Chemistry and biological activities of 1,3-benzothiazoles

Mini-Reviews in Organic Chemistry

Volumn 9, Issue 1, 2012, Pages 44-53

  Facchinetti, Victor ^a,b   da Reis, Raísa R ^a   Gomes, Claudia R B ^b   Vasconcelos, Thatyana R A ^a  

^a FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

^b INSTITUTO OSWALDO CRUZ   (Brazil)

Author keywords

1; 3 benzothiazoles; Biological activity; Drugs; Synthesis

Indexed keywords

EID: 83455218321     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157019312799079929     Document Type: Article

References (59)

1. Katritzky, A. R. Preface. Tetrahedron, 1996, 52 (9), xiii.
2. Katritzky, A. R.; Rees, C. W. Comprehensive Heterocyclic Chemistry-Structure, Reactions, Synthesis and Uses of Heterocyclic Compounds. Pergamon Press Oxford, 1984, vol. 1, pp. 143-152.
3. Gunwardana, G. P.; Kohmoto, S.; Gunasekera, S. P., McConnell, O. J.; Koehn F. E. Dercitin, a new biologically active acridine alkaloid from a deep water marine sponge, Dercitus sp. J. Am. Chem. Soc., 1988, 110, 4856-4858.
4. Rana, A., Siddiqui, N., Khan, S. A.; Benzothiazoles: a new profile of biological activities. Indian J. Pharm. Sci., 2007, 69 (1), 10-17.
5. Caleta, I.; Kralj, M.; Marjanovic, M.; Bertosa, B.; Tomic, S.; Pavilovic, G.; Pavelic, K.; Karminski-Zamola, G. Novel cyano- and amidinobenzothiazole derivatives: synthesis, antitumor evaluation, and X-ray and quantitative structure-activity relationship (QSAR) analysis. J. Med. Chem., 2009, 52, 1744-1756.
6. Ben-Alloum, A.; Bakkasa, S.; Soufiaoui, M. Nouvelle Voie de Synthese des 2-arylbenzothiazoles transfert d'electrons active par micro-ondes. Tetrahedron Lett., 1997, 38(36), 6395-6396.
7. Boger, D. L. A convenient preparation of 2-substituted benzothiazoles. J. Org. Chem., 1978, 43, 2296-2297.
8. Li, Y.; Wang, Y. L.; Wang, J. W. A simple iodine-promoted synthesis of 2-substituted benzothiazoles by condensation of aldehydes with 2-aminothiophenol. Chem. Lett., 2006, 35, 460-461.
9. Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis of fused imidazoles and benzothiazoles from (hetero)aromatic ortho-diamines or ortho-aminothiophenol and aldehydes promoted ny chlorotrimethylsilane. Synthesis, 2006, 21, 3715-3726.
10. Praveen, C.; Hemanthkumar, K.; Muralidharan, D.; Perumal, P. T. Oxidative cyclization of thiophenolic and phenolic Schiff's bases promoted by PCC: a new oxidant for 2-substituted benzothiazoles and benzoxazoles. Tetrahedron, 2008, 64, 2369-2374.
11. Downer, N. K., Jackson, Y. A. Synthesis of benzothiazoles via ipso substitution of ortho-methoxythiobenzamides. Org. Biomol. Chem., 2004, 2, 3039-3043.
12. Jacobson, P. Ueber bildung von anhydroverbindungen des orthoamidophenylmercaptans aus thioaniliden. Ber. Dtsch. Chem. Ges., 1886, 19, 1067-1070.
13. Stevens, M. F. G., McCall, C. J., Lelieveld, P., Alexander, P., Richter, A., Davies, D. E. Structural studies on bioactive compounds.23.Synthesis of polyhydroxylated 2-phenylbenzothiazoles and a comparison of their cytotoxicities and pharmacological properties with genistein and quercertin. J. Med. Chem., 1994, 37, 1689-1695.
14. Metzger, J., Planck, H. Methods of synthesis of benzothiazoles. Chim. Ind. (Paris), 1956, 75, 929-939.
15. Downer, N. K., Jackson, Y. A. Iodine-mediated cyclisation of thiobenzamides to produce benzothiazoles and benzoxazoles. Tetrahedron, 2007, 63, 10276-10281.
16. Itoh, T., Mase, T. A novel practical synthesis of benzothiazoles via Pdcatalyzed thiol cross-coupling. Org. Lett., 2007, 9 (18), 3687-3689.
17. Pratap, U. R.; Mali, J. R.; Jawale, D. V.; Mane, R. A. Bakers' yeast catalyzed synthesis of benzothiazoles in an organic medium. Tetrahedron Lett., 2009, 50, 1352-1354.
18. Aliyan, H.; Fazaeli, R.; Fazaeli, N.; Mssah, A. R.; Naghash, H. J.; Alizadeh, M.; Emani, G. Facile route for the synthesis of benzothiazoles and benzimidazoles in the presence of tungstophosphoric acid impregnated zirconium phosphate under solvent-free conditions. Heteroat. Chem., 2009, 20, 202-207.
19. Ding, Q.; Huang, X.; Wu, J. Facile synthesis of benzothiazoles via cascade reactions of 2-iodoanilines, acid chlorides and Lawesson's reagent. J. Comb. Chem., 2009, 11, 1047-1049.
20. Yuan, Q.; Ma, D. A one-pot coupling/hydrolysis/condensation process to pyrrolo[1,2-a]quinoxaline. J. Org. Chem., 2008, 73, 5159-5162.
21. Chen, Y.; Wang, Y.; Sun, Z.; Ma, D. Elaboration of 2-(trifluoromethyl) indoles via a cascade coupling/condensation/deacylation process. Org. Lett., 2008, 10, 625-628.
22. Mourtas, S.; Gatos, D.; Barlos, K. Solid phase synthesis of benzothiazolyl compounds. Tetrahedron Lett., 2001, 42, 2201-2204.
23. Hioki, H.; Matsushita, K.; Kubo, M.; Kodama, M. Combinatorial synthesis of benzothiazoles and benzimidazoles using a traceless aniline linker. J. Comb. Chem., 2006, 8, 462-463.
24. Guo, H. Y.; Li, J. C.; Shang, Y. L. A simple and efficient synthesis of 2- substituted benzothiazoles catalyzed by H2O2/HCl. Chin. Chem. Lett., 2009, 20, 1408-1410.
25. Kumar, A.; Sharma, S.; Maurya, R. A. Bienzymatic synthesis of benzothia/(oxa)zoles in aqueous medium. Tetrahedron Lett., 2010, 51, 6224-6226.
26. Jaseer, E. A.; Prasad, D. J. C.; Dandapat, A.; Sekar, G. An efficient copper(II)-catalyzed synthesis of benzothiazoles through intramolecular coupling-cyclization of N-(2-chlorophenyl)benzothioamides. Tetrahedron Lett., 2010, 51, 5009-5012.
27. Fan, X.; Wang, Y.; He, Y.; Zhang, X.; Wang, J. Ru(III)-catalyzed oxidative reaction in ionic liquid: an efficient and practical route to 2-substituted benzothiazoles and their hybrids with pyrimidine nucleoside. Tetrahedron Lett., 2010, 51, 3493-3496.
28. Li, C. L.; Zhang, X. G.; Tang, R. Y.; Zhong, P.; Li, J. H. Copper-catalyzed thiolation annulations of 1,4-dihalides with sulfides leading to 2-trifluoromethyl benzothiophenes and benzothiazoles. J. Org. Chem., 2010, 75, 7037-7040.
29. Zhu, J.; Chen, Z.; Xie, H.; Li, S.; Wu, Y. A general and straightforward method for the synthesis of 2-trifluoromethylbenzothiazoles. Org. Lett., 2010, 12(10), 2434-2436.
30. Yang, X. L.; Xu, C. M.; Lin, S. M.; Chen, J. X.; Ding, J. C.; Wu, H. Y.; Su, W. K. Eco-friendly synthesis of 2-substituted benzothiazoles catalyzed by cetyltrimethyl ammonium bromide (CTAB) in water. J. Braz. Med. Chem., 2010, 21, 37-42.
31. Mylari, B. L.; Larson, E. R.; Beyer, T. A.; Zembrowski, W. J.; Aldinger, C. E.; Dee, M. F.; Siegel, T. W.; Singleton, D.H. Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]-methyl]-1-phthalazineacetic acid (zopolrestat) and congeners. J. Med. Chem., 1991, 34, 108-122.
32. Siddiqui, N.; Rana, A.; Khan, S. A.; Bhat, M. A.; Haque, S. E. Synthesis of benzothiazole semicarbazones as novel anticonvulsants-The role of hydrophobic domain. Bioorg. Med. Chem. Lett., 2007, 17, 4178-4182.
33. Shashank, D.; VIshawanth, T.; Pasha, A. Md.; Balasubramaniam, V.; Nagendra, A.; Perumal, P.; Suthakaran, R. Synthesis of some substituted benzothiazole derivatives and its biological activities. Int. J. ChemTech Res., 2009, 1(4), 1224-1231.
34. Jeon, R.; Kim, Y.; Cheon, Y.; Ryu, J. Synthesis and biological activity of [[(Heterocycloamino)alkoxy]benzyl]-2,4-thiazolidinediones as PPART agonists. Arch. Pharm. Res., 2006, 29(5), 394-399.
35. Ren, P.; Liu, Y.; Li, L.; Chan, K.; Wilson, T. E. Benzothiazole kinase inhibitors and methods of use. WO/2009/114874, September 19, 2009.
36. Dörwald, F. C.; Andersen, K. E.; Hohlweg, R.; Christensen, I. T.; Lundbeck, J. M. Benzothiazoles having histamine H3 receptor activity. WO/2007/110364, October 04, 2007.
37. Sjö, P.; Storm, P. Novel use of benzothiazole derivatives. WO/2004/016600, February 26, 2004.
38. Bondock, S.; Fadaly, W.; Metwally, M. A. Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. Eur. J. Med. Chem., 2010, 45, 3692-3701.
39. Aggarwal, R.; Kumar, V.; Tyagi, P.; Singh, S. P. Synthesis and antibacterial activity of some new 1-heteroaryl-5-amino-3H/methyl-4-phenylpyrazoles. Bioorg. Med. Chem., 2006, 14, 1785-1791.
40. Moy, T. I.; Conery, A. L.; Larkins-Ford, J.; Wu, G.; Mazitschek, R.; Casadei, G.; Lewis, K.; Carpenter, A. E.; Ausubel, F. M. High-throughput screen for novel antimicrobials using a whole animal infection model. ACS Chem. Biol., 2009, 4, 527.
41. Stella, A.; Segersb, K.; De Jonghea, S.; Vanderhoydoncka, B.; Rozenskia, J.; Anne, J.; Herdewijn, P. Synthesis and antibacterial evaluation of a novel series of 2-(1,2-Dihydro-3-oxo-3H-pyrazol-2-yl)benzothiazoles. Chem. Biodivers., 2011, 8, 253-265.
42. Franchini, C.; Muraglia, M.; Corbo, F.; Florio, M. A.; Di Mola, A.; Rosato, A.; Matucci, R.; Nesi, M.; van Bambeke, F.; Vitali, C. Synthesis and biological evaluation of 2-Mercapto-1,3-benzothiazole derivatives with potential antimicrobial activity Arch. Pharm. Chem. Life Sci., 2009, 342, 605-613.
43. Sharma, V.; Sharma, K. V. Synthesis and biological activity of some 3,5-Diaryl-1-benzothiazolopyrazoline derivatives: reaction of chalcones with 2-Hydrazinobenzothiazoles. Eur. J. Chem., 2009, 6(2), 348-356.
44. Asati, V.; Sahu, N. K.; Rathore, A.; Sahu, S.; Kohli, D. V. Synthesis, characterization and antimicrobial evaluation of some 1,3-benzothiazole-2-yl-hydrazone derivatives. Arabian J. Chem., 2011, doi:10.1016/j.arabjc.2011.01.036
45. Yamazaki, K.; Kaneko, Y.; Suwa, K.; Ebara, S.; Nakazawa, K.; Yasuno, K. Synthesis of potent and selective inhibitors of Candida albicans Nmyristoyltransferase based on the benzothiazole structure. Bioorg. Med. Chem., 2005, 13, 2509-2522.
46. Saeed, S.; Rashid, N.; Jones, P. G.; Ali, M.; Hussain, R. Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents. Eur. J. Med. Chem., 2010, 45, 1323-1331.
47. Sattigeri, J. A.; Kumar, N.; Yadav, A.; Sharma, L.; Cliffe, I. A.; Varughese, S. B.; Shabbir, S. R.; Raj, V. S.; Upadhyay, D. J.; Bhatnagar, P. K. Benzothiazoles and aza-analogues thereof use as antibacterial agents. WO/2009/156966, December 30, 2009.
48. World Health Organization. www.who.int/cancer/en/ (Accessed May 23, 2011).
49. Vicini, P.; Geronikaki, A.; Incerti, M.; Busonera, B.; Poni, G.; Cabras, C. A.; La Colla, P. Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases. Bioorg. Med. Chem., 2003, 11, 4785-4789.
50. Caleta, I.; Kralj, M.; Marjanovic, M.; Bertosa, B.; Tomic, S.; Pavlovic, G.; Pavelic, K.; Karminski-Zamola, G. Novel cyano- and amidinobenzothiazole derivatives: synthesis, antitumor evaluation, and X-ray and Quantitative Structure-Activity Relationship (QSAR) analysis. J. Med. Chem., 2009, 52, 1744-1756.
51. de Souza, M. V. N. New natural products able to act on the stabilization of microtubules, an important target against cancer. Quim. Nova, 2004, 27(2), 308-312.
52. Bhuva, H. A.; Kinib, S. G. Synthesis, anticancer activity and docking of some substituted benzothiazoles as tyrosine kinase inhibitors J. Mol. Graph. Mod., 2010, 29, 32-37.
53. Hutchinson, I.; Jennings, S. A.; Vishnuvajjala, B. A.; Westwell, A. D.; Stevens, M. F. G.; Antitumor benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-Aminophenyl)benzothiazole amino acid prodrugs. J. Med. Chem., 2002, 45, 744-747.
54. Lion, C. J.; Matthews, C. S.; Wells, G.; Bradshaw, T. D.; Stevens, M. F. G.; Westwell, A. D. Antitumour properties of fluorinated benzothiazolesubstituted hydroxycyclohexa-2,5-dienones ('quinols'). Bioorg. Med. Chem. Lett., 2006, 16, 5005-5008.
55. Mortimer, C. G.; Wells, G.; Crochard, J; Stone, E. L.; Bradshaw, T. D.; Stevens, M. F. G.; Westwell, A. D. Antitumor benzothiazoles. 26. 2-(3,4-Dimethoxyphenyl)-5-fluorobenzothiazole (GW 610, NSC 721648), a simple fluorinated 2-Arylbenzothiazole, shows potent and selective inhibitory activity against lung, colon, and breast cancer cell lines. J. Med. Chem., 2006, 49, 179-185.
56. Aiello, S.; Wells, G.; Stone, E. L.; Kadri, H.; Bazzi, R.; Bell, D. R.; Stevens, M. F. G.; Matthews, C. S.; Bradshaw, T. D.; Westwell, A. D. Synthesis and biological properties of benzothiazole, benzoxazole, and Chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648). J. Med. Chem., 2008, 51, 5135-5139.
57. Kamal, A.; Reddy, K. S.; Khan, M. N. A.; Shetti, R. V. C. R. N. C.; Ramaiah M. J.; Pushpavalli, S.N.C.V.L.; Srinivas, C.; Pal-Bhadra, M.; Chourasia, M.; Sastry, G. N.; Juvekar, A.; Zingde, S.; Barkume, M. Synthesis, DNA-binding ability and anticancer activity of benzothiazole/benzoxazole-pyrrolo[2,1-c][1,4]benzodiazepine conjugates. Bioorg. Med. Chem., 2010, 18, 4747-4761.
58. Reis, R. R.; Azevedo, E. C.; de Souza, M. C. B. V.; Ferreira, V. F.; Montenegro, R. C.; Araújo, A. J.; Pessoa, C.; Costa-Lotufo, L. V.; de Moraes, M. O.; Filho, J. D. B. M.; de Souza, A. M. T.; de Carvalho, N. C.; Castro, H. C.; Rodrigues, C. R.; Vasconcelos, T. R. A. Synthesis, anticancer activities and SAR studies of some novel 2-(benzo[d]thiazol-2-yl)-8-substituted-2H-pyrazolo[4,3-c]quinolin-3(5H)-ones. Eur. J. Med. Chem., 2011, 46, 1448-1452.
59. Nogueira, A. F.; Azevedo, E. C.; Ferreira, V. F.; Araújo, A. J.; dos Santos, E. A.; Pessoa, C.; Costa-Lotufo, L. V.; Montenegro R. C.; de Moraes, M. O.; Vasconcelos, T. R. A. Synthesis and antitumor evaluation of (E)-2-Benzothiazole hydrazones. Lett. Drug. Des. Discov., 2010, 7, 551-555.