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. 1958 Dec;13(4):404–410. doi: 10.1111/j.1476-5381.1958.tb00229.x

Antiviral action of derivatives of ω-aminoacetophenone

J Brug, C A De Bock, H D Moed, A J Klein
PMCID: PMC1481883  PMID: 13618544

Abstract

Numerous structural analogues of 3-amino-4-hydroxy-ω-methylaminoacetophenone were tested for their effect on the multiplication of influenza virus (FM1 strain) in embryonated eggs, infected via the allantoic cavity. Antiviral activity was found in ω-aminoacetophenones containing an amino and hydroxyl group in the aromatic nucleus in the ortho or para positions to each other. The most powerful antiviral activity was found in the series of ω-alkylamino-5-amino-2:4-dihydroxyacetophenones. Derivatives of acetophenone with other substituents in the aromatic nucleus or in the aliphatic chain were without activity. In vitro, several analogues inactive in the egg test, as well as those which were active, exerted a virucidal and to a lesser extent a haemagglutinin-destroying action. Antiviral action in the allantoic test could not be prevented or inhibited by simultaneous administration of reducing substances, or of some amino-acids or vitamins. No inhibition of virus multiplication occurred in embryonated eggs infected via the yolk sac, or in mice infected intranasally with FM1 virus. The activity in the allantoic test could be explained by the virucidal action of the compounds on the virus present in the allantoic fluid. No satisfactory interpretation of the empirical relationship between chemical structure and antiviral activity could be found.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Barber M. The antibacterial activity of simple derivatives of 2-aminophenol. Biochem J. 1945;39(4):285–287. [PMC free article] [PubMed] [Google Scholar]
  2. FAUCONNIER B. Développement du virus grippal et pH du liquide allantoïque de l'oeuf embryonne. III. Action favorisante du carbonate de magnésium. Ann Inst Pasteur (Paris) 1955 Jan;88(1):96–103. [PubMed] [Google Scholar]
  3. GROUPE V., ENGLE C. G., GAFFNEY P. E., MANAKER R. A. Virucidal activity of representative antiinfective agents against influenza A and vaccinia viruses. Appl Microbiol. 1955 Nov;3(6):333–336. doi: 10.1128/am.3.6.333-336.1955. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. HANNOUN C. Action de certains inhibiteurs enzymatiques sur la multiplication du virus la grippe. C R Hebd Seances Acad Sci. 1952 Dec 1;235(22):1445–1446. [PubMed] [Google Scholar]
  5. KRAMER P. E., ROBBINS M. L., SMITH P. K. Phenolic compounds as chemotherapeutic agents against poliomyelitis virus in tissue culture. J Pharmacol Exp Ther. 1955 Mar;113(3):262–271. [PubMed] [Google Scholar]
  6. KUROYA M., ISHIDA N., KONNO J., SHIRATORI T., MIURA M., YOSHINARI Y. Antiviral activity of several quinone and isoquinoline derivatives. Yokohama Med Bull. 1953 Apr;4(2):73–77. [PubMed] [Google Scholar]
  7. LIU O. C., MALSBERGER R. G., CARTER J. E., DESANCTIS A. N., WIENER F. P., HAMPIL B. Studies on the chemotherapy of viral infections. I. The activity of caprochlorone on influenza viral infection in the de-embryonated egg. J Immunol. 1957 Mar;78(3):214–221. [PubMed] [Google Scholar]
  8. PHILIPPE J. Les applications des méthodes statistiques aux titrages bactériologiques. Ann Pharm Fr. 1955 Mar;13(3):215–235. [PubMed] [Google Scholar]
  9. PIZZI M. Sampling variation of the fifty percent end-point, determined by the Reed-Muench (Behrens) method. Hum Biol. 1950 Sep;22(3):151–190. [PubMed] [Google Scholar]
  10. RANDLES C. A., Jr, ROMANOFF A. L. The buffering capacities of allantoic and amniotic fluids of the chick. Arch Biochem Biophys. 1954 Mar;49(1):160–167. doi: 10.1016/0003-9861(54)90177-0. [DOI] [PubMed] [Google Scholar]
  11. RASMUSSEN A. F., Jr, STOKES J. C. Chemical inhibition of the growth of the virus of influenza in embryonated eggs. J Immunol. 1951 Feb;66(2):237–247. [PubMed] [Google Scholar]
  12. RUFFILLI D. Azione dell'ambiente biochimico sulla riproduzione del virus influenzale in culture di tessuti. VI. Primi dati sull'importanza della concentrazione ioni idrogeno. Boll Soc Ital Biol Sper. 1952 Jul;28(7):1397–1400. [PubMed] [Google Scholar]
  13. TAKEMOTO K. K., ROBBINS M. L., SMITH P. K. The experimental chemotherapy of influenza viruses. J Immunol. 1954 Feb;72(2):139–147. [PubMed] [Google Scholar]

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