2(1H)-pyrimidinone, tetrahydro-4-hydroxy-1-beta-D-ribofuranosyl-

Base Information

• Chemical Name: 2(1H)-pyrimidinone, tetrahydro-4-hydroxy-1-beta-D-ribofuranosyl-
• CAS No.: 18771-50-1
• Molecular Formula: C9H16 N2 O6
• Molecular Weight: 248.236
• NSC Number: 741900,112907
• NCI Thesaurus Code: C868
• Metabolomics Workbench ID: 130007
• ChEMBL ID: CHEMBL27798
• Mol file: 18771-50-1.mol

Synonyms:NSC 112907;NSC-112907;NSC112907;Tetrahydrouridine

Chemical Property of 2(1H)-pyrimidinone, tetrahydro-4-hydroxy-1-beta-D-ribofuranosyl-

Chemical Property:

• Vapor Pressure: 0.65mmHg at 25°C
• Boiling Point: 668.6°Cat760mmHg
• PKA: 12.50±0.40(Predicted)
• Flash Point: 358.2°C
• PSA: 130.33000
• Density: 1.622g/cm³
• LogP: -2.73000
• Storage Temp.: -20°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 248.10083623
• Heavy Atom Count: 17
• Complexity: 301

Purity/Quality:

99%, ^*data from raw suppliers

3,4,5,6-Tetrahydrouridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(C(=O)NC1O)C2C(C(C(O2)CO)O)O
• Description: Tetrahydrouridine is a competitive, reversible inhibitor of cytidine deaminase (Ki values = 54 and 240 nM for human and E. coli enzymes, respectively).Its use, alone or in combination with the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine, is being evaluated in animal models and clinical trials for diseases, including cancer and mitochondrial DNA depletion syndrome. Tetrahydrouridine is a competitive, reversible inhibitor of cytidine deaminase (Ki values = 54 and 240 nM for human and E. coli enzymes, respectively). Its use, alone or in combination with the DNA methyltransferase inhibitor 5-fluoro-2’-deoxycytidine, is being evaluated in animal models and clinical trials for diseases, including cancer and mitochondrial DNA depletion syndrome.
• Uses: 3,4,5,6-Tetrahydrouridine, is a derivative of Uridine (U829910). Tetrahydrouridine (THU), is a potent inhibitor of cytidine. It inhibits cell proliferation through cell cycle regulation regardless of cytidine deaminase expression levels deaminase (CDA), and thus can be used as a potential and promising treatment for tumors with highly expressed CDA.

Technology Process of 2(1H)-pyrimidinone, tetrahydro-4-hydroxy-1-beta-D-ribofuranosyl-

There total 3 articles about 2(1H)-pyrimidinone, tetrahydro-4-hydroxy-1-beta-D-ribofuranosyl- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5,6-dihydrouridine (5627-05-4) → Tetrahydrouridine (18771-50-1)

Guidance literature:

With sodium borohydrid; acetic acid; In water;

Reference yield:

5,6-dihydrouridine (5627-05-4) → 1-(β-D-ribofuranosyl)hexahydropyrimidin-2-one (19149-48-5) + Tetrahydrouridine (18771-50-1)

Guidance literature:

With ammonia; In 2-butanol-water; water;

Reference yield:

→ Tetrahydrouridine (18771-50-1)

Guidance literature:

Cytidin, H2, Rhodium/Al2O3 (ueber intermediaeres Tetrahydro-cytidin);

DOI:10.1021/ja01001a057

upstream raw materials:

5,6-dihydrouridine

Refernces

• 1、 -. "Organic compounds and process". . . Retrieved 2008/06/13.