Synthesis of novel mast cell-stabilising and anti-allergic 1,2,3,4-tetrahydro-1-naphthalenols and related compounds

European Journal of Medicinal Chemistry

Volumn 46, Issue 5, 2011, Pages 1545-1554

  Barlow, James W ^a   McHugh, Aengus P ^a   Woods, Orla ^a   Walsh, John J ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

Anti Allergic; Indan; Mast cell; Tetralin

Indexed keywords

(3,4 DIHYDRO 1 NAPHTHALENYLOXY)(TRIMETHYL)SILANE; 1',3' DIHYDRO SPIRO[[1,3]DIOXOLANE 2,2' INDENE]; 2 (1 METHOXY 2 PHENYLETHYL) 1,2,3,4 TETRAHYDRO 1 NAPHTHALENONE; 2 (1,2,3,4 TETRAHYDRO 2 NAPHTHALENYLIDEN) 1 INDANONE; 2 (1H 2 INDENYL) 2 METHYL 1,3 DIPHENYL 1 PROPANOL; 2 (1H 2 INDENYL) 2 METHYL 1,3 DIPHENYL 1 PROPANONE; 2 (3,4 DIHYDRO 1 NAPHTHALENYL) 1,2,3,4 TETRAHYDRO 1 NAPHTHALENONE; 2 (3,4 DIHYDRO 2 NAPHTHALENYL) 1,2,3,4 TETRAHYDRO 1 NAPHTHALENONE; 2 (3,4 DIHYDRO 2 NAPHTHALENYL) 2 METHYL 1,3 DIPHENYL 1 PROPANOL; 2 (4 HYDROXYETHYLBENZYL) 2 (2 PHENYL 1 ETHENYL) 1,2,3,4 TETRAHYDRO 1 NAPHTHALENOL; 2 (4 METHYLBENZYL) 2 (2 PHENYL 1 ETHENYL) 1,2,3,4 TETRAHYDRO 1 NAPHTHALENOL; 2 (4 METHYLBENZYL) 2 (2 PHENYL 1 ETHENYL) 1,2,3,4 TETRAHYDRO 1 NAPHTHALENONE; 2 (4 TRIFLUOROMETHOXYBENZYL) 2 (2 PHENYL 1 ETHENYL) 1,2,3,4 TETRAHYDRO 1 NAPHTHALENOL; 2 (4 TRIFLUOROMETHOXYBENZYL) 2 (2 PHENYL 1 ETHENYL) 1,2,3,4 TETRAHYDRO 1 NAPHTHALENONE; 2 [2 (2 HYDROXYETHOXY) 1,2,3,4 TETRAHYDRO 2 NAPHTHALENYL] 1 PHENYL 1 PROPANONE; 2 [2 (2 HYDROXYETHOXY) 2,3 DIHYDRO 1H 2 INDENYL] 1 PHENYL 1 PROPANONE; 2 [2 (2 HYDROXYETHOXY) 2,3 DIHYDRO 1H 2 INDENYL] 1,2,3,4 TETRAHYDRO 1 NAPHTHALENONE; 2 BENZYL 2 (1H 2 INDENYL)1,2,3,4 TETRAHYDRO 1 NAPHTHALENOL; 2 BENZYL 2 (1H 2 INDENYL)1,2,3,4 TETRAHYDRO 1 NAPHTHALENONE; 2 BENZYL 2 (3,4 DIHYDRO 2 NAPHTHALENYL) 1 INDANOL; 2 BENZYL 2 (3,4 DIHYDRO 2 NAPHTHALENYL) 1 INDANONE; 2 BENZYL 2 [2 PHENYL 1 ETHENYL] 1,2,3,4 TETRAHYDRO 1 NAPHTHALENOL; 2 BENZYL 2 [2 PHENYL 1 ETHENYL] 1,2,3,4 TETRAHYDRO 1 NAPHTHALENONE; 2 BENZYL 2 METHYL 1,4 DIPHENYL 3 BUTEN 1 OL; 2 BENZYL 2 METHYL 1,4 DIPHENYL 3 BUTEN 1 ONE; 3 METHOXY 2 METHYL 1,4 DIPHENYL 1 BUTANONE; ANTIALLERGIC AGENT; ANTIINFLAMMATORY AGENT; INDOMETACIN; METHYL 2 [4 [(1,2,3,4 TETRAHYDRO 1 OXO 2 STYRYLNAPHTHALEN 2 YL)METHYL]PHENYL]ACETATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; EAR DISEASE; EAR EDEMA; EDEMA; IN VITRO STUDY; IN VIVO STUDY; MALE; MAST CELL; MOUSE; NONHUMAN;

ANIMALS; ANTI-ALLERGIC AGENTS; ARACHIDONIC ACID; CELL COUNT; CELL SURVIVAL; EAR DISEASES; EDEMA; HYPERSENSITIVITY; MALE; MAST CELLS; MICE; MICE, INBRED STRAINS; MOLECULAR STRUCTURE; NAPHTHOLS; RATS; STEREOISOMERISM;

EID: 79953185321     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.01.073     Document Type: Article

References (28)

1. E.B. Cook, J.L. Stahl, N.P. Barney, and F.M. Graziano Curr. Drug Targets Inflamm. Allergy 1 2 2002 167 180
2. J.J. Walsh, N. Frankish, H. Sheridan, R. Farrell, W. Byrne, U.S. Patent 6,300,376, Oct. 9 (2001);
3. H. Sheridan, J.J. Walsh, M. Jordan, C. Cogan, and N. Frankish Eur. J. Med. Chem. 44 12 2009 5018 5022
4. Helen Sheridan, J.J. Walsh, C. Cogan, M. Jordan, T. McCabe, E. Passante, and N.H. Frankish Bioorg. Med. Chem. Lett. 19 2009 5927 5930
5. P.F. Juby, W.R. Goodwin, T.W. Hudyma, and R.A. Partyka J. Med. Chem. 15 12 1972 1297 1306
6. Ching-Yuh Chern, Yung-Lee Yek, Yu-Lin Chen, and Wai-Ming Kan J. Chin. Chem. Soc. 55 2008 846 853
7. W.C. Black, C-S. Li, D. Guay, P. Prasit, P. Roy, U.S. Patent 5,409,944, April 25 (1995).
8. J.W. Barlow, and J.J. Walsh Eur. J. Med. Chem. 43 2008 2891 2900
9. J.W. Barlow, and J.J. Walsh Eur. J. Med. Chem. 45 2010 25 37
10. G.A. Olah, B.G. Balaram Gupta, S.C. Narang, and R. Malhotra J. Org. Chem. 44 24 1979 4272 4275
11. P.G. Gassman, S.J. Burns, and K.B. Pfister J. Org. Chem. 58 1993 1449 1457
12. F.F. Caserio, and J.D. Roberts J. Am. Chem. Soc. 80 1958 5837 5841
13. T.H. Chan, M.A. Brook, and T. Chaly Synthesis 1983 203 205
14. T. Mukaiyama, and M. Murakami Synthesis 12 1987 1043 1054
15. R.C. Cambie, D.S. Larsen, C.E.F. Rickard, P.S. Rutledge, and P.D. Woodgate Aust. J. Chem. 39 1986 487 502
16. M. Honda, W. Oguchi, M. Segi, and T. Nakajima Tetrahedron 58 2002 6815 6823
17. E. Nakamura, and I. Kuwajima Chem. Lett. 1983 59 62
18. E. Nakamura, and I. Kuwajima Tetrahedron. Lett. 24 32 1983 3347 3350
19. J.N. Moorthy, S. Samanta, A.L. Koner, S. Saha, and W.M. Nau J. Am. Chem. Soc. 130 41 2008 13608 13617
20. J.M. Springer, C.W. Hinman, E.J. Eisenbraun, P.W.K. Flanagan, and M.C. Hamming J. Org. Chem. 35 5 1970 1260 1264
21. M. Goto, K. Akimoto, K. Aoki, M. Shindo, and K. Koga Tetrahedron. Lett. 40 1999 8129 8132
22. N. Frankish, R. Farrell, and H. Sheridan J. Pharm. Pharmacol. 56 11 2004 1423 1427
23. Z. Ovary J. Immunol. 81 1958 355 357
24. S. Katayama, H. Shionoya, and S. Ohtake Jpn. J. Pharmacol. 1978 Suppl. 25:103 pp.
25. J.M. Young, D.A. Spires, C.J. Bedord, B. Wagner, S.J. Ballaron, and L.M. De Young J. Invest. Dermatol. 82 1984 367 371
26. B.K. Banik, M. Chapa, J. Marquez, and M. Cardona Tetrahedron. Lett. 46 2005 2341 2343
27. S. Dayan, J. Almog, O. Khodzhaev, and S. Rozen J. Org. Chem. 63 8 1998 2752 2754
28. C.H. Heathcock, S.K. Davidsen, K.T. Hug, and L.A. Flippin J. Org. Chem. 51 1986 3027 3037