Preparation of 5-Selenocyanatouracil by a more convenient method and evaluation of some pharmacological properties

Sahar Muayad Noori; Nadheerah F. Neamah; Shaker A. N. Al-Jadaan

doi:10.53730/ijhs.v6nS8.13379

Authors

Sahar Muayad Noori
Saharalshemary@gmail.com
Pharmacology &Toxicology -Department, College of Pharmacy/ University of Basrah, Iraq
Nadheerah F. Neamah Pharmacology &Toxicology -Department, College of Pharmacy/ University of Basrah, Iraq
Shaker A. N. Al-Jadaan Pharmaceutical Chemistry- Department, College of Pharmacy/ University of Basrah, Iraq

Keywords:

uracil, selenium, potassium selenocyanate, DPPH, antimicrobials

Abstract

A convenient method for preparation of 5-Selenocyanatouracil (5-SeU), this compound gains importance because it is similar to 5-Fluorouracil which is one of the famous uracil derivatives as an anticancer drug. Some of invitro pharmacological activities such as DPPH antioxidant effects and antimicrobial activity, in addition to median lethal dose (LD50) were estimated. The study aimed to use a convenient synthesis procedure, and evaluation of in vitro pharmacological activity, also to determine the median lethal dose of 5-SeU. 5-SeU synthesis was carried out in very good yield through a direct reaction between 5-Iodouracil and freshly prepared potassium selenocyanate in refluxing aqueous solution to give light-gray crystalline. Antimicrobial measured by disc diffusion method. LD50was determine using Albino rats. 5-SeU compound was branded by FT-IR; ¹³C- NMR and ¹H- NMR spectroscopic data. The results showed no antibacterial effects for most of test bacteria with a low inhibition effect on Staph. Aureus, and Pseudomonas aeruginosa, with moderate inhibition zone at candida culture.

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References

Abdul-Jabar, R., Al-Fadal, S. A. M., & Hameed, B. (2020). The antioxidant and DNA damage protection activity of Hibiscus sabdariffa L. Plant Cell Biotechnology and Molecular Biology, 21, 10-23

Abonia, R., Gutierrez, L., Zwarycz, A., Smits, S., & Laali, K. (2019). An Efficient Selectfluor-Mediated Oxidative Thio- A nd Selenocyanation of Diversely Substituted Indoles and Carbazoles. Heteroatom Chemistry, 2019, 1- 10. doi: 10.1155/2019/1459681

Baliyan, S., et al., Determination of Antioxidants by DPPH Radical Scavenging Activity and Quantitative Phytochemical Analysis of Ficus religiosa. Molecules, 2022. 27(4): p. 1326

Baquedano, Y.; Alcolea, V.; Toro, M.A.; Gutierrez, K.J.; Nguewa, P.; Font, M.; Moreno, E.; Espuelas, S.; Jimenez-Ruiz, A.; Palop, J.A.; Sanmartin, C. Novel heteroaryl selenocyanates and diselenides as potent antileishmanial agents. Antimicrob Agents Chemother 2016, 60, 3802-3812

Brogi, S., Ibba, R., Rossi, S., Butini, S., Calderone, V., Gemma, S., & Campiani, G. (2022). Covalent Reversible Inhibitors of Cysteine Proteases Containing the Nitrile Warhead: Recent Advancement in the Field of Viral and Parasitic Diseases. Molecules, 27(8), 2561.

Cao, Q.-Q., Fu, Y.-Q., Zhang, C.-B., Zhu, Y., Yin, J.-F., Granato, D., . . . Xu, Y.-Q. (2022). Effect of Brewing Water on the Antioxidant Capacity of Green Tea Infusion with DPPH Assay. Journal of Chemistry, 2022, 7736117. doi: 10.1155/2022/7736117

Chandra, M., Raj, J., Dogra, T. d., Rajvanshi, A. C., & Raina, A. (2014). Determination of median lethal dose of Triazophos with DMSO in wistar rats. Asian J Pharm Clin Res, 7(4). doi: https://www.researchgate.net/publication/265378795

Dawoud, H., & Shayoub, M. (2015). Acute Toxicity Studies of Ethanolic Extract of Eucalyptus Camaldulensis Dehnh Leaves. Journal of Network Communications and Emerging Technologies, 2

Hadjiivanov, K. I., Panayotov, D. A., Mihaylov, M. Y., Ivanova, E. Z., Chakarova, K. K., Andonova, S. M., & Drenchev, N. L. (2021). Power of Infrared and Raman Spectroscopies to Characterize Metal-Organic Frameworks and Investigate Their Interaction with Guest Molecules. Chemical Reviews, 121(3), 1286-1424. doi: 10.1021/acs.chemrev.0c00487

Huang, L., Xuan, W., Sarna, T., & Hamblin, M. R. (2019). Comparison of thiocyanate and selenocyanate for potentiation of antimicrobial photodynamic therapy. J Biophotonics, 12(1), e201800092. doi: 10.1002/jbio.201800092

Jaszczak, E., Polkowska, Ż., Narkowicz, S., & Namieśnik, J. (2017). Cyanides in the environment-analysis-problems and challenges. Environ Sci Pollut Res Int, 24(19), 15929-15948. doi: 10.1007/s11356-017-9081-7

Jia, Y., & Zhao, L. (2021). The antibacterial activity of fluoroquinolone derivatives: An update (2018–2021). European Journal of Medicinal Chemistry, 224, 113741. doi: https://doi.org/10.1016/j.ejmech.2021.113741

Kariyil, B., & A. Usha, P. (2020). Acute oral toxicity studies of methanolic extract and chloroform fraction of methanolic extract of seeds of Annona muricata. Pharmacognosy Magazine, 16(72), 757-763. doi: 10.4103/pm.pm_118_20

Loo, Y.Y., et al., In Vitro Antimicrobial Activity of Green Synthesized Silver Nanoparticles Against Selected Gram-negative Foodborne Pathogens. Frontiers in Microbiology, 2018. 9

Martín-Escolano, R., Molina-Carreño, D., Plano, D., Espuelas, S., Rosales, M., Moreno, E., . . . Marin, C. (2021). Library of Selenocyanate and Diselenide Derivatives as In Vivo Antichagasic Compounds Targeting Trypanosoma cruzi Mitochondrion. Pharmaceuticals, 14, 419. doi: 10.3390/ph14050419

More, G.K. and R.T. Makola, In-vitro analysis of free radical scavenging activities and suppression of LPS-induced ROS production in macrophage cells by Solanum sisymbriifolium extracts. Scientific Reports, 2020. 10(1): p. 6493.

Morris-Schaffer, K. and M.J. McCoy, A Review of the LD50 and Its Current Role in Hazard Communication. ACS Chemical Health & Safety, 2021. 28(1): p. 25-33

Nadheerah F. Neamah, Abdul-Razzak .Naaeem Khudair, Shaker. A. N. Al-Jadaan Synthesis, (2020); Characterization, Antimicrobial Activity And Acute Toxicity Test of Anovel 4̄,4̄̄ - (4, 5, 6, 7-Tetrahydro- [1, 2, 3 -] Selenad Iazolo [4, 5 e] Pyridine-4, 6-Diyl) Bis (Benzene-1, 3-Diol). Egypt. J. Chem. Vol. 63, No.2. pp. 669-681

Qamar, N., P. John, and A. Bhatti, Emerging role of selenium in treatment of rheumatoid arthritis: An insight on its antioxidant properties. Journal of Trace Elements in Medicine and Biology, 2021. 66: p. 126737

Razzaq, A., et al., Synthesis of PVA capped naproxen conjugated MgO nanoparticles and its bioactivity screening. Journal of Drug Delivery Science and Technology, 2022. 73: p. 103429.

Serebrianyi, A.M.; Sal'nikova, L.E.; Bakhitova, L.M.; Pashin Iu, B. Potassium cyanate modification of the toxic and mutagenic effects of gamma radiation and benzo(a)pyrene. Radiobiologiia 1989, 29, 235-240 .

Singh, S., Mosslemin, M. H., & Hassanabadi, A. (2018). Synthesis of 5-Aryl-1,3- Dimethyl-7-Selenoxopyrimidino[4,5-d]Pyrimidine-2,4(1H,3H)-Dione. Journal of Chemical Research, 42(5), 264-266. doi: 10.3184/174751918X15265512038216

van Duin, D., & Paterson, D. L. (2020). Multidrug-Resistant Bacteria in the Community: An Update. Infectious disease clinics of North America, 34(4), 709- 722. doi: 10.1016/j.idc.2020.08.002

Wiaam M. Ahmed, NuhaH. Al-Saadawy and Mohammed I. Abowd.Synthesis and Characterization of a New Organoselenium and Organotellurium Compounds Depending on 9-Chloro-10-Nitro-9,10-Dihydroanthracene Annals of R.S.C.B. Vol. 25, Issue 4, 2021, Pages. 11035 – 11043.

Zhang, H., Li, Z., Dai, C., Wang, P., Fan, S., Yu, B., & Qu, Y. (2021). Antibacterial properties and mechanism of selenium nanoparticles synthesized by Providencia sp. DCX. Environmental Research, 194, 110630. doi: https://doi.org/10.1016/j.envres.2020.110630

Zhang, Y.-Y., Huang, Y.-F., Liang, J., & Zhou, H. (2022). Improved up-and- down procedure for acute toxicity measurement with reliable LD50 verified by typical toxic alkaloids and modified Karber method. BMC Pharmacology and Toxicology, 23(1), 3. doi: 10.1186/s40360-021-00541-7

Zhao, W., F. Zhai, and J. Han, Effects of Selenium on Differentiation and Antioxidant Activity of Sclerotium of Penicillium thomii Q1 Strain. BioMed Research International, 2020. 2020: p. 2368245.