128496-21-9

Usage

Chemical structure

A complex compound with several key functional groups, including a dihydrofuran ring, a fluoro group, a trityloxy group, and a pyrimidine-2,4-dione moiety.

Chirality

The compound has a chiral center, as denoted by the (2R,5S) prefix, indicating that it has two stereocenters in its structure.

Potential biological activity

Given its structural features and resemblance to certain pharmacologically active compounds, this chemical likely has potential biological activity.

Further investigation

The specific properties and potential applications of 1-{(2R,5S)-3-fluoro-5-[(trityloxy)methyl]-2,5-dihydrofuran-2-yl}-5-methylpyrimidine-2,4(1H,3H)-dione would need to be further investigated through experimental studies.

Fluoro group

The presence of a fluoro group (F) in the compound may contribute to its biological activity and properties.

Trityloxy group

The trityloxy group (C6H5)3COis a bulky protecting group that can influence the reactivity and stability of the compound.

Pyrimidine-2,4-dione moiety

This moiety is a common structural element in many biologically active compounds, including some nucleosides and antiviral drugs.

Stereochemistry

The stereochemistry of the compound, as indicated by the (2R,5S) prefix, is important for its potential biological activity and interactions with target molecules.

Synthesis

The synthesis of this complex compound likely involves multiple steps and the use of various protecting groups and synthetic strategies to achieve the desired structure.

Upstream product

• 128114-98-7 1-(2-deoxy-2-fluoro-3-O-mesyl-5-O-triphenylmethyl-β-D-arabinofuranosyl)thymine 
• 1251064-57-9 1-(2-deoxy-2-fluoro-3-O-mesyl-5-O-trityl-β-D-ribofuranosyl)-5-methyluracil 
• 69256-17-3 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine 
• 128114-98-7 1-(2-deoxy-2-fluoro-3-O-(methylsulfonyl)-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 128114-99-8 2,3'-anhydro-1-(2-deoxy-2-fluoro-5-O-trityl-β-D-lyxofuranosyl)thymine 

Relevant academic research and scientific papers

Modified nucleosides for the treatment of viral infections and abnormal cellular proliferation

The disclosed invention is a composition for and a method of seating a Flaviviridae (including BVDV and HCV), Orthomyxoviridae (including Influenza A and B) or Paramyxoviridae (including RSV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans, using a nucleoside of general formula (I)-(XXIII) or its pharmaceutically acceptable salt or prodrug. This invention also provides an effective process to quantify the viral load, and in particular BVDV, HCV or West Nile Virus load, in a host, using real-time polymerase chain reaction (“RT-PCR”). Additionally, the invention discloses probe molecules that can fluoresce proportionally to the amount of virus present in a sample.

Antiviral activity of various 1-(2′-Deoxy-β- d -lyxofuranosyl), 1-(2′-Fluoro-β- d -xylofuranosyl), 1-(3′-Fluoro-β- d -arabinofuranosyl), and 2′-fluoro-2′,3′-didehydro-2′, 3′-dideoxyribose pyrimidine nucleoside analogues against duck hepatitis B virus (DHBV) and human hepatitis B virus (HBV) replication

Despite the existence of successful vaccine and antiviral therapies, infection with hepatitis B virus (HBV) continues to be a major global cause of acute and chronic liver disease and high mortality. We synthesized and evaluated several lyxofuranosyl, 2′-fluoroxylofuranosyl, 3′- fluoroarabinofuranosyl, and 2′-fluoro-2′,3′-didehydro- 2′,3′-dideoxyribose pyrimidine nucleoside analogues for antiviral activities against hepatitis B virus. Among the compounds examined, 1-(2-deoxy-β-d-lyxofuranosyl)thymine (23), 1-(2-deoxy-β-d- lyxofuranosyl)-5-trifluoromethyluracil (25), 1-(2-deoxy-2-fluoro-β-d- xylofuranosyl)uracil (38), 1-(2-deoxy-2-fluoro-β-d-xylofuranosyl)thymine (39), 2′,3′-dideoxy-2′,3′-didehydro-2′- fluorothymidine (48), and 2′,3′-dideoxy-2′,3′-didehydro- 2′-fluoro-5-ethyluridine (49) were found to possess significant anti-HBV activity against DHBV in primary duck hepatocytes with EC50 values of 4.1, 3.3, 40.6, 3.8, 0.2, and 39.0 μM, respectively. Compounds 23, 25, 39, 48, and 49 (EC50 = 41.3, 33.7, 19.2, 2.0-4.1, and 39.0 μM, respectively) exhibited significant activity against wild-type human HBV in 2.2.15 cells. Intriguingly, 25, 39, 48, and 49 retained sensitivity against lamivudine-resistant HBV containing a single mutation (M204I) and 48 emerged as an effective inhibitor of drug-resistant HBV with an EC50 of 4.1 μM. In contrast, 50% inhibition could not be achieved by lamivudine at 44 μM concentration in the drug-resistant strain. The compounds investigated did not show cytotoxicity to host cells up to the highest concentrations tested.

Fluorinated sugar analogues of potential anti-HIV-1 nucleosides

In order to obtain agents with therapeutic indices superior to those of AZT, FLT, or D4T, several analogues of anti-HIV-1 nucleosides were synthesized. These include 2',3'-dideoxy-2',3'-difluoro-5-methyluridine (13), its arabino analogue 19, arabino-5-met

Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1)

A range of 2'-fluoro and 2',3'-difluoro analogues of pyrimidine deoxyribonucleosides have been synthesized and evaluaed against human immunodeficiency virus (HIV-1) in a human lymphoblastoid cell line. Among these compounds, 1-(2,3-dideoxy-2-fluoro-β-D-threopentofuranosyl)cytosine (12), 2',3'-didehydro-2',3'-dideoxy-2'-fluorocytidine (35), 1-(2,3-dideoxy-2,3-difluoro-β-D-arabinofuranosyl)cytosine (41), and 3'-deoxy-2',3'-didehydro-2'-fluorothymidine (45) were found to have significant antiviral activity, with IC50 values of 0.65, 10, 10, and 100 μM, respectively. The structure-activity relationships are discussed.