3249-94-3

Usage

Uses

Used in Pharmaceutical Industry:
2,2'-Anhydro-1-(5'-O-triphenylmethyl-beta-D-arabinofuranosyl)-uracil is used as a potential antiviral agent for its ability to inhibit the replication of viral DNA or RNA, offering a therapeutic approach to combat viral infections.
Used in Oncology:
In the field of oncology, 2,2'-Anhydro-1-(5'-O-triphenylmethyl-beta-D-arabinofuranosyl)-uracil is used as a potential antineoplastic agent, targeting the replication mechanisms of cancer cells and thereby exhibiting potential in the treatment of certain types of cancers.
Used in Preclinical Research:
2,2'-Anhydro-1-(5'-O-triphenylmethyl-beta-D-arabinofuranosyl)-uracil is utilized as a subject of preclinical studies to explore its efficacy and safety in medical applications, with the aim of advancing its development as a therapeutic agent for viral infections and cancers.

Upstream product

• 76-83-5 trityl chloride 
• 58-96-8 uridine 
• 3736-77-4 2,2'-Anhydrouridine 

Downstream Products

• 3736-77-4 2,2'-Anhydrouridine 
• 34407-66-4 1-(2-azido-2-deoxy-5-O-(triphenylmethyl)-β-L-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione 
• 276870-92-9 Diazo-acetic acid (2R,3R,3aS,9aR)-6-oxo-2-trityloxymethyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-yl ester 
• 276870-93-0 C₃₀H₂₄N₂O₆ 
• 204688-13-1 1-((2R,3R,4S,5R)-3-Amino-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 1426142-20-2 1-{(5aR,6R,8R,8aS)-5a,6,8,8a-tetrahydro-6-[(triphenylmethoxy)methyl]-4H-furo[3,4-b][1,2,3]triazolo[1,5-d][1,4]oxazin-8-yl}pyrimidine-2,4(1H,3H)-dione 
• 1426142-26-8 4-amino-1-{(5aR,6R,8R,8aS)-5a,6,8,8a-tetrahydro-6-[(triphenylmethoxy)methyl]-4H-furo[3,4-b][1,2,3]-triazolo[1,5-d][1,4]oxazin-8-yl}pyrimidin-2(1H)-one 
• 95906-49-3 1-(5'-O-triphenylmethyl-3'-deoxy-β-D-threopentofuranosyl)uracil 
• 130860-08-1 1-(3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)cytosine 
• 130860-07-0 1-(2-O-acetyl-3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)-4-(1,2,4-triazolyl)pyrimidinone 

Relevant academic research and scientific papers

Versatile synthesis of 2′-amino-2′-deoxyuridine derivatives with a 2′-amino group carrying linkers possessing a reactive terminal functionality

2,2′-Anhydrouridine has been successfully converted into the appropriate 2′-amino-2′-deoxyuridine derivatives in a reaction with isothiocyanates obtained from amino acids or α,ω-diaminoalkanes. The initially formed oxazolidine-2-thione ring is cleaved under basic conditions into the corresponding 2′-amino(substituted)-2′-deoxyuridine derivatives. The implemented additional terminal functionality in the substituent attached to the 2′-amino group allows further modifications with e.g., fluorophore moiety.

Study on the thermolysis of 5′-O-trityl-2′,3′-O-triphenylphosphoranediyluridine

A new method is introduced by thermolysis of 5′-O-trityl2′,3′-O-triphenylphosphoranediyluridine (4) with or without the presence of methanol to afford the 3-N-methyl-5′-O-trityluridine (9) and 5′-O-trityl-2,2′-cyclouridine (5), respectively. Mechanism for this thermolysis is also proposed.

Uracil- and thymine-substituted thymidine and uridine derivatives

The four possible 3'-uracil-1-yl and 3'-thymin-1-yl derivatives of 3'- deoxythymidine and the four analogous derivatives of 2'-deoxyuridine have been synthesised from thymidine and uridine, respectively. Advantages of the 2-(methoxycarbonyl)vinyl group to prevent the formation of anhydronucleosides and SnCl2/PhSH/Et3N in relation to H2/Pd for the reduction of most azido groups are disclosed.

Synthesis and Anticancer Activity of Various 3'-Deoxy Pyrimidine Nucleoside Analogues and Crystal Structure of 1-(3-Deoxy-β-D-threo-pentofuranosyl)cytosine

Various 3'-deoxy pyrimidine nucleoside analogues have been synthesized for evaluation as potential anticancer and antiviral agents.Among these compounds, 1-(3-deoxy-β-D-threo-pentofuranosyl)cytosine (10, 3'-deoxy-ara-C) and 3'-deoxycytidine (22) had significant anticancer activity against CCRF-CEM, L1210, P388, and S-180 cancer cell lines in vitro, producing ED50 values of 2,10,5,and 34 μM, respectively, for 3'-deoxy-ara-C (10); and 25, 5, 2.5, and 15μM, respectively, for 3'-deoxycytidine (22).Thus, 3'-deoxy-ara-C (10) was 12.5 times more active against CCRF-CEM cells than 3'-deoxycytidine (22).The 2'-O-acetyl, 5'-O-acetyl, and 2',5'-di-O-acetyl derivatives of 3'-derivatives of 3'-deoxy-ara-C (10), compounds 34, 31, and 30, demonstrated anticancer activity in the same range as 3'-deoxy-ara-C (10) against CCRF-CEM, L1210, P388, and S-180 cells.The 5'-O-acetyl derivative (31) had significantly greater activity against CCRF-CEM with an ED50 value of 0.4 but this compound also showed similar activity, as did 3'-deoxy-ara-C against L1210, P388, and S-180 with ED50 values of 3, 3, and 13 μM, respectively. 3'-Deoxy-ara-C was also evaluated in vitro against HSV-2, HCMV, and GPCMV viruses and was found to be not very active with respective IC50 values of 110, 220, and 1000 μM.The single-crystal structure of 3'-deoxy-ara-C (10) was determined by X-ray crystallography.There are two molecules of the nucleoside and one molecule of water in the asymmetric unit.The sugar moieties of two nucleoside molecules adopt different conformations.In molecule A, the ring pucker is C3'-endo with P=18.7 deg and τm= 37.3 deg, while the CH2OH side chain is gauche+.In molecule B, the ring pucker is C2'-endo with P= 156.8 deg and τm = 37.8 deg and the side chain is trans.