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

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

Open Access
|Jan 2018

References

  1. 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.2011.05.014
  2. 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.2012.06.116350113023175584
  3. 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/jr9490001064
  4. 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/CT9099502167
  5. 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.19100430117
  6. 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.19100430219
  7. 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.2007.08.036
  8. 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/10.1080/00397911.2015.1095929
  9. 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.2006.12.00117239490
  10. 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.2007.04.00317442576
  11. https://doi.org/10.1016/j.bmc.2007.04.00310.1016/j.bmc.2007.04.003
  12. 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.2015.04.01525934508
  13. 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/10.3109/14756366.2012.68804310.3109/14756366.2012.68804322651798
  14. 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.
  15. 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.2016.07.06227494167
  16. 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/10.1080/1475636080251955810.1080/1475636080251955819469712
  17. 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.2007.01.00317321639
  18. 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/jm00092a0061635057
  19. 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.
  20. 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)332
  21. 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.
  22. 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.2016.05.05927262600
  23. 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.2015.11.00226599534
  24. 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.26006108385050391
  25. 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_2
  26. 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.2016.62009
  27. 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.2012.05.00822727810
  28. 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/a0012720259672719045976
  29. 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.0b013e318157c66818157015
DOI: https://doi.org/10.1515/acph-2017-0040 | Journal eISSN: 1846-9558 | Journal ISSN: 1330-0075
Language: English
Page range: 495 - 510
Accepted on: Oct 8, 2017
Published on: Jan 11, 2018
Published by: Croatian Pharmaceutical Society
In partnership with: Paradigm Publishing Services
Publication frequency: 4 issues per year
Related subjects:

© 2018 Rafat M. Mohareb, Amira E. M. Abdallah, Ebtsam A. Ahmed, published by Croatian Pharmaceutical Society
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.