Synthesis and antimicrobial activity of new adamantane derivatives I

• Autorzy: Orzeszko A. , Gralewska R. , Starosciak B.J. , Kazimierczuk Z.
• Języki publikacji: EN

Abstrakty

EN

A series of fourteen derivatives of adamantane was synthesised. The new compound 4-(adamant-1-ylmethoxycarbonyl)phthalanhydride obtained from 1-adamantane- methanol and trimellitic anhydride chloride appeared very useful for preparation of a number of N-substituted phthalimides. Antimicrobial activity of the newly obtained derivatives such as, for example, 4-(adamant-1-ylmethoxycarbonyl)-N-(5-carboxypentamethylene)phthalimide or 4-(adamant-1-ylmethoxycarbonyl)-N-(L-alanyl)phthalimide was tested against Staphylococcus aureus, Bacillus sp., Micrococcus flavus and Enterococcus faecium. The minimal inhibitory concentration (MIC) for these compounds against S. aureus were 0.022 and 0.05 µg/ml, respectively.

Słowa kluczowe

EN

tumour necrosis factor-alpha; 4-[adamant-1-ylmethoxycarbonyl]phthalanhydride; adamantane derivative; trimellitic acid anhydride; Micrococcus flavus; Staphylococcus aureus; Bacillus; antimicrobial activity; Enterococcus faecium; trimellitic anhydride chloride; 1-adamantanemethanol

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 2000
• Tom: 47
• Numer: 1
• Opis fizyczny: p.87-94

Twórcy

autor

Orzeszko A.

• Agricultural University, Rakowiecka 26-30, 02-528 Warsaw, Poland

autor

Gralewska R.

autor

Starosciak B.J.

autor

Kazimierczuk Z.

Bibliografia

• 1. Bialecka-Florjanczyk, E. & Orzeszko, A. (1993) Some novel liquid crystalline derivatives of 4-carboxyphthalimide. Liq. Cryst. 15, 255- 258.
• 2. Bialecka-Florjanczyk, E., Orzeszko, A. & Sledzinska, I. (1997) Cholesteryl ester imides with oxyethylene and methylene tails. Mol. Cryst. Liq. Cryst. 300, 1-8.
• 3. Bialecka-Florjanczyk, E., Orzeszko, A., Sledzinska, I. & Gorecka, E. (1999) Evidence of the smectic antiphase in 4-decyloxybiphenyl ester imide derivatives. J. Mater. Chem. 9, 371-374.
• 4. Sledzinska, I., Bialecka-Florjanczyk, E. & Orzeszko, A. (1996) Synthesis and liquid crystalline properties of cholesteryl bisester imides with poly(ethylene oxide)s as central spacer. Eur. Polym. J. 32, 1345-1350.
• 5. Kricheldorf, H.R. (1999) Liquid-crystalline polyimides. Adv. Polym. Sci. 141, 84-188.
• 6. Loncrini, D.F. (1966) Aromatic poly(ester imide)s. J. Polym. Sci. Part A-1. 4, 1531-1541.
• 7. Kricheldorf, H.R. (1994) Liquid-crystalline polyimides. Mol. Cryst. Liq. Cryst. 254, 87-108.
• 8. Kricheldorf, H.R. & Pakull, R. (1988) New polymer synthesis. 20. Liquid-crystalline poly(ester imide)s derived from trimellitic anhydride, alpha,w-diaminoalkanes and 4,4'-dihydroxybiphenyl. Macromolecules 21, 551-557.
• 9. Mallawaarachchi, W., Simmonds, R.J. & Parry, D.E. (1989) The geometry of N-hydroxymethyl compounds. Part 3: Geometries of N-(hydroxymethyl)amides related to reactivities. Anti-Cancer Drug Des. 4, 233-240.
• 10. Davies, W.L., Grunert, R.R., Haff, R.F., McGahen, J.W., Neumayer, E.M., Paulshock, M., Watts, J.C., Wood, T.R., Hermann, E.C. & Hoffmann, C.E. (1964) Antiviral activity of 1-adamantanamine (amantidine). Science 144, 862-863.
• 11. Schwab, R.S., England, A.C., Jr., Poskanzer, D.C. & Young, R.R. (1969). Amantadine in the treatment of Parkinson's disease. J. Am. Med. Assoc. 208, 1168-1170.
• 12. Plachta, D. & Starosciak, B. (1994) Synthesis of some 1-alkylamino-2,4-adamantylphenoxy)ethane derivatives. Acta Polon. Pharm. 51, 51-54.
• 13. Papadaki-Valiraki, A., Papakonstantinou- Garoufalias, S., Makaros, P., Chytyroglou- Lada, A., Hosoya, M., Balzarini, J. & De Clercq, E. (1993) Synthesis, antifungal, antibacterial and antiviral effects of some adamantaneketoxime ethers. Il Farmaco 48, 1091-1102.
• 14. Wang, J.-J., Wang, S.-S., Lee, Ch.-F., Chung, M.-A. & Chern, Y.-T. (1997; In vitro antitumor and antimicrobial activities of N-substituts of maleimide by adamantane and diamantane. Chemotherapy 43, 182-189.
• 15. Takatori, Y. (1992) N-1-adamantylmaleimide. Jpn. Kokai Tokyo Koho, Japan Pat. 6028961.
• 16. Sabata, Y., Shichita, M., Sasaki, K., Hashimoto, Y. & Iwasaki, S. (1995) N-Alkylphthalimides: Structural requirement of thalidomidal action on 12-0-tetradecanoylphorbol-13-acetate-induced tumor necrosis factor a production by human leukemia HL-60 cells. Chem. Pharm. Bull. 43, 177-179.
• 17. National Committee for Clinical Laboratory Standards NCCLS Approved Standard Document M7-A. (1985) Villanova, PA, U.S.A.
• 18. National Committee for Clinical Laboratory Standards 5th edn. Approved Standard NCCLS Document M2-A5. (1993) Villanova, PA, U.S.A.
• 19. Bialecka-Florjanczyk, E. & Orzeszko, A. (1999) Sposob wytwarzania cieklokrystalicznego bezwodnika 4-cholesteryloksykarbonyloftalowego. Pol. Patent 175659 (in Polish).
• 20. Bialecka-Florjanczyk, E. & Orzeszko, A. (1999) Sposob wytwarzania cieklokrystalicznych estrow cholesterolowych pochodnych bezwodnika 4-cholesteryloksykarbonyloftalowego. Pol. Patent 176084 (in Polish).
• 21. Kalodera, Z., Popejnak, S., Blazevic, N., Petrak, T. (1997) Chemical composition and antimicrobial activity of Tanacetum parthenium essential oil. Pharmazie 52, 885-886.
• 22. Kada, T., Hirano, K. & Shirazu, Y. (1980) Screening of environmental chemical mutagens by the rec-assay system with Bacillus subtilis. Chemical Mutagens (de Serres, F.J. & Hollaender, A., eds.) vol. 6, pp. 149-173, Plenum Pub. Co., New York.