Synthesis and correlations between experimental and calculated lipophilic indices of new 1,2-benzisothiazole derivatives with potential antimicrobial activity

Archiv der Pharmazie

Volumn 333, Issue 5, 2000, Pages 135-144

  Vicini, Paola ^a   Fisicaro, Emilia ^a   Lugari, Maria Teresa ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

1,2 Benzisothiazolylhydrazones; Capacity factor; Lipophilicity; Log P; RP HPLC

Indexed keywords

1,2 BENZISOTHIAZOLE DERIVATIVE; 1,2 BENZISOTHIAZOLYLHYDRAZONE DERIVATIVE; ANTIINFECTIVE AGENT; HYDRAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CONTROLLED STUDY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROPHOBICITY; LIPOPHILICITY; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ALDEHYDES; ANTI-INFECTIVE AGENTS; HYDRAZINES; HYDRAZONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SOLUBILITY; THIAZOLES;

EID: 0034083224     PISSN: 03656233     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-4184(20005)333:5<135::AID-ARDP135>3.0.CO;2-U     Document Type: Article

References (44)

1. Asish De in Progress in Medicinal Chemistry (G.P. Ellis, G.B. West, Eds.), vol. 18, Elsevier, North-Holland Biomedical Press, 1981, 117-133.
2. P. Vicini, Farmaco Ed. Sc. 1986 41, 808-818.
3. P. Vicini, L. Amoretti, M. Chiavarini, M. Impicciatore, Farmaco Ed. Sc. 1990, 45, 933-943.
4. P. Vicini, E. Fisicaro, Arch. Pharm. 1991, 324, 927-931.
5. P. Vicini, L. Amoretti, A. Caretta, Farmaco 1992, 47, 265-274.
6. P. Vicini, L. Amoretti, V. Ballabeni, E. Barocelli, M. Chiavarini, Eur. J. Med. Chem. 1995 30, 809-814.
7. P. Vicini, C. Manotti, A. Caretta, L. Amoretti, Arzneim-Forsch/Drug Res. 1997, 47, 1218-1221.
8. P. Vicini, C. Manotti, A. Caretta, L. Amoretti, Arzneim-Forsch/Drug Res. 1999, 49, 896-899.
9. P. Vicini, P. Mazza, Farmaco 1989, 44, 511-517.
10. G. Massimo, F. Zani, E. Coghi, A. Bellotti, P. Mazza, Farmaco 1990, 45, 439-446
11. F. Zani, P. Vicini, Arch. Pharm. Pharm. Med. Chem. 1998, 331, 219-223.
12. M. Davis in Advances in Heterocyclic Chemistry (Katritzky A. R., Boulton A.J. Eds.), Vol. 38, Academic Press, New York, 1985 114-116.
13. P. Borgna, M. L. Carmellino, M. Natangelo, G. Pagani, F. Pastoni, M. Pregnolato, M. Terreni, Eur. J. Med. Chem. 1996, 31, 919-925.
14. C. Yamagami, N. Takao, T. Fujita, Quant. Struct.-Act. Relat. 1990, 9, 313-320.
15. R. Mannhold, R. F. Rekker, C. Sonntag, A. M. Ter Laak, Dross K., E. E. Polymeropoulos, J. Pharm. Sci 1995, 84, 1410-1419.
16. J. Jurgen, H. Schedletzky, P. Heisig, J.K. Seydel, B. Wiedemann, U. Holzgrabe, Arch. Pharm. Pharm. Med. Chem. 1996, 329, 179-190.
17. A. Niewiiadomy, J. Matysiak, A. Zabinska, J.K. Rozylo, B. Senczyna, K. Jozwiak J. Chromatogr. 1998, 828 431-438.
18. F. Barbato, M.I. La Rotonda, F. Quaglia, Eur. J. Med. Chem. 1996, 31, 311-318.
19. N. El Tayar, H. Van de Waterbeemd, B. Testa, J. Chromatogr. 1985, 320, 305-312.
20. D. Reymond, G. N. Chung, J. M. Mayer, B. Testa, J. Chromatogr. 1987, 391, 97-109.
21. M. A. Al-Haj, P. Haber, R. Kaliszan, B. Buszewski, M. Jezierska, Z. Chilmonzyk, J. Pharm. Biomed. Anal. 1998, 18, 721-728.
22. R. Kaliszan, A. Kaliszan, I.W. Wainer, J. Pharm. Biomed. Anal. 1993, 11, 505-511.
23. A.Tanaka, K. Nakamuro, I. Nakanishi, H. Fujiwara, J. Med. Chem. 1994, 37, 4563-4566
24. T. Braumann, J. Chromatogr. 1986, 373, 191-226.
25. a) C. Yamagami, N. Takao, Chem. Pharm. Bull. 1993, 41, 694-698.
26. b) C. Yamagami, N. Katashiba, Chem. Pharm. Bull. 1996, 44, 1338-1343.
27. M. Bona, P. Boudeville, P. Zekri, M.O. Christen, J.L. Burgot, J. Pharm. Sci. 1995, 84, 1107-1112.
28. A.J. Leo, C. Hansch, D. Elkins, Chem. Rev. 1971, 71, 525-616.
29. C. Hansch, A.J. Leo, S.H. Unger, K. Hwan Kim, D. Nikaitani, E.J. Lien, J. Med. Chem. 1973, 16, 1201-1216
30. A.J. Leo in Comprehensive Medicinal Chemistry, (C. Hansch, P.G. Sammes, J.B. Taylor Eds), vol 4 (Ramsden C.A., volume ed.), Pergamon Press, New York, 1990, 295-319.
31. A. J. Leo, Chem Rev 1993, 93, 1281-1306.
32. H. Kubinyi in QSAR: Hansh Analysis and Related Approaches, (R. Mannhold, P. Krogsgaard-Larsen, H. Timmerman Eds.), VCH, Weinheim/New York, 1991.
33. R.F. Rekker, R. Mannhold, Calculation of Drug Lipophilicity, VCH, Weinheim New York, 1992.
34. [331 H. Van de Waterbeemd, R. Mannhold, Quant. Struct.-Act. Relat. 1996, 15, 410-412.
35. T. Vitali, C.A. Maggiali, C.F. Laureri, M.T. Lugari Mangia, Ateneo Parmense Acta Naturalia 1971, 7, 115-126.
36. Beil. 27, II 378.
37. T. Vitali, M.R. Mingiardi, C.A. Maggiali, Farmaco Ed. Sc. 1973, 28, 8-18.
38. L. Amoretti, P.L. Catellani, M. Impicciatore, A. Cavaggioni, Farmaco Ed. Sc. 1972, 27, 855-869.
39. T. Vitali, L. Amoretti, Boll. Soc. It. Biol. Sper. 1971, 47, 790-793.
40. P. Vicini, unpublished results.
41. P. Boudeville, M. Bona, J.L. Burgot, J. Pharm. Sci. 1996, 85, 990-998.
42. R. Collander, Acta Chem. Scand. 1951, 5, 774-781
43. G. Cimpan, F. Irimie, S. Gocan, H.A. Claesens, J. Chromatogr. B 1998, 714, 247-261.
44. K. Nagano, H. Tsukahara, H. Kinoshita, Z. Tamura, Chem. Pharm. Bull. 1963, 6, 797-805.