5-Phenyl-2-(benzalhydrazonyl)-1,3,4-thiadiazoles, potential trypanocidal agents: Consistent dimer formation via N - H ⋯ N intermolecular hydrogen bonds

Zeitschrift fur Kristallographie

Volumn 224, Issue 12, 2009, Pages 598-606

  Carvalho, Samir A ^a   Harrison, William T A ^b   Fraga, Carlos A M ^c   Da Silva, Edson F ^a   Wardell, James L ^a   Wardell, Solange M S V ^a  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

^b UNIVERSITY OF ABERDEEN   (United Kingdom)

^c FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

stacking interactions; Chagas' disease; Hydrazones; Hydrogen bonding; Single crystal structure analysis; Synchrotron X ray radiation; Thiadiazoles

Indexed keywords

EID: 74049149302     PISSN: 00442968     EISSN: None     Source Type: Journal    
DOI: 10.1524/zkri.2009.1203     Document Type: Article

References (43)

1. Pink, R.; Hudson, A.; Mouries, M.-A.; Bending, M.: Opportunities and Challenges in Antiparasitic Drug Discovery. Nat. Rev. Drug Disc. 4 (2005) 727-740.
2. Croft, S.; Barrett, M. P.; Urbina, J. A.: Chemotherapy oftrypano-somiases and leshmaniasis. Trends Parasitol. 21 (2005) 508-512.
3. Berkelhammer, G.; Asato, G.: 2-Amino-5-(l-methyl-5-nitro-2-imidazolyl)-1, 3,4-thiadiazole: A New Antimicrobial Agent. Science 162 (1968) 1146.
4. Filardi, L. S.; Brener, Z.: A nitroimidazole-thiadiazole derivative with curative action in experimental Trypanosoma cruzi infections. Ann. Trop. Med. Parasitol. 76 (1982) 293-297.
5. European Cooperation in the Field of Scientific and Technical Research, Chemotherapy of. Protozoal Infections, Action B9, 2002. http://cost.cordis.lu/ src/home.cfm
6. Nesslany, R; Brugier, S.; Mouries, M. A.; Le Curieux, R; Marzin, D.: In vitro and in vivo chromosomal aberrations induced by megazol. Mutat. Res. 560 (2004) 147-158.
7. Poli, P.; de Mello, M. A.; Buschini, A.; Mortara, R. A.; de Albuquerque, C. N.; Silva, S.; Rossi, C; Zucchi, T. M. A. D.: Cytotoxic and genotoxic effects of megazol, an anti-Chagas' disease drug, assessed by different short-term tests. Biochem. Pharmacol. 64 (2002) 1617-1627.
8. Chauviere, G.; Bouteille, B.; Enanga, B.; de Albuquerque, C; Croft, S. L.; Dumas, M.; Perié J.: Synthesis and Biological Activity of Nitro Heterocycles Analogous to Megazol, a Trypanocidal Lead. J. Med. Chem. 46 (2003) 427-440.
9. Boechat, N.; Carvalho, A. S.; Fernandez-Ferreira, E.; Soares, R. O.; Souza, A. S.; Gibaldi, D.; Bozza, M.; Pinto, A. C: Novel nitroimidazoles with trypanocidal and cell growth inhibition activities. Cytobios 105 (2001) 83-90.
10. Carvalho, A. S.; Gibaldi, D.; Pinto, A. C; Bozza, M.; Boechat, N.: Synthesis and Trypanocidal Evaluation of New 5-[N-(3-(5-Substituted)-1,3,4- Thiadiazolyl)] Amino-1 -Methyl-4-Nitroi-midazoles. Lett. Drug Des. Discovery 3 (2006) 98-101.
11. Carvalho, A. S.; Menna-Barreto, R. F. S.; Romeiro, N. C; de Castro, S. L.; Boechat, N.: Design, synthesis and activity against Trypanosoma cruzi of azaheterocyclic analogues of megazol. Med. Chem. 3 (2007) 460-465.
12. Carvalho, A. S.; da Silva, E. R; Santa-Rita, R. M.; de Castro, S. L.; Fraga, C. A. M.: Synthesis and antitrypanosomal profile of new functionalized l,3,4-thiadiazole-2-arylhydrazone derivatives, designed as non-mutagenic megazol analogues. Bioorg. Med. Chem. Lett. 14 (2004) 5967-5970.
13. Carvalho, S. A.; Lopes, F. A. S.; Salomaõ, K.; Romeiro, N. C; Wardell, S. M. S. V.; de Castro, S. L.; da Silva, E. R; Fraga, C. A. M.: Studies toward the structural optimization of new brazili-zone related trypanocidal l,3,4-thiadiazole-2-arylhydrazone derivatives. Bioorg. Méd Chem. 16 (2008) 413-421.
14. Camerman, A.; Hempel, A.; Mastropaolo, D.; Camerman, N.: Stereochemical basis for activity in thiadiazole anticonvulsants: 1-[5-(bi-phenyl-2-yl)-1,3,4- thiadiazol-2-yl]-methanaminium chloride and two inactive analogues, 2-(biphenyl-4-yl)-5-[2-(1-methylethylidene)hydrazino]-1,3,4-thiadiazole and the methanol solvate of its hydrochloride salt. Acta Crystallogr. C61 (2005) o427-o430.
15. Nassar, A. A.; Valdés-Martínez, J.; Hernández- Ortega, S.; West, D. X.: 2-([l-(2-Arninophenyl)ethylidene]hydrazino}-5- piperidyl-1,3,4-thiadiazole. Acta Crystallogr. E58 (2002) o694-o695.
16. Khoo, T.-J.; Cowley, A. R.; Watkin, D.J.; Ibrahim, M.; Tahir, M.; Crouse, K.A. N-(3-Pyridylmethylene)-N'-[5-(3-pyridyl-methylsulfanyl)-1,3,4-thiadiazol- 2-yl]hydrazine. Acta Crystallogr. E61 (2005) o3414-o3415.
17. (a) Liu, J.; Deng, Y.-H.; Li, P.-Z.; Jin, Q.-H.: N- [Phenyl(piperidin-1-yl)methyl]-1,3,4-thiadiazol-2-amine. Acta Crystl-logr. E63 (2007) o4849;
18. (b) Seena, E. B.; Kurup, M. R. P. 2-[5- (Cyclohexylamino)-1,3,4- thiadiazol-2-yl]phenol. Acta Crystallogr. E62 (2006) o5627-o5629.
19. Zhan, J.-Y; Xiong, D.-J.; Wang, Y.-G.; Li, H.-B.: 2-(o-Toly-loxy)-N-[5- (trifluoromethyl)-1,3,4-thiadiazol-2-yl]acetamide. Acta Crystallog. E63 (2007) o2184-o2185
20. Tan, Z.W; Tan, X.-H.; Song, X.-J.: 1-(3-Methylphenyl)-3-{5-[4- (trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}-urea. Acta Crystallogr. E63 (2007) o3641.
21. Wan, R.; Han, R; Zhang, J.-J.; Cao, L.; Wang, J.-T.: 3,5-Di-methyl-N-(5- m-tolyl-1,3,4-thiadiazol-2-yl)benzamide. Acta Crystallogr. E63 (2007) o885-o886.
22. Lynch, D. E.; McClenaghan, I.: 2-Acetamido-4-p-tolyl-1,3-thia-zole and 2-amino-4-p-toIyl-1,3-thiazolium chloride dehydrate. Acta Crystallogr. C60 (2004) o815-o817.
23. Yin, L.-H.; Wan.R.; Han, R; Wang, B.; Wang, J.-T.: Diethyl {(4-memoxyphenyl)[5-(4-nitrophenyl)-l,3,4-thiadiazol-2-ylami-no]methyl} phosphonate. Acta Crystallogr. E64 (2008) ol376.
24. Khusenov, K. S.; Umarov, B. B.; Ishankhodzhaeva, M. M.; Par-piev, N. A.; Talipov, S. A.; Ibragimov, B. T.: Crystal Structure of 2-Amino-1,3,4-Thiadiazole and Its Zn(II) Complex. Russ. J. Coord. Chem. 23 (1997) 555-559.
25. 6(20) rings. Acta Crystallogr. C62 (2006) o42-o44.
26. Lynch, D. E.: 2-Amino-5-methyl-l,3,4-thiadiazole and 2-amino-5-ethyl-l,3, 4-thiadiazole. Acta Crystallogr. C57 (2001) 1201-1203.
27. Shen, X.-Q.; Li, Z.-J.; Zhang, H.Y.; Qiao, H.-B.; Wu, Q.-A.; Wang, H.-Y; Zu, Y: Structure and thermal behaviors of organic crystals based on substituted 1,3,4-thiadiazoles. J. Phys. Chem. Solids 66 (2005) 1755-1760.
28. Choudhury, A. R.; Mruthyunjayaswamy, B. H. M.; Ijare, O. B.; Jadegoud, Y; Row, T. N. R.: 2-Amino-5-propyl-1,3,4-thiadiazole. Acta Crystallogr. E58 (2002) ol237-ol238.
29. Öztürk, S.; Akkurt, M.; Cansiz, A.; Koparir, M.; Sekerci, M.; Heinemann, R W: 2-Amino-5-phenyl-1,3,4-thiadiazole at 110 K. Acta Crystallogr. E60 (2004) o820-o821.
30. Ishankhodzhaeva, M. M; Kadyrova, Sh. A.; Surazhskaya, M. D.; Parpiev, N. A.; Koz'min, P. A.: Crystalline and Molecular Structure of 2-Amino-5-phenyl-1,3, 4-thiadiazole. Russ. J. Org. Chem. 37 (2001) 721-723.
31. Wan, R.; Han, R; Wu, R; Zhang, J.-J.; Wang, J.-T.: 5-(4-Fluoro-phenyl)-1, 3,4-thiadiazol-2-ylamine. Acta Crystallogr. E62 (2006) o5547-o5548.
32. Han, F; Wan, R.; Wu, W.-Y; Zhang, J.-J.; Wang, J.-T: 5-m-Tolyl-1, 3,4-thiadiazol-2-ylamine. Acta Crystallogr. E63 (2007) o717-o718.
33. Yin, L.-H.; Wan, R.; Wang.Y; Han, R; Wang, J.-T: 5-(2-Bromophenyl)-1,3,4- thiadiazol-2-amine. Acta Crystallogr. E64 (2008) 01884.
34. Guo, Z.; Yang, M.; Zhang, R.; Sun, Y: 2-Amino-5-(salicylide-neamino)-1,3, 4-thiadiazole. Acta CrystaUogr. E63 (2007) o4817.
35. Spek, A. L.: Single-crystal structure validation with the program PLATON. J. Appl. Crystallogr. 36 (2003) 7-13
36. Hooft, R. W. W.: COLLECT, data collection software. Nonius BV, Delft, The Netherlands, (1998).
37. Otwinowski, Z.; Minor, W: Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods in Enzymology. Vol. 276. In: Macromolecular Crystallography. Part A. (Eds. Carter Jr, C. W; Sweet, R. M.) pp. 307-326. New York: Academic Press, (1997).
38. Sheldrick, G. M.: SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA. (2004).
39. APEX2, Bruker AXS Inc., Madison, USA, (2004).
40. SAINT, Bruker AXS Inc., Madison, USA, (2004).
41. Farrugia, L. J.: Ortep-3 for Windows - A version of ORTEP-III with a Graphical User Interface. J. Appl. Crystallogr. 30 (1997) 565.
42. Sheldrick, G. M.: SHELXS97. Program for the Solution of Crystal Structures. University of Göttingen, Germany, (1997).
43. Sheldrick, G. M.: SHELXL-97, Program for crystal structure analysis. University of Göttingen, Germany, (1997).