Highly lipophilic benzoxazoles with potential antibacterial activity
Language English Country Switzerland Media electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
18007347
PubMed Central
PMC6147629
DOI
10.3390/10070783
PII: 10070783
Knihovny.cz E-resources
- MeSH
- Anti-Bacterial Agents pharmacology MeSH
- Antifungal Agents pharmacology MeSH
- Antitubercular Agents pharmacology MeSH
- Benzoxazoles chemistry pharmacology MeSH
- Isomerism MeSH
- Isoniazid pharmacology MeSH
- Molecular Conformation MeSH
- Models, Molecular MeSH
- Mycobacterium tuberculosis drug effects MeSH
- Solubility MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Anti-Bacterial Agents MeSH
- Antifungal Agents MeSH
- Antitubercular Agents MeSH
- Benzoxazoles MeSH
- Isoniazid MeSH
A series of lipophilic 2-substituted 5,7-di-tert-butylbenzoxazoles was prepared in average yields by the reaction of 3,5-di-tert-butyl-1,2-benzoquinone with amino acids and dipeptides bearing N-terminal glycine. Dipeptides having other N-terminal amino acids undergo oxidative deamination. 5,7-Di-tert-butylbenzoxazoles have shown activity against Mycobacterium tuberculosis and some nontuberculous strains where isoniazid has been inactive. Antifungal activity was mediocre.
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Temiz O., Oren I., Sener E., Yalcin I., Ucartürk N. Il Farmaco. 1998;53:337–341. PubMed
Oren I., Temiz O., Yalcin I., Sener E. A., Altanlar N. Eur. J. Pharm. Sci. 1998;7:153–160. PubMed
Kumar D., Jacob M. R., Reynolds M. B., Kerwin S. M. Bioorg. Med. Chem. 2002;10:3997–4004. doi: 10.1016/S0968-0896(02)00327-9. PubMed DOI
Kim J. S., Sun Q., Gatto B., Yu Ch., Liu A., Liu L. F., LaVoie E. J. Bioorg. Med. Chem. 1996;4:621–630. doi: 10.1016/0968-0896(96)00047-8. PubMed DOI
Hoffman J. M., Smith A. M., Rooney C. S., Fisher T. E., Wai J. S., Thomas C. M., Bamberger D. L., Barne J. L., William T. M., Jobes H. H., Olson B. D., O´Brien J. A., Goldman M. E., Nunberg J. H., Quintero J. C., Schleif W. A., Emini E. A., Anderson P. S. J. Med. Chem. 1993;36:953–966. doi: 10.1021/jm00060a002. PubMed DOI
Perrin L., Rakik A., Yearly S., Baumberger C., Kinloch-deLoies S., Pechiere M., Hirschel B. AIDS. 1996;10:1233–1239. PubMed
Holler M. G., Campo L. F., Brandelli A., Stefani V. J. Photochem. Photobiol. A: Chemistry. 2002;149:217–225. doi: 10.1016/S1010-6030(02)00008-4. DOI
Laber B., Usunow G., Wiecko E., Franke W., Franke H., Köhn A. Pesticide Biochem. Physiol. 1999;63:173–184.
Dunwell D. W., Evans D. J. Med. Chem. 1977;20:797–801. doi: 10.1021/jm00216a011. PubMed DOI
Vinsova J., Horak V. Chem. Listy. 2001;97:1157–1167.
Voleva V. B., Belostotskaya I. S., Bundel A. Yu., Komissarova N. L., Erskov V. V. Russ. Chem. Bull. 1997;46:385–386.
Horak V., Mermersky Y., Guirguis D. B. Collect. Czech Chem. Commun. 1994;59:227–230.
Corey E. J., Achiwa K. J. Am. Chem. Soc. 1969;91:1429–1432.
National Committee for Clinical Laboratory Standards: Reference method for broth dilution antifungal susceptibility testing of yeast: Approved Standard, NCCLS document, M27-A. NCCLS; Villanova, PA: 1997.
Haeussler H., Jadamus H. Chem. Ber. 1964;97:3051–3055. doi: 10.1002/cber.19640971113. DOI
Gilchrist T.L., Harris C. J., King F. D., Peek M. E., Rees Ch. W. J. Chem. Soc. Perkin Trans 1. 1988:2169–2174. doi: 10.1039/p19880002169. DOI
Wieland T., Klu, Hi Shin, Heinke B. Chem. Ber. 1958;91:483–487. doi: 10.1002/cber.19580910304. DOI
Errera M., Greenstein J. P. Arch. Biochem. 1947;14:477–478. PubMed