Novel Oxadiazole Thioglycosides As Potential Anti- Agents

Overview

Journal Iran J Pharm Res

Publisher Brieflands

Specialty Pharmacology

Date 2017 Mar 1

PMID 28243273

Citations 1

Authors

Karim Akbari Dilmaghani

Fazel Nasuhi Pur

Majid Mahammad Pour

Jafar Mahammad Nejad

Affiliations

Soon will be listed here.

Abstract

The glycosylation of 1,3,4-oxadiazole-2-thiones has been performed with peracetylated β-pyranosyl bromide in the presence of potassium carbonate. Deprotection of acetylated thioglycosides was necessary for increasing their antibacterial effects. The structures of nucleosides were confirmed by H NMR, C NMR and HRMS. The anomeric protons of nucleosides c were assigned to the doublet, confirming the β-configuration. The synthesized compounds were tested for their antimicrobial activity against (Gram-negetive) strain in comparison with Ampicillin as a reference drug which is normally used for treating such infections. The synthetic compounds showed different inhibition zones against tested bacterial strain. Thioglycoside derivatives of 1,3,4-oxadiazole-2-thiones (c set) were more active against ATCC 23055 than "parent" 1,3,4-oxadiazole-2-thiones (a set), confirming the relation between glyco-conjugation and increasing of antiproliferative activity of antibiotic agents. The best result belonged to nucleoside bearing 2-furyl moiety in its heterocyclic nucleus (c). The existence of -PhNO group as Ar in structures of a set and their corresponding sugar derivatives decreased the antibacterial activity of them in comparison with the rest of synthetic compounds.

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References

Kitov P, Sadowska J, Mulvey G, Armstrong G, Ling H, Pannu N . Shiga-like toxins are neutralized by tailored multivalent carbohydrate ligands. Nature. 2000; 403(6770):669-72. DOI: 10.1038/35001095. View

Lee R, Lee Y . Affinity enhancement by multivalent lectin-carbohydrate interaction. Glycoconj J. 2001; 17(7-9):543-51. DOI: 10.1023/a:1011070425430. View

Ahmad R, Iqbal R, Akhtar H, Zia-Ul-Haq , Duddeck H, Stefaniak L . Synthesis and structure determination of some oxadiazole-2-thione and triazole-3-thione galactosides. Nucleosides Nucleotides Nucleic Acids. 2001; 20(9):1671-82. DOI: 10.1081/NCN-100105903. View

Andre S, Pieters R, Vrasidas I, Kaltner H, Kuwabara I, Liu F . Wedgelike glycodendrimers as inhibitors of binding of mammalian galectins to glycoproteins, lactose maxiclusters, and cell surface glycoconjugates. Chembiochem. 2002; 2(11):822-30. DOI: 10.1002/1439-7633(20011105)2:11<822::AID-CBIC822>3.0.CO;2-W. View

Nagahori N, Lee R, Nishimura S, Page D, Roy R, Lee Y . Inhibition of adhesion of type 1 fimbriated Escherichia coli to highly mannosylated ligands. Chembiochem. 2002; 3(9):836-44. DOI: 10.1002/1439-7633(20020902)3:9<836::AID-CBIC836>3.0.CO;2-2. View

Woller E, Walter E, Morgan J, Singel D, Cloninger M . Altering the strength of lectin binding interactions and controlling the amount of lectin clustering using mannose/hydroxyl-functionalized dendrimers. J Am Chem Soc. 2003; 125(29):8820-6. DOI: 10.1021/ja0352496. View

Vrasidas I, Andre S, Valentini P, Bock C, Lensch M, Kaltner H . Rigidified multivalent lactose molecules and their interactions with mammalian galectins: a route to selective inhibitors. Org Biomol Chem. 2003; 1(5):803-10. DOI: 10.1039/b210923a. View

Autar R, Salam Khan A, Schad M, Hacker J, Liskamp R, Pieters R . Adhesion inhibition of F1C-fimbriated Escherichia coli and Pseudomonas aeruginosa PAK and PAO by multivalent carbohydrate ligands. Chembiochem. 2003; 4(12):1317-25. DOI: 10.1002/cbic.200300719. View

Wittmann V, Seeberger S . Spatial screening of cyclic neoglycopeptides: identification of polyvalent wheat-germ agglutinin ligands. Angew Chem Int Ed Engl. 2004; 43(7):900-3. DOI: 10.1002/anie.200352055. View

10.

El din Awad O, Attia W, El Ashry E . Comparative evaluation of D-glucosyl thiouronium, glucosylthio heterocycles, Daonil, and insulin as inhibitors for hepatic glycosidases. Carbohydr Res. 2004; 339(3):469-76. DOI: 10.1016/j.carres.2003.11.009. View

11.

DEFAYE J, Guillot J, Biely P, Vrsanska M . Positional isomers of thioxylobiose, their synthesis and inducing ability for D-xylan-degrading enzymes in the yeast Cryptococcus albidus. Carbohydr Res. 1992; 228(1):47-64. DOI: 10.1016/s0008-6215(00)90548-2. View

12.

Arosio D, Vrasidas I, Valentini P, Liskamp R, Pieters R, Bernardi A . Synthesis and cholera toxin binding properties of multivalent GM1 mimics. Org Biomol Chem. 2004; 2(14):2113-24. DOI: 10.1039/b405344c. View

13.

Joosten J, Loimaranta V, Appeldoorn C, Haataja S, El Maate F, Liskamp R . Inhibition of Streptococcus suis adhesion by dendritic galabiose compounds at low nanomolar concentration. J Med Chem. 2004; 47(26):6499-508. DOI: 10.1021/jm049476+. View

14.

Orgeret C, Seillier E, Gautier C, DEFAYE J, Driguez H . 4-Thiocellooligosaccharides. Their synthesis and use as ligands for the separation of cellobiohydrolases of Trichoderma reesei by affinity chromatography. Carbohydr Res. 1992; 224:29-40. DOI: 10.1016/0008-6215(92)84090-f. View

15.

Schnaar R, Lee Y . Polyacrylamide gels copolymerized with active esters. A new medium for affinity systems. Biochemistry. 1975; 14(7):1535-41. DOI: 10.1021/bi00678a030. View

16.

Tabatabai S, Barghi Lashkari S, Zarrindast M, Gholibeikian M, Shafiee A . Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives. Iran J Pharm Res. 2013; 12(Suppl):105-11. PMC: 3813377. View

17.

Tabatabai S, Rezaee Zavareh E, Reyhanfard H, Alinezhad B, Shafaghi B, Sheikhha M . Evaluation of Anxiolytic, Sedative-hypnotic and Amnesic Effects of Novel 2-phenoxy phenyl-1,3,4-oxadizole Derivatives Using Experimental Models. Iran J Pharm Res. 2015; 14(Suppl):51-7. PMC: 4499426. View

18.

Dilmaghani K, Nasuhi Pur F, Hatami Nezhad M . Synthesis and Antibacterial Evaluation of New Thione Substituted 1,2,4-Triazole Schiff Bases as Novel Antimicrobial Agents. Iran J Pharm Res. 2015; 14(3):693-9. PMC: 4518097. View

19.

Mammen M, Choi S, Whitesides G . Polyvalent Interactions in Biological Systems: Implications for Design and Use of Multivalent Ligands and Inhibitors. Angew Chem Int Ed Engl. 2018; 37(20):2754-2794. DOI: 10.1002/(SICI)1521-3773(19981102)37:20<2754::AID-ANIE2754>3.0.CO;2-3. View

20.

Mereyala H, Gurijala V . Use of 2-pyridyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-beta-D-glucopyranoside as a glycosyl donor and methyl iodide as an activator for the synthesis of 1,2-trans-linked saccharides. Carbohydr Res. 1993; 242:277-80. DOI: 10.1016/0008-6215(93)80041-c. View