Synthesis and antiprotozoan evaluation of new alkyl-linked bis(2-thioxo-[1,3,5]thiadiazinan-3-yl) carboxylic acids

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 10, 2005, Pages 3413-3421

  Coro, Julieta ^a   Pérez, Rolando ^b   Rodríguez, Hortensia ^a   Suárez, Margarita ^a   Vega, Celeste ^c   Rolón, Miriam ^c   Montero, David ^c   Nogal, Juan José ^c   Gómez Barrio, Alicia ^c  

^a UNIVERSITY OF HAVANA   (Cuba)

^b Instituto Cubano de Investigaciones de los Derivados de la Cana de Azucar   (Cuba)

^c UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Antiparasitics; Chemotherapy; Thiadiazine 2 thione

Indexed keywords

2 [5 [3 [5 (1 CARBOXY 2 PHENYLETHYL) 2 THIOXO[1,3,5]THIADIAZINAN 3 YL] 2,2 DIMETHYLPROPYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL] 3 PHENYLPROPIONIC ACID; 2 [5 [3 [5 (1 CARBOXY 3 METHYLBUTYL) 2 THIOXO[1,3,5]THIADIAZINAN 3 YL] 2,2 DIMETHYLPROPYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL] 4 METHYLPENTANOIC ACID; 2 [5 [3 [5 (1 CARBOXY 3 METHYLSULFANYLPROPYL) 2 THIOXO[1,3,5]THIADIAZINAN 3 YL] 2,2 DIMETHYLPROPYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL] 4 METHYLSULFANYLBUTYRIC ACID; 2 [5 [3 [5 [[(1 CARBOXYMETHYLCARBAMOYL)METHYL] 2 THIOXO[1,3,5]THIADIAZINAN 3 YL] 2,2 DIMETHYLPROPYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL]ACETYLAMINO]ACETIC ACID; 2 [5 [6 [5 (1 CARBOXY 2 PHENYLETHYL) 2 THIOXO[1,3,5]THIADIAZINAN 3 YL]HEXYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL] 3 PHENYLPROPIONIC ACID; 2 [5 [6 [5 (1 CARBOXY 3 METHYLBUTYL) 2 THIOXO[1,3,5]THIADIAZINAN 3 YL]HEXYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL] 4 METHYLPENTANOIC ACID; 2 [5 [6 [5 (1 CARBOXY 3 METHYLSULFANYLPROPYL) 2 THIOXO[1,3,5]THIADIAZINAN 3 YL]HEXYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL] 4 METHYLSULFANYLBUTYRIC ACID; 2 [5 [6 [5 [[(1 CARBOXYMETHYLCARBAMOYL)METHYL] 2 THIOXO[1,3,5]THIADIAZINAN 3 YL]HEXYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL]ACETYLAMINO]ACETIC ACID; 3 [5 [6 [5 (1 CARBOXYMETHYL 2 AMINOPROPYL) 2 THIOXO[1,3,5]THIADIAZINAN 3 YL]HEXYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL] 4 AMINOPENTANOIC ACID; 3 [5 [6 [5 (1 CARBOXYMETHYL 2 OXOPROPYL) 2 THIOXO[1,3,5]THIADIAZINAN 3 YL]HEXYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL] 4 OXOPENTANOIC ACID; 3 [5 [6 [5 (2 CARBOXYETHYL) 2 THIOXO[1,3,5]THIADIAZINAN 3 YL]HEXYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL]PROPIONIC ACID; 4 CARBAMOYL 2 [5 [6 [5 (3 CARBAMOYL 1 CARBOXYPROPYL) 2 THIOXO[1,3,5] THIADIAZINAN 3 YL]HEXYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL]BUTYRIC ACID; 5 [5 [6 [5 (5 CARBOXYBUTYL) 2 THIOXO[1,3,5]THIADIAZINAN 3 YL]HEXYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL]PENTANOIC ACID; 6 [5 [3 [5 (5 CARBOXYPENTYL) 2 THIOXO[1,3,5]THIADIAZINAN 3 YL] 2,2 DIMETHYLPROPYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL]HEXANOIC ACID; 6 [5 [6 [5 (5 CARBOXYPENTYL) 2 THIOXO[1,3,5]THIADIAZINAN 3 YL]HEXYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL]HEXANOIC ACID; ANTIPARASITIC AGENT; ANTIPROTOZOAL AGENT; METRONIDAZOLE; NIFURTIMOX; UNCLASSIFIED DRUG; [5 [3 (5 CARBOXYMETHYL 2 THIOXO[1,3,5]THIADIAZINAN 3 YL) 2,2 DIMETHYLPROPYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL]ACETIC ACID; [5 [5 (5 CARBOXYMETHYL 2 THIOXO[1,3,5]THIADIAZINAN 3 YL)HEXYL] 6 THIOXO[1,3,5]THIADIAZINAN 3 YL]ACETIC ACID;

ANTIMICROBIAL ACTIVITY; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; NONHUMAN; STRUCTURE ACTIVITY RELATION; TRICHOMONAS VAGINALIS; TRYPANOSOMA CRUZI;

TRICHOMONAS VAGINALIS; TRYPANOSOMA; TRYPANOSOMA CRUZI;

EID: 17444377502     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.03.009     Document Type: Article

References (26)

1. E. Ilhan, G. Capan, and N. Ergenc Il Fármaco 50 11 1995 787
2. M. Ertan, B.A. Tayhan, and N. Yulug Arch. Pharm. 323 1990 605
3. M. Ertan, A.A. Bilgil, and E. Palaska Arzneim.-Forsch./Drug Res. 42 1 1992 160
4. M. Ertan, H.G. Ayyildiz, and N. Yulug Arzneim.-Forsch./Drug Res. 41 I 1991 1182
5. M. Vitangelo, and N. Vovlas Fithopathology 25 1975 17
6. T. Zsolnai Arzneim.-Forsch./Drug Res. 18 II 1968 1319
7. A. El-Shorbagi Eur. J. Med. Chem. 29 1994 11
8. T. Aboul-Fadl, and A. El-Shorbagi Eur. J. Med. Chem. 31 1996 165
9. M.I. Abd-Elrahman, M.O. Ahmed, S.M. Ahmed, T. Aboul-Fadl, and A. El-Shorbagi Biophys. Chem. 97 2-3 2002 113
10. A. El-Shorbagi Bull. Pharm. Sci., Assiut Univ. 23 1 2000 31
11. G. Chen, J. He, F. Zhang, Y. Li, and Y. Li Shoudu Yike Daxue Xuebao 23 2 2002 107
12. A. El-Shorbagi Arch. Pharm. (Weinheim) 333 9 2000 281
13. T. Aboul-Fadl, and K. Hassanin Pharmazie 54 4 1999 244
14. C. Ochoa, E. Pérez, R. Pérez, M. Suárez, E. Ochoa, H. Rodríguez, A.G. Barrio, S. Muelas, J.J. Nogal, and R.A. Martínez Arzneim.-Forschung./Drug Res. 49 II 1999 464
15. S. Muelas, M. Suárez, R. Pérez, H. Rodríguez, C. Ochoa, J.A. Escario, and A. Gómez-Barrio Mem. Inst. Oswaldo Cruz, Rio de Janeiro 97 2 2002 269
16. R. Pérez, H. Rodríguez, E. Pérez, M. Suárez, O. Reyes, L.J. González, A. De Cerain, O. Ezpeleta, C. Pérez, and C. Ochoa Arzneim.-Forschung./Drug Res. 50 II 2000 854
17. L. Monzote, A.M. Montalvo, L. Fonseca, R. Pérez, M. Suárez, and H. Rodríguez Mem. Inst. Oswaldo Cruz, Rio de Janeiro 99 3 2004 329
18. Monzote, L.; Montalvo, A. M.; Fonseca, L.; Pérez R.; Suárez, M.; Rodríguez, H. Arzneim.-Forschung./Drug Res., in press
19. M.J. North, J.C. Mottran, and G.H. Coombs Parasitol. Today 6 1990 270
20. J. Goksoyr Acta Chem. Scand. 18 1964 1341
21. P. Kristian, and J. Bernat Tetrahedron Lett. 6 1968 679
22. R. Pérez, O. Reyes, M. Suárez, H.E. Garay, L.J. Cruz, H. Rodríguez, M.D. Molero-Vilchez, and C. Ochoa Tetrahedron Lett. 41 2000 613
23. D. Molero, R. Pérez, H. Rodríguez, M. Suárez, N. Martín, R. Martínez, and C. Seoane Magn. Reson. Chem. 39 2001 222
24. R. Pérez, M. Suárez, H. Rodríguez, N. Martín, C. Seoane, H. Novoa, N. Blaton, O. Peeters, and C. De Ranter Tetrahedron 57 2001 9543
25. F.S. Buckner, C.L. Verlinde, A.C. La Flamme, and W.C. van Voorhis Antimicrob. Agent. Chemother. 1996 40
26. V.V. Kouznetsov, L.Y. Mendez, B. Tibaduiza, C. Ochoa, D.M. Pereira, J.J. Ruiz, C.F. Portillo, S.M. Serrano, A. Gómez Barrio, A. Bahsas, and J. Amaro-Luis Arch. Pharm. (Weinheim) 337 2004 127