23220-74-8 Usage
Description
4-Hydroxy-1-(2-O,3-O,5-O-tribenzoyl-β-D-ribofuranosyl)pyridin-2(1H)-one is a complex organic compound that serves as a protected intermediate in the synthesis of various biologically active molecules. It is characterized by its unique structure, which includes a pyridinone core with a β-D-ribofuranosyl moiety and three benzoyl groups attached to specific hydroxyl groups. 4-Hydroxy-1-(2-O,3-O,5-O-tribenzoyl-β-D-ribofuranosyl)pyridin-2(1H)-one plays a crucial role in the development of pharmaceuticals due to its ability to be transformed into therapeutically relevant molecules.
Uses
Used in Pharmaceutical Synthesis:
4-Hydroxy-1-(2-O,3-O,5-O-tribenzoyl-β-D-ribofuranosyl)pyridin-2(1H)-one is used as a protected intermediate for the synthesis of 3-Deazauridine (D203240), a structural analog of uridine. This nucleoside analog has demonstrated the ability to inhibit the biosynthesis of Cytidine-5''-Triphosphate by competitively inhibiting Cytidine Triphosphate synthetase, which is considered its primary mode of action. The compound has potential applications in the treatment of various diseases, particularly those involving abnormal cell proliferation.
Used in Antiviral Applications:
As a precursor to 3-Deazauridine, 4-Hydroxy-1-(2-O,3-O,5-O-tribenzoyl-β-D-ribofuranosyl)pyridin-2(1H)-one may also be used in the development of antiviral drugs. 3-Deazauridine has shown potential as an antiviral agent, particularly against viruses that rely on the synthesis of Cytidine-5''-Triphosphate for replication. This makes it a valuable compound for the development of new antiviral therapies.
Used in Research and Development:
In addition to its pharmaceutical applications, 4-Hydroxy-1-(2-O,3-O,5-O-tribenzoyl-β-D-ribofuranosyl)pyridin-2(1H)-one may also be used in research and development settings. Its unique structure and reactivity make it a valuable tool for studying the synthesis and properties of various biologically active molecules, as well as for exploring new methods of drug design and synthesis.
Used in Drug Delivery Systems:
Similar to gallotannin, 4-Hydroxy-1-(2-O,3-O,5-O-tribenzoyl-β-D-ribofuranosyl)pyridin-2(1H)-one may also be employed in the development of novel drug delivery systems. These systems could potentially improve the delivery, bioavailability, and therapeutic outcomes of the compounds synthesized from this intermediate, such as 3-Deazauridine.
Check Digit Verification of cas no
The CAS Registry Mumber 23220-74-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,2,2 and 0 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 23220-74:
(7*2)+(6*3)+(5*2)+(4*2)+(3*0)+(2*7)+(1*4)=68
68 % 10 = 8
So 23220-74-8 is a valid CAS Registry Number.
InChI:InChI=1/C31H25NO9/c33-23-16-17-32(25(34)18-23)28-27(41-31(37)22-14-8-3-9-15-22)26(40-30(36)21-12-6-2-7-13-21)24(39-28)19-38-29(35)20-10-4-1-5-11-20/h1-18,24,26-28,34H,19H2
23220-74-8Relevant articles and documents
High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries
Bookser, Brett C.,Raffaele, Nicholas B.
, p. 173 - 179 (2007/10/03)
The Vorbrueggen glycosylation reaction was adapted into a one-step 5 min/130 °C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl inflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield ± SD was 26 ± 16%, and the average purity ± SD was 95 ± 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.
