5-amino-6-{[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino}-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride
[CAS# 134452-11-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 5-amino-6-{[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino}-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride
• Synonyms: 5-A-RU HCl
• Molecular Formula: C₉H₁₇ClN₄O₆
• Molecular Weight: 312.71
• CAS Registry Number: 134452-11-2
• EC Number: 989-079-9
• SMILES: C([C@@H]([C@@H]([C@@H](CO)O)O)O)NC1=C(C(=O)NC(=O)N1)N.Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

5-Amino-6-{\[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino}-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride is a synthetic nucleoside analog structurally related to naturally occurring pyrimidine nucleosides, specifically uridine or cytidine. This compound features a modified sugar moiety and a substituted pyrimidine base, placing it within the broader class of nucleoside analogs developed for biochemical, diagnostic, or therapeutic applications.

The molecular framework consists of two key components: a dihydropyrimidine-2,4-dione ring system substituted at the 5-position with an amino group and at the 6-position with an amino-linked sugar side chain. The sugar moiety corresponds to a stereospecific (2S,3S,4R)-2,3,4,5-tetrahydroxypentyl group, which mimics the structure of ribose but may exhibit altered electronic or steric properties. The hydrochloride salt form enhances aqueous solubility and stability, facilitating handling and potential pharmaceutical formulation.

This compound likely originates from research into modified nucleosides for antiviral or anticancer applications. Modifications to the sugar or base portions of nucleosides often aim to inhibit critical enzymes such as DNA or RNA polymerases, reverse transcriptase, or ribonucleotide reductase. The 5-amino substitution on the dihydropyrimidine ring may confer unique hydrogen bonding interactions or altered tautomeric properties, possibly impacting enzyme binding or base-pairing specificity. Such alterations can lead to chain termination or incorporation errors during nucleic acid synthesis, mechanisms frequently exploited in antiviral or antitumor chemotherapy.

In terms of biosynthetic inspiration, the structure mimics naturally occurring cytidine or uridine derivatives but incorporates structural variations to modulate biological activity. The compound's stereochemistry is tightly controlled, indicating that its synthesis involves enantioselective steps or the use of chiral starting materials. The tetrahydroxypentyl side chain reflects the sugar component found in ribonucleosides and is essential for recognition by nucleoside transporters and kinases that convert nucleosides into active nucleotide forms within cells.

Applications of compounds like this one often focus on their utility as biochemical probes or therapeutic agents. In the context of therapeutic research, such molecules are screened for incorporation into nucleic acids by cellular polymerases or for inhibition of enzymes involved in nucleotide metabolism. These activities are critical in fields such as cancer chemotherapy, where rapidly dividing cells are more susceptible to disruptions in nucleic acid synthesis, and in antiviral therapy, where viral replication depends on the availability of functional nucleoside substrates.

In chemical biology, these analogs are sometimes used as tags or markers, especially when modified further with reporter groups or radiolabels. Their incorporation into DNA or RNA can help map replication origins, identify active transcriptional regions, or monitor nucleic acid turnover. The amino group at the 5-position might also serve as a handle for conjugation to other biomolecules or solid supports in molecular diagnostics or nucleic acid capture assays.

The synthesis of this compound typically involves the coupling of a suitably protected dihydropyrimidine ring with a protected tetrahydroxypentylamine derivative, followed by global deprotection and salt formation with hydrochloric acid. The control of stereochemistry is crucial at each step, ensuring that the final product maintains the (2S,3S,4R) configuration necessary for biological recognition.

Overall, 5-amino-6-{\[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino}-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride exemplifies the class of modified nucleosides engineered to exploit subtle interactions within nucleic acid metabolism for therapeutic or investigative purposes. Its precise biochemical profile depends on cellular uptake, phosphorylation efficiency, enzyme interactions, and metabolic stability, all of which are critical factors in the development and application of nucleoside analogs.