Substituted benzothiazoles: Synthesis and medicinal characteristics

Heterocyclic Communications

Volumn 19, Issue 2, 2013, Pages 89-99

  Henary, Maged ^a   Paranjpe, Shirish ^a   Owens, Eric A ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

Benzothiazole; Heterocyclic compounds; PET probes; Review; Synthesis

Indexed keywords

EID: 84876538810     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/hc-2013-0026     Document Type: Review

References (28)

1. Henary, M.; Paranjpe, S.; Owens, E. A. Synthesis and application of benzothiazole containing cyanine dyes. Heterocycl. Commun. 2013, 19, 1-11.
2. Robbins, K.; Liu, G.; Lin, G.; Lazo, N. Detection of strongly bound thioflavin T species in amyloid fibrils by ligand-detected 1 H NMR. J. Phys. Chem. Lett. 2011, 2, 735 - 740.
3. Sisodia, S.; Price, D. Role of the β -amyloid protein in Alzheimer's disease. FASEB J. 1995, 9, 366 - 370.
4. Yan, P.; Bero, A.; Cirrito, J.; Xiao, Q.; Hu, X.; Wang, Y.; Gonzales, E.; Holtzman, D.; Lee, J. -M. Characterizing the appearance and growth of amyloid plaques in APP/PS1 mice. J. Neurosci. 2009, 29, 10706 - 10714.
5. Klunk, W.; Engler, H.; Nordberg, A.; Wang, Y.; Blomqvist, G.; Holt, D.; Bergström, M.; Savitcheva, I.; Huang, G.-F.; Estrada, S.; et al. Imaging brain amyloid in Alzheimer ' s disease with Pittsburgh compound-B. Ann. Neurol. 2004, 55, 306 - 319.
6. Klunk, W.; Wang, Y.; Huang, G.-F.; Debnath, M.; Holt, D.; Mathis, C. Uncharged thioflavin-T derivatives bind to amyloid- β protein with high affinity and readily enter the brain. Life Sciences 2001, 69, 1471 - 1484.
7. Landau, S.; Breault, C.; Joshi, A.; Pontecorvo, M.; Mathis, C.; Jagust, W.; Mintun, M. For the Alzheimer ' s Disease Neuroimaging Initiative. Amyloid- β imaging with Pittsburgh compound B and florbetapir: comparing radiotracers and quantification methods. J. Nucl. Med. 2013, 54, 476-490.
8. Wilson, A.; Garcia, A.; Chestakova, A.; Kung, H.; Houle, S. A rapid one-step radiosynthesis of the β -amyloid imaging radiotracer N -methyl-[11C]2-(4′ -methylaminophenyl)-6-hydroxybenzothiazole ([11C]-6-OH-BTA-1). J. Label. Compd. Rad. 2004, 47, 679- 682.
9. Yousefi, B.; Manook, A.; Drzezga, A.; Reutern, B.; Schwaiger, M.; Wester, H.-J.; Henriksen, G. Synthesis and evaluation of 11C-labeled imidazo[2,1-b]benzothiazoles (ibts) as PET tracers for imaging β -amyloid plaques in Alzheimer ' s disease. J. Med. Chem. 2011, 54, 949 - 956.
10. Ribeiro Morais, G.; Paulo, A.; Santos, I. A synthetic overview of radiolabeled compounds for β -amyloid targeting. Eur. J. Org. Chem. 2012, 7, 1279 - 1293.
11. Yadav, P.; Devprakash; Senthilkumar, G. Benzothiazole: different methods of synthesis and diverse biological activities. Int. J. Pharm. Sci. Drug Res. 2011, 3, 1 - 7.
12. Ouyang, L.; Huang, Y.; Zhao, Y.; He, G.; Xie, Y.; Liu, J.; He, J.; Liu, B.; Wei, Y. Preparation, antibacterial evaluation and preliminary structure-activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives. Bioorg. Med. Chem. 2012, 22, 3044 - 3049.
13. Bandyopadhyay, P.; Sathe, M.; Ponmariappan, S.; Sharma, A.; Sharma, P.; Srivastava, A.; Kaushik, M. Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents. Bioorg. Med. Chem. 2011, 21, 7306 - 7309.
14. Shi, X.-H.; Wang, Z.; Xia, Y.; Ye, T.-H.; Deng, M.; Xu, Y.-Z.; Wei, Y.-Q.; Yu, L.-T. Synthesis and biological evaluation of novel benzothiazole-2-thiol derivatives as potential anticancer agents. Molecules 2012, 17, 3933 - 3944.
15. Mortimer, C.; Wells, G.; Crochard, J.-P.; Stone, E.; Bradshaw, T.; Stevens, M.; Westwell, A. Antitumor benzothiazoles. 26. 1 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.
16. D ' Angelo, N.; Kim, T.-S.; Andrews, K.; Booker, S.; Caenepeel, S.; Chen, K.; D ' Amico, D.; Freeman, D.; Jiang, J.; Liu, L.; et al. Discovery and optimization of a series of benzothiazole phosphoinositide 3-kinase (PI3K)/mammalian target of rapamycin (mTOR) dual inhibitors. J. Med. Chem. 2011, 54, 1789 - 1811.
17. Shafi, S.; Mahboob Alam, M.; Mulakayala, N.; Mulakayala, C.; Vanaja, G.; Kalle, A.; Pallu, R.; Alam, M. Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: their anti-inflammatory and anti-nociceptive activities. Eur. J. Med. Chem. 2012, 49, 324 - 333.
18. Gilani, S.; Khan, S. Synthesis and pharmacological evaluation of N -(6-chlorobenzo[d]-thiazol-2-yl)hydrazine carboxamide derivatives of benzothiazole. Med. Chem. Res. 2012, 19, 1 - 13.
19. Kosugi, T.; Mitchell, D.; Fujino, A.; Imai, M.; Kambe, M.; Kobayashi, S.; Makino, H.; Matsueda, Y.; Oue, Y.; Komatsu, K.; et al. Mitogen-activated protein kinase-activated protein kinase 2 (MAPKAP-K2) as an antiinflammatory target: discovery and in vivo activity of selective pyrazolo[1,5- a]-pyrimidine inhibitors using a focused library and structure-based optimization approach. J. Med. Chem. 2012, 55, 6700 - 6715.
20. Van Zandt, M.; Jones, M.; Gunn, D.; Geraci, L.; Jones, J.; Sawicki, D.; Sredy, J.; Jacot, J.; DiCioccio, A.; Petrova, T.; et al. Discovery of 3-[(4,5,7-trifluorobenzo-thiazol-2-yl)methyl] indole- N -acetic acid (Lidorestat) and congeners as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications. J. Med. Chem. 2005, 48, 3141 - 3152.
21. Moreno-Díaz, H.; Villalobos-Molina, R.; Ortiz-Andrade, R.; Díaz-Coutiño, D.; Medina-Franco, J.; Webster, S.; Binnie, M.; Estrada-Soto, S.; Ibarra-Barajas, M.; León-Rivera, I.; et al. Antidiabetic activity of N -(6-substituted-1,3-benzothiazol- 2-yl)benzen-esulfonamides. Bioorg. Med. Chem. 2008, 18, 2871 - 2877.
22. Massari, S.; Daelemans, D.; Barreca, M.; Knezevich, A.; Sabatini, S.; Cecchetti, V.; Marcello, A.; Pannecouque, C.; Tabarrini, O. A 1,8-naphthyridone derivative targets the HIV-1 Tat-mediated transcription and potently inhibits the HIV-1 replication. J. Med. Chem. 2010, 53, 641 - 648.
23. Jonckers, T.; Rouan, M.-C.; Haché, G.; Schepens, W.; Hallenberger, S.; Baumeister, J.; Sasaki, J. Benzoxazole and benzothiazole amides as novel pharmacokinetic enhancers of HIV protease inhibitors. Bioorg. Med. Chem. 2012, 22, 4998 - 5002.
24. Spadaro, A.; Frotscher, M.; Hartmann, R. Optimization of hydroxybenzothiazoles as novel potent and selective inhibitors of 17 β -HSD1. J. Med. Chem. 2012, 55, 2469 - 2473.
25. Anzini, M.; Chelini, A.; Mancini, A.; Cappelli, A.; Frosini, M.; Ricci, L.; Valoti, M.; Magistretti, J.; Castelli, L.; Giordani, A.; et al. Synthesis and biological evaluation of amidine, guanidine, and thiourea derivatives of 2-amino(6- trifluoromethoxy)-benzothiazole as neuroprotective agents potentially useful in brain diseases. J. Med. Chem. 2010, 53, 734 - 744.
26. Ugale, V.; Patel, H.; Wadodkar, S.; Bari, S.; Shirkhedkar, A.; Surana, S. Quinazolino-benzothiazoles: fused pharmacophores as anticonvulsant agents. Eur. J. Med. Chem. 2012, 53, 107 - 113.
27. Azam, F.; Prasad, M.; Thangavel, N. Structure-based design, synthesis, and molecular modeling studies of 1-(benzo[d] thiazol-2-yl)-3-(substituted aryl)urea derivatives as novel anti-Parkinsonian agents. Med. Chem. Res. 2012, 21, 2630 - 2643.
28. Karal i, N.; Güzel,ö.;özsoy, N.;özbey, S.; Salman, A. Synthesis of new spiroindolinones incorporating a benzothiazole moiety as antioxidant agents. Eur. J. Med. Chem. 2010, 45, 1068 - 1077.