Synthesis and crystal structure determination of 6-(N-isopropyl)amidino-2- methylbenzothiazole hydrochloride monohydrate and 2-amino-6-(N-isopropyl) amidinobenzothiazole hydrochloride

Structural Chemistry

Volumn 14, Issue 6, 2003, Pages 587-595

  Ćaleta, Irena ^a   Cetina, Mario ^b   Hergold Brundić, Antonija ^c   Nagl, Ante ^b   Karminski Zamola, Grace ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

^b UNIVERSITY OF ZAGREB   (Croatia)

^c UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

Amidinobenzothiazole derivatives; Synthesis; X ray structure analysis

Indexed keywords

2 AMINO 6 (N ISOPROPYL)AMIDINOBENZOTHIAZOLE; 6 (N ISOPROPYL)AMIDINO 2 METHYLBENZOTHIAZOLE; BENZOTHIAZOLE; SODIUM CHLORIDE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; CRYSTALLIZATION; DATA ANALYSIS; DRUG DETERMINATION; DRUG SYNTHESIS; HYDROGEN BOND; INFRARED RADIATION; X RAY ANALYSIS;

EID: 1842721264     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:STUC.0000007570.93128.c2     Document Type: Article

References (40)

1. deZwart, M. A. H.; van der Goot, H.; Timmerman, H. J. Med. Chem. 1989, 32, 487.
2. Canto-Cavalheiro, M. M.; Echevarria, A.; de Souza, M. A. S.; Cysne-Finkelstein, L.; Torres, M. A. D.; Leon L. L. Arzneim. Forsch. 2000, 50, 925.
3. Okumura, K.; Shimazaki, T.; Aoki, Y.; Yamashita, H. J. Med. Chem. 1998, 41, 4036.
4. Ku, T. W.; Miller, W. H.; Bondinell, W. E.; Erhard, K. F.; Keenan, R. M.; Nicholas, A. J.; Peishoff, C. E.; Samanen, J. M.; Wong, A. S.; Huffman, W. F. J. Med. Chem. 1995, 38, 9.
5. El Ashry, E. S. H.; Rashed, N.; Shobier, A. H. S. Pharmazie 2000, 55, 403.
6. Sielecki, T. M.; Liu, J.; Mousa, S. A.; Racanelli, A. L.; Hausner, E. A.; Wexler, R. R.; Olson, R. E. Bioorgan. Med. Chem. Lett. 2001, 11, 2201.
7. Ewing, W. R.; Becker, M. R.; Manetta, V. E.; Davis, R. S.; Pauls, H. W.; Mason, H.; Choi-Sledeski, Y. M.; Green, D.; Cha, D.; Spada, A. P.; Cheney, D. L.; Mason, J. S.; Maignan, S.; Guilloteau, J. P.; Brown, K.; Colussi, D.; Bentley, R.; Bostwick, J.; Kasiewski, C. J.; Morgan, S. R.; Leadley, R. J.; Dunwiddie, C. T.; Perrone, M. H.; Chu, V. J. Med. Chem. 1999, 42, 3557.
8. Ferroni, R.; Simoni, D.; Manfredini, S.; Guarneri, M.; Orlandini, P.; Barbieri, M.; Franzè, G. P.; Mugelli, A. Arzneim. Forsch. 1995, 45, 665.
9. Mellor, J. M.; Rataj, H. Tetrahedron Lett. 1996, 37, 2619.
10. Rudolph M. J.; Illig, C. R.; Subasinghe, N. L.; Wilson, K. J.; Hoffman, J. B.; Randle, T.; Green, D.; Molloy, C. J.; Soll, R. M.; Lewandowski, F.; Zhang, M.; Bone, R.; Spurlino, J. C.; Deckman, I. C.; Manthey, C.; Sharp, C.; Maguire, D.; Grasberger, B. L.; Des-Jarlais, R. L.; Zhou, Z. Bioorgan. Med. Chem. Lett. 2002, 12, 491.
11. Echevarria, A.; Santos, L. H.; Miller, J.; Mahmood, N. Bioorgan. Med. Chem. Lett. 1996, 6, 1901.
12. Lown, J. W.; Krowicki, K.; J. Org. Chem. 1985, 50, 3774.
13. Baraldi P. G.; Cacciari, B.; Guiotto, A.; Romagnoli, R.; Spalluto, G.; Leoni, A.; Bianchi, N.; Feriotto, G.; Rutigliano, C.; Mischiati, C.; Gambari, R. Nucleosides Nudeotides Nucleic Acids 2000, 19, 1219.
14. Baraldi, P. G.; Cozzi, P.; Geroni, C.; Mongelli, N.; Romagnoli, R.; Spalluto, G. Bioorgan. Med. Chem. 1999, 7, 251.
15. Janciene, R.; Kosychova, L.; Bukelskiene, V.; Domkus, V.; Strumbreiciute, Z.; Ragaleviciene, V.; Puodziunaite B. D. Arzneim. Forsch. 2002, 52, 475.
16. Mizuno, Y.; Adachi, K. J. Pharm. Soc. Jpn. 1952, 72, 739.
17. Stephens, F. F; Wibberley, D. G. J. Chem. Soc. 1950, P. 3336.
18. Farley, T. A.; Tidwell, R. R.; Donkor, I.; Naiman, N. A.; Ohemeng, K. A.; Lomberdy, R. J.; Bentley, J. A.; Cory, M. J. Med. Chem. 1993, 36, 1746.
19. Sawhney, S. N.; Boykin, D. W. J. Org. Chem. 1979, 44, 1136.
20. Katritzky, A. R.; Takeuchi, Y. Organ. Magn. Reson. 1970, 2, 569.
21. Stoe & Cie, STADI4, Diffractometer Control Program, 1995, Darmstadt, Germany.
22. Stoe & Cie, X-RED, Diffractometer Reduction Program, 1995, Darmstadt, Germany.
23. Sheldrick, G. M. SHELXS-97, Program for the Solution of Crystal Structures, 1997, University of Göttingen, Germany.
24. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures, 1997, University of Göttingen, Germany.
25. Nardelli, M. J. Appl. Crystallogr. 1995, 28, 659.
26. Spek, A. L. PLATON98 for Windows, 1998, University of Utrecht The Netherlands.
27. Sawusch, S.; Schilde, U. Z. Naturforsch. 1999, B54, 881.
28. Soon-Beng, T.; Siang-Guan, T.; Okechukwu, R. C.; Hoong-Kun, F. J. Organomet. Chem. 1993, 454, 67.
29. Chen, W. J. Organomet. Chem. 1994, 471, 69.
30. Armstrong, D. R.; Bennett, S.; Davidson, M. G.; Snaith, R.; Stalke, D.; Wright, D. S. Chem. Commun. 1992, 262.
31. Jan-nhuknan, J.; Karipides, A. G.; Hughes, J. M.; Cantrell, J. S. Acta Crystallogr. 1997, C53, 381.
32. Lynch, D. E.; Smith, G.; Byriel, K. A.; Kennard, C. H. L. Aust. J. Chem. 1998, 51, 587.
33. Lokaj, J.; Vrabél, Y.; Ilavsky, D.; Bartovič, A. Acta Crystallogr. 1996, C52, 1040.
34. Allen, F. H.; Kennard, O. Chem. Des. Autom. News 1993, 8, 31.
35. Blaton, N. M.; Peeters, O. M.; De Ranter, C. J. Acta Crystallogr. 1995, C51, 991.
36. Kim, S.; Bishop, R.; Craig, D. C.; Dance, I. G.; Scudder, M. L. J. Org. Chem. 1990, 55, 355.
37. Drexler, K.; Dehne, H.; Reinke, H.; Michalik, M. Liebigs Ann. Chem. 1997, 269.
38. Müller, G.; Dürner, G.; Bats, J. W.; Göbel, M. W. Liebigs Ann. Chem. 1994, 1075.
39. Papoutsakis, D.; Kirby, J. P.; Jackson, J. E.; Nocera, D. G. Chem. Europ. J. 1999, 5, 1474.
40. Reck, G.; Hagen, V.; Wagner, G. Crystallogr. Struct. Commun. 1982, 11, 1099.