Synthesis and cytotoxicity evaluation of thiazole derivatives obtained from 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene- 3-carbonitrile

1. I. Lagoja, C. Pannecouque, G. Griffioen, S. Wera, V. M. Rojasdelaparra and A. V. Aerschot, Substituted 2-aminothiazoles are exceptional inhibitors of neuronal degeneration in tau-driven models of Alzheimer’s disease, Eur. J. Med. Chem. 43 (2011) 386-392; https://doi.org/org/10.1016/j.ejps.2011.05.014Search in Google Scholar

2. S. Kamila, K. Mendoza and E. R. Biehl, Microwave-assisted Hantzsch thiazole synthesis of Nphenyl- 4-(6-phenylimidazo[2,1-b]thiazol-5-yl)thiazol-2-amines from the reaction of 2-chloro-1-(6- phenylimidazo[2,1-b]thiazol-5-yl)ethanones and thioureas, Tetrahedron Lett. 53 (2012) 4921-4924; https://doi.org/10.1016/j.tetlet.2012.06.11610.1016/j.tetlet.2012.06.116350113023175584Search in Google Scholar

3. A. H. Cook, I. Heilbron, S. F. Macdonald and A. P. Mahadevan, 226. Studies in the azole series. Part XII. Some thiazolopyrimidines, J. Chem. Soc. 1949, 1064-1068; https://doi.org/10.1039/JR949000106410.1039/jr9490001064Search in Google Scholar

4. R. Robinson, CCXXXII. - A new synthesis of oxazole derivatives, J. Chem. Soc. 95 (1909) 2167-2174; https://doi.org/org/10.1039/CT909950216710.1039/CT9099502167Search in Google Scholar

5. S. Gabriel, Eine Synthese von Oxazolen und Thiazolen. I, Ber. Dtsch. Chem. Ges. 43 (1910) 134-138; https://doi.org/10.1002/cber.1910043011710.1002/cber.19100430117Search in Google Scholar

6. S. Gabriel, Synthese von Oxazolen und Thiazolen II, Ber. Dtsch. Chem. Ges. 43 (1910) 1283-1287; https://doi.org/10.1002/cber.1910043021910.1002/cber.19100430219Search in Google Scholar

7. T. M. Potewar, S. A. Ingale and K. V. Srinivasan, Efficient synthesis of 2,4-disubstituted thiazoles using ionic liquid under ambient conditions: a practical approach towards the synthesis of fanetizole, Tetrahedron 63 (2007) 11066-11069; https://doi.org/10.1016/j.tet.2007.08.03610.1016/j.tet.2007.08.036Search in Google Scholar

8. M. V. B. Reddy, D. Srinivasulu, K. Peddanna, Ch. Apparao and P. Ramesh, Synthesis and antioxidant activity of new thiazole analogues possessing urea, thiourea, and selenourea functionality, Synth. Commun. 45 (2015) 2592-2600; https://doi.org/org/10.1080/00397911.2015.1095929Search in Google Scholar

9. M. Shiradkar, G. V. S. Kumar, V. Dasari, S. Tatikonda, K. C. Akula and R. Shah, Clubbed triazoles: a novel approach to antitubercular drugs, Eur. J. Med. Chem. 42 (2007) 807-816; https://doi.org/10.1016/j.ejmech.2006.12.00110.1016/j.ejmech.2006.12.00117239490Search in Google Scholar

10. M. R. Shiradkar, K. K. Murahari, H. R. Gangadasu, T. Suresh, C. A. Kalyan, D. Panchal, R. Kaur, P. Burange, J. Ghogare, V. Mokale and M. Raut, Synthesis of new S-derivatives of clubbed triazolyl thiazole as anti-Mycobacterium tuberculosis agents, Bioorg. Med. Chem. 15 (2007) 3997-4008;10.1016/j.bmc.2007.04.00317442576Search in Google Scholar

https://doi.org/10.1016/j.bmc.2007.04.00310.1016/j.bmc.2007.04.003Search in Google Scholar

11. A. Ayati, S. Emami, A. Asadipour, A. Shafiee and Al. Foroumadi, Recent applications of 1,3-thiazole core structure in the identification of new lead compounds and drug discovery, Eur. J. Med. Chem. 97 (2015) 699-718; http://dx.doi.org/10.1016/j.ejmech.2015.04.01510.1016/j.ejmech.2015.04.01525934508Search in Google Scholar

12. L. Yurttas, Y. Özkay, Z. A. Kaplancikli, Y. Tunali and H. Karaca, Synthesis and antimicrobial activity of some new hydrazone bridged thiazole-pyrrole derivatives, J. Enzyme Inhib. Med. Chem. 28 (2013) 830-835; https://doi.org/10.3109/14756366.2012.68804310.3109/14756366.2012.68804322651798Search in Google Scholar

13. B. Ghasemi and M. Najimi, Antibacterial effect of thiazole derivatives on Rhodoccocus equi, Brucella abortus, and Pasteurella multocida, Iran. J. Vet. Med. 10 (2016) 47-52.Search in Google Scholar

14. G. M. Reddy, J. R. Garcia, V. H. Reddy, A. M. de Andrade, A. Jr. Camilo, R. A. P. Ribeiro and S. R. de Lazaro, Synthesis, antimicrobial activity and advances in structure-activity relationships (SARs) of novel tri-substituted thiazole derivatives, Eur. J. Med. Chem. 123 (2016) 508-513; https://doi.org/10.1016/j.ejmech.2016.07.06210.1016/j.ejmech.2016.07.06227494167Search in Google Scholar

15. R. N. Sharma, F. P. Xavier, K. K. Vasu, S. C. Chaturvedi and S. S. Pancholi, Synthesis of 4-benzyl- 1,3-thiazole derivatives as potential anti-inflammatory agents: an analogue-based drug design approach, J. Enzyme Inhib. Med. Chem. 24 (2009) 890-897; https://doi.org/10.1080/1475636080251955810.1080/1475636080251955819469712Search in Google Scholar

16. J. Balzarini, B. Orzeszko, J. K. Maurin, and A. Orzeszko, Synthesis and anti-HIV studies of 2-adamantyl- substituted thiazolidin-4-ones, Eur. J. Med. Chem. 42 ( 2007) 9 93-1003; https://doi.org/10.1016/j.ejmech.2007.01.00310.1016/j.ejmech.2007.01.00317321639Search in Google Scholar

17. W. C. Patt, H. W. Hamilton, M. D. Taylor, M. J. Ryan, D. G. Jr. Taylor, C. J. C. Connolly, A. M. Doherty, S. R. Klutchko, I. Sircar, B. A. Steinbaugh, B. L. Batley, C. A. Painchaud, S. T. Rapundalo, B. M. Michniewicz and S. C. J. Olson, Structure-activity relationships of a series of 2-amino-4- thiazole containing renin inhibitors, J. Med. Chem. 35 (1992) 2562-2572; https://doi.org/10.1021/jm00092a00610.1021/jm00092a0061635057Search in Google Scholar

18. H. Cousse, G. Mouzin, B. Bonnaud, J. P. Tarayre and J. P. Couzinier, Studies of arylthiazole oxamates in relation to oral antiallergic activity, Arzneimittelforschung 36 (1986) 1391-1393.Search in Google Scholar

19. N. Ergenç, G. Capan, N. S. Günay, S. Ozkirimli, M. Güngör, S. Ozbey and E. Kendi, Synthesis and hypnotic activity of new 4-thiazolidinone and 2-thioxo-4,5-imidazolidinedione derivatives, Arch. Pharm. (Weinheim) 332 (1999) 343-347; https://doi.org/10.1002/(SICI)1521-4184(199910)332Search in Google Scholar

20. F. Bonina, F. Guerrera, M. C. Sarvà, M. A. Siracusa, A. Caruso, M. G. Leone and M. A. Roxas, Synthesis and analgesic antiinflammatory activities of 2-aryl-ethenyl-4-aryl-thiazole-5-acetic acids, Farmaco Sci. 42 (1987) 905-913. Search in Google Scholar

21. H. He, X. Wang, L. Shi, W. Yin, Z. Yang, H. He and Y. Liang, Synthesis, antitumor activity and mechanism of action of novel 1,3-thiazole derivatives containing hydrazide-hydrazone and carboxamide moiety, Bioorg. Med. Chem. Lett. 26 (2016) 3263-3270; https://doi.org/10.1016/j.bmcl.2016.05.05910.1016/j.bmcl.2016.05.05927262600Search in Google Scholar

22. G. Turan-Zitouni, M. D. Altıntop, A. Özdemir, Z. A. Kaplancıklı, G. A. Çiftçi and H. E. Temel, Synthesis and evaluation of bis-thiazole derivatives as new anticancer agents, Eur. J. Med. Chem. 107 (2016) 288-294; https://doi.org/10.1016/j.ejmech.2015.11.00210.1016/j.ejmech.2015.11.00226599534Search in Google Scholar

23. I. Nabih, F. El-Hawary and H. Zoorob, Structure and activity of thiazole-type schistosomicidal agents, J. Pharm. Sci. 61 (1972) 1327-1328; https://doi.org/10.1002/jps.260061083810.1002/jps.26006108385050391Search in Google Scholar

24. R. R. Gupta, M. Kumar and V. Gupta, Heterocyclic Chemistry - Volume II: Five-Membered Heterocycles, 1st ed., Springer-Verlag, Berlin-Heidelberg 1999, pp. XI-638.10.1007/978-3-662-07757-3_2Search in Google Scholar

25. E. M. Samir, A. S. Abouzied and F. I. Hamed, The synthesis and cytotoxicity of novel thiophene derivatives derived from 2-(4-oxo-4,4-dihydrothiazol-2-yl) acetonitrile, Int. J. Org. Chem. 6 (2016) Article ID 66590 (10 pages); https://doi.org/10.4236/ijoc.2016.6200910.4236/ijoc.2016.62009Search in Google Scholar

26. V. Combes, G. J. Guillemin, T. Chan-Ling, N. H. Hunt and G. E. R. Grau, The crossroads of neuroinflammation in infectious diseases: endothelial cells and astrocytes, Trends Parasitol. 28 (2012) 311-319; https://doi.org/10.1016/j.pt.2012.05.00810.1016/j.pt.2012.05.00822727810Search in Google Scholar

27. L. Roemer, S. M. Orsillo and K. Salters-Pedneault, Efficacy of an acceptance-based behavior therapy for generalized anxiety disorder: evaluation in a randomized controlled trial, J. Consult. Clin. Psychol. 76 (2008) 1083-1089; https://doi.org/10.1037/a001272010.1037/a0012720259672719045976Search in Google Scholar

28. J. Li, B. Mookerjee and J. Wagner, Purification of melanoma reactive T cell by using a monocytebased solid phase T-cell selection system for adoptive therapy, J. Immunother. 31 (2008) 81-88; https://doi.org/10.1097/CJI.0b013e318157c66810.1097/CJI.0b013e318157c66818157015Search in Google Scholar