Nucleic acid components and their analogs: Design and synthesis of novel cytosine thioglycoside analogs

Abstract

The synthesis of a new category of novel cytosine 4-thioglycoside analogs has been first accomplished. The main step of this strategy is the synthesis of sodium pyrimidine-4-thiolate through the condensation of 2-cyano-N-arylacetamides with sodium cyanocarbonimidodithioate, followed by coupling with α-bromo-sugars to afford the corresponding cytosine 4-thioglycoside analogs. The free thioglycosides were also prepared. Subsequent studies on the application of this strategy for the preparation of other potent pyrimidine thioglycosides are reported.

Discovery of NewS‐Glycosides andN‐Glycosides of Pyridine‐biphenyl System with Antiviral Activity and Induction of Apoptosis inMCF7 Cells

“…Treatment of pyridine-2-thione derivatives 1a-d [38] with aq. KOH in acetone furnished the corresponding potassium salts of 2-thioxopyridines (2a-d), which in turn were treated with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (3a) or 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (3b) to afford the S-glycosylated [15,[39][40][41][42][43][44][45][46][47] compounds 4a-h in good to high yields (50-99%) (Scheme 1). The structures of the S-glycoside 4a-h were confirmed by elemental analysis and spectral data (IR, 1 H-NMR, 13 C-NMR).…”

An unexpected tautomer: synthesis and crystal structure of N-[6-amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamide

“…Continuing with our project of developing synthetic strategies for the design and synthesis of efficient antimetabolites (Elgemeie & Mohamed-Ezzat, 2022), focussing on derivatives of sulfonamides, we describe here a new approach (Fig. 1) that generates novel substituted triazine sulfonamides starting from the highly reactive compound dimethyl cyanocarboimidodithioate (2), which has shown its effectiveness in synthesizing various heterocycles (Elgemeie & Mohamed, 2014;Mohamed-Ezzat et al, 2021), in particular nucleoside and non-nucleoside pyrimidine analogues (Elgemeie et al, 2015(Elgemeie et al, , 2017(Elgemeie et al, , 2019.…”

Synthesis and crystal structure of N-phenyl-2-(phenylsulfanyl)acetamide

“…Acetamide-containing drugs are used for inflammation control, cyclooxygenase (COX) enzyme inhibition, and as antiviral drugs (Agrawal et al, 2010;Orzalesi et al, 1977). Recently, starting from acetamides, we have synthesized various heterocyclic compounds that exhibit diverse activities, including anti-SARS CoV-2 (Mohamed-Ezzat & Elgemeie, 2023), antimicrobial (Elgemeie et al, 2017a,b), antitumor properties (Elgemeie & Mohamed-Ezzat, 2022;Mohamed-Ezzat et al, 2023a,b), as well as potential for other applications (Elgemeie et al, 2015(Elgemeie et al, , 2017a(Elgemeie et al, ,b, 2019Mohamed-Ezzat et al, 2021, 2023a.…”