Synthesis of 5-(ethylsulfonyl)-2-methoxyaniline: An important pharmacological fragment of VEGFR2 and other inhibitors

Beilstein Journal of Organic Chemistry

Volumn 9, Issue , 2013, Pages 173-179

  Murár, Miroslav ^a   Addová, Gabriela ^a   Boháč, Andrej ^a,b  

^a Physics and Informatics   (Slovakia)

^b Biomagi Ltd   (Slovakia)

Author keywords

Angiogenesis; Pharmacophoric ligand; Synthesis of 5 (ethylsulfonyl) 2 methoxyaniline; VEGFR2 tyrosine kinase inhibitors

Indexed keywords

EID: 84873420690     PISSN: None     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.9.20     Document Type: Article

References (23)

1. SciFinder. http://scifinder.cas.org/scifinder/view/scifinder/ (accessed Nov 14, 2012).
2. Carmeliet, P. Oncology 2005, 69 (Suppl. 3), 4-10. doi:10.1159/000088478 (Pubitemid 41680947)
3. Finley, S. D.; Popel, A. S. AAPS J. 2012, 14, 500-509. doi:10.1208/s12248-012-9363-4
4. Harris, P. A.; Cheung, M.; Hunter, R. N., III; Brown, M. L.; Veal, J. M.; Nolte, R. T.; Wang, L.; Liu, W.; Crosby, R. M.; Johnson, J. H.; Epperly, A. H.; Kumar, R.; Luttrell, D. K.; Stafford, J. A. J. Med. Chem. 2005, 48, 1610-1619. doi:10.1021/jm049538w (Pubitemid 40364567)
5. Protein data bank. http://www.rcsb.org/pdb/explore.do?structureId=1y6a (accessed Nov 2, 2012).
6. Accelrys. http://accelrys.com/products/discovery-studio/visualization- download.p hp (accessed Nov 1, 2012).
7. Remko, M.; Boháč, A.; Kováčiková, L. Struct. Chem. 2011, 22, 635-648. doi:10.1007/s11224-011-9741-z
8. AldrichCPR - a collection of Sigma-Aldrich third party vendors building blocks. http://www.sigmaaldrich.com/chemistry/chemistry-services/aldrichcpr-b uilding.html (accessed Nov 3, 2012).
9. Reaxys and SciFinder Scholar. http://www.reaxys.com (accessed Oct 30, 2012).
10. And http://scifinder.cas.org/ (accessed Oct 30, 2012).
11. Onozuka, T.; Tanaka, M.; Fujiwara, T.; Tamura, M.; Satake, S. Process for production of aromatic sulfonyl chloride compound. WO-Patent Appl. WO2011058915A1, May 19, 2011.
12. Chauhan, S. S.; Joshi, Y. C. Org. Chem.: Indian J. 2009, 5, 424-428.
13. Morgan, M. S.; Cretcher, L. H. J. Am. Chem. Soc. 1948, 70, 375-378. doi:10.1021/ja01181a116
14. Birchall, J. D.; Glidewell, C. J. Chem. Soc., Dalton Trans. 1977, 10-14. doi:10.1039/DT9770000010
15. Liu, J.; Zhou, X.; Rao, H.; Xiao, F.; Li, C.-H.; Deng, G.-J. Chem.-Eur. J. 2011, 17, 7996-7999. doi:10.1002/chem.201101252
16. Guzzo, P. R.; Henderson, A. J.; Nacro, K.; Isherwood, M. L.; Ghosh, A.; Xiang, K. Epiminocycloalkyl[b]indole derivatives as serotonin sub-type 6 (5-HT6) modulators and uses thereof. WO-Patent Appl. WO2011/44134 A1, April 14, 2011.
17. Austad, T. Acta Chem. Scand., Ser. A 1976, 30, 579-585. doi:10.3891/acta.chem.scand.30a-0579
18. Suter, C. M.; Hansen, H. L. J. Am. Chem. Soc. 1932, 54, 4100-4104. doi:10.1021/ja01349a040
19. Maccagnani, T. Boll. Sci. Fac. Chim. Ind. Bologna 1965, 23, 381-393.
20. Acher, J.; Bulteau, G.; Monier, J.-C. Verfahren zur Herstellung von 2-Alkoxy-5-alkylsulfonylbenzoesaeuren. Ger. Patent DE2327194, Dec 20, 1973.
21. Chem. Abstr. 1974, 80, 82414.
22. Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D.; Maiolo, F. Tetrahedron 1982, 38, 2721-2724. doi:10.1016/0040-4020(82)80028-8
23. Simonet, J.; Fourets, O.; Pilard, J.-F. Tetrahedron Lett. 2000, 41, 1763-1766. doi:10.1016/S0040-4039(00)00049-6 (Pubitemid 30163718)