5334-23-6

Usage

Chemical Properties

YELLOW AMORPHOUS POWDER

InChI:InChI=1/C5H4N4S/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)/p-1

Upstream product

• 315-30-0 Allopurinol 
• 5399-92-8 4-chloro-1H-pyrazolo[3,4-d]pyrimidine 

Downstream Products

• 5418-10-0 4-methylthio-1H-pyrazolo[3,4-d]pyrimidine 
• 42755-02-2 4-benzylsulfanyl-1⁽²⁾H-pyrazolo[3,4-d]pyrimidine 
• 328390-36-9 1-[1-(2-acetoxyethoxy)methyl-1,2,3-triazol-4-ylmethyl]-4-benzylthio-1H-pyrazolo[3,4-d]pyrimidine 
• 328390-37-0 1-[1-(2-acetoxyethoxy)methyl-1,2,3-triazol-5-ylmethyl]-4-benzylthio-1H-pyrazolo[3,4-d]pyrimidine 
• 1309386-98-8 C₂₄H₂₅FN₆O₄ 
• 1309377-75-0 C₂₄H₂₅FN₆O₄ 
• 1309377-74-9 C₁₃H₈FN₅O₂S 
• 1309377-73-8 C₁₃H₈FN₅S 
• 125345-79-1 1-(1,2-Epoxy-3-propanyl)-4-[1-(diphenylmethylpiperazin-4-yl]-2-hydroxy-3-propanylthio]-1H-pyrazolo[3,4-d]pyrimidine 
• 64372-72-1 (2R,3R,4S,5R)-2-(4-Allylsulfanyl-pyrazolo[3,4-d]pyrimidin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 60355-67-1 4-(methylthio)-1-β-D-ribofuranosyl-1H-pyrazolo<3,4-d>pyrimidine 
• 380897-88-1 benzoic acid 1-acetoxymethyl-2-[4-(1-ethoxycarbonyl-propylsulfanyl)-pyrazolo[3,4-d]pyrimidin-1-ylmethoxy]-ethyl ester 
• 380897-87-0 benzoic acid 1-acetoxymethyl-2-[4-(1-ethoxycarbonyl-ethylsulfanyl)-pyrazolo[3,4-d]pyrimidin-1-ylmethoxy]-ethyl ester 
• 54524-71-9 4-mercapto-1-β-D-ribofuranosyl-1H-pyrazolo<3,4-d>pyrimidine 

Relevant academic research and scientific papers

Synthesis and antibacterial activity of new spiro[thiadiazoline-(pyrazolo[3,4-d]pyrimidine)] derivatives

New heterocyclic compounds spiroderivatives of allopurinol of biological interest were prepared from allopurinol via thionation and 1,3-dipolar cycloaddition and were produced in high to excellent yields. These compounds were characterized on the basis of spectral and spectroscopic data (1H NMR, 13C, IR, and MS). The antibacterial activity of the synthesized products was studied using bacterial strains: Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa. Compounds having an ethyl group showed the best activity with MIC value of 31.25 μg/mL against Staphylococcus aureus and Streptococcus fasciens.

Synthesis and biological activity of 4-substituted 1-[1-(2-hydroxyethoxy)-methyl-1,2,3-triazol-(4 & 5)-Ylmethyl]-1H-pyrazolo[3,4-d]pyrimidines

The chemical synthesis of some 4-substituted 1-[1-(2-hydroxyethoxy)-methyl-1,2,3-triazol-(4 and 5)-ylmethyl]-1H-pyrazolo[3,4-d]pyrimidines 12a,b, 13a,b and 14-23 as acyclic nucleosides is described. Treatment of (2-acetoxyethoxy)methylbromide with sodium azide afforded (2-acetoxyethoxy)methylazide 9. The heterocycles 6a,b were alkylated, separately, with propargyl bromide to obtain, regioselectively, 4-(methyl and benzyl)thio-1-(prop-2-ynyl)-1H-pyrazolo[3,4-d] pyrimidines 7a,b. These N1alkylated products were condensed with compound 9 via a 1,3-dipolar cycloaddition reaction to obtain, after separation and deprotection, 1,4-and 1,5-regioisomers 12a,b and 13a,b. The deprotected acyclic nucleosides 12a and 13a served as precursors for the preparation of 4-amino (14 and 15), 4-methylamino (16 and 17), 4-benzylamino (18 and 19), 4-methoxy (20 and 21) and 4-hydroxy (22 and 23) analogues. Compounds 7a,b and all deprotected acyclic nucleosides were evaluated for their inhibitory effects against the replication of HIV-1(IIIB) and HIV-2(ROD) in MT-4 cells and for their anti-tumor activity. No marked activity was found. However, initial evaluation of 6a,b, 7a,b, 12a,b, 13a,b and 14-23 showed that compound 7b has marked activity against M. tuberculosis.