84472-83-3

Basic information

• Product Name: 1-(2-deoxy-5-O-tritylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione
• Synonyms: 2,4(1H,3H)-pyrimidinedione, 1-[2-deoxy-5-O-(triphenylmethyl)pentofuranosyl]-; 5'-O-Trityl-2'-Deoxyuridine
• CAS NO: 84472-83-3
• Molecular Formula: C₂₈H₂₆N₂O₅
• Molecular Weight: 470.5164
• Mol File: 84472-83-3.mol
• Article Data: 4

Chemical Properties

• Density: 1.3g/cm³
• Refractive Index: 1.63
• CAS DataBase Reference: 1-(2-deoxy-5-O-tritylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-deoxy-5-O-tritylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione(84472-83-3)
• EPA Substance Registry System: 1-(2-deoxy-5-O-tritylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione(84472-83-3)

Safety Data

• Hazardous Substances Data: 84472-83-3(Hazardous Substances Data)

Usage

Description

1-(2-deoxy-5-O-tritylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione, commonly known as thymine, is a pyrimidine derivative that is an integral part of the genetic code in DNA and RNA. It is characterized by the presence of a pentofuranose sugar attached to it. Thymine plays a vital role in the storage and transmission of genetic information, as it forms hydrogen bonds with adenine, its complementary base, to stabilize the DNA double helix structure. It is also involved in essential biological processes such as DNA replication and repair and serves as a target for certain anti-cancer drugs that interfere with DNA synthesis.

Uses

Used in Pharmaceutical Industry:
1-(2-deoxy-5-O-tritylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione is used as a target for the development of anti-cancer drugs. The expression is: 1-(2-deoxy-5-O-tritylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione is used as a target molecule for the development of anti-cancer drugs for its role in DNA synthesis and its interaction with adenine.
Used in Genetic Research:
1-(2-deoxy-5-O-tritylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione is used as a fundamental component in genetic research. The expression is: 1-(2-deoxy-5-O-tritylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione is used as a nucleobase in genetic research for its role in the storage and transmission of genetic information and its involvement in DNA replication and repair.
Used in DNA and RNA Analysis:
1-(2-deoxy-5-O-tritylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione is used as a reference molecule in the analysis of DNA and RNA structures. The expression is: 1-(2-deoxy-5-O-tritylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione is used as a reference molecule in DNA and RNA analysis for its role in stabilizing the DNA double helix structure through hydrogen bonding with adenine.

Upstream product

• 5983-03-9 3'-O-(methylsulfonyl)-5'-O-trityl-2'-deoxyuridine 
• 188559-36-6 2-((2R,3R)-5-Benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-3H-pyrimidin-4-one 
• 134485-39-5 (E)-5,5-Bis-benzyloxy-pent-2-enoic acid ethyl ester 
• 188559-06-0 C₃₈H₃₆O₃ 
• 188559-31-1 4-Allyloxy-2-((2R,3R)-5-benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-pyrimidine 
• 188559-09-3 (2R,3R)-5,5-Bis-benzyloxy-1-trityloxy-pentane-2,3-diol 
• 14270-73-6 O^5'-trityl-2'-deoxy-uridine 

Downstream Products

• 6038-53-5 1-<2-deoxy-3-O-methanesulfonyl-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl>uracil 
• 13039-99-1 1-[2-deoxy-β-D-threo-pentofuranosyl]uracil 
• 6038-55-7 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)uracil 
• 515138-01-9 2',3'-dideoxy-3'-fluoro-5'-O-(triphenylmethyl)uridine 
• 84472-84-4 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)uracil 
• 84472-86-6 3'-amino-2',3'-dideoxyuridine 
• 84472-90-2 3'-amino-2',3'-dideoxycytidine 
• 84472-89-9 3'-azido-2',3'-dideoxycytidine 
• 84472-87-7 3'-azido-2',3'-dideoxy-5'-O-acetyluridine 

Relevant articles and documents

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 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.