Synthesis and anti-inflammatory activity evaluation of novel AZT and adenosine derivatives
220 viewsDOI:
https://doi.org/10.54939/1859-1043.j.mst.VITTEP.2022.30-36Keywords:
Adenosine; AZT; Quinazolinone; Click chemistry; Anti-inflammatory.Abstract
A five-step procedure was used to synthesize four novel conjugates of AZT and adenosine with quinazolinone scaffold. In the last step, alkynes-1 of quinazolinone were coupled to adenosine azide and AZT by Click chemistry to yield the designed conjugates. Their structures were characterized by full-length data of spectra including 1H-, 13C-NMR and MS. Screening for their in vitro anti-inflammatory activity was performed using Murine macrophage RAW 264.7 cells. The relationship between structure and biological activity was also discussed.
References
[1]. H. C. Kolb et al, “The growing impact of click chemistry on drug discovery,” Drug Discov. Today. Vol. 8, No. 24, pp. 1128-1137, (2003). DOI: https://doi.org/10.1016/S1359-6446(03)02933-7
[2]. X. Jiang et al, “Recent applications of click chemistry in drug discovery,” Expert Opin. Drug Discov. Vol. 14, No. 8, pp. 779-789, (2019). DOI: https://doi.org/10.1080/17460441.2019.1614910
[3]. Y. W. He et al, “1,2,3-Triazole-containing derivatives of rupestonic acid: click-chemical synthesis and antiviral activities against influenza viruses,” Eur. J. Med. Chem. Vol. 76, pp. 245-255, (2014). DOI: https://doi.org/10.1016/j.ejmech.2014.02.029
[4]. M. F. Mady et al, “Ultrasound-assisted synthesis of novel 1,2,3-triazoles coupled diaryl sulfone moieties by the Cu-AAC reaction, and biological evaluation of them as antioxidant and antimicrobial agents,” Eur. J. Med. Chem. No. 84, pp. 433-443, (2014). DOI: https://doi.org/10.1016/j.ejmech.2014.07.042
[5]. F. J. Pan et al, “Synthesis of 4-phenylthieno[2,3-e][1,2,4]triazolo[4,3-a]pyrimidine-5(4H)-one derivatives and evaluation of their anti-inflammatory activity,” Lett. Drug Des. Discov. Vol. 13, No. 2, pp. 141-148, (2016). DOI: https://doi.org/10.2174/1570180812666150630184439
[6]. L. V. Chinh et al, “New Chalcones Containing 5-Fluorouracil Exhibiting in vitro Anti-Cancer Activity,” Lett. Org. Chem. Vol. 12, No. 4, pp. 251-261, (2015). DOI: https://doi.org/10.2174/1570178612666150226230109
[7]. Z. Xu et al, “1,2,3-Triazole-containing hybrids as potential anticancer agents: Current developments, action mechanisms and structure-activity relationships,” Eur. J. Med. Chem. Vol. 183, pp. 111700, (2019). DOI: https://doi.org/10.1016/j.ejmech.2019.111700
[8]. M. Serafini et al, “Advances in Heterocyclic Chemistry” Academic Press, pp. 101-148, (2021). DOI: https://doi.org/10.1016/bs.aihch.2020.10.001
[9]. L. P. Jordheim et al, “Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases,” Nat. Rev. Drug Discov Vol. 12, pp. 447-464, (2013). DOI: https://doi.org/10.1038/nrd4010
[10]. A. A. Zenchenko et al, “Antiviral and Antimicrobial Nucleoside Derivatives: Structural Features and Mechanisms of Action,” Mol. Biol. Vol. 55, pp. 786-812, (2021). DOI: https://doi.org/10.1134/S0026893321040105
[11]. T. D. Thinh et al, “New quinazolinone derivatives: Synthesis and in vitro cytotoxic activity”, Vietnam J. Sci. Technol. Vol. 58, No. 1, pp. 12-20, (2020). DOI: https://doi.org/10.15625/2525-2518/58/1/14391
[12]. D. Tsikas, “Analysis of nitrite and nitrate in biological fluids by assays based on the Griess reaction: appraisal of the Griess reaction in the L-arginine/nitric oxide area of research,” J. Chromatogr. B. Vol. 815, No. 1-2, pp. 51-71, (2007). DOI: https://doi.org/10.1016/j.jchromb.2006.07.054
[13]. L. G. Chen et al, “Anti-inflammatory activity of mangostins from Garcinia mangostana,” Food Chem. Toxicol. Vol. 46, No. 2, pp. 688-693, (2008). DOI: https://doi.org/10.1016/j.fct.2007.09.096
