Antimicrobial, anti-inflammatory and analgesic activities of 2-amino-6-ethyl-4,6-dihydropyrano[3,2-c][2,1]benzothiazine 5,5-dioxides and triethylammonium 3-[1-(4-hydroxy-1-ethyl-2,2-dioxido-1h-2,1-benzothiazin-3-yl)-3-(het)arylmethyl]-1-ethyl-1h-2,1-benzo

Authors

  • D. A. Lega National University of Pharmacy, Ukraine
  • N. I. Filimonova National University of Pharmacy, Ukraine
  • I. A. Zupanets National University of Pharmacy, Ukraine
  • S. K. Shebeko National University of Pharmacy, Ukraine
  • V. P. Chernykh National University of Pharmacy, Ukraine
  • L. A. Shemchuk National University of Pharmacy, Ukraine

DOI:

https://doi.org/10.24959/nphj.16.2111

Keywords:

2, 1-benzothiazine 2, 2-dioxide, 2-amino-4H-pyran, antimicrobial activity, anti-inflammatory activity, analgesic activity

Abstract

The search and development of new bioactive compounds, possessing antimicrobial, anti-inflammatory and analgesic activities, are the topical issues of current medicinal chemistry. 2,1-Benzothiazine 2,2-dioxides condensed with 2-amino-3-R-4-(het)aryl-4H-pyran core and triethylammonium 3-[1-(4-hydroxy-1-ethyl-2,2-dioxido-1H-2,1-benzothiazin-3-yl)-3-(het)arylmethyl]-1-ethyl-1H-2,1-benzothiazin-4-olat 2,2-dioxides were tested to possess antimicrobial activity. As it was established condensed derivatives don’t have any antibacterial activity. Simultaneously, this group of compounds possesses pronounced antifungal activity against C. albicans. Ethyl 2-amino-4-{2-[2-oxo-2-(N-R-amino)ethoxy]phenyl}-6-ethyl-4,6-dihydropyrano[3,2-c][2,1]benzothiazine-3-carboxylate 5,5-dioxides were proposed for further synthetic and screening researches. Among the evaluated triethylammonium salts, triethylammonium 3-[1-(4-hydroxy-1-ethyl-2,2-dioxido-1H-2,1-benzothiazin-3-yl)-3-arylmethyl]-1-ethyl-1H-2,1-benzothiazin-4-olat 2,2-dioxides were displayed a high level of antimicrobial activity against E. coli, P. aeruginosa and C. albicans. The study of anti-inflammatory and analgesic activities of compounds related to different groups of 2-amino-3-R-4-R′-6-ethyl-4,6-dihydropyrano[3,2-c][2,1]benzothiazine 5,5-dioxides showed that they have anti-inflammatory activity at that 2-amino-3-ethoxycarbonyl-4-(4-chlorophenyl)-6-ethyl-4,6-dihydropyrano[3,2-c][2,1]benzothiazine 5,5-dioxide was as active as reference drug Piroxicam. Level of analgesic activity for tested compounds was not less than it was for reference drug. These facts allow to consider 2-amino-3-R-4-R′-6-ethyl-4,6-dihydropyrano[3,2-c][2,1]benzothiazine 5,5-dioxides as promising compounds for further search among them new substances displaying anti-inflammatory and analgesic activity.

Author Biographies

D. A. Lega, National University of Pharmacy

postgraduate student

N. I. Filimonova, National University of Pharmacy

Head of the Department of Microbiology, Virology and Immunology

I. A. Zupanets, National University of Pharmacy

Head of the Department of Clinical Pharmacology and Clinical Pharmacy

V. P. Chernykh, National University of Pharmacy

Rector

L. A. Shemchuk, National University of Pharmacy

Head of the Department of Organic Chemistry

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Published

2016-09-02

Issue

No. 3(87) (2016)

Section

Experimental and Clinical Pharmacology

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