A series of newly 1,3,4-oxadiazole-2-thioglycoside derivatives were synthesized. The key step of this protocol is the coupling between 5-herteroaryl-1,3,4-oxadiazole-2-thione and activated sugars (cyclic or acyclic sugar analogues) in the presence of basic medium. Among of the synthesized compounds, compounds 7, 10, 11 and 13 were screened for them in vitro anticancer activity against four human cancer cells. MCF-7 (Breast), HEPG2 (Liver), HCT116 (Colon) and HEP2 (Larynx) carcinoma cell lines with IC50 values ranging from 2.08 - 8.72 μg/well. Compounds 11 and 13 were highly specific and potent for four cell lines (MCF-7, HCT116, HEPG2 and HEP2).
S. Eckhardt, “Recent Progress in the Development of Anti Cancer Agents,” Current Medicinal Chemistry, Vol. 2, No. 3, 2002, pp. 419-439.
V. Jakubkiene, M. M. Burbuliene, C. Mekuskiene, E. Udrenaite, P. gaidelis and P. Vainilavicius, “Synthesis and Anti-Inflammatory Activity of 5-(6-Methyl-2-substituted 4-Pyrimidinyloxymethyl)-1,3,4-oxadiazole-2- thiones and Their 3-Morpholinomethyl Derivatives,” IL Far- maco, Vol. 58, No. 4, 2003, pp. 323-328. doi:10.1016/S0014-827X(02)00022-8
E. Palaska, G. Sahin, P. Kelicen, N. T. Durlu and G. Altinok, “Synthesis and Anti-Inflammatory Activity of 1-Acylthiosemicarbazides, 1,3,4-Oxadiazoles, 1,3,4-Thia- diazoles and 1,2,4-Triazole-3-thiones,” IL Farmaco, Vol. 57, No. 2, 2002, pp. 101-107. doi:10.1016/S0014-827X(01)01176-4
B. Jayashan-kar, K. M. L. Rai, N. Baskaran and H. S. Sathish, “Synthesis and Pharmacological Evaluation of 1,3,4-Oxadiazole Bearing Bis(heterocycle)derivatives as Anti-Inflammatory and Analgesic Agents,” European Journal of Medicinal Chemistry, Vol. 44, No. 10, 2009, pp. 3898-3902. doi:10.1016/j.ejmech.2009.04.006
D. Kumar, S. Sundaree, E. O. Johnson and K. Shah, “An Efficient Synthesis and Biological Study of Novel In-dolyl-1,3,4-oxadiazoles as Potent Anticancer Agents,” Bioorganic & Medicinal Chemistry Letters, Vol. 19, No. 15, 2009, pp. 4492-4494. doi:10.1016/j.bmcl.2009.03.172
W. S. Li, S. V. More, C. H. Wang, Y. C. Jen, C. F. Yao, T. F. Wang, C. C. Hung and S. C. Jao, “Synthesis and Structure-Activity Relationships of Novel Furazan-3,4- diamide Analogs as Potent Anti-Cancer Agents,” Bioorganic & Medicinal Chemistry Letters, Vol. 20, No. 3, 2010, pp. 1148-1152. doi:10.1016/j.bmcl.2009.12.017
M. A. Abu-Zaied, E. M. El-Telbani, G. H. Elgemeie and G. A. M. Nawwar, “Synthesis and in Vitro Anti-Tumor Activity of New Oxadiazole Thioglycosides,” European Journal of Medi-cinal Chemistry, Vol. 46, No. 1, 2011, pp. 229-235. doi:10.1016/j.ejmech.2010.11.008
T. M. C. Tan, Y. Chen, K. H. Kong, J. Bai, Y. Li, S. G. Lim, T. H. Ang and Y. Lam, “Synthesis and the Biological Evaluation of 2-Benzenesulfonylalkyl-5-substituted- sul-fanyl-[1,3,4]-oxadiazoles as Potential Anti-Hepatitis B Virus Agents,” Antiviral Research, Vol. 71, No. 1, 2006, pp. 7-14. doi:10.1016/j.antiviral.2006.02.007
M. A. Ali and M. Shaharyar, “Oxadiazole Mannich Bases: Syn-thesis and Antimycobacterial Activity,” Bioorganic & Medicinal Chemistry Letters, Vol. 17, No. 12, 2007, pp. 3314-3316. doi:10.1016/j.bmcl.2007.04.004
A. S. Aboraia, H. M. Abdel-Rahman, N. M. Mahfouz and M. A. El-Gendy, “Novel 5-(2-Hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole—2-Thione Derivatives: Promising Anticancer Agents,” Bioorganic & Medicinal Chemistry Letters, Vol. 14, 2006, pp. 1236-1246. doi:10.1016/j.bmc.2005.09.053
Y. Li, J. Liu, H. Zhang, X. Yang and Z. Liu, “Stereoselective Synthesis and Fungicidal Activities of (E)-Alpha-(me-thoxyimino)-benzeneacetate Derivatives Containing 1,3,4-Oxadiazole Ring,” Bioorganic & Medicinal Chemistry Letters, Vol. 16, No. 8, 2006, pp. 2278-2282. doi:10.1016/j.bmcl.2006.01.026
M. T. H. Khan, M. I. Choudhary, K. M. Khan, M. Rani and A. U. Rahman, “Structure-Activity Relationships of Tyrosinase Inhibitory Combinatorial Library of 2,5-Disubstituted-1,3,4-oxadiazole Analogues,” Bioorganic & Medi-cinal Chemistry, Vol. 13, No. 6, 2005, pp. 3385-3395. doi:10.1016/j.bmc.2005.03.012
J. T. Palmer, B. L. Hirschbein, H. Cheung, J. McCarter, J. W. Janc, Z. W. Yu and G. Wesolowski, “Keto-1,3,4- oxadiazoles as Ca-thepsin K Inhibitors,” Bioorganic & Medicinal Chemistry Letters, Vol. 16, No. 11, 2006, pp. 2909-2914. doi:10.1016/j.bmcl.2006.03.001
G. Pratviel, J. Bernadou and B. Meunie, “Carbon-Hydrogen Bonds of DNA Sugar Units as Targets for Chemical Nudeases and Drugs,” Angewandte Chemie International Edition, Vol. 34, 1995, pp. 746-769. doi:10.1002/anie.199507461
R. A. Dwek, “Glyco-biology toward Understanding the Function of Sugars,” Chemical Reviews, Vol. 96, No. 2, 1996, pp. 683-720. doi:10.1021/cr940283b
J. Kralora, J. Koivukorpi, Z. Kejik, P. PoucKova, E. Sievanen, E. Kolehmainen and V. Kral, “Porphyrin-Bile Acid Conjugates: From Saccharide Recognition in the Solution to the Selective Cancer Cellfluorescence Detection,” Organic & Biomolecular Chemistry, Vol. 6, No. 9, 2008, pp. 1548-1552. doi:10.1039/b717528k
T. Minko, S. S. Dharap, R. I. Pakunlu and Y. wang, “Molecular Targeting of Drug Delivery Systems to Cancer,” Current Drug Targets, Vol. 5, No. 4, 2004, pp. 389- 406. doi:10.2174/1389450043345443
H. N. Hafez, A. B. A. El-Gazzar and G. A. M. Nawwar, “Synthesis, Biological and Medicinal Significance of S-Glycosido-thieno[2,3-d]-pyrimidines as New Anti-Inflammatory and Analgesic Agents,” European Journal of Medicinal Chemistry, Vol. 45 , No. 4, 2010, pp. 1485-1493. doi:10.1016/j.ejmech.2009.12.056
H. N. Hafez, A. B. El-GAzzar and G. A. M. Nawwar, “New Acyclic Nucleosides Analogues as Potential Anal- gesic, Anti-Inflammatory, Anti-Oxidant and Anti-Microbial De-rived from Pyrimido[4,5-b]quinolines,” European Journal of Medicinal Chemistry, Vol. 44, No. 4, 2009, pp. 1427-1436. doi:10.1016/j.ejmech.2008.09.030
E. S. M. Yakout, Y. A. Allam and G. A. M. Nawwar, “Simple Syntheses of Benzothiazol-2-Ylazoles,” Heteroatom Chemistry, Vol. 10, No. 3, 1999, pp. 177-182. doi:10.1002/(SICI)1098-1071(1999)10:3 3.0.CO;2-D
E. M. El-Telbani, R. H. Swellem and G. A. M. Nawwar, “Facile Synthesis of 6-Heteroaryl [1,2,4] Triazolo [3,4-b][1,3,4] Thiadiazoles and 7-Hetaryl[1,3,4] Triadiazolo[2,3-c][1,2,4]thiazines with Fungicidal Activity,” Russian Journal of Organic Chemistry, Vol. 43, No. 12, 2007, pp. 1815-1820. doi:10.1134/S1070428007120135
A. M. Attia and G. H. Elgemeie, “A New Class of Dihy Dropyridine Thioglycosides via Piperidinium Salts,” Synthetic Communications, Vol. 33, No. 13, 2003, pp. 2243- 2255. doi:10.1081/SCC-120021503
I. W. J. Still, N. Plavac, D. M. Mackinnon and M. S. Chauhan, “Carbon-13 Nuclear Magnetic Resonance Spectra of Organic Sulfur Compounds. Comparison of Chemical Shifts for Carbonyl and Thiocarbonyl Compounds in the Pyrone, Thiopyrone, and Pyridone Series,” Canadian Journal of Chemistry, Vol. 54, No. 2, 1976, pp. 280-289. doi:10.1139/v76-042
L. Stefaniak, “14N and 13C NMR of Tautomeric Systems of Mercapto- and Ami-no-Pyridines,” Organic Magnetic Resonance, Vol. 12, No. 6, 1979, pp. 379-382. doi:10.1002/mrc.1270120611
P. Skehan, R. Strong, D. Scadiaro, A. Monks, J. Mc- Mahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenney and M. R. Boyed, “New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening,” Journal of the National Cancer Institute, Vol. 82, No. 13, 1990, pp. 1107-1112. doi:10.1093/jnci/82.13.1107
G. R. Pettit, J. C. Knight, D. L. Herald, R. Davenport, R. K. Pettit, B. E. Tucker and J. M. Schmidt, “Isolation of Labradorins 1 and 2 from Pseudomonas Syringae pv. Coronafaciens,” Journal of Natural Products, Vol. 65, No. 12, 2002, pp. 1793-1797. doi:10.1021/np020173x