in understanding their potential therapeutic effects and identifying new targets for drug development.
Used in Antiviral Applications:
In antiviral therapy, 1-(3,5-ANHYDRO-2-DEOXY-BETA-D-THREO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE is used as an antiviral agent for its ability to inhibit viral replication by interfering with the synthesis of viral nucleic acids, thereby preventing the spread of viral infections.
Used in Anticancer Applications:
In oncology, 1-(3,5-ANHYDRO-2-DEOXY-BETA-D-THREO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE is used as an anticancer agent for its potential to disrupt the replication and proliferation of cancer cells, leading to the inhibition of tumor growth and progression.

InChI:InChI=1/C10H12N2O4/c1-5-3-12(10(14)11-9(5)13)8-2-6-7(16-8)4-15-6/h3,6-8H,2,4H2,1H3,(H,11,13,14)

Upstream product

• 63914-08-9 3',5'-bis-O-(p-tolylsulfonyl)thymidine 
• 6979-97-1 3',5'-diacetylthymidine 
• 452-51-7 D-2-deoxyribose 
• 4594-52-9 1,3,5-tri-O-acetyl-2-deoxyribose 
• 50-89-5 thymidine 
• 56822-33-4 3',5'-di-O-mesylthymidine 

Downstream Products

• 124685-30-9 1-((2R,4R,5R)-4-Hydroxy-5-pentyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 65-71-4 thymin 
• 3056-17-5 stavudin 
• 117901-57-2 1-<2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl>thymine 
• 124685-31-0 1-[(2R,4R,5R)-5-(2,2-Dimethyl-propyl)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 118778-33-9 1-(2,5-dideoxy-β-D-threo-pentofuranosyl)thymine 
• 204326-27-2 1-((2R,4R,5R)-5-{2-[(1,1-Diethoxy-ethyl)-phenyl-phosphinoyl]-ethyl}-4-hydroxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 162880-50-4 Benzoic acid (2R,3S,5R)-2-(2-ethoxyphosphinoyl-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 500018-97-3 1-[(3'S,4'R)-3'-O-benzoyl-2',5',6'-trideoxy-6'-(ethoxyhydroxyphosphinyl)-β-hexofuranosyl]thymine 
• 500018-96-2 1-[(3'S,4'R)-3'-O-benzoyl-2',5',6'-trideoxy-6'-(diethoxyphosphinyl)-β-hexofuranosyl]thymine 
• 500018-93-9 [(2S,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-ylmethyl]-{2-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-phosphinic acid ethyl ester 
• 500018-99-5 2'-Deoxy-O^P-ethyl-5'-O-(4,4'-dimethoxytrityl)thymidylylmethylene-(3'->5')-2',5'-dideoxythymidine 
• 500018-89-3 C₄₇H₅₇N₄O₁₁PSi 
• 500018-87-1 C₄₇H₅₇N₄O₁₂PSi 

Relevant academic research and scientific papers

SYNTHESIS AND IMPROVEMENT OF A NUCLEOSIDE ANALOGUE AS AN ANTI-CANCER AND ANTI-VIRAL DRUG

The invention is a drug for anticancer and antiviral therapy, comprising a nucleoside analogue (7) comprising a furan ring irreversibly bound to the RNA/DNA synthesis chain by phosphodiester bonds and having SP3 hybridization, and folic acid (A) bound to the nucleoside analogue (7) comprising furan ring. The synthesis method of the said nucleoside analogue is also contained within the scope of the invention. In this work, a nucleoside-analogue was transformed after converting the furan-ring hybridization from Sp2 to Sp3 to make it more selectivity with different enzymes and linking it via site 5 with the effective folic acid towards entering the substances inside the cells and to become the final compound possessing anti-cancer and anti- virus properties after controlling the replication and reproduction process in DNA.

Synthesis and antiviral activity of boranophosphonate isosteres of AZT and d4T monophosphates

We report synthesis, in vitro antiviral activity, and stability studies in biological media of original boranophosphonate isosteres of AZT and d4T monophophates. A convenient route for the synthesis of 3′-Azido-3′-deoxythymidine-5′-boranophosphonate 8 and 2′,3′-Didehydro-3′-dideoxythymidine-5′-boranopho sphonate 12 is described. H-phosphinates 7 and 11, and α-boranophosphonates 8 and 12 exhibited no significant in vitro activity against HIV-infected cells, neither against a broad panel of viruses, up to 200 μM. The absence of activity of target compounds 8 and 12 can be partially explained by their short half-life in culture medium.

The synthesis and NMR investigation on novel boron derivatives of stavudine

Preparation and spectroscopic properties of novel boron-containing derivatives of anti-HIV agent stavudine are presented, The new compounds, (5′-O-(4,4,5,5-tetramethyl-1,3,2-dioxaboronate)-2′-3′-didehydro-2′-3′-dideoxythymidine and 5′-O-(dihydroxyboronate)-2′-3′-didehydro-2′-3′-dideoxythymidine), were prepared by direct reaction between stavudine and reagents containing B{single bond}H moieties - pinacolborane and borane-dimethylsulfide complexes, respectively. The boron coordination equilibrium of those compounds was analyzed by water titration monitored by NMR. Results of the DFT calculations and NMR experiments pointed to structural and electronic similarity of tetrahedral boron complexes to phosphate group.

Synthesis and anti-HIV-1 activities of novel podophyllotoxin derivatives

In order to explore the range of biological activities of the podophyllotoxin compound class, a novel series of derivatives of podophyllotoxin, which were conjugates containing stavudine and different structural podophyllotoxin analogues, were designed, synthesized, and evaluated for their anti-HIV-1 activities in vitro. Among these compounds, 19d and 19c showed the highest anti-HIV-1 activities with EC50 values of 0.17 and 0.29 μM and TI values of 466.9 and 354.5, respectively.

Simple and efficient method for the synthesis of 2′,3′-didehydro-3′-deoxythymidine (d4T)

2′,3′-Didehydro-3′-deoxythymidine (d4T) is an orally active antiviral drug used in the treatment of AIDS. A novel two-step synthetic method was developed for the synthesis of d4T using inexpensive reagents. An improvement in the yield was achieved for the conversion of the intermediate oxetane to d4T. This is the first simple and efficient method for the large-scale synthesis of d4T.

Synthesis of new homo and heterodinucleosides containing the 2′,3′-dideoxynucleosides AZT and D4T

The synthesis of new dinucleosides of AZT and D4T is described.

Synthesis of 5'-ethynyl-2'-deoxynucleoside analogues as building block for antisense oligonucleotide

New nucleosides and nucleoside analogue dimers were prepared using 5'- ethynyl-2'-deoxynucleoside as starting material.

Conversion of Some Pyrimidine 2'-Deoxyribonucleosides into the Corresponding 2',3'-Didehydro-2',3'-dideoxynucleosides

Thymidine 4b was converted into 2,3'-anhydro-1-(2'-deoxy-β-D-threo-pentofuranosyl)thymine 7b in ca. 65percent isolated yield by being heated at 155 deg C with an excess of diphenyl sulfite and 1-methylimidazole in N,N-dimethylacetamide solution. 2'-Deoxyuridine 4a, 2'-deoxy-5-ethyluridine 4c and 2'-deoxy-5-fluorouridine 4d were similarly converted into 2,3'-anhydronucleosides which were isolated as their 5'-O-(tert-butyldimethylsilyl) derivatives 8a, 8c and 8d in 51, 50 and 59percent yield, respectively.When the oxetane derivatives 5a-d, prepared by the literature procedure from the parent 2'-deoxynucleosides 4a-d, were heated with an excess of sodium hydride in N,N-dimethylacetamide solution at 100 deg C, they were converted into the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides 6a-d in 68, 76, 69 and 74percent isolated yield, respectively.The latter compounds were similarly prepared from the 2,3'-anhydronucleosides 7a-d in 71, 81, 69 and 74percent isolated yield, respectively. 2,3'-Anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-5-(trifluoromethyl)- and -5-iodo-1-(β-D-threo-pentofuranosyl)uracil 8e and 8f, which were themselves prepared from the parent 2'-deoxynucleosides 4e and 4f, respectively, in ca. 60 and 50percent yield, were converted by a three-step procedure via the intermediate 2'-deoxy-3'-(phenylseleno) derivatives 10e and 10f into the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides 6e and 6f in 52 and 49percent overall yield, respectively.Compound 8e was also converted into 2',3'-dideoxy-5-(trifluoromethyl)uridine 11b and 3'-azido-2',3'-dideoxy-5-(trifluoromethyl)uridine 11c in 49 and 66percent overall yield, respectively.

Production of 2',3'-dideoxy-2',3'-didehydronucleosides

There are disclosed novel processes for producing 2',3'-dideoxy-2'3'-didehydronucleosides, for example, 2',3'-dideoxy-2',3'-didehydrothymidine in high yields and on a large scale. The compounds so-produced are useful as antiviral agents, especially as agents effective against the human immunodeficiency viruses (HIV).

1 (2,3 Dideoxy β-D-glycero-pent-2-enofuranosyl)thymine. A highly potent and selective anti-HIV agent

The nucleoside analogue 1 (2,3 dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine (d4T, 1) was prepared by ring opening of the 3',5'-anhydro compound 5. This method has been refined such that it can be used to prepare d4T (1) on a large scale. The triphosphate of d4T (8) was also synthesized from 1 in order to examine the mode of action. The in vitro inhibitory activity of d4T was found to be comparable to that of AZT in HIV-infected CEM cells. The triphosphate of d4T (8) and that of AZT inhibited the HIV reverse transcriptase with poly(rA):oligo(dT) as the template:primer with K(i) values of 0.032 and 0.007 μM, respectively. The in vitro toxicity of d4T against normal human hematopoietic progenitor cells (CFU-GM) was measured in comparison to AZT. While d4T reduces colony-forming units by 50% at a concentration of 100 μM, it takes only 1 μM AZT to have a similar toxic effect. With erythrocyte burst forming units (BFU-E) the in vitro toxicities for d4T and AZT have comparable ID50 values of 10 and 6.7 μM, respectively.