Hemi-synthesis, in-vitro and in-silico bioactivities of new chiral-Schiff bases and benzodiazepine derivatives from Ammodaucus leucotrichus(S)-perillaldehyde
authors Khalfaoui, M; Chebrouk, F; Ziani, BEC; Bennamane, N; Cherfaoui, B; Frites, W; Valega, M; Mendes, RF; Paz, FAA; Chebout, R; Bachari, K; Talhi, O; Silva, AMS
nationality International
journal JOURNAL OF MOLECULAR STRUCTURE
author keywords Ammodaucus leucotrichus; Amines; Hemi-synthesis; Essential oil; NMR; Single-crystal X-ray diffraction; Chiral-HPLC; Biological activity; Molecular docking; (S)-(-)-perillaldehyde
keywords BIOLOGICAL-ACTIVITIES; CHEMICAL-COMPOSITION; ANTICANCER ACTIVITY; ESSENTIAL OIL; IONIC LIQUID; 1,5-BENZODIAZEPINES; LEUCOTRICHUS; EFFICIENT; CATALYST; ANTIOXIDANT
abstract A new series of benzodiazepines and chiral Schiff bases have been prepared by an in situ condensation of (S)-(-)-perillaldehyde, occurring naturally in the essential oil of Ammodaucus leucotrichus subsp. Leucotrichus, with various amines, hydrazines, and oxalyl dihydrazide. Pure enantiomeric compounds TK16 have been obtained in moderate to good yields, after spontaneous precipitation in ethanol. The structures have been identified by one-and two-dimensional NMR experiments, FTIR, and single-crystal X-ray. To confirm the formation of unique Schiff base enantiomers and diastereomeric mixtures of benzodiazepines, chiral HPLC was used. All the new derivatives were screened for their antioxidant and antibacterial activities. The antioxidant activity has been evaluated using the DPPH-scavenging activity method, in which the benzodiazepines show an excellent activity compared to gallic acid. The antimicrobial studies revealed the highest inhibition of the chloro-benzodiazepine derivative against MSSA, MRSA, and M. luteus with MIC values between 0.125-0.25mg/mL when compared with metronidazole used as reference. Molecular docking performed on the penicillin-binding protein (PBP2a) from methicillin-resistant S. aureus MRSA has demonstrated sensitivity towards the novel Schiff Bases. (c) 2021 Elsevier B.V. All rights reserved.
publisher ELSEVIER
issn 0022-2860
isbn 1872-8014
year published 2021
volume 1241
digital object identifier (doi) 10.1016/j.molstruc.2021.130690
web of science category 10
subject category Chemistry, Physical
unique article identifier WOS:000670212600014
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journal impact factor 2.463
5 year journal impact factor 2.121
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