Nucléosides et Nucléotides

Applications 5’-O-Benzoyl Ribavirin is an impurity of Ribavirin (R414475). Ribavirin impurity E.
References Zakharieva., et al.: Bioorganic. Medicinal. Chem., 1994, 4, 2831 (1994), Reichard., et al.: The Lancet, 351, 83 (1998),

Impurity Ganciclovir EP Impurity A
Applications 9-[[2-chloroprop-2-en-1-yl)oxy]methyl]guanine (Ganciclovir EP Impurity A) is an impurity of Ganciclovir (G235000).

Applications Ganciclovir derivative.

Applications Labelled 5-Methyl Uridine. A primary degradation product of tRNA, an urinary nucleoside as biological marker for patients with colorectal cancer.
References Borek, E., et al.: Cancer Res., 37, 3362 (1977), Sander, G., et al.: Clin. Sci.,71, 367 (1986), Sander, G., et al.: Ann. Nutr. Metab., 30, 137 (1986), Rasmuson, T., et al.: Acta Oncol., 34, 61 (1995),

Applications L-Alanine 2-Ethylbutyl Ester Hydrochloride is used in the synthesis of phosphoramidate prodrug of a pyrrolo[2,1-f][triazin-4-amino] adenine C-nucleoside (GS-5734) for the treatment of ebola and emerging viruses.
References Siegel, D., et al.: J. Med. Chem., 60, 1648-1661 (2017)

Applications Labelled Azathioprine (A803350). An immunosuppressive antimetabolite. Also active as disease modifying antirheumatic drug (DMARD).
References Mitrou, P.S., et al.: Arzneim.-Forsch., 29, 483, 662 (1979), Ding, T.L., et al.: Drug. Metab. Dispos., 7, 373 (1979), Chan, G.L.C., et al.: Pharmacotherapy, 7, 165 (1987), Sandborn, W.J., et al.: : Scand. J. Gastroenterol., 33, Suppl. 225, 92 (1998,)

Applications 5'-Deoxy-5'-chloroadenosine is an intermediate in the synthesis of 5'-Deoxy-5'-(methylthio)adenosine (D242600), a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethionine (AdoMet) and methionine salvage pathways.
References Olopade, O., et al.: Cancer Res., 53, 2410 (1993), Hartmann, S., et al.: Clin. Chem., 52, 1127 (2006), Penner, N., et al.: J. Pharm. Biomed. Anal., 52, 534 (2010),

Applications A 2-substituted 2’-Deoxyadenosine (D231620). Used in the synthesis of oligonucleotides.
References Ishikawa, F., et al.: J. Mol. Biol., 70, 475 (1972), Hattori, M., et al.: Biochemistry, 13, 2754 (1974), Kazimierczuk, Z., et al.: J. Med. Chem., 33, 1683 (1990),

Applications A novel labelled HIV reverse transcriptase inhibitor useful in treatment of HIV infection.
References Scholler-Gyure, M., et al.: J. Clin. Pharmacol., 48, 322 (2008), Thakur, A., et al.: Eur. J. Med. Chem., 43, 471 (2008),

Impurity Penciclovir Impurity F
Applications 6-Chloro Desacetyl Famciclovir is a prodrug of Penciclovir (P221500); an antiviral.
References Weinberg, A., et al.: Antimicrob. Ag. Chemother., 36, 2037 (1992); McMeekin, J.R., et al.: Anal. Proc., 29, 178 (1992)

Applications Gemcitabine intermediate.
References Balzarini, J., et al.: Biochem. Pharmacol., 1988, 37, 2847 (1988), Hertel, L., et al.: Cancer Res., 50, 4417 (1990), Marquez, V., et al.: J. Med. Chem., 33, 978 (1990),

Impurity Lamivudine EP Impurity B
Applications 2’-Epi-Lamivudine (Lamivudine EP Impurity B) is an epimer of Lamivudine (L172500); an antiviral that inhibits HIV-reverse transcriptase.
References Lin, T. et al.: J. Med. Chem., 39, 1757 (1996); Schinazi, R.F. et al.: Antimicrob. Agents Chemother.,36, 672 (1992);

Applications 6,7-Dimethylpterin, a derivative of Folic Acid (F680300) is used as a biomarker for a non-invasive cancer diagnosis. Also can function as chromophores in light sensitive proteins allowing for analysis of target cells.
References Kritskii, M.S. et al.: Dokl. Akad. Nauk., 380, 408 (2001); Gamagedara, S. et al.: Clin. Chim. Acta., 412, 128 (2011);

Applications Folic acid dihydrate

Applications 2,5,6-Triamino-4(3H)-pyrimidinone Sulfate is used in the preparation of guanines and other purine derivatives with antiviral activities.
References Hemmati, S. et al.: Int. J. Chem. Sci., 2, 9 (2004); Chetsanga, C.J. et al.: Chem.-Biol. inter., 58, 117 (1986);

Applications 3-(3-Azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione is an impurity of Zidovudine (A825000). Zidovudine is an antiviral agent used in the clinical treatment of HIV infections.
References Radatus, B.K., Org. Process. Res. Dev., 15, 1281 (2011)

Stability Moisture Sensitive, Unstable in Solution
Applications 2-Deoxy-3,5-di-O-p-toluoyl-α-L-ribofuranosyl Chloride (cas# 141846-57-3) is a compound useful in organic synthesis.

Stability Hygroscopic
Applications Dapagliflozin C2 Epimer is an intermediate used in the synthesis of Dapagliflozin (D185370), a sodium-glucose transporter 2 inhibitor.
References Majewski, A., et al.: Przemysl Chemiczny, 95, 1129 (2016); Kasichayanula, S. et al.: Diabetes, Obesity and Metabolism 13, 47 (2011)

Applications An impurity from the synthesis of Gemcitabine.
References Haufman, et al.: Science, 145, 585 (1964), Prusoff, et al.: Biochim. Biophys. Acta, 32, 295 (1959)

Applications An intermediate used in the preparation of Zanamivir derivatives.
References Andrews, D., et al.: Eur. J. Med. Chem., 34, 563 (1999), Altamore, T., et al.: Bioorg. Med. Chem., 14, 1126 (2006),

Applications Possesses antiviral activity. It is an inhibitor of leukocyte adhesion to TNF-treated endothelial cells.
References Jurgensen, C.H., et al.: J. Immunol., 144, 653 (1990), Flexner, C.W., et al.: Lancet, 339, 438 (1992), Reddy, M., et al.: Prot. Sci., 17 2134 (2008),

Intermediate in the synthesis of ribavirin

Triphenylmethanol (TPM) is an inhibitor of the enzyme alcohol dehydrogenase. It is synthesized by reacting p-hydroxybenzoic acid with a hydroxyl group in the presence of trifluoroacetic acid and potassium carbonate. The reaction solution was then analyzed by x-ray crystallography, revealing the molecular structure of TPM. TPM binds to the metal ion in a hydroxyl group, preventing alcohol dehydrogenase from oxidizing ethanol to acetaldehyde. This mechanism also explains why TPM inhibits other enzymes that use this same metal ion cofactor such as carboxypeptidase A and aminopeptidase P, which are involved in protein synthesis and degradation.