Abstract
Herein, a series of novel 1H-1,2,3-triazole and carboxylate derivatives of metronidazole (5a–i and 7a–e) were synthesized and evaluated for their antimicrobial activity in vitro. All the newly synthesized compounds were characterized by 1H NMR, 13C NMR, HRMS, and 19F NMR (5b, 5c and 5h) spectroscopy wherever applicable. The structures of compounds 3, 5c and 7b were unambiguously confirmed by single crystal X-ray analysis diffraction method. Single crystal X-ray structure analysis supported the formation of the metronidazole derivatives. The antimicrobial (antifungal and antibacterial) activity of the prepared compounds was studied. All compounds (except 2 and 3) showed a potent inhibition rate of fungal growth as compared to control and metronidazole. The synthetic compounds also showed higher bacterial growth inhibiting effects compared to the activity of the parent compound. Amongst the tested compounds 5b, 5c, 5e, 7b and 7e displayed excellent potent antimicrobial activity. The current study has demonstrated the usefulness of the 1H-1,2,3-triazole moiety in the metronidazole skeleton.
Highlights
Metronidazole (1) is an important antimicrobial agent which has been clinically used successfully for a long time
In this regard we suggested the modification of the alcohol tail of metronidazole by incorporating an N-heterocyclic moiety
The first step was initiated by the protection of the primary hydroxy group of metronidazole (1) with p-toluenesulfonyl chloride in dry DCM in the presence of triethylamine at 0 °C to room temperature
Summary
Metronidazole (1) is an important antimicrobial agent which has been clinically used successfully for a long time. Corporation of the 1H-1,2,3-triazole moiety is well known to impact on the physical, chemical and biological potential properties of organic molecules Due to this reason, many efforts have been exerted to develop new synthetic methodologies toward the 1H-1,2,3-triazole group containing organic entities. Nitrogen-containing heterocycles play a vital role in agrochemicals and pharmaceuticals [3] Among these heterocyclic systems, the 1H-1,2,3-triazoles are very important in organic chemistry due to their broad spectrum of applications in biochemical, biomedicinal, pharmaceuticals, and materials sciences [4]. The 1H-1,2,3-triazoles are very important in organic chemistry due to their broad spectrum of applications in biochemical, biomedicinal, pharmaceuticals, and materials sciences [4] Their chemistry underwent a substantial growth over the past decades [5]. The choice of 1H-1,2,3-triazole was based on its known activities and its broad range of applications in biochemical, pharmaceutical, biomedicinal and materials sciences [4,5]
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