Novel synthesis and anti-inflammatory activities of 2,5-disubstituted- dioxacycloalkanes

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 19, 2005, Pages 5640-5646

  Bi, Lanrong ^a   Zhang, Yue ^b   Zhao, Ming ^b   Wang, Chao ^b   Chan, Priscilla ^c   Tok, Jeffrey B H ^c   Peng, Shiqi ^a  

^a CAPITAL MEDICAL UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

^c LAWRENCE LIVERMORE NATIONAL LABORATORY   (United States)

Author keywords

2,5 Disubstituted dioxacycloalkanes; Acetalization; Anti inflammatory activity

Indexed keywords

3,3 DIMETHOXYPROPANAL; [N (2 CARBONYLMETHYL 1,3 DIOXAN 5 YL)]PHENYLAMIDE; [N (2 CARBONYLMETHYL) 1,3 DIOXACYCLOHEPTAN 5 YL]PHENYLAMIDE; [N (2 CARBONYLMETHYL) 1,3 DIOXACYCLOOCTAN 5 YL]PHENYLAMIDE; [N (2 CARBONYLMETHYL) 4 METHYL 1,3 DIOXAN 5 YL]PHENYLAMIDE; [N 2 (1,3 DIOXOLAN 2 YL)METHYL 1,3 DIOXAN 5 YL]PHENYLACETAMIDE; [N 2 (2 ETHOXY 2 METHOXYETHYL) 1,3 DIOXAN 5 YL]PHENYLACETAMIDE; ACETYLSALICYLIC ACID; ALDEHYDE; CARBOXYMETHYLCELLULOSE; CYCLOALKANE DERIVATIVE; N [2 (2,2 DIMETHOXYETHYL) 1,3 DIOXACYCLOHEPTAN 5 YL]PHENYLACETAMIDE; N [2 (2,2 DIMETHOXYETHYL) 1,3 DIOXACYCLOOCTAN 5 YL]PHENYLACETAMIDE; N [2 (2,2 DIMETHOXYETHYL) 1,3 DIOXAN 5 YL]PHENYLACETAMIDE; N [2 (2,2 DIMETHOXYETHYL) 1,3 DIOXAN 5 YL]PHENYLAMIDE; N [2 (2,2 DIMETHOXYETHYL) 4 METHYL 1,3 DIOXAN 5 YL]PHENYLACETAMIDE; N [2 HYDROXY 1 (HYDROXYMETHYL)ETHYL]PHENYLACETAMIDE; N [2 HYDROXY 1 (HYDROXYMETHYL)PROPYL]PHENYLACETAMIDE; N [3 HYDROXY 1 (HYDROXYMETHYL)PROPYL]PHENYLACETAMIDE; N [4 HYDROXY 1 (HYDROXYMETHYL)BUTYL]PHENYLACETAMIDE; N,N' METHYLENE(4 METHYL 1,3 DIOXAN 2,5 DIYL)(1,3 DIOXACYCLOOCTAN 2,5 DIYL)BISPHENYLACETAMIDE; N,N' METHYLENEBIS(4 METHYL 1,3 DIOXAN 2,5 DIYL)BISPHENYLACETAMIDE; UNCLASSIFIED DRUG; XYLENE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; EAR; EDEMA; MALE; MONITORING; MOUSE; NONHUMAN; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CYCLOPARAFFINS; EAR DISEASES; EDEMA; MALE; MICE; MICE, INBRED STRAINS; MOLECULAR CONFORMATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; XYLENES;

EID: 23944519935     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.05.032     Document Type: Article

References (21)

1. S. Kuchera, H. Barth, P. Jacobson, A. Metz, C. Schaechtele, and D. Schrier Agents Actions 39 1993 169
2. A. Basu Pharmacol. Ther. 59 1993 257
3. U. Amon, and K.R. Dietz Arch. Dermatol. Res. 284 1992 8
4. G.J. Fisher, A. Tavakkol, and K. Leach J. Invest. Dermatol. 101 1993 553
5. H.H. Rasmussen, and J.E. Celis J. Invest. Dermatol. 101 1993 560
6. P.G. Goekjian, and M.R. Jirousek Curr. Med. Chem. 6 1999 877 903
7. N. Reynolds J. Arch. Dermatol. Res. 289 1997 520
8. P.L. Stanley, S. Steiner, M. Havens, and K.M. Tramposch Skin Pharmacol. 4 1991 262
9. M. Scott, V. Jayasree, and A.S. Roshantha J. Med. Chem. 44 2001 281
10. H. Tamamura, D.M. Sigano, P.M. Blumberg, and V.E. Marquez J. Med. Chem. 47 2004 644
11. K. Nacro, B. Bienfait, J. Lee, K. Han, J. Kang, S. Benzaria, N.E. Lewin, D.K. Bhattacharyya, P.M. Blumberg, and V.E. Marquez J. Med. Chem. 43 2000 921
12. J. Lee, K.-C. Han, J.-H. Kang, L.L. Pearce, N.E. Lewin, S. Yan, S. Benzaria, M.C. Nicklaus, P.M. Blumberg, and V.E. Marquez J. Med. Chem. 46 2003 2794
13. G.R. Pettit, S. Ducki, R. Tan, R.S. Gardella, J.B. McMahon, M.R. Boyd, G.R. Pettit III, P.M. Blumberg, N.E. Lewin, D.L. Doubek, L.P. Tackett, and M.D. Williams J. Nat. Prod. 65 2002 1262 1265
14. J.-H. Kang, M.A. Siddiqui, D.M. Sigano, K. Krajewski, N.E. Lewin, Y. Pu, P.M. Blumberg, J. Lee, and V.E. Marquez Org. Lett. 6 2004 2413
15. Jiang, J. B.; Johnson, M. G.; Nichols, US Patent 5,360,818, 1994.
16. L. Bi, M. Zhao, C. Wang, and S. Peng Eur. J. Org. Chem. 2000 2669
17. L. Bi, M. Zhao, C. Wang, S. Peng, and E. Winterfeldt J. Org. Chem. 67 2002 22
18. Zhao, M.; Wang, C.; Peng, S.; Unpublished results.
19. H. Firouzabadi, N. Iranpoor, and H.R. Shaterian Bull. Chem. Soc. Jpn. 75 2002 2195 2205
20. C. Romay, N. Ledon, and R. Gonzalez Inflamm. Res. 47 1998 334 338
21. D.E. Griswold, L.D. Martin, A.M. Badger, J. Breton, and M. Chabot-Fletcher Inflamm. Res. 47 1998 56 61