Synthesis and Biological Evaluation of Some Pyrrolo[2,3‐d]pyrimidines

Abstract

Pyrrolo[2,3-d]pyrimidine and tetrazolopyrimidine derivatives 2a, b-5a, b were prepared. Also, acyclic and cyclic C-nucleosides 7a, b-12a, b were prepared by treating compound 6 with some aldoses. All prepared products were tested for antiviral activity against hepatitis-A virus (HAV, MBB-cell culture adapted strain) and herpes simplex virus type-1 (HSV-1). Plaque reduction infectivity assay was used to determine virus count reduction as a result of treatment with tested compounds. Compound 2a showed the highest effect on HAV, while compound 11b showed the highest effect on the HSV-1 virus.

Synthesis and anti-HSV-1 evaluation of some pyrazoles and fused pyrazolopyrimidines

“…The IR spectra of compounds 12a and 12b revealed the absence of hydroxyl groups and showed absorption bands due to (NH) and (C]O). Also, the 1 H NMR and 13 Meanwhile, stirring of compounds 11a and 11b with acetic anhydride, in dry pyridine at 70 C, gave two sets of products: the O-acetylated sugar hydrazone derivatives 12a (42%) and 12b (39%) and the O-acetylated cyclic C-nucleosides 13a (54%) and 13b, (56%), respectively (Scheme 2, Section 3). However, heating of derivatives 11a and 11b with acetic anhydride using water bath, gave products assigned to the structures of compounds 13a and 13b, respectively.…”

“…This could be explained via acetylation of the hydrazone derivatives 11a and 11b to give their corresponding O-acetylated sugar hydrazone derivatives 12a and 12b, and then followed by oxidative cyclization [13,15,17] to give the O-acetylated cyclic Cnucleosides 13a and 13b, respectively.…”

“…Moreover, C-nucleosides were reported to be of great value from the biological point of view [13,14], and many of their derivatives have been synthesized as potential antibacterial [15], antifungal agents [16,17] and were tested also against herpes simplex viruses (HSV-1 and HSV-2) [13].…”

Synthesis, Isomerization, and Antimicrobial Evaluation of Some Pyrazolopyranotriazolopyrimidine Derivatives

“…Thus, nitrosation of the hydrazino group of compound 5, afforded 5,10-dimethyl-11-(p-nitrophenyl)-9,11-dihy- [1,5-c]pyrimidine derivatives are still not known (to the best of our knowledge) in the literature. In continuation of our previous work in preparing various cyclic and acyclic nucleosides of different heterocyclic compounds [17,18,20,22,27], in this report, we described the synthesis of …”

“…Condensation of compound 5 with p-nitrobenzaldehyde, p-methoxybenzaldehyde in the presence of a few drops of piperidine and also with aldohexose [22,23], namely D-glucose, in the presence of a catalytic amount of glacial acetic acid took place by heating under reflux in ethanol, where the corresponding hydrazones 12a-c were produced. Attemps to cyclize the latter compounds to their corresponding [1,2,4]triazolo [4,3-c]pyrimidine derivatives by refluxing with bromine in glacial acetic acid failed.…”