This review summarizes recent literature (2000-2015) on the synthesis and pharmaceutical properties of pyrrolopyrimidines. These modified pyrimidine bases, fused to a pyrrole ring, and their corresponding nucleosides display a broad applicability in medicinal chemistry. This overview is divided into three main sections, according to the respective isomers: pyrrolo[2,3-d]pyrimidines, pyrrolo[3,2-d]pyrimidines, and pyrrolo[3,4-d]pyrimidines. Each section contains a description of common retro-synthetic strategies, with particular attention for newly reported synthetic entries to the scaffold. Next, the synthetic strategies and the ways in which the scaffolds can be further modified are exemplified according to the biological properties of the obtained products.
Awareness of the impact of microbiota in both health and disease is growing. Using a new in vitro oral mucosa co-culture model, we recently showed a clear inhibition of epithelial wound healing in the presence of an oral microbial community. In this paper, we have used the same model in combination with specific oral microbial species to obtain a better insight into the role of the oral microbiota in wound healing. Monocultures of Klebsiellaoxytoca and Lactobacillus salivarius significantly inhibited wound healing with ~20%, whereas Streptococcus mitis and S. oralis enhanced the healing process with ~15% in 24 h. Yet, neither S. oralis or S. mitis were able to counteract the inhibitory effects from K.oxytoca on wound healing. Other tested microbial species had no effect on wound healing. Apart from this species-dependency, the inhibitory effect on wound healing depended on a microbial threshold concentration. Further mechanistic experiments with K.oxytoca excluded different microbial factors and hypothesized that quorum sensing molecules might play a role in the inter-kingdom signalling during wound healing. These results are important for the development of new strategies for the management of (infected) wounds and ulcerations.Electronic supplementary materialThe online version of this article (doi:10.1186/s13568-015-0116-5) contains supplementary material, which is available to authorized users.
In this work, the synthesis of oxazolo[4,5‐d]pyrimidines and oxazolo[5,4‐d]pyrimidines is reviewed. The review is focused on the construction of the scaffold rather than on its further modification. Nevertheless, selected examples illustrate some of the most common modifications of these scaffolds. The synthetic part is complemented by an overview of their biological activity. This review covers literature and patents from 1967 until the present.
A series of novel 2-(thiazol-2-yl)-octahydropyrrolo [3,4-c]pyrroles was synthesized by reaction of octahydropyrrolo [3,4-c]pyrrole N-benzoylthiourea derivatives and α-haloketones in subcritical water at 130 °C in 75-91% yield. Both the thiourea intermediates and the end products were synthesized in subcritical water, which proved a suitable green alternative to acetone by delivering the desired compounds in much shorter reaction times and practically the same yields. The antimicrobial activity of the compounds was determined against five bacterial strains and three fungal strains, and MIC values of 15.62-250 g/mL were observed. Moreover, the compounds exhibited antimycobacterial activity against M. tuberculosis H37Rv with MIC values of 7.81-62.5 µg/mL.
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