SYNTHESIS AND ANTIMICROBIAL EVALUATION OF NOVEL POLYHETEROCYCLIC SYSTEMS DERIVED FROM CYCLOPENTA[4',5']PYRIDO[3',2':4,5]FURO[3,2-<i>d</i>]PYRIMIDINE

Authors

  • Samvel N. Sirakanyan Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Science of Republic of Armenia, Institute of Fine Organic Chemistry of A. L. Mnjoyan, 26 Azatutyan Ave., Yerevan 0014, Armenia
  • Domenico Spinelli Dipartimento di Chimica G. Ciamician, Alma Mater Studiorum-Università di Bologna, Via F. Selmi 2, Bologna 40126, Italy
  • Athina Geronikaki Aristotle University of Thessaloniki, School of Pharmacy, Thessaloniki 54124, Greece
  • Victor G. Kartsev InterBioScreen Ltd., P. O. Box 218, Moscow 119019, Russia
  • Hrachya M. Stepanyan Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Science of Republic of Armenia, Institute of Fine Organic Chemistry of A. L. Mnjoyan, 26 Azatutyan Ave., Yerevan 0014, Armenia
  • Elmira K. Hakobyan Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Science of Republic of Armenia, Institute of Fine Organic Chemistry of A. L. Mnjoyan, 26 Azatutyan Ave., Yerevan 0014, Armenia
  • Anush A. Hovakimyan Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Science of Republic of Armenia, Institute of Fine Organic Chemistry of A. L. Mnjoyan, 26 Azatutyan Ave., Yerevan 0014, Armenia

DOI:

https://doi.org/10.1007/5924

Keywords:

7-azidofuro[3, 2-d]pyrimidine, cyclopenta[4', 5']pyrido[3', 2', 4, 5]furo[3, 2-d]pyrimidin-7-amines, furo[2, 3-e][1, 2, 4]triazolo[4, 3-c]pyrimidine, antimicrobial activity, azide-tetrazole equilibrium, Dimroth rearrangement.

Abstract

The synthesis of new cyclopenta[4',5']pyrido[3',2':4,5]furo[3,2-d]pyrimidin-7-amines have been carried out to study their antimicrobial activity. The biological tests evidenced that some of the synthesized compounds exhibit pronounced antimicrobial properties. A study of the structure–activity relationship revealed that the 3,5-dimethyl-1H-pyrazol-1-yl moiety linked to the carbon C-9 of the pyrimidine plays a decisive role in the manifestation of activity. The influence of 3,5-dimethyl-1H-pyrazol-1-yl group on the Dimroth rearrangement and azide-tetrazole equilibrium has also been examined.

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Published

2021-01-26

Issue

Vol. 57 No. 1 (2021)

Section

Original Papers