Cent Eur J Public Health 2004, 12(Supplement):S57-S59

Biological Activity of 2-Hydroxythiobenzanilides and Related Compounds

Kubicová L., Šustr M., Pravda M., Waisser K.
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University in Prague, Czech Republic

Thiobenzanilides substituted in thioacyl moiety with one or more hydroxy groups are interesting for their biological effects depending on the substitution pattern. New findings in mechanisms of action of 2-hydroxybenzanilides insert 2-hydroxybenzanilides and their analogues, e.g. substituted thiobenzanilides, among interesting compounds in the development of new potential antimicrobial drugs. The present review paper with 32 references links up with our previous communications which reviewed biological activity of 2-hydroxybenzanilides and related compounds, and includes the research of mono-, di-, and trihydroxythiobenzanilides carried out in the last period.

Keywords: thiobenzanilides, mycobacteria, fungi, alga, photosynthesis-inhibiting activity, toxicity

Published: March 1, 2004  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
Kubicová L, Šustr M, Pravda M, Waisser K. Biological Activity of 2-Hydroxythiobenzanilides and Related Compounds. Cent Eur J Public Health. 2004;12(Supplement):S57-59. PubMed PMID: 15141980.
Share...
Download citation
  • BibTeX (.bib)
  • Bookends (.ris)
  • EasyBib (.ris)
  • EndNote (.enw)
  • EndNote 8 (.xml)
  • ISI WoS (.isi)
  • Medlars (.medlars)
  • Mendeley (.ris)
  • MODS (.xml)
  • Papers (.ris)
  • RefWorks (.txt)
  • RefManager (.ris)
  • RIS (.ris)
  • MS Word (.xml)
  • Zotero (.ris)
    • Open full article

    References

    1. Macielag MJ, Demers JP, Frago-Spano SA, Hlasta DJ, Johnson SG, Kanojia RM, Russell RK, Sui Z, Weidner-Wells A, Werblood H, Foleno BD, Goldschmidt RM, Loeloff MJ, Webb GC, Barrett JF: Substituted salicylanilides as inhibitors of two-component regulatory systems in bacteria. J Med Chem 1998; 41: 2939. Go to original source... Go to PubMed...
    2. Kauppi AM, Nordfelth R, Hagglund U, Wolf-Watz H, Elofsson M: Salicylanilides are potent inhibitors of type III secretion in Yersinia.Adv Exp Med Biol 2003; 529: 97-100. Go to original source...
    3. Waisser K, Kubicová L, Dostál H: Biological effects of substances similar to salicylanilides: Thiobenzanilides. Folia Pharm Univ Carol 1998; 23: 59-66.
    4. Waisser K, Kubicová L: Biologicacl effects of substances similar to salicylanilides. 3-aryl-2H,4H-benz[e][1,3]oxazin-2,4-dions and thiosalicylanilides. Čs Farm 1993; 42: 218-222. (In Czech.)
    5. Waisser K, Kubicová L, Gregor J, Buďová J, Andrlová A, Dršata J, Odlerová Ž: Relationship between chemical structure of substances and their antimycobacterial activity against atypical strains. XIII. Thiosalicylanilides. Čes-Slov Farm 1998; 47: 84-86. (In Czech.)
    6. Kuneš J, Balšánek V, Pour M, Waisser K, Kaustová J: On the relationship between the substitution pattern of thiobenzanilides and their antimycobacterial activity. Farmaco 2002; 57: 777-782. Go to original source... Go to PubMed...
    7. Kolář P, Foltýn M, Látalová M, Šustr M, Kubicová L, Kaustová J: Antimycobacterial activity of thioanthranilamides. Chem Listy 2002; 96: 418. (In Czech.)
    8. Kubicová L, Šustr M, Macháček M, Waisser K, Buchta V, Kubanová P, Kaustová J, Kráľová K: Synthesis of 5-chloro-2-hydroxythiobenzanilides and their antimycobacterial, antifungal, and photosynthesis-inhibiting activity. 5th Int Elect Conf Synth Org Chem, www.mdpi.org/ecsoc-5.htm, C0010. Basel, 2001.
    9. Šustr M, Kubicová L, Kaustová J, Waisser K:Antimycobacterial 3,5dichlorosalicylanilides. Chem Listy 2002; 96: 417.
    10. Waisser K, Hladůvková J, Kuneš J, Kubicová L, Klimešová V, Karajannis P, Kaustová J: Synthesis and antimycobacterial activity of salicylanilides substituted in position 5. Chem Papers 2001; 55: 121-129.
    11. Šustr M, Macháček M, Kubicová L, Kubanová P:Activity of chlorthiosalicylanilides against Absidia corymbifera. Chem Listy 2001; 95: 760.
    12. Nippon Soda Co., Ltd.: Jpn. Kokai Tokkyo Koho JP 2003048876 (2003).
    13. Hanusek J, Šustr M, Kubanová P, Buchta V, Sedlák M: Biological activity of substituted 2-aminothiobenzamides and quinazolin-4-thiones. Folia Pharm Univ Carol 2003; 29/30; 55-64.
    14. Šustr M, Kráľová K, Kubicová L, Waisser K: Synthesis and herbicidal activity of thiosalicylanilides. Chem Listy 2000; 94: 937.
    15. Kubicová L, Kráľová K, Fargašová A, Šustr M: Antialgal activity of thiosalicylanilides. Chem Listy 2000; 94: 1065. (In Czech.)
    16. Niewiadomy A, Matysiak J, Macik-Niewiadomy G: The antibacterial activity of some 2,4-dihydroxythiobenzanilides substituted in the N-aryl ring. Pestycydy 2000; (3-4): 43-51.
    17. Matysiak J, Niewiadomy A, Macik-Niewiadomy G., Kornilowicz T: Dependence of fungistatic activity of 2,4-dihydroxythiobenzanilides on the structure and lipophilic nature of the compounds. Eur J Med Chem 2000; 35: 393-404. Go to original source...
    18. Matysiak J, NiewiadomyA, Macik-Niewiadomy G: In vitro inhibition properties of a new group of thiobenzanilides in relation to yeasts. Eur J Pharm Sci 2000; 10: 119-123. Go to original source...
    19. Matysiak J, NiewiadomyA, Macik-Niewiadomy G: In vitro evaluation of 2,4-dihydroxythiobenzanilides against various moulds. Eur J Pharm Sci 2001; 13: 243-248. Go to original source...
    20. Legocki J, Matysiak J, Niewiadomy A, Kostecka M-L: Synthesis and fungistatic activity of new groups of 2,4-dihydroxythiobenzoyl derivatives against phytopathogenic fungi. J Agric Food Chem 2003; 51: 362-368. Go to original source... Go to PubMed...
    21. Matysiak J, Niewiadomy A, Zabinska A, Rozylo JK: Structure and retention of 2,4-dihydroxythiobenzanilides in a reversed-phase system. J Chromatogr A 1999; 830: 491-496. Go to original source...
    22. Garcia-Domenech R, CatalaAL, Garcia-GarciaA, SorianoA, Perez-MondejarV, Galvez J: QSAR by molecular topology of 2,4-dihydroxythiobenzanilides - a virtual screening approach to optimize the antifungal activity. Indian J Chem, Sect B 2002; 41: 2376-2384.
    23. Matysiak J, Krajewska-Kulak E, Karczewski J, Niewiadomy A: N-heterocyclic derivatives of 2,4-dihydroxybenzcarbothioamide as antimycotic agents. J Agric Food Chem 2001; 49: 5251-5257. Go to original source... Go to PubMed...
    24. Matysiak J, Niewiadomy A: Synthesis and antimycotic activity of N-azolyl-2,4-dihydroxythiobenzamides. Bioorg Med Chem 2003; 11: 2285-2291. Go to original source...
    25. Kleinrok Z, Niewiadomy A, Matysiak J: Evaluation of toxic activity of 2,4-dihydroxythiobenzanilides. Pharmazie 2002; 57: 198-200. Go to PubMed...
    26. Kowalska-Pylka H, Majer-Dziedzic B, Niewiadomy A, Matysiak J: Evaluation of the toxicity of substituted benzthioanilides by using in vitro tests. ATLA-Altern. Lab Anim 2001; 29: 547-556. S59 Go to original source... Go to PubMed...
    27. Matysiak J, Kwiatkowska-Drabik B, Wojcierowski J, NiewiadomyA: The nature of interaction of 4'-[(N-benzoyl)aminomethanocarboxy]2,4-dihydroxybenzcarbothioamide with blood lymphocytes. Pharmazie 2002; 57: 774-775. Go to original source... Go to PubMed...
    28. Yoneyama K,Asami T, Crow WD, Takahashi N,Yoshida S: Inhibition of photosynthesis by 3-acyl-2,4,6-trihydroxythiobenzamide derivatives. Agric Biol Chem 1989; 53: 471-475. Go to original source...
    29. Honda I,Yoneyama K, Konnai M, Takahashi N,Yoshida S: Syntheses of 3-nitro-2,4,6-trihydroxybenzamide and thiobenzamide derivatives as highly potent inhibitors of photosynthetic electron transport. Agric Biol Chem 1990; 54: 1071-1072. Go to original source...
    30. Yoneyama K, Konnai M: Phloroglucinol derivatives as potent photosystem II inhibitors. Zeit Naturforsch C 1990; 45: 317-321. Go to original source...
    31. Honda I, Yoneyama K, Iwamura H, Konnai M, Takahashi N, Yoshida S: Structure-activity relationship of 3-nitro-2,4,6-trihydroxybenzamide derivatives in photosynthetic electron transport inhibition. Agric Biol Chem 1990; 54: 1227-1233. Go to original source...
    32. Takasaki M, Konoshima T, Kozuka M, Yoneyama K, Yoshida S, Tokuda H, Nishino H, Iwashima A: Inhibitors of skin-tumor promotion. XIII. Inhibitory effects of euglobals and their related compounds on Epstein-Barr virus activation and on two-stage carcinogenesis of mouse skin tumors. Biol Pharm Bull 1995; 18: 288-294. Go to original source... Go to PubMed...

    Return to the content