So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Felczak, Krzysztof; Drabikowska, Alicja; Vilpo, Juhani A.; Kulikowski, Tadeusz; Shugar, David researched the compound: 4-Methyl-6-(methylthio)pyrimidin-2-ol( cas:16710-11-5 ).Formula: C6H8N2OS.They published the article 《6-Substituted and 5,6-Disubstituted Derivatives of Uridine: Stereoselective Synthesis, Interaction with Uridine Phosphorylase, and in Vitro Antitumor Activity》 about this compound( cas:16710-11-5 ) in Journal of Medicinal Chemistry. Keywords: structure activity nucleoside antitumor phosphorylase substrate; uridine preparation antitumor cytotoxicity phosphorylase substrate; nucleoside preparation antitumor cytotoxicity phosphorylase substrate. We’ll tell you more about this compound (cas:16710-11-5).
Stereoselective procedures are described for the synthesis of 6-alkyluridines, e.g. I (R = F, OH, R1 = H, F), by Lewis acid-catalyzed condensation of trimethylsilylated 6-alkyl-4-alkylthiouracils with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (ABR) and trimethylsilylated 6-alkyl-3-benzyluracils with ABR. For all the foregoing nucleosides in the fixed syn conformation about the glycosyl bond, 1H NMR spectroscopy further demonstrated that the pentose rings exist predominantly in the conformation N (3′-endo). Most of the nucleosides were weak substrates of Escherichia coli pyrimidine nucleoside phosphorylase. The 5-fluoro-6-substituted uridines were the poorest substrates. Cytotoxicities of the nucleosides were examined vs the human tumor cell lines MOLT-3, U-937, K-562, and IM-9, as well as PHA-stimulated human lymphocytes. Two of the analogs, 5-fluoro-6-(fluoromethyl)uridine and 5-fluoro-6-(hydroxymethyl)uridine, exhibited cytotoxicities comparable to that of 5-fluorouracil.
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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem