Design, synthesis, anti-schistosomal activity and molecular docking of novel 8-hydroxyquinoline-5-sufonyl 1,4-diazepine derivatives

Bioorganic Chemistry

Volumn 46, Issue 1, 2013, Pages 17-25

  Eweas, Ahmad F ^a,b   Allam, Gamal ^b,c   Abuelsaad, Abdelaziz S A ^b,c   Alghamdi, Abdul Hamid ^b   Maghrabi, Ibrahim A ^b  

^a NATIONAL RESEARCH CENTRE   (Egypt)

^b TAIF UNIVERSITY   (Saudi Arabia)

^c Beni Suef University   (Egypt)

Author keywords

1,4 Diazepines; 8 Hydroxyquinoline; Anti schistosoma; Molecular docking; Thioredoxin glutatione reductase (TGR)

Indexed keywords

2 [(8 HYDROXYQUINOLIN 5 YL)SULFONYL]1,3 DIPHENYLPROPANE 1,3 DIONE; 3 [(8 HYDROXYQUINOLIN 5 YL)SULFONYL]PENTANE 2,4 DIONE; 5 [(2,4 DIMETHYL 3H BENZO[B][1,4]DIAZEPIN 3 YL)SULFONYL]QUINOLIN 8 OL; 5 [(2,4 DIMETHYL 3H PYRIDO[3,4 B][1,4]DIAZEPIN 3 YL)SULFONYL]QUINOLIN 8 OL; 5 [(2,4 DIPHENYL 3H BENZO[B][1,4]DIAZEPIN 3 YL)SULFONYL]QUINOLIN 8 OL; 5 [(2,4 DIPHENYL 3H PYRIDO[3,4 B][1,4]DIAZEPIN 3 YL)SULFONYL]QUINOLIN 8 OL; 5 [(5,7 DIMETHYL 3,6 DIHYDRO 2H 1,4 DIAZEPIN 6 YL)SULFONYL]QUINOLIN 8 OL; 5 [(5,7 DIPHENYL 3,6 DIHYDRO 2H 1,4 DIAZEPIN 6 YL)SULFONYL]QUINOLIN 8 OL; 8 HYDROXYQUINOLINE 5 SUFONYL 1,4 DIAZEPINE DERIVATIVE; ANTISCHISTOSOMAL AGENT; DIAZEPINE DERIVATIVE; GLUTATHIONE REDUCTASE; OXIDOREDUCTASE INHIBITOR; PRAZIQUANTEL; THIOREDOXIN REDUCTASE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ANTISCHISTOSOMAL ACTIVITY; ARTICLE; BINDING AFFINITY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; EGG LAYING; ENZYME INHIBITION; ENZYME STRUCTURE; HYDROGEN BOND; IN VITRO STUDY; MOLECULAR DOCKING; NONHUMAN; PARASITE SURVIVAL; PRIORITY JOURNAL; SCORING SYSTEM;

ANIMALS; AZEPINES; DRUG DESIGN; GLUTATHIONE REDUCTASE; HUMANS; HYDROXYQUINOLINES; MODELS, MOLECULAR; MOLECULAR DOCKING SIMULATION; SCHISTOSOMA; SCHISTOSOMIASIS; SCHISTOSOMICIDES; THIOREDOXIN-DISULFIDE REDUCTASE;

SCHISTOSOMA;

EID: 84870821717     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2012.10.003     Document Type: Article

References (42)

1. J. Utzinger, B.S. Raso, D. De Savigny, M. Tanner, N. Ornbjerg, B.H. Singer, and E.K. N'goran Parasitology 136 2009 1859 1874
2. D.J. Gray, D.P. McManus, Y. Li, G.M. Williams, R. Bergquist, and A.G. Gross Lancet Infect. Dis. 10 2010 733 736
3. J. Patz, T. Graczyk, N. Geller, and A. Vittor Int. J. Parasitol. 30 2000 1395 1405
4. M.J. Doenhof, J.R. Kusel, G.C. Coles, and D. Cioli Trans. Roy. Soc. Trop. Med. Hyg. 96 2002 465 469
5. F. Angelucci, A. Basso, A. Bellelli, M. Brunori, L. Pica-Mattoccia, and C. Valle Parasitology 134 2007 1215 1221
6. M. Ismail, S. Botros, A. Metwally, and S. William Am. J. Trop. Med. Hyg. 6 1999 932 935
7. L. Pica-Mattoccia, and D. Cioli Int. J. Parasitol. 34 2004 527 533
8. D.L. Boros Clin. Microbiol. 2 1989 250 269
9. D. Engels, L. Chitsulo, A. Montresor, and L. Savioli Acta Trop. 82 2002 139 146
10. C.R. Caffrey Curr. Opin. Chem. Biol. 11 2007 433 439
11. M. Doenhoff, D. Cioli, and J. Utzinger Curr. Opin. Infect. Dis. 21 2008 659 667
12. D. Cioli, C. Valle, F. Angelucci, and A.E. Miele Trends Parasitol. 24 2008 379 382
13. F. Angelucci, A.A. Sayed, D.L. Williams, G. Boumis, M. Brunori, D. Dimastrogiovanni, A.E. Miele, F. Pauly, and A. Bellelli J. Biol. Chem. 284 42 2009 28977 28985
14. K. Mekouar, J.F. Mouscadet, and D. Desmaele J. Med. Chem. 41 1998 2846 2857
15. M. Ouali, C. Laboulais, and H. Leh J. Med. Chem. 43 2000 1949 1957
16. C.S. Chen, S.Y. Lai, and P.S. Hsu Chin. Pharm. J. 54 2002 353 374 (Taipei, Taiwan)
17. M.A. Fakhfakh, A. Fournet, and E. Prina Bio-org. Med. Chem. 11 2003 5013 5023
18. Z. Dardari, M. Lemrani, and A. Bahloul Farmaco 59 2004 195 199
19. S.S. Chhajed, P. Manisha, V.A. Bastikar, H. Animeshchandra, V.N. Ingle, C.D. Upasani, and S.S. Wazalwar Bioorg. Med.Chem. Lett. 20 2010 3640 3644
20. S. Raafat, and A.H. Nibal J. Pharm. Sci. 68 1979 1377 1381
21. R. Soliman, H.M. Mokhtar, and S. K el Sadany J. Pharm. Sci. 73 3 1984 403 405
22. A.F. Eweas, G. Allam, A.S.A. Abu-elsaad, I.A. Maghrabi, and A.H. Al-Ghamdi Anti-infective Agents 11 2013 In press
23. H.M. Alger, and D.L. Williams Mol. Biochem. Parasitol. 121 2002 129 139
24. A.N. Kuntz, C.E. Davioud, A.A. Sayed, L.L. Califf, J. Dessolin, E.S. Arnér, and D.L. Williams PLoS Med. 4 e206 2007 1071 1086
25. M. Sharma, S. Khanna, G. Bulusu, and A. Mitra J Mol. Graph. Model. 27 2009 665 675
26. Y.C. Joshi, S. Saingar, J.P. Kavita, and R. Kumar J. Korean Chem. Soc. 55 4 2011 638 643
27. R.G.W. Hollingstead Oxine and its Derivatives vols. I-IV 1954-1956 Butterworths London
28. J.P. Phillips Chem. Rev. 56 1956 271 297
29. M.K. Jones, D.P. McManus, P. Sivadorai, A. Glanfield, L. Moertel, S.I. Belli, and G.N. Gobert Int. J. Biochem. Cell Biol. 39 2007 1646 1658
30. S.K. Jonas, and P.A. Riley Cell Biochem. Funct. 9 1991 245 253
31. A.K. Jacob, R.S. Hotchkiss, S.L. DeMeester, M. Hiramatsu, I.E. Karl, P.E. Swanson, J.P. Cobb, and T.G. Buchman Surgery 122 1997 243 253
32. P. Leanderson, and C. Tagesson Carcinogenesis 17 1996 545 550
33. I. Ebersberger, J. Knobloch, and W. Kunz Dev. Genes Evol. 215 2005 261 267
34. J.S. Cordingley Parasitol. Today 3 1987 341 344
35. F. Eshete, and P.T. LoVerde J. Parasitol. 79 1993 309 317
36. H. Yamamoto, S. Kuno, A. Nagai, A. Nishida, S. Yamauchi, and K. Ikeda Int. J. Biol. Micromoles 12 1990 305 310
37. C. Sun, and J.H. Waite J. Biol. Chem. 280 2005 39332 39336
38. J.P. Pierre, P. Baret, and G. Serratrice Curr. Med. Chem. 10 2003 1077 1084
39. M.A. Stirewalt, and J.F. Bronson J. Parasitol. 41 1955 328
40. S.R. Smithers, and R.J. Terry Parasitology 55 1965 695 700
41. S.H. Xiao, J. Keiser, J. Chollet, J. Utzinger, Y. Dong, Y. Endriss, J.L. Vennerstrom, and M. Tanner Antimicrob. Agents Chemother. 51 2007 1440 1445
42. L.G. Magalhaes, and C.B.M. Machado Rezende Parasitol. Res. 104 2009 1197 1201