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Novel thiophene derivatives with sulfonamide, isoxazole, benzothiazole, quinoline and anthracene moieties as potential anticancer agents Cover

Novel thiophene derivatives with sulfonamide, isoxazole, benzothiazole, quinoline and anthracene moieties as potential anticancer agents

Open Access
|Dec 2014

References

  1. 1. S. Abbas, M. Hussain, S. Ali, M. Parvez, A. Raza, A. Haider and J. Iqbal, Structural, enzyme inhibition, antibacterial and DNA protection studies of organotin(IV) derivatives of thiophene-2- carboxylic acid, J. Organometallic Chem. 724 (2013) 255-261; DOI: 10.1016/j.jorganchem.2012.11.033.
  2. 2. A. M. Asiri and S. A. Khan, Synthesis and antibacterial activities of a bis-chalcone derived from thiophene and its bis-cyclized products, Molecules 16 (2011) 523-531; DOI: 10.3390/molecules160 10523.
  3. 3. A. M. Khalil, M. A. Berghot and M. A. Gouda, Synthesis and antibacterial activity of some new thiazole and thiophene derivatives, Eur. J. Med. Chem. 44 (2009) 4434-4440; DOI: 10.1016/j.ejmech. 2009.06.002.
  4. 4. S. Deka, S. Mohan, J. Saravanan, M. Kakati, A. Talukdar, B. J. Sahariah, B. K. Dey and R. K. Sarma, Syntheses, characterization and in-vitro anti-Inflammatory activity of some novel thiophenes, Maced. J. Med. Sci. 5 (2012) 159-163; DOI: org/10.3889/MJMS.1957-5773.2012.0225.
  5. 5. R. A. Forsch, J. E. Wright and A. Rosowsky, Synthesis and in vitro antitumor activity of thiophene analogues of 5-chloro-5,8-dideazafolic acid and 2-methyl-2-desamino-5-chloro-5,8-dideazafolic acid, Bioorg. Med. Chem. 10 (2002) 2067-2076; DOI: org/10.1016/S0968-0896(02)00018-4.
  6. 6. H. A. Saad, M. M. Youssef and M. A. Mosselhi, Microwave assisted synthesis of some new fused 1,2,4-triazines bearing thiophene moieties with expected pharmacological activity, Molecules, 16 (2011) 4937-4957; DOI: 10.3390/molecules16064937.
  7. 7. A. E. Rashad, A. H. Shamroukh, R. E. Abdel-Megeid, A. Mostafa, R. El-Shesheny, A. Kandeil, M. A. Ali and K. Banert, Synthesis and screening of some novel fused thiophene and thienopyrimidine derivatives for anti-avian influenza virus (H5N1) activity, Eur. J. Med. Chem. 45 (2010) 5251-5257; DOI: 10.1016/j.ejmech.2010.08.044.
  8. 8. M. M. Ghorab, F. A. Ragab and M. M. Hamed, Synthesis and docking studies of some novel quinoline derivatives bearing a sulfonamide moiety as possible anticancer agents, Arzneimittelforschung. Drug Res. 60 (2010) 141-148; DOI: 10.1055/s-0031-1296263.
  9. 9. M. M. Ghorab, F. A. Ragab, H. I. Heiba and R. M. El-Hazek, Anticancer and radio-sensitizing evaluation of some new thiazolopyrane and thiazolopyranopyrimidine derivatives bearing a sulfonamide moiety, Eur. J. Med. Chem. 46 (2011) 5120-5126; DOI: 10.1016/j.ejmech.2011.08.026.
  10. 10. M. M. Ghorab, F. A. Ragab and M. M. Hamed, Design, synthesis and anticancer evaluation of novel tetrahydroquinoline derivatives containing sulfonamide moiety, Eur. J. Med. Chem. 44 (2009) 4211-4217; DOI: 10.1016/j.ejmech.2009.05.017.
  11. 11. J. T. Arcari, J.S. Beebe, M. A. Berliner, V. Bernardo, M. Boehm, G. V. Borzillo, T. Clark, B. D. Cohen, R. D. Connell, H. N. Frost, D. A. Gordon, W. M. Hungerford, S. M. Kakar, A. Kanter, N. F. Keene, E. A. Knauth, S. D. LaGreca, Y. Lu, L. Martinez-Alsina and M. A. Marx, Discovery and synthesis of novel 4-aminopyrrolopyrimidine Tie-2 kinase inhibitors for the treatment of solid tumors, Bioorg. Med. Chem. Lett. 23 (2013) 3059-3063; DOI: 10.1016/j.bmcl.2013.03.012.
  12. 12. K. S. Abou-Melha, Octahedral Co(II) and Ni(II) complexes of schiff bases, semicarbazone and thiosemicarbazone, synthesis, biological, spectral, and thermal studies, J. Coordination Chem. 61 (2008) 2053-2067; DOI: 10.1080/00958970701862167.
  13. 13. S. S. Mohamed, S. A. Mohamed, E. S. Shalfoh and O. Fhid, Microwave assisted one-pot synthesis and screening of some schiff’s bases of sulfanilamide, J. Chem. Pharmaceutical. Res. 4 (2012) 2512-2516; DOI: 5-2012/JCPR-2012-4-5-2512-2516.
  14. 14. G. D. Simone and C. T. Supuran, Carbonic anhydrase IX: Biochemical and crystallographic characterization of a novel antitumor target, Biochim. Biophys. Acta 1804 (2010) 404-409; DOI: 10.1016/j. bbapap.2009.07.027.
  15. 15. S. M. Marques, E. A. Enyedy, C. T. Supuran, N. I. Krupenko, S. A. Krupenko and M. A. Santos, Pteridine-sulfonamide conjugates as dual inhibitors of carbonic anhydrases and dihydrofolate reductase with potential antitumor activity, Bioorg. Med. Chem. 18 (2010) 5081-5089; DOI: 10.1016/j. bmc.2010.05.072.
  16. 16. H. M. Said, C. T. Supuran, C. Hageman, A. Staab, B. Polat, A. Katzer, A. Scozzafava, J. Anacker, M. Flentje and D. Vordermark, Modulation of carbonic anhydrase 9 (CA9) in human brain cancer, Curr. Pharm. Des. 16 (2010) 3288-3299; DOI: 10.2174/138161210793429788.
  17. 17. W. R. Chegwidden, S. J. Dodgson and I. M. Spencer, The roles of carbonic anhydrase in metabolism, cell growth and cancer in animals, EXS 90 (2000) 343-363; DOI: 10.1016/pubmed.11268523.
  18. 18. B. E. Maryanoff and M. J. Costan, Inhibitors of proteases and amide hydrolases that employ an α-ketoheterocycle as a key enabling functionality, Bioorg. Med. Chem. 16 (2008) 1562-1595; DOI: 10.1016/j.bmc.2007.11.015.
  19. 19. S. Bondock, W. Fadaly and M. A. Metwally, Enaminonitrile in heterocyclic synthesis: Synthesis and antimicrobial evaluation of some new pyrazole, isoxazole and pyrimidine derivatives incorporating a benzothiazole moiety, Eur. J. Med. Chem. 44 (2009) 4813-4818; DOI: 10.1016/j.ejmech.2009.07.024.
  20. 20. P. J. Bindu, K. M. Mahadevan and T. R. Ravikumar Naik, An efficient one-pot synthesis and photoinduced DNA cleavage studies of 2-chloro-3-(5-aryl-4,5-dihydroisoxazol-3-yl)quinolines, Bioorg. Med. Chem. Lett. 22 (2012) 6095-6098; DOI: 10.1016/j.bmcl.2012.08.034.
  21. 21. M. S. Al-Dosari, M. M. Ghorab, M. S. Alsaid, Y. M. Nissan and A. B. Ahmed, Synthesis and anticancer activity of some novel trifluoromethylquinolines carrying a biologically active benzenesulfonamide moiety, Eur. J. Med. Chem. 69 (2013) 373-383; DOI: 10.1016/j.ejmech.2013.08.048
  22. 22. M. Sankaran, C. Kumarasamy, U. Chokkalingam and P. S. Mohan, Synthesis, antioxidant and toxicological study of novel pyrimidoquinoline derivatives from 4-hydroxy-3-acyl quinolin-2- one, Bioorg. Med. Chem. Lett. 20 (2010) 7147-7151; DOI: 10.1016/j.bmcl.2010.09.018.
  23. 23. A.R. Ellanki, A. Islam, V. S. Rama, R. P. Pulipati, D. Rambabu, G. R. Krishna, M. C. Reddy, K. Mukkanti, G. R. Vanaja, A. M. Kalle, S. K. Kumar and P. Manojit, Solvent effect on copper-catalyzed azide-alkyne cycloaddition (CuAAC): Synthesis of novel triazolyl substituted quinolines as potential anticancer agents, Bioorg. Med. Chem. Lett. 22 (2012) 3455-3459; DOI: 10.1016/j.bmcl.2012. 03.091.
  24. 24. L. Wang, M. Switalska, Z. Mei, W. Lu, Y. Takahara, X. Feng, I. E. El-Sayed, J. Wietrzyk and T. Inokuchi, Synthesis and in vitro antiproliferative activity of new 11-aminoalkylamino-substituted 5H- and 6H-indolo[2,3-b]quinolines; structure-activity relationships of neocryptolepines and 6-methyl congeners, Bioorg. Med. Chem. 20 (2012) 4820-4829; DOI: 10.1016/j.bmc.2012.05.054.
  25. 25. L. Fu, W. Lin, P. Xu, Y. Xi, M. Wang and D. Shi, Novel and efficient synthesis of substituted quinoline-1-oxides and the complex compounds SnL2Cl2 (L=2-aminoquinoline-1-oxides) with the aid of stannous chloride, Tetrahedron. 68 (2012) 7782-7786; DOI: 10.1016/j.tet.2012.07.049.
  26. 26. T. Yamaguchi, S. Watanabe, Y. Matsumura, Y. Tokuoka and A. Yokoyama, Oxovanadium com complexes with quinoline and pyridinone ligands: Syntheses of the complexes and effect of alkyl chains on their apoptosis-inducing activity in leukemia cells, Bioorg. Med. Chem. 20 (2012) 3058-3064; DOI: 10.1016/j.bmc.2012.02.063.
  27. 27. S. A. F. Rostom, Synthesis and in vitro antitumor evaluation of some indeno[1,2-c]pyrazol(in)es substituted with sulfonamide, sulfonylurea(-thiourea) pharmacophores and some derived thiazole ring systems, Bioorg. Med. Chem. 14 (2006) 6475-6485; DOI: 10.1016/j.bmc.2006.06.020.
  28. 28. J. E. Payne, C. Bonnefous, C. A. Hassig, K. T. Symons, X. Guo, P. M. Nguyen, T. Annable, P. L. Wash, T. Z. Hoffman, T. S. Rao, A. K. Shiau, J. W. Malecha, S. A. Noble, J. H. Hager and N. D. Smith, Identification of KD5170: a novel mercaptoketone-based histone deacetylase inhibitor, Bioorg. Med. Chem. Lett. 18 (2008) 6093-6096; DOI: 10.1016/j.bmcl.2008.10.029.
  29. 29. M. M. Ghorab, F. A. Ragab, H. I. Heiba, R. K. Arafa and E. M. El-Hossary, Docking study, in vitro anticancer screening and radiosensitizing evaluation of some new fluorine-containing quinoline and pyrimidoquinoline derivatives bearing a sulfonamide moiety, Med. Chem. Res. 20 (2011) 388-400; DOI: 10.1007/s00044-010-9332-3.
  30. 30. M. S. Alsaid, M. S. Bashandy, S. I. Alqasomi and M. M. Ghorab, Anti-breast cancer activity of some novel 1,2- dihydropyridine, thiophene and thiazole derivatives, Eur. J. Med. Chem. 46 (2011) 137-141; DOI: 10.1016/j.ejmech.2010.10.024.
  31. 31. M. S. Alsaid, M. S. Bashandy and M. M. Ghorab, Novel quinolines bearing biologically active trimethoxyphenyl moiety as a new class of antitumor agents, Arzneimittel-Forschung Drug Res. 61 (2011) 527-531; DOI: 10.1055/s-0031-1296239.
  32. 32. M. S. Bashandy, M. S. Alsaid, S. I. Alqasoumi and M. M. Ghorab, Design and synthesis of some novel hydrazide, 1,2-dihydropyridine, chromene derivative carrying active sulfone moieties with potential anticancer activity, Arzneimittel-Forschung Drug Res. 61 (2011) 521-526; DOI: 10.1055/s-0031-1296238.
  33. 33. M. S. Alsaid, M. M. Ghorab, M. S. Al-Dosari and M. M. Hamed, Synthesis and in vitro anticancer evaluation of some novel hexahydroquinolinederivatives having a benzenesulfonamide moiety, Eur. J. Med. Chem. 46 (2011) 201-207; DOI: 10.1016/j.ejmech.2010.11.002.
  34. 34. F. Al-Omran, N. Al-Awadi, M. M. Abdel-Khalik, K. Kaul, A. A. El-Khair and M. H. Elnagdi,. 1-Substituted 3-dimethylaminoprop-2-en-1-ones as building blocks in heterocyclic synthesis: Routes to 6-aryl- and 6-heteroaryl-2H-pyran-2-ones and 6- and 4-arylpyridin-2(1H)-ones, J. Chem. Res. (S), 84 (1997) 84-85.
  35. 35. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenny and M. R. Boyd, New colorimetric cytotoxicity assay for anticancer-drug screening, J. Natl. Cancer Inst. 82 (1990) 1107-1112; DOI: 10.1093/jnci/82.13.1107
DOI: https://doi.org/10.2478/acph-2014-0035 | Journal eISSN: 1846-9558 | Journal ISSN: 1330-0075
Language: English
Page range: 419 - 431
Accepted on: Jul 3, 2014
Published on: Dec 20, 2014
Published by: Croatian Pharmaceutical Society
In partnership with: Paradigm Publishing Services
Related subjects:

© 2014 Mostafa M. Ghorab, Mahmoud S. Bashandy, Mansour S. Alsaid, published by Croatian Pharmaceutical Society
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.