Spiro[benzo[е]pyrano[3,2-c][1,2]oxathiin-4,3’-indolil]-3-carbonitrile 5,5-dioxides: synthesis and the biological activity study

Authors

  • G. V. Grygoriv National University of Pharmacy, Ukraine
  • D. A. Lega National University of Pharmacy, Ukraine https://orcid.org/0000-0002-4505-3646
  • I. A. Zupanets National University of Pharmacy, Ukraine
  • S. K. Shebeko National University of Pharmacy, Ukraine
  • S. M. Zimin National University of Pharmacy, Ukraine
  • I. L. Starchikova National University of Pharmacy, Ukraine
  • L. A. Shemchuk National University of Pharmacy, Ukraine

DOI:

https://doi.org/10.24959/ophcj.19.182954

Keywords:

1, 2-benzoxathiin-4(3H)-one 2, 2-dioxide, isatins, spiro compounds, analgesic activity, anti-inflammatory activity, antimicrobial activity

Abstract

The development of medicines with several pharmacological activities, including the analgesic, anti-inflammatory and antimicrobial properties, is one of the challenging tasks of modern medicinal chemistry.
Aim. To expand the range of novel spiro-condensed derivatives of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide, and study the biological activity of the substances obtained.
Results and discussions. The target compounds were synthesized as a result of the interaction of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide, malononitrile and isatins. When using ethyl cyanoacetate the interaction appeared to be much more complicated and requires further research. The study of the biological activity has revealed the compounds with the analgesic properties and the antimicrobial effect against gram-positive strains.
Experimental part. Two new 2-amino-2’-oxospiro[4H-pyrano[3,2-c][1,2]benzoxathiine-4,3’-indoline]-3-carbonitrile 5,5-dioxides were synthesized by the three-component reaction based on 1,2-benzoxathiin-4(3H)-one 2,2-dioxide. The anti-inflammatory activity was studied on the model of the carrageenan induced paw edema, and the analgesic activity was assessed on the model of the local inflammatory hyperalgesia. The study of the antimicrobial activity of the compounds obtained was performed by the agar well diffusion method.
Conclusions. New spiro[benzo[е]pyrano[3,2-c][1,2]oxathiin-4,3’-indolil]-3-carbonitrile 5,5-dioxides have been synthesized. The compounds obtained have revealed high levels of the analgesic properties and the antimicrobial activity. The latter exceeds the activity of the reference drugs, and has appeared to be higher against grampositive bacteria.

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Published

2019-11-21

How to Cite

(1)
Grygoriv, G. V.; Lega, D. A.; Zupanets, I. A.; Shebeko, S. K.; Zimin, S. M.; Starchikova, I. L.; Shemchuk, L. A. Spiro[benzo[е]pyrano[3,2-c][1,2]oxathiin-4,3’-Indolil]-3-Carbonitrile 5,5-Dioxides: Synthesis and the Biological Activity Study. J. Org. Pharm. Chem. 2019, 17, 53-61.

Issue

Vol. 17 No. 4(68) (2019)

Section

Original Researches

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