“…As we have reported [ 36 ], in the case of 6-methyluracil 2 the reaction of its bissilylated derivative 5 with a propargyl bromide unexpectedly led to the mixture of N 1- and N 3-substituted products. Therefore, N 1-propargyl derivatives of uracil 1 , 6-methyluracil 2 , thymine 3 , as well as N 1-ω-alkynyl derivatives of 3,6-dimethyluracil 6 (compounds 1a , 2a , 3a , 6a – c , respectively) were synthesized by the alkylation of monosodium salts 7 [ 36 ] (Scheme 1 ). Scheme 1 Synthesis of pyrimidine derivatives containing an ω-alkyne substituent at the N 1 or the C5 position of the pyrimidine ring …”
Section: Resultsmentioning
confidence: 66%
“…Alkyne derivatives of uracil (1b,c; 2b,c), thymine (3b,c) and quinazolin-2,4-dione (4a-c) were obtained in 33-64% yield. As we have reported [36], in the case of 6-methyluracil 2 the reaction of its bissilylated derivative 5 with a propargyl bromide unexpectedly led to the mixture of N1-and N3-substituted products. Therefore, N1-propargyl derivatives of uracil 1, 6-methyluracil 2, thymine 3, as well as N1-ω-alkynyl derivatives of 3,6-dimethyluracil 6 (compounds 1a, 2a, 3a, 6a-c, respectively) were Scheme 1 Synthesis of pyrimidine derivatives containing an ω-alkyne substituent at the N1 or the C5 position of the pyrimidine ring synthesized by the alkylation of monosodium salts 7 [36] (Scheme 1).…”
Section: Synthetic Chemistrymentioning
confidence: 71%
“…At first, we focused on the synthesis of alkyne components of the CuAAC reaction, namely pyrimidine derivatives 1a – c , 2a – c , 3a – c , 4a – c , 6a – c with ω-alkyne substituents at the N 1 atom. They were prepared according to the method reported previously [ 36 ]. Starting pyrimidines uracil ( 1 ), 6-methyluracil ( 2 ), thymine ( 3 ) and condensed uracil derivative, namely quinazoline-2,4-dione ( 4 ), were reacted with an excess of hexamethyldisilazane (HMDS) in toluene in the presence of H 2 SO 4 at reflux for 8 h to afford bissilylated derivatives 5 which were then engaged in the alkylation with ω-iodo-alk-α-ynes without purification (Scheme 1 ).…”
Section: Resultsmentioning
confidence: 99%
“…The azide component of the CuAAC reaction, namely azido ribofuranose 9c, was prepared based on the published procedure [36] (Scheme 2). D-ribose was converted into methyl b-ribofuranoside 9a by reacting with methanol and subsequent acetylation.…”
Section: Synthetic Chemistrymentioning
confidence: 99%
“…Coupling the alkyne components 1a-c, 2a-c, 3a-c, 4a-c, 6a-c, 8 with the azido component 9c was accomplished by a CuAAC reaction in according with a procedure already described [36] (Scheme 3). The 1,2,3-triazolyl analogues 1-4, 6, 8 with acetyl protection were obtained in good yields (60-96%).…”
Based on the fact that a search for influenza antivirals among nucleoside analogues has drawn very little attention of chemists, the present study reports the synthesis of a series of 1,2,3-triazolyl nucleoside analogues in which a pyrimidine fragment is attached to the ribofuranosyl-1,2,3-triazol-4-yl moiety by a polymethylene linker of variable length. Target compounds were prepared by the Cu alkyne-azide cycloaddition (CuAAC) reaction. Derivatives of uracil, 6-methyluracil, 3,6-dimethyluracil, thymine and quinazolin-2,4-dione with ω-alkyne substituent at the N1 (or N5) atom and azido 2,3,5-triO -acetyl-D-β-ribofuranoside were used as components of the CuAAC reaction. All compounds synthesized were evaluated for antiviral activity against influenza virus A/PR/8/34/(H1N1) and coxsackievirus B3. The best values of IC 50 (inhibiting concentration) and SI (selectivity index) were demonstrated by the lead compound 4i in which the 1,2,3-triazolylribofuranosyl fragment is attached to the N1 atom of the quinazoline-2,4-dione moiety via a butylene linker (IC 50 = 30 μM, SI = 24) and compound 8n in which the 1,2,3-triazolylribofuranosyl fragment is attached directly to the N5 atom of the 6-methyluracil moiety (IC 50 = 15 μM, SI = 5). According to theoretical calculations, the antiviral activity of the 1,2,3-triazolyl nucleoside analogues 4i and 8n against H1N1 (A/PR/8/34) influenza virus can be explained by their influence on the functioning of the polymerase acidic protein (PA) of RNA-dependent RNA polymerase (RdRP).
“…As we have reported [ 36 ], in the case of 6-methyluracil 2 the reaction of its bissilylated derivative 5 with a propargyl bromide unexpectedly led to the mixture of N 1- and N 3-substituted products. Therefore, N 1-propargyl derivatives of uracil 1 , 6-methyluracil 2 , thymine 3 , as well as N 1-ω-alkynyl derivatives of 3,6-dimethyluracil 6 (compounds 1a , 2a , 3a , 6a – c , respectively) were synthesized by the alkylation of monosodium salts 7 [ 36 ] (Scheme 1 ). Scheme 1 Synthesis of pyrimidine derivatives containing an ω-alkyne substituent at the N 1 or the C5 position of the pyrimidine ring …”
Section: Resultsmentioning
confidence: 66%
“…Alkyne derivatives of uracil (1b,c; 2b,c), thymine (3b,c) and quinazolin-2,4-dione (4a-c) were obtained in 33-64% yield. As we have reported [36], in the case of 6-methyluracil 2 the reaction of its bissilylated derivative 5 with a propargyl bromide unexpectedly led to the mixture of N1-and N3-substituted products. Therefore, N1-propargyl derivatives of uracil 1, 6-methyluracil 2, thymine 3, as well as N1-ω-alkynyl derivatives of 3,6-dimethyluracil 6 (compounds 1a, 2a, 3a, 6a-c, respectively) were Scheme 1 Synthesis of pyrimidine derivatives containing an ω-alkyne substituent at the N1 or the C5 position of the pyrimidine ring synthesized by the alkylation of monosodium salts 7 [36] (Scheme 1).…”
Section: Synthetic Chemistrymentioning
confidence: 71%
“…At first, we focused on the synthesis of alkyne components of the CuAAC reaction, namely pyrimidine derivatives 1a – c , 2a – c , 3a – c , 4a – c , 6a – c with ω-alkyne substituents at the N 1 atom. They were prepared according to the method reported previously [ 36 ]. Starting pyrimidines uracil ( 1 ), 6-methyluracil ( 2 ), thymine ( 3 ) and condensed uracil derivative, namely quinazoline-2,4-dione ( 4 ), were reacted with an excess of hexamethyldisilazane (HMDS) in toluene in the presence of H 2 SO 4 at reflux for 8 h to afford bissilylated derivatives 5 which were then engaged in the alkylation with ω-iodo-alk-α-ynes without purification (Scheme 1 ).…”
Section: Resultsmentioning
confidence: 99%
“…The azide component of the CuAAC reaction, namely azido ribofuranose 9c, was prepared based on the published procedure [36] (Scheme 2). D-ribose was converted into methyl b-ribofuranoside 9a by reacting with methanol and subsequent acetylation.…”
Section: Synthetic Chemistrymentioning
confidence: 99%
“…Coupling the alkyne components 1a-c, 2a-c, 3a-c, 4a-c, 6a-c, 8 with the azido component 9c was accomplished by a CuAAC reaction in according with a procedure already described [36] (Scheme 3). The 1,2,3-triazolyl analogues 1-4, 6, 8 with acetyl protection were obtained in good yields (60-96%).…”
Based on the fact that a search for influenza antivirals among nucleoside analogues has drawn very little attention of chemists, the present study reports the synthesis of a series of 1,2,3-triazolyl nucleoside analogues in which a pyrimidine fragment is attached to the ribofuranosyl-1,2,3-triazol-4-yl moiety by a polymethylene linker of variable length. Target compounds were prepared by the Cu alkyne-azide cycloaddition (CuAAC) reaction. Derivatives of uracil, 6-methyluracil, 3,6-dimethyluracil, thymine and quinazolin-2,4-dione with ω-alkyne substituent at the N1 (or N5) atom and azido 2,3,5-triO -acetyl-D-β-ribofuranoside were used as components of the CuAAC reaction. All compounds synthesized were evaluated for antiviral activity against influenza virus A/PR/8/34/(H1N1) and coxsackievirus B3. The best values of IC 50 (inhibiting concentration) and SI (selectivity index) were demonstrated by the lead compound 4i in which the 1,2,3-triazolylribofuranosyl fragment is attached to the N1 atom of the quinazoline-2,4-dione moiety via a butylene linker (IC 50 = 30 μM, SI = 24) and compound 8n in which the 1,2,3-triazolylribofuranosyl fragment is attached directly to the N5 atom of the 6-methyluracil moiety (IC 50 = 15 μM, SI = 5). According to theoretical calculations, the antiviral activity of the 1,2,3-triazolyl nucleoside analogues 4i and 8n against H1N1 (A/PR/8/34) influenza virus can be explained by their influence on the functioning of the polymerase acidic protein (PA) of RNA-dependent RNA polymerase (RdRP).
Herein, the synthesis and crystal structure identification of thymine‐modified β‐cyclodextrin (mono‐(6‐Thymine‐6‐deoxy)‐β‐CD, Thy‐CD) are reported. The catalyst system (Pd@Thy‐CD) was prepared by using the thymine‐modified β‐cyclodextrin as ligand and palladium acetate (Pd(OAc)2) as palladium source. The as‐obtained Pd@Thy‐CD catalyst was characterized by NMR, IR, SEM, and XPS analysis. The catalyst can efficiently catalyze the aqueous phase Suzuki coupling reaction in situ. Under mild reaction conditions, the catalyst system provides excellent yields for the Suzuki coupling reaction of aryl halides, including with aryl chlorides and aryl boronic acids in water. The major advantages of this technique are the ease of preparation of the palladium catalyst, the aqueous phase coupling reaction, the broad functional group tolerance, and the easy recyclability.
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