5983-03-9

Basic information

• Product Name: 1-[2-deoxy-3-O-(methylsulfonyl)-5-O-tritylpentofuranosyl]pyrimidine-2,4(1H,3H)-dione
• CAS NO: 5983-03-9
• Molecular Formula: C₂₉H₂₈N₂O₇S
• Molecular Weight: 548.6068
• Mol File: 5983-03-9.mol

Chemical Properties

• Density: 1.4g/cm³
• Refractive Index: 1.662
• CAS DataBase Reference: 1-[2-deoxy-3-O-(methylsulfonyl)-5-O-tritylpentofuranosyl]pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2-deoxy-3-O-(methylsulfonyl)-5-O-tritylpentofuranosyl]pyrimidine-2,4(1H,3H)-dione(5983-03-9)
• EPA Substance Registry System: 1-[2-deoxy-3-O-(methylsulfonyl)-5-O-tritylpentofuranosyl]pyrimidine-2,4(1H,3H)-dione(5983-03-9)

Safety Data

• Hazardous Substances Data: 5983-03-9(Hazardous Substances Data)

Usage

Chemical structure

A modified form of the nucleoside 2'-deoxyuridine with a methylsulfonyl group attached to the 3rd position and a trityl-protected hydroxyl group at the 5th position of the pentofuranosyl moiety.

Usage

Commonly used in nucleoside synthesis and organic chemistry.

Applications

Potential applications in the development of nucleoside analogs for use in antiviral and anticancer drugs, as well as in the study of DNA modifications and epigenetics.

Unique structure

The presence of a methylsulfonyl group and a trityl-protected hydroxyl group in the pentofuranosyl moiety provides a unique structure that is valuable for research and drug development in the field of nucleoside chemistry.

Functional groups

The compound contains a methylsulfonyl group (-SO2CH3) and a trityl group (C6H5)3C-, which contribute to its unique properties and potential applications.

Research significance

The compound serves as a valuable tool for research in the field of nucleoside chemistry, particularly in the development of new antiviral and anticancer drugs, as well as in the study of DNA modifications and epigenetics.

Synthesis

The compound is synthesized through the modification of the nucleoside 2'-deoxyuridine, involving the attachment of a methylsulfonyl group and a trityl-protected hydroxyl group to specific positions in the pentofuranosyl moiety.

Stability

The trityl-protected hydroxyl group in the compound provides increased stability during chemical reactions, making it a useful intermediate in the synthesis of other nucleoside analogs.

Purity

The compound is typically synthesized and used in a pure form to ensure accurate results in research and drug development applications.

Upstream product

• 951-78-0 2'-deoxyuridine 
• 124-63-0 methanesulfonyl chloride 
• 14270-73-6 O^5'-trityl-2'-deoxy-uridine 
• 76-83-5 trityl chloride 

Downstream Products

• 5964-40-9 2,3'-anhydro-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil 
• 84472-84-4 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)uracil 
• 101039-95-6 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil 
• 84472-83-3 1-[2-deoxy-5-O-(triphenylmethyl)-β-D-xylofuranosyl]uracil 
• 859206-78-3 3'-amino-5'-O-trityl-2',3'-dideoxyuridine 
• 859206-79-4 3'-acetylamino-5'-O-trityl-2',3'-dideoxyuridine 
• 1251064-14-8 5-chloro-3'-O-(methylsulfonyl)-5'-O-trityl-2'-deoxyuridine 
• 101039-96-7 1-(3-azido-2,3-dideoxy-β-D-threo-pentofuranosyl)uracil 
• 6038-53-5 1-<2-deoxy-3-O-methanesulfonyl-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl>uracil 
• 84472-87-7 3'-azido-2',3'-dideoxy-5'-O-acetyluridine 
• 84472-89-9 3'-azido-2',3'-dideoxycytidine 
• 84472-90-2 3'-amino-2',3'-dideoxycytidine 
• 84472-86-6 3'-amino-2',3'-dideoxyuridine 
• 162894-42-0 2',3'-dideoxy-2-O-ethyl-3'-(phenylseleno)uridine 

Relevant articles and documents

Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogues of pyrimidine deoxyribonucleoside

Several new 3'-azido and 3'-amino nucleosides (8, 9, 12, and 13) have been synthesized and their biological activities evaluated. Among them, 3'-amino-2',3'-dideoxycytidine (13) was found to exhibit potent cytotoxic activity against both L1210 and S-180 cells in vitro with an ID50 of 0.7 and 4.0 μM, respectively. Furthermore, 13 has also shown antitumor activity against L1210 tumor bearing mice with a T/C x 100 value of 283.

Modified 5'-Trityl Nucleosides as Inhibitors of Plasmodium falciparum dUTPase

2'-Deoxyuridine triphosphate nucleotidohydrolase (dUTPase) is a potential drug target for the treatment of malaria. We previously reported the discovery of 5'-tritylated analogues of deoxyuridine as selective inhibitors of this Plasmodium falciparum enzyme. Herein we report further structure-activity studies; in particular, variations of the 5'-trityl group, the introduction of various substituents at the 3'-position of deoxyuridine, and modifications of the base. Compounds were tested against both the enzyme and the parasite. Variations of the 5'-trityl group and of the 3'-substituent were well tolerated and yielded active compounds. However, there is a clear requirement for the uracil base for activity, because modifications of the uracil ring result in loss of enzyme inhibition and significant decreases in antiplasmodial action. Fewer trips to the dUMP: dUTPase is a potential drug target for the treatment of malaria. We previously reported the discovery of 5'-tritylated analogues of deoxyuridine as selective inhibitors of this P.falciparum enzyme. Herein we report further structure-activity studies of the 5'-trityl group, the introduction of various substituents at the 3'-position of deoxyuridine, and modifications of the base.

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.

Synthesis of pyrimidine 2'3'-dideoxy-2-thionucleosides

2'-Deoxyuridine 8a and thymidine 8b were converted in eight steps and in satisfactory overall yields into 2',3'-dideoxy-2-thiouridine (ddTU) 6a and 3'-deoxy-2-thiothymidine (ddTT) 6b, respectively. A three-step procedure is described for the conversion of ddTU 6a and ddTT 6b into the corresponding 2',3'-dideoxycytidine derivatives (ddTC 7a and ddMTC 7b, respectively) in good overall yield.