Use of phosphonyl carbanions in the synthesis of anti-inflammatory active phosphorus-containing fused heterocycles and relevance phosphonates

European Journal of Medicinal Chemistry

Volumn 45, Issue 11, 2010, Pages 5217-5224

  Abdou, Wafaa M ^a   Kamel, Azza A ^a   Shaddy, Abeer A ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

Condensative cyclization reaction; Diphosphor esters for inflammatory inhibition; Five and six membered phosphorus heterocycles; Phosphonyl carbanions

Indexed keywords

2 BROMO 5 ETHOXY 7 METHYL 5H THIENO[3,2 D][1,2]OXAPHOSPHININE 4 CARBONITRILE 5 OXIDE; 2 ETHOXY 3A,6A DIMETHYL 6 OXO 3,3A,6,6A TETRAHYDRO 2H CYCLOPENTA[D][1,2] OXAPHOSPHOLE 3 CARBONITRILE 2 OXIDE; ANTIINFLAMMATORY AGENT; DIETHYL [(5 ACETYL 2 THIENYL)(CYANO)METHYL]PHOSPHONATE; DIETHYL [1 CYANO 2 (5' METHYL 2' FURYL)PROP 1 EN 1 YL]PHOSPHONATE; DIETHYL [2 (5 ETHOXY 4,7 DIMETHYL 5 OXIDO 5H THIENO[3,2 D][1,2]OXAPHOSPHININ 2 YL)VINYL]PHOSPHONATE; DIETHYL [CARBOETHOXY (4 CARBOMETHOXY 5 ETHOXY 7 METHYL 5 OXIDO 5H THIENO[3,2 D][1,2]OXAPHOSPHININ 2 YL)METHYL]PHOSPHONATE; DIETHYL [CARBOMETHOXY (4 CARBOMETHOXY 5 ETHOXY 7 METHYL 5 OXIDO 5H THIENO[3,2 D][1,2]OXAPHOSPHININ 2 YL)METHYL]PHOSPHONATE; DIETHYL[CYANO (4 CYANO 5 ETHOXY 7 METHYL 5 OXIDO 5H THIENO[3,2 D][1,2]OXAPHOSPHININ 2 YL)METHYL]PHOSPHONATE; ETHYL (2 (DIETHOXYPHOSPHORYL) 3 (5' METHYL 2' FURYL)BUT 2 ENOATE; ETHYL (5 ACETYL 2 THIENYL)(DIETHOXYPHOSPHORYL)ACETATE; ETHYL 2 BROMO 5 ETHOXY 7 METHYL 5H THIENO[3,2 D][1,2]OXAPHOSPHININE 4 CARBOXYLATE 5 OXIDE; ETHYL 2 ETHOXY 3A,6A DIMETHYL 6 OXO 3,3A,6,6A TETRAHYDRO 2H CYCLOPENTA[D][1,2] OXAPHOSPHOLE 3 CARBOXYLATE 2 OXIDE; INDOMETACIN; METHYL (2 (DIETHOXYPHOSPHORYL) 3 (5' METHYL 2' FURYL)BUT 2 ENOATE; METHYL (5 ACETYL 2 THIENYL)(DIETHOXYPHOSPHORYL)ACETATE; METHYL 2 BROMO 5 ETHOXY 7 METHYL 5H THIENO[3,2 D][1,2]OXAPHOSPHININE 4 CARBOXYLATE 5 OXIDE; METHYL 2 ETHOXY 3A,6A DIMETHYL 6 OXO 3,3A,6,6A TETRAHYDRO 2H CYCLOPENTA[D][1,2] OXAPHOSPHOLE 3 CARBONITRILE 2 OXIDE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG INHIBITION; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; MALE; NONHUMAN; PAW EDEMA; RAT;

ANIMALS; ANIONS; ANTI-INFLAMMATORY AGENTS; CARRAGEENAN; DOSE-RESPONSE RELATIONSHIP, DRUG; EDEMA; FEMALE; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; PHOSPHONIC ACIDS; RATS; RATS, INBRED F344; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 77957841192     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.08.036     Document Type: Article

References (31)

1. L.D. Quin The Heterocyclic Chemistry of Phosphorus 1981 John Wiley & Sons New York Chapter 2, pp. 83-99, and Chapt. 3, pp. 131-152
2. H. Yang, and R. Lu Synth. Commun. 24 1994 59 63
3. L.N. He, F. Cai, R.Y. Chen, and J. Zhou Phosphorus Sulfur Silicon Relat. Elem. 130 1997 65 71
4. T.B. Huang, L.F. Liu, W.Q. Yang, X.M. Yu, X.H. Qian, and J.L. Zhang Phosphorus Sulfur Silicon Relat. Elem. 122 1997 299 305
5. M.S. Singh, G. Mishra, and K.N. Mehrotra Phosphorus Sulfur Silicon Relat. Elem. 63 1997 177 180
6. J.L. Pirat, D. Virieux, L. Clarion, J.N. Volle, N. Bakalara, M. Mersel, J. Montbrun, H.J. Cristau, Patent WO/2009/004096 (2009).
7. Y.H. Babu, M.A. Kumar, K. Srinivasulu, C.S. Reddy, and C.N. Raju ARKIVOC 15 2006 189 197
8. L.A. Cates, V.S. Li, D.R. Powell, and D. Van der Helm J. Med. Chem. 27 1984 397 401
9. V.H. Arnold, F. Bourseaux, and N. Brock Arzneimittel-Forsch. 11 1961 143 158
10. R.W. Marsh Systemic Fungicides 1972 Longmans London
11. G.N. Vasilev, M. Kirilov, Kh. Angelov, and Z.O. Dimcheva Dokl. Bolg. Akad. Nauk. 33 1980 667 670
12. Chem. Abstr. 94 1981 42514
13. W.M. Abdou, M.A.I. Salem, and A.A. Sediek ARKIVOC 14 2005 102 117
14. W.M. Abdou, A.A. Sediek, and M.D. Khidre Monatsh. Chem. 139 2008 617 623
15. W.M. Abdou, and A.A. Shaddy Lett. Org. Chem. (LOC) 5 2008 569 575
16. W.M. Abdou, A.A. Shaddy, and A.A. Sediek J. Chem. Res. 2009 8 13
17. W.M. Abdou, M.D. Khidre, and R.E. Khidre Eur. J. Med. Chem. (EJMECH) 44 2009 526 532
18. W.M. Abdou, and R.E. Khidre Monatsh. Chem. 141 2010 in press
19. A.N. Pudovik, and N.M. Lebedeva Dokl. Akad. Nauk. SSSR. 90 1953 799 802
20. Chem. Abstr. 50 1960 2429
21. S. Patia, and A. Schwartz J. Org. Chem. 25 1960 1232 1234
22. D.L. Wright G.W. Gribble, J.A. Joule, Furans as Versatile Synthons for Target-Oriented and Diversity-Oriented Synthesis, Progress in Heterocyclic Chemistry vol. 17 2005 Elsevier
23. J. Barluenga, A. de Prado, J. Santamria, and M. Tomas Chem. Eur. J. 13 2007 1326 1331
24. J. Barluenga, A. Gomez, A. de Prado, N. Panday, J. Santamria, and M. Tomas Tetrahedron 63 2007 6542 6547
25. S.W. Li, and R.A. Batey Chem. Commun. 2007 3759 3761
26. K. Tokumaru, S. Arai, and A. Nishida Org. Lett. 8 2006 27 30
27. J.B. Sperry, I. Ghiviriga, and D.L. Wright Chem. Commun. 2006 194 196
28. W.M. Abdou, and A.A. Kamel Tetrahedron 56 2000 7573 7580
29. 3D-Molecular Modeling Softwares Alchemy II, Tripos Associates, Inc., Subdivision of Evans and Sutherland (1992).
30. I.L. Finar Organic Chemistry vol. 1 1962 The English Language Book Society and Longman Group Limited England 77-82
31. D. Hadjipavlou-Litina Res. Commun. Chem. Pathol. Pharmacol. 81 1993 1091 1102