Synthesis, degradation kinetics and in vitro antimicrobial activity of tetrahydro-2H-1,3,5- thiadiazine-2-thione derivatives of some β-amino acids

Arzneimittel-Forschung/Drug Research

Volumn 53, Issue 7, 2003, Pages 526-531

  Aboul Fadl, Tarek ^a   Khallil, Abdel Raouf ^b  

^a Assiut University   (Egypt)

^b Assiut University   (Egypt)

Author keywords

Tetrahydro 2H 1,3,5 thiadiazine 2 thione derivatives, antimicrobial activity in vitro, degradation kinetics, lipophilicity; Alanine; Phenylalanine

Indexed keywords

3,5 DIMETHYLTETRAHYDRO 2H 1,3,5 THIADIAZINE 2 THIONE; BETA AMINO ACID; SULBENTINE; TETRAHYDRO 2H 1,3,5 THIADIAZINE 2 THIONE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; DEGRADATION KINETICS; DERIVATIZATION; DERMATOPHYTE; DRUG EFFECT; ENZYME STABILITY; FINITE ELEMENT ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPOPHILICITY; SYNTHESIS;

EID: 0042668298     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1297144     Document Type: Article

References (23)

1. Reiche, A., Hilgetag, G., Martini, A. et al., New compounds with bactericidal, fungicidal, and virostatic activity. I. 2-Thiotetrahydro-1,3,5-thiadiazine (carbothialdine) and dithiocarbamic acid salts. Arch. Pharm. 293, 957 (1960)
2. Reiche, A., Hilgetag, G., Martini, A. et al., New compounds with bactericidal, fungicidal and inhibitory effects on the growth of viruses. II. Thiourethane. Arch. Pharm. 294, 201 (1961)
3. Weuffen, W., Martin, D., Schade, W., Relation between chemical structure and antimicrobial action. 1. Studies on the bacteriostatic properties of some 2-thiotetrahydro-1,3,5-thiadiazines. Pharmazie 18, 420 (1963)
4. Zsolanai, T., Antimicrobial effect of potential isothiocyanate components. Arzneim.-Forsch./Drug Res. 18, 1319 (1968)
5. Schorr, M., Durrcheimer, W., Klatt, P. et al., New tetrahydro-1,3,5-thiadiazine-2-thiones with antimycotic, antibacterial and anthelmintic effect. Arzneim.-Forsch./Drug Res. 19, 1807 (1969)
6. Zsolnai, T., Antimicrobial effects of thiocyanates, isothiocyanates and potential isothiocyanate forming substances. Arzneim.-Forsch./Drug Res. 21, 121 (1971)
7. Ertan, M., The synthesis and biological studies on some novel semisynthetic β-lactam antibiotics I. Acta Pharm. Turc. 27, 82 (1985)
8. El-Shorbagi, A., New tetrahydro-2H-1,3,5-thiadiazine-2-thione derivatives as potential antimicrobial agents. Arch. Pharm. Pharm. Med. Chem. 333, 281 (2000)
9. Manohar, V., Murthy, S., Sirsi, M. et al., Antidermatophytic activity of 2-thiotetrahydro-1,3,5-thiadiazines and isothiocyanates. J. Pharm. Sci. 64, 164 (1975)
10. Ertan, M., Ertan, R., Üreten, M. et al., Studies on the synthesis of some 3,5-disubstituted tetrahydro-2H-1,3,5-thiadiazine-2-thione derivatives and their fungicide activities against Phytophthora capsici Leon. Acta Pharm. Turc. 28, 65 (1986)
11. Schmidt, U., Beyer, E., Martin, D., Modification of virus diseases by synthetic mustard-oil forming substances. Dtsch. Akad. Wiss. 6, 458 (1964)
12. Rada, B., Hanusovska, T., Drobinca, L. et al., Inhibition of virus multiplication by selected isothiocyanates. Acta Virol. 15, 329 (1971)
13. Odlerova, Z., Evaluations of the antimycobacterial effectiveness of natural and synthetic drugs using growth curves. Stud. Pneumol. Phtiseol. Gzech. 36, 156 (1976)
14. Aboul-Fadl, T., Hassanin, K., Tetrahydro-2H-1,3,5-thiadiazine-5-(4-pyridylcarboxamide)-2-thione derivatives as prodrugs for isoniazid. Synthesis, investigations, and in vitro antituberculous activity. Pharmazie 54, 244 (1999)
15. Schade, W., Reiche, A., Synthetic oils of mustard. VII. Studies on the mechanism of action of 2-thion-tetrahydro1,3,5-thiadiazine. Arch. Pharm. 299, 589 (1966)
16. Goksøyr, J., Chemical and fungicidal reactions of 3,5-dimethyltetrahydro-1,3,5-thiadizine-2-thione (3,5-D). A. Comparison with sodium N-methyl dithiocarbamate and methyl isothiocyanate. Acta Chem. Scand. 18, 1341 (1964)
17. Leo, A. J., Calculating log Poct from structures. Chem. Rev. 93, 1281 (1993)
18. Pai, S. T., Platt, M. W., Antifungal effects of Allium sativum (garlic) extract against the Aspergillus species involved in otomycosis. Lett. Appl. Microbiol. 20, 14 (1995)
19. Pliska, V., Testa, B., Waterbeemd, H. (eds.), Lipophilicity in Drug Action and Toxicology, A Series Monographs of Methods and Principles in Medicinal Chemistry, Vol. 4. VCH, Weinheim-New York etc. (1996)
20. Møss, J., Bundgaard, H., Prodrugs of peptides. 7. Transdermal delivery of thyrotropin-releasing hormone (TRH) via prodrugs, Int. J. Pharm. 66, 39 (1990)
21. Seydel, J. K., Schaper, K. J., The problem of resistance in the treatment of Mycobacterium infections: new experimental results and combinations for the treatment of tuberculosis and leprosy. Pharmazie in unserer Zeit 24, 313 (1995)
22. Aboul-Fadl, T., El-Shrobagi, A., New prodrug approach for amino acids and amino-acid-like drugs. Eur. J. Med. Chem. 31, 165 (1996)
23. Aboul-Fadl, T., El-Shrobagi, A., New carriers for representative peptides and peptide drugs. Arch. Pharm. Pharm. Med. Chem. 330, 327 (1997)