Synthesis, antimalarial activity, structure-activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 7, 2008, Pages 3661-3674

  Barazarte, Arthur ^a   Camacho, José ^a   Domínguez, José ^a   Lobo, Gricela ^a   Gamboa, Neira ^b   Rodrigues, Juan ^b   Capparelli, Mario V ^c   Álvarez Larena, Ángel ^d   Andujar, Sebastian ^e   Enriz, Daniel ^e   Charris, Jaime ^a  

^a UNIVERSIDAD CENTRAL DE VENEZUELA   (Venezuela)

^b UNIVERSIDAD CENTRAL DE VENEZUELA   (Venezuela)

^c FACULTAD DE CIENCIAS   (Venezuela)

^d UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^e UNIVERSIDAD NACIONAL DE SAN LUIS   (Argentina)

Author keywords

1,4 Benzothiazines; Antimalarial; Cyclization; SAR study; Thieno

Indexed keywords

BENZOTHIAZINE DERIVATIVE; BETA HEMATIN; CHLOROQUINE; ETHYL 3 AMINO 6 CHLORO 9 (2' METHYLPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 6 CHLORO 9 (2',5' DIMETHYLPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 6 CHLORO 9 (3' CHLOROPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 6 CHLORO 9 (3' METHOXYLPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 6 CHLORO 9 (3',4' DICHLOROPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 6 CHLORO 9 (4' CHLOROPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 6 CHLORO 9 (4' METHOXYLPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 6 CHLORO 9 (4' METHYLPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 6 CHLORO 9 PHENYLTHIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 7 CHLORO 9 (2' METHYLPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 7 CHLORO 9 (2',5' DIMETHYLPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 7 CHLORO 9 (3' CHLOROPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 7 CHLORO 9 (3' METHOXYLPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 7 CHLORO 9 (3',4' DICHLORPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 7 CHLORO 9 (4' CHLOROPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 7 CHLORO 9 (4' METHOXYLPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 7 CHLORO 9 (4' METHYLPHENYL)THIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; ETHYL 3 AMINO 7 CHLORO 9 PHENYLTHIENO[3,2 B]BENZOTHIAZINE 4,4 DIOXIDE 2 CARBOXYLATE; HEMATIN; HEMOGLOBIN; LEUPEPTIN; PEPSTATIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DECARBOXYLATION; DRUG EFFICACY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; MALARIA; MALE; MOUSE; NONHUMAN; PLASMODIUM BERGHEI; PROTEIN HYDROLYSIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIMALARIALS; BENZENE; CRYSTALLOGRAPHY, X-RAY; ELECTROSTATICS; GLOBINS; HEMEPROTEINS; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDES; PLASMODIUM BERGHEI; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZINES;

PLASMODIUM BERGHEI; RODENTIA;

EID: 41649110228     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.02.011     Document Type: Article

References (49)

1. WHO World Malaria Report 2005, http://rbm.who.int/wmr 2005.
2. Miller L.H., Baruch D.I., Marsh K., and Doumbo O.K. Nature (London) 415 (2002) 673
3. Joshi A.A., and Viswanathan C.L. Anti-Infec. Agents Med. Chem. 5 (2006) 105
4. Domi{dotless}́nguez J.N. Curr. Trop. Med. Chem. 2 (2002) 1171
5. Sullivan D.J., Gluzman I.Y., Russell D.G., and Goldberg D.E. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 11865
6. Tilley L., Loria P., and Foley M. Chloroquine and other quinoline antimalarials. In: Rosenthal P.J. (Ed). Antimalarial Chemotherapy (2001), Humana Press Inc., Totowa, NJ 87
7. Slater A., Swiggard W., Orton B., Flitter W., Goldberg D., Cerami A., and Henderson G. Proc. Natl. Acad. Sci. U.S.A. 88 (1991) 325
8. Pagola S., Stephens P., Bohle D., Kosar A., and Madesen S. Nature (London) 404 (2000) 307
9. Egan T.J. J. Inorg. Chem. 100 (2006) 916
10. Anquetin G., Rouquayrol M., Mahmoudi N., Santillana-Hayat M., Gonzalbes R., Greiner J., Farhati K., Derouin F., Guedj R., and Vierling P. Bioorg. Med. Chem. Lett. 14 (2004) 2773
11. Charris J.E., Domi{dotless}́nguez J.N., Gamboa N., Rodrigues J., and Angel J.E. Heterocycl. Commun. 11 (2005) 419
12. Charris J., Barazarte A., Domi{dotless}́nguez J., Lobo G., Camacho J., Ferrer R., Gamboa N., Rodrigues J., and Capparelli M. J. Heterocycl. Chem. 44 (2007) 639
13. Leysen D.C., Zhang M.Q., Haemers A., and Bollaert W. Pharmazie 46 (1991) 485
14. Brown C., and Davinson R.M. Adv. Heterocycl. Chem. 38 (1985) 135
15. Teller J. Methods Org. Chem. (Houben-Weyl) E9 (1997) 450
16. Karchgaudhuri N., De A., and Mitra A.K. J. Chem. Res. (S) (2001) 180
17. Kappe C.O. Angew. Chem. Int. Ed. 43 (2004) 6250
18. Bourgin K., Loupy A., and Soufiaoui M. J. Photochem. Photobiol. C: Phochem. Rev. 6 (2005) 139
19. Kappe C.O., and Stadler A. Microwave in organic and medicinal chemistry. In: Mannhold R., Kubinyi H., and Folkers G. (Eds) (2005), Whiley-VCH Verlag Gmbh & Co. KGaA, Weinhein
20. Microwave-Assisted Synthesis of Heterocycles Series: Topics in Heterocyclic Chemistry, Gupta, R. R., Series Ed.; Van der Eycken, E., Kappe, C. O., Volume Editors; Springer, 2006; Vol. 1.
21. Gómez L., Charris J., Domi{dotless}́nguez J., Lobo G., Basante W., Riggione F., Sánchez E., and Duerto Z. Rev. Fac. Farmacia 64 (2001) 56
22. Unpublished results. Crystallographic data is deposited with the Cambridge Crystallographic Data Centre (3c: CCDC 650288, 3e: CCDC 650289).
23. Charris J., Barazarte A., Domi{dotless}́nguez J., and Gamboa N. J. Chem. Res. (2005) 27
24. Charris J., Barazarte A., Ferrer R., Camacho J., Gamboa N., Rodrigues J., Atencio R., and González T. J. Chem. Res. (2007) 16
25. Kirsch G., Cagniant Mme D., and Cagniant P. J. Heterocycl. Chem. 19 (1982) 443
26. Zambias R., and Hammond M. Synth. Commun. 21 (1991) 859
27. Sthephens C., Price M., and Sowell W. J. Heterocycl. Chem. 36 (1999) 659
28. Comel A. J. Heterocycl. Chem. 38 (2001) 1167
29. Owton W.J. Tetrahedron Lett. 44 (2003) 7147
30. Allen F.H., Kennard O., Watson D.G., Brammer L., Orpen A.G., and Taylor R. J. Chem. Soc. Perkin Trans. II (1987) 1-19
31. Polilzer P., and Truhlar D.G. Chemical Applications of Atomic and Molecular Electrostatic Potential (1991), Plenum, New York
32. Carrupt P.A., El Tayar N., Karlé A., and Festa B. Methods Enzymol. 202 (1991) 638
33. In: Politzer P., Murray J.S., Lipkowitz K.B., and Boyd D.B. (Eds). Reviews in Computational Chemistry Vol. 2 (1991), Springer, New York Chapter 7
34. Naray-Szabo G., and Ferenczy G.G. Chem. Rev. 95 (1995) 829
35. Bruker. SMART, version 5.63. Bruker AXS Inc., Madison, WI, USA, 2002.
36. Bruker. SAINT, version 6.22. Bruker AXS Inc., Madison, WI, USA, 2001.
37. Bruker. SADABS, version 2.05. Bruker AXS Inc., Madison, WI, USA, 2001.
38. Sheldrick, G. M. SHELXS-A Program for Crystal Structure Solution. Release 97-2. University of Göttingen, Germany, 1997.
39. Sheldrick, G.M. SHELXL-A Program for Crystal Structure Refinement. Release 97-2. University of Göttingen, Germany, 1997.
40. Farrugia L.J. J. Appl. Crystallogr. 30 (1997) 565
41. Farrugia L.J. J. Appl. Crystallogr. 32 (1999) 837
42. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A., Vreven Jr. T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03 Revision B.05 (2003), Gaussian, Inc., Pittsburgh, PA
43. Flükiger, P.; Lüthi, H. P.; Portmann, S.; Weber, J. MOLEKEL 4.0; Swiss Center for Scientific Computing: Manno, Switzerland, 2000.
44. Baelmans R., Deharo E., Muñoz V., Sauvain M., and Ginsburg H. Exp. Parasitol. 96 (2000) 243
45. Dorn A., Stoffel R., Matile H., Bubendorf A., and Ridley R. Nature (London) 374 (1995) 269
46. Deharo E., Gautret P., Ginsburg H., Chabaud A., and Landau I. Parasitol. Res. 80 (1994) 159
47. Rosenthal P. Exp. Parasitol. 80 (1995) 272
48. Peters W., and Robinson B.L. Parasitic infection models. In: Zak O., and Sande M. (Eds). Handbook of Antimalarial Models of Infection (1999), Academic Press, London 757
49. Graph Pad Prism Software Inc. 4.02 for windows. May 17th, 1992-2004.