Synthesis of Novel Homo-N-Nucleoside Analogs Composed of a Homo-1,4-Dioxane Sugar Analog and Substituted 1,3,5-Triazine Base Equivalents

Abstract

Enantioselective syntheses from dimethyl tartrate of 1,3,5-triazine homo-N-nucleoside analogs, containing a 1,4-dioxane moiety replacing the sugar unit in natural nucleosides, were accomplished. The triazine heterocycle in the nucleoside analogs was further substituted with combinations of NH2, OH and Cl in the 2,4-triazine positions.

Synthesis, molecular docking, ctDNA interaction, DFT calculation and evaluation of antiproliferative and anti-Toxoplasma gondii activities of 2,4-diaminotriazine-thiazole derivatives

“…Multiple-point hydrogen bonding is responsible for the formation of base pairs in the double helix of DNA and determines the stability of DNA double helix. Diaminotriazine can form a highly stable complex with two molecules of thymine or uracil interacting through six hydrogen bonds (Yu et al 2008 ; Mao and Bong 2015 ; Zeng et al 2012 ). Because of the serious side effects of existing drugs, specific recognition of DNA by drug molecules is a key factor in the design of DNA-target drugs.…”

“…Some triazines have already found medical use, e.g., hexamethylmelamine (Altretamine), which is used in refractory ovarian cancer (Damia and D’lncalci 1995 ). Triazine derivatives are also known to form highly stable complexes through hydrogen-bonding interaction with thymine–thymine or uracil–uracil (T–T, U–U) mismatch sites, thus acting as purine mimics (Yu et al 2008 ; Mao and Bong 2015 ; Zeng et al 2012 ).…”

The synthesis of polymeric s-Triazine schiff bases and investigation of [(Fe(III)/Mn(III)(Salen)Cl] metal complexes

“…In addition, striazine Schiff base compounds are used in medicine, especially as molecular magnetic materials and such heterocyclic compounds are used as active ingredients of antitumor and anticancer drugs (Koc and Uysal, 2016;Arslaner et al, 2017;Ozer et al, 2023). Melamine compounds have gained importance in environmental chemistry, metalorganic lattice structures and gas storage (Yu et al, 2008).…”

Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction

“…Nucleoside analogs represent a potentially important class of antiviral anticancer agents [ 1 , 2 , 3 , 4 , 5 ] with antimicrobial and cholinesterase inhibitory activities [ 6 , 7 , 8 , 9 , 10 ] and are commonly used to treat hepatitis B virus [ 11 , 12 ], hepatitis C virus [ 13 , 14 ], herpes simplex [ 15 , 16 ], Human Immunodeficiency Virus (HIV) and neoplasms [ 17 , 18 ]. Zalcitabine (2′,3′-dideoxycytidine, ddc), Abacavir, Stavudine (2′,3′-didehydro-2′,3′-didehydro-2′,3′-dideoxythymidine, d4T), Didanosine (2′,3′-dideoxyinosine, ddI), Emtricitabine (FTC) and Zidovudine (azidothymidine, AZT) ( Figure 1 ) are among the essential antiretroviral nucleoside analogue reverse transcriptase inhibitors (NRTIs) that are used to treat HIV/Acquired Immune Deficiency Syndrome (AIDS) infections [ 19 ].…”