Author(s): Taghreed S. Hussein, Mohammed R. Ahamad

Email(s): ted38456@gmail.com

DOI: 10.52711/0974-360X.2021.00919   

Address: Taghreed S. Hussein, Mohammed R. Ahamad
Department of Chemistry, College of Science, Baghdad University, Baghdad, Iraq.
*Corresponding Author

Published In:   Volume - 14,      Issue - 10,     Year - 2021


ABSTRACT:
Preparation of new S-glycosides including thiouracil derivatives as heterobase. The main step of this work is the formation of thiouracil derivatives [1-3] by the condensation reaction of ethyl cyanoacetate, aromatic aldehydes and thiourea to form target compounds [1-3], after protection of the hydroxyl groups in sugar (D-fructose, L- sorbose, and D-galactose), react with hydrobromic acid 45% in glacial acetic acid give different Bromo sugars [a-c], which coupled with prepares thiouracil derivatives [1-3] and propylthiouracil [4] in the presence of K2CO3 to afford the corresponding product S-glycoside analogs [1-4a, 1-4b, 1-4c]. deprotection of the S-glycoside analogs in acid and base medium, led to the free S-glycoside derivatives [1-4d,1-4e,1-4f]. The obtained compounds were tested for their antibacterial and antifungal actives.


Cite this article:
Taghreed S. Hussein, Mohammed R. Ahamad. Synthesis of S-glycosides analogues containing Thiouracil unite and Evaluated as antibacterial and Antifungal active. Research Journal of Pharmacy and Technology. 2021; 14(10):5274-9. doi: 10.52711/0974-360X.2021.00919

Cite(Electronic):
Taghreed S. Hussein, Mohammed R. Ahamad. Synthesis of S-glycosides analogues containing Thiouracil unite and Evaluated as antibacterial and Antifungal active. Research Journal of Pharmacy and Technology. 2021; 14(10):5274-9. doi: 10.52711/0974-360X.2021.00919   Available on: https://rjptonline.org/AbstractView.aspx?PID=2021-14-10-37


REFERENCE:
1.    Lian, G.; Zhang, X.; Yu, B., Thioglycosides in carbohydrate research. Carbohydrate research 2015, 403, 13-22.
2.    Matsuoka, K.; Onaga, T.; Mori, T.; Sakamoto, J.-I.; Koyama, T.; Sakairi, N.; Hatano, K.; Terunuma, D., Synthesis of a useful lauryl thioglycoside of sialic acid and its application. Tetrahedron letters 2004; 45: 9383-9386.
3.    Yousif, M. N.; El-Sayed, W. A.; Abbas, H.-A. S.; Awad, H. M.; Yousif, N. M., Anticancer activity of new substituted pyrimidines, their thioglycosides and thiazolopyrimidine derivatives. J Appl Pharm Sci 2017; 7: 021-032.
4.    Dilmaghani, K. A.; Pur, F. N., Novel oxadiazole thioglycosides as potential anti-Acinetobacter agents. Iranian journal of pharmaceutical research: IJPR 2016; 15: 777.
5.    Chen, Q.; Kong, F., Stereoselective glycosylation using fully benzylated pyrimidin-2-yl 1-thio-β-d-glycopyranosides. Carbohydrate research 1995; 272: 149-157.
6.    Ding, X.; Yang, G.; Kong, F., Synthesis and glycosylation of pyrimidin-2-yl 1-thio-α-d-manno-and-α-l-rhamnopyranoside. Carbohydrate research 1998; 310: 135-139.
7.    Autar, R.; Khan, A. S.; Schad, M.; Hacker, J.; Liskamp, R. M.; Pieters, R. J., Adhesion inhibition of F1C‐fimbriated Escherichia coli and Pseudomonas aeruginosa PAK and PAO by multivalent carbohydrate ligands. Chem Bio Chem 2003; 4: 1317-1325.
8.    Arosio, D.; Vrasidas, I.; Valentini, P.; Liskamp, R. M.; Pieters, R. J.; Bernardi, A., Synthesis and cholera toxin binding properties of multivalent GM1 mimics. Organic and biomolecular chemistry 2004; 2: 2113-2124.
9.    Nagahori, N.; Lee, R. T.; Nishimura, S. I.; Pagé, D.; Roy, R.; Lee,
Y. C., Inhibition of adhesion of type 1 fimbriated Escherichia coli to highly mannosylated ligands. Chem Bio Chem 2002; 3: 836- 844.
10.    Woller, E. K.; Walter, E. D.; Morgan, J. R.; Singel, D. J.; Cloninger, M. J., Altering the strength of lectin binding interactions and controlling the amount of lectin clustering using mannose/hydroxyl-functionalized dendrimers. Journal of the American Chemical Society 2003; 125: 8820-8826.
11.    Fathalla, O.; Zeid, I.; Haiba, M.; Soliman, A.; Abd-Elmoez, S. I.; El-Serwy, W., Synthesis, antibacterial and anticancer evaluation of some pyrimidine derivatives. World J Chem 2009; 4: 127-132.
12.    Jain, K.; Chitre, T.; Miniyar, P.; Kathiravan, M.; Bendre, V.; Veer, V.; Shahane, S.; Shishoo, C., Biological and medicinal significance of pyrimidines. Current Science 2006; 793-803.
13.    Kotaiah, S.; Ramadevi, B.; Naidu, A.; Dubey, P., Studies on synthesis of 2-(1-(1H-benzo (d) imidazol-2-yl) ethylthio)-6- methylpyrimidin-4-ol of potential pharmacological interest. Der Pharma Chemica 2011; 3: 198-201.
14.    Cui, P.; Li, X.; Zhu, M.; Wang, B.; Liu, J.; Chen, H., Design, synthesis and antimicrobial activities of thiouracil derivatives containing triazolo-thiadiazole as SecA inhibitors. European journal of medicinal chemistry 2017; 127: 159-165.
15.    Gokavi, N. M.; Pattar, V. P.; Bagoji, A. M.; Nandibewoor, S. T., Square wave voltammetric determination of 2-thiouracil in pharmaceuticals and real samples using glassy carbon electrode. International Journal of Electrochemistry 2013; 2013.
16.    Cai, D.; Zhang, Z.-H.; Chen, Y.; Yan, X.-J.; Zhang, S.-T.; Zou, L.- J.; Meng, L.-H.; Li, F.; Fu, B.-J., Synthesis of some new thiazolo [3, 2-a] pyrimidine derivatives and screening of their in vitro antibacterial and antitubercular activities. Medicinal Chemistry Research 2016; 25: 292-302.
17.    Abdelghani, E.; Said, S. A.; Assy, M.; Hamid, A. M. A., Heterocyclization of thiouracil derivative: synthesis of thiazolopyrimidines, tetrazolopyrimidines and triazolopyrimidines of potential biological activity. Journal of the Iranian Chemical Society 2015; 12: 1809-1817.
18.    Sharba, A. H. K.; Askar, F. W.; Al-Fattahi, Y. A., Synthesis of New Carbohydrate Derivatives Via 1, 3-Dipolarcycloaddition Reaction. Al-Nahrain Journal of Science 2011; 14: 1-9.
19.    Midland, M. M.; Asirwatham, G.; Cheng, J. C.; Miller, J. A.; Morell, L. A., Synthesis and Conformational Analysis of (6R)-[6- 2H1]-1, 2: 3, 4-Di-O-isopropylidene-. alpha. D-galactopyranose. NMR and Molecular Modeling Studies. The Journal of Organic Chemistry 1994; 59: 4438-4442.
20.    Srour, A. M.; Ismail, A. E.-H. A.; El-Kosy, S. M., Antiviral and antischistosomal evaluation of newly synthesized thioglycosides and their acyclic analogues. Zeitschrift für Naturforschung C 2009; 64: 483-489.
21.    Woon, S.-A.; Fisher, D., Antimicrobial agents–optimising the ecological balance. BMC medicine 2016; 14: 1-9.

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