Incorporation of diarylbutylamine pharmacophore into indeno- or naphtho[1,2-b]pyran ring systems

European Journal of Organic Chemistry

Volumn , Issue 12, 2004, Pages 2707-2714

  Maertens, Faye ^a   Toppet, Suzanne ^a   Compernolle, Frans ^a   Hoornaert, Georges J ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Epoxidation; Furans; Heterocyclic compounds; Pyrans

Indexed keywords

ALCOHOL DERIVATIVE; BUTYLAMINE; CHROMENE DERIVATIVE; FURAN DERIVATIVE; METHYL 2 (3 BUTENYL) 1 HYDROXY 1 PHENYL 1,2,3,4 TETRAHYDRONAPHTHALENE 2 CARBOXYLATE; METHYL 2 (3 BUTENYL) 1 HYDROXY 1 PHENYLINDANE 2 CARBOXYLATE; METHYL 2 (3 BUTENYL) 1 OXOINDANE 2 CARBOXYLATE; METHYL 2 (HYDROXYMETHYL) 10B PHENYL 3,4,6,10B TETRAHYDRO 2H BENZO[H]CHROMENE 4A(5H) CARBOXYLATE; METHYL 2 (HYDROXYMETHYL) 8B PHENYL 2,3,4,8 TETRAHYDRO 3AH INDENO[1,2 B]FURAN 3A CARBOXYLATE; METHYL 2 (HYDROXYMETHYL) 9B PHENYL 2,3,5,9B TETRAHYDRONAPHTHOL[1,2 B]FURAN 3A(4H) CARBOXYLATE; METHYL 2 (HYDROXYMETHYL) 9B PHENYL 3,4,5,9B TETRAHYDROINDENO[1,2 B]PYRAN 4A(2H) CARBOXYLATE; METHYL 2 [(METHYLAMINO)METHYL] 10B PHENYL 3,4,6,10B TETRAHYDRO 2H BENZO[H]CHROMENE 4A(5H) CARBOXYLATE; METHYL 2 [(METHYLAMINO)METHYL] 8B PHENYL 2,3,4,8B TETRAHYDRO 3AH INDENO[1,2 B]FURAN 3A CARBOXYLATE; METHYL 2 [(METHYLAMINO)METHYL] 9B PHENYL 2,3,5,9B TETRAHYDRONAPHTHO[1,2 B]FURAN 3A(4H) CARBOXYLATE; METHYL 2 [(METHYLAMINO)METHYL] 9B PHENYL 3,4,5,9B TETRAHYDROINDENO[1,2 B]PYRAN 4A(2H) CARBOXYLATE; METHYL 2 [[(METHYLSULFONYL)OXY]METHYL] 10B PHENYL 3,4,6,10B TETRAHYDRO 2H BENZO[H]CHROMENE; METHYL 2 [[(METHYLSULFONYL)OXY]METHYL] 8B PHENYL 2,3,4,8B TETRAHYDRO 3AH INDENO[1,2 B]FURAN 3A CARBOXYLATE; METHYL 2 [[(METHYLSULFONYL)OXY]METHYL] 9B PHENYL 2,3,5,9B TETRAHYDRONAPHTHO[1,2 B]FURAN 3A(4H) CARBOXYLATE; METHYL 2 [[(METHYLSULFONYL)OXY]METHYL] 9B PHENYL 3,4,5,9B TETRAHYDROINDENO[1,2 B]PYRAN 4A(2H) CARBOXYLATE; METHYL 2 ALLYL 1 HYDROXY 1 PHENYL 1,2,3,4 TETRAHYDRONAPHTHALENE 2 CARBOXYLATE; METHYL 2 ALLYL 1 HYDROXY 1 PHENYLINDANE 2 CARBOXYLATE; METHYL 2 ALLYL 1 OXO 1,2,3,4 TETRAHYDRONAPHTHALENE 2 CARBOXYLATE; METHYL 2 ALLYLOXO 1,2,3,4 TETRAHYDRONAPHTHALENE 2 CARBOXYLATE; METHYL 2 HYDROXYMETHYL 9B PHENYL 3,4,5,9B TETRAHYDROINDENO[1,2 B]PYRAN 4A(2H) CARBOXYLATE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; EPOXIDATION; PHARMACOPHORE; SUBSTITUTION REACTION;

EID: 4544251220     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400096     Document Type: Article

References (12)

1. D. M. Mottola, G. Laiten, V. J. Watts, A. Tropsha, S. D. Wyrick, D. E. Nichols, R. B. Mailman, J. Med. Chem. 1996, 39, 285-296.
2. F. Claudi, G. M. Cingolani, A. Di Stefano, G. Giorgioni, F. Amenta, P. Barili, F. Ferrari, D. Giuliani, J. Med. Chem. 1996, 39, 4238-4246.
3. C. Hansch, P. G. Sammes, J. B. Taylor, Comprehensive Medicinal Chemistry: The Rational Design, Mechanistic Study & Therapeutic Application of Chemical Compounds, vol. 3, Membranes & Receptors, Pergamon Press, 1991.
4. W. R. Hardie, J. Hidalgo, R. E. Allen, J. Med. Chem. 1966, 9, 127-136.
5. A. L. Coppell, S. Pei, T. S. C. Zetterström, Neuropharmacology 2003, 44, 903-910.
6. W. M. Welch, C. A. Harbert, B. K. Koe, A. R. Kraska, US Pat. 4 556 676, 1985; Chem. Abstr 1986, 105, 12113.
7. P. Mailliet, C. Salagnad, PCT Int. Appl., 200100 7408, 2001; Chem. Abstr. 2001, 134, 147495.
8. D. Binder, C. R. Noe, Monatsh. Chem. 1977, 108, 839-851.
9. W. T. Jiaang, H. C. Lin, K. H. Tang, L. B. Chang, Y. M. Tsai, J. Org. Chem. 1999, 64, 618-628.
10. J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry, Oxford University Press, Oxford, 2001, chapter 34, p. 895-896.
11. J. L. Broeker, R. W. Hoffmann, K. N. Houk, J. Am. Chem. Soc. 1991, 113, 5006-5017.
12. K. Van Emelen, T. De Wit, G. J. Hoornaert, F. Compernolle, Org. Lett. 2000, 2, 3083-3086.