The synthesis and biological evaluation of a range of novel functionalised benzopyrans as potential potassium channel activators

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 3, 2008, Pages 1237-1240

  Tyrrell, Elizabeth ^a   Tesfa, Kibur Hunie ^a   Greenwood, Iain ^b   Mann, Alistair ^a  

^a KINGSTON UNIVERSITY   (United Kingdom)

^b ST GEORGE'S UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Benzopyrans; Chiral; Cromakalim; Nicholas reaction; Potassium channel activators; Rat thoracic tissue; Smooth muscle relaxation

Indexed keywords

ADENOSINE TRIPHOSPHATE SENSITIVE POTASSIUM CHANNEL; BENZOPYRAN DERIVATIVE; CROMAKALIM; PHENYLEPHRINE; POTASSIUM CHANNEL STIMULATING AGENT;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DETERMINATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; MOUSE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; THORACIC AORTA;

ANIMALS; ANTIHYPERTENSIVE AGENTS; AORTA, THORACIC; BENZOPYRANS; COMBINATORIAL CHEMISTRY TECHNIQUES; CROMAKALIM; MOLECULAR STRUCTURE; MUSCLE RELAXATION; MYOCYTES, SMOOTH MUSCLE; POTASSIUM CHANNELS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS;

EID: 38749092597     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.11.135     Document Type: Article

References (21)

1. Hamilton T.C., Weir S.W., and Weston A.H. Br. J. Pharmacol. 88 (1986) 103
2. Emfield J.R., and Russell K. Annu. Rep. Med. Chem. (1995) 81
3. Roxburgh C.J. Synthesis (1996) 307
4. Cho H., Katoh S., Sayama S., Murakami K., Nakanishi H., Kajimoto Y., Ueno H., Kawasaki H., Aisaka K., and Uchida I. J. Med. Chem. 39 (1996) 3797
5. Andersson K.-E. Pharmacol. Toxicol. 70 (1992) 244
6. Drizin I., Holladay M.W., Lin Y., Zhang H.Q., Gopalakrishnan S., Gopalakrishnan M., Whiteaker K.L., Buckner S.A., Sullivan J.P., and Carroll W.A. Bioorg. Med. Chem. Lett. 12 (2002) 1481
7. Mann A., Muller C., and Tyrrell E. J. Chem. Soc., Perkin Trans. (1998) 1427
8. As well as SAR data in Ref. 3 see. Russell K. Bioorg. Med. Chem. Lett. 6 (1996) 913
9. Nicholas K.M. Acc. Chem. Res. 20 (1987) 207
10. Tyrrell E., Skinner G.A., and Bashir T. Synlett 12 (2001) 1929
11. Tyrrell E., and Tillett C. Tetrahedron Lett 39 (1998) 9535
12. Berge J., Claridge S., Mann A., Muller C., and Tyrrell E. Tetrahedron Lett. 38 (1997) 685
13. Tyrrell E., Millet J., Hunie Tesfa K., Williams N., Mann A., et al. Tetrahedron 63 (2007) 12769
14. Frantz D.E., and Carriera E.M. J. Am. Chem. Soc. 122 (2000) 1806
15. Anand N.K., and Carreira E.M. J. Am. Chem. Soc. 123 (2001) 9687
16. Boyall D., Frantz D., and Carreira E.M. Org. Lett. 4 (2002) 2605
17. Tyrrell E., Hunie Tesfa K., Millet J., and Muller C. Synthesis 18 (2006) 3099
18. Tyrrell E., Hunie Tesfa K., Mann A., and Singh K. Synthesis 10 (2007) 1491
19. The cis stereochemistry for compounds 7a-h was based upon the coupling constant J for the methine protons which was found to be between 5.1 and 5.8 Hz. In contrast the coupling constants derived from the 1H NMR spectrum for the corresponding methine protons in compounds 2 and 3 were found to be 10 and 11 Hz, respectively.
20. Aschcroft F.M., and Gribble F.M. Trends Pharm. Sci. 21 (2005) 439
21. Cechetti V., Tabarrini O., and Sabatini S. Curr. Top. Med. Chem. 6 (2006) 1049