52522-97-1

Upstream product

• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 611-08-5 2,4-dihydroxy-5-nitropyrimidine 
• 611-08-5 5-nitrobarbituric acid 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 23392-16-7 5-nitrouridine 2',3',5'-tri-O-benzoate 
• 2857-97-8 trimethylsilyl bromide 
• 81777-44-8 Acetic acid 2-(5-nitro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-ethyl ester 
• 124314-20-1 1-[(4S,5R)-5-Benzyloxymethyl-4-(2-methanesulfinyl-ethoxy)-tetrahydro-furan-2-yl]-5-nitro-1H-pyrimidine-2,4-dione 
• 158966-45-1 3',5'-di-O-benzoyl-2'-O-methyl-5-nitrouridine 
• 338742-29-3 1-(3,5-O-dibenzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)-5-nitrouracil 
• 81797-05-9 5-nitroacyclouridine 
• 66782-11-4 C₅₆H₄₃N₃O₁₈ 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of Some 5-Nitro- and 5-Amino Derivatives of 2′-Deoxycytidine, 2′,3′-Dideoxyuridine, and 2′,3′-Dideoxycytidine

In this article, we describe the synthesis of 5-nitro-1-(2-deoxy-α -D-erythro-pentofuranosyl)cytosine (4α), 5-nitro-1-(2-deoxy-β -D-erythro-pentofurano syl)cytosine (4β), 5-amino-1-(2-deoxy-α -D-erythro-pentofuranosyl)cytosine (5α), 5-nitro-1-(2-deoxy-β -D-erythro-pentofuranosyl)cytosine (5β), 5-nitro-1-(2,3-dideoxy-β -D-ribofuranosyl)uracil (6β), 5-amino-1-(2,3-dideoxy-α, β-D-ribofuranosyl)uracil (7), 5-nitro-1-(2,3-dideoxy-α,β -D-ribofuranosyl)cytosine (8) and 5-amino-1-(2,3-dideoxy-β -D-ribofuranosyl)cytosine (9β). The prepared compounds were tested for their activity against HIV and HBV viruses, but they did not show significant activity.

Synthesis of 2',3'-dideoxy-3'-fluorouridines with potential anti-HIV activity according to neural network calculations

Methyl 2, 3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythropentofuranoside was condensed with trimethylsilylated 5-substituted uracils to give nucleosides using trimethylsilyl trifluoromethanesulfonate as catalyst. In the case of 5-nitrouracil an acyclic nucleoside believed to be an intermediate for the corresponding nucleoside was isolated. The 5-substituents were selected from neural network calculations on compounds with potential activity against HIV-1. All compounds from the condensation reactions were deacylated by treatment with sodium methoxide in methanol.

Chitosan–silica sulfate nanohybrid: a highly efficient and green heterogeneous nanocatalyst for the regioselective synthesis of N-alkyl purine, pyrimidine and related N-heterocycles via presilylated method

Abstract: The presilylation of purine and pyrimidine nucleobases as well as other related N-heterocycles with HMDS utilizing chitosan–silica sulfate nanohybrid (CSSNH) is described. CSSNH is proved to be a useful, highly efficient and eco-friendly heterogeneous nanohybrid catalyst for silylation of nucleobases. The presilylated nucleobases then underwent the reaction with different sources of carbon electrophiles to afford the desired N-alkyl-substituted derivatives in good-to-excellent yields. CSSNH exhibits several advantageous involving ease of handling and preparation, low cost, reusability and environmental benignity. These unique properties render the CSSNH to be an ideal candidate for use in green industrial processes. Graphic abstract: [Figure not available: see fulltext.].

A solid-supported acidic oxazolium perchlorate as an easy-handling catalyst for the synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation

A solid-supported acidic oxazolium perchlorate was investigated as a heterogeneous catalyst in N-glycosylation reactions using silylated modified pyrimidines and an acylated ribose or glucose to afford the corresponding pyrimidine nucleosides. This salt is a nonhygroscopic and stable powder whose activity is comparable to that of 2-methyl-5-phenylbenzoxazolium perchlorate. A reaction with this polymer catalyst can be conducted on a gram scale. Reusability of the solid-supported catalyst was also investigated.

Synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation catalyzed by 2-methyl-5-phenylbenzoxazolium perchlorate

Several acidic azolium salts prepared from oxazole, thiazole, and imidazole derivatives were investigated as catalysts in N-glycosylation reaction using a silylated modified pyrimidine and an acylated ribose or glucose to afford the corresponding pyrimidine nucleoside. Among the salts, 2-methyl-5- phenylbenzoxazolium perchlorate showed the highest catalytic activity. This salt is a nonhygroscopic crystalline compound that shows higher activity than the frequently used trimethylsilyl triflate. Reactions with this salt can be conducted in gram scales.

One-flow, multistep synthesis of nucleosides by Bronsted acid-catalyzed glycosylation

Nucleosides in flow: A general, scalable method of Bronsted acid-catalyzed nucleoside formation is described. Because of the high reaction temperatures readily available to the flow reaction format, mild Bronsted acids, particularly pyridinium triflates, can be used. A one-flow multistep synthesis of unprotected nucleosides is also reported (see scheme).

Silica sulfuric acid (SSA) as a highly efficient heterogeneous catalyst for persilylation of purine and pyrimidine nucleobases and other N-heterocycles using HMDS

Purine and pyrimidine nucleobases and other N-heterocycles have been silylated with HMDS in excellent yields in the presence of a catalytic amount of silica sulfuric acid (SSA) as a heterogeneous catalyst. SSA utilizes a shorter reaction time and higher yields of silylated nucleobases. SSA is reusable for several times without a decrease in reactivity or yield of silylated adducts. Copyright

Inhibition of hepatitis B virus (HBV) replication by pyrimidines bearing an acyclic moiety: Effect on wild-type and mutant HBV

Chronic hepatitis B virus (HBV) infection remains a major health problem worldwide. The main clinical limitation of a current antiviral drug for HBV, lamivudine, is the emergence of drug-resistant viral strains upon prolonged therapy. A group of 5-, 6-, or 5,6-substituted acyclic pyrimidine nucleosides with a 1-[(2-hydroxyethoxy)methyl] moiety were synthesized and evaluated for antiviral activities. The target compounds were prepared by the reaction of silylated uracils possessing a variety of substituents at the C-5 or C-6 positions or both with 1,3-dioxolane in the presence of potassium iodide and chlorotrimethylsilane by a convenient and single-step synthesis. Among the compounds tested, 5-chloro and 5-bromo analogues possessing an acyclic glycosyl moiety were the most effective and selective antiviral agents in the in vitro assays against wild-type duck HBV (EC50 = 0.4-2.2 and 3.7-18.5 μM, respectively) and human HBV-containing 2.2.15 cells (EC50 = 4.5-45.4 and 18.5-37.7 μM, respectively). These compounds were also found to retain sensitivity against lamivudine-resistant HBV containing a single mutation (M204I) and double mutations (L180M/M204V). The compounds investigated did not show cytotoxicity to host HepG2 and Vero cells, up to the highest concentration tested. The results presented here confirm and accentuate the potential of acyclic pyrimidine nucleosides as anti-HBV agents and extend our previous observations. We herein report the capability of acyclic pyrimidine nucleosides to inhibit the replication of both wild-type and drug-resistant mutant HBV.

Experimental evidence for intramolecular attractive nonbonded C-F ··· H-C interactions in 2',3'-dideoxy-4'-(fluoromethyl)nucleosides - Through- space J(CF) and J(HF) NMR coupling constants, correlation with empirical parameters of solvent polarity and single-crystal X-ray structures

A collection of 5'-O-benzyl-2',3'-dideoxy-4'-(fluoromethyl)nucleosides carrying both purinic and pyrimidinic nucleobases (uracil, 5-Br-uracil, 5- O2N-uracil, 6-Cl-purine and inosine) were synthesized in both the α and the β form. Through-space-transmitted 6J(CF) NMR coupling constants between F and C-6 (pyrimidinic base) or C-8 (purinic base) were observed for all of the α anomers of the compounds examined, whilst the corresponding 7J(HF) coupling constants were resolved only for the 5-substituted uracil derivatives. The absolute values of all the through-space couplings were found to decrease monotonically with increasing solvent polarity (CDCl3, MeOD, [D6]acetone, [D6]DMSO). This trend suggests that the through-space interaction is mediated by an intramolecular (sp3)C-F ··· H-C(sp2) hydrogen bond. The possibility of any relevant solvent-induced conformational change influencing the F/base mutual spatial relationship in the molecules investigated was ruled out by heteronuclear steady-state 1H{19F}-NOE experiments. A linear correlation was observed between 6J(CF) and 7J(HF) coupling constants and the Kamlet-Taft's hydrogen bond basicity parameter β. The crystal structures of the α and β anomers of the 5-nitrouracil nucleoside show evidence that the H-6 of the nucleobase forms hydrogen-bond- like interactions involving the O-benzyl oxygen atom in the β anomer, and that in the case of the α anomer this is replaced by the F atom of the fluoromethyl group.

General preparative synthesis of 2'-O-methylpyrimidine ribonucleosides

A convergent and general approach to synthesizing 2'-O-methylpyrimidine ribonucleosides 4a-e-, 6, 7 on a multigram scale is described which begins with an improved procedure for making larger quantities of 2-O-methyl-1,3,5-tri-O-benzoyl-α-D-ribose. The sugar was reacted with the desired silylated pyrimidines at room temperature under Vorbruggen conditions. The crude products contained less than 10% of the α anomers and the desired β anomers were isolated by crystallization. The blocked nucleosides were then deprotected and isolated by standard methods.