Synthesis and biological activity of hydrazones of o- and p-hydroxybenzoic acids. Spatial structure of 5-Bromo-2-hydroxybenzylidene-4-hydroxybenzohydrazide

Abstract

A series of hydrazones based on hydrazides of o-and p-hydroxybenzoic acids have been prepared. N-(5-Bromo-2-hydroxybenzylidene)-4-hydroxybenzohydrazide has been studied by X-ray diffraction analysis; its molecule forms hydrogen bond with a solvating ethanol molecule. Biological activity of the synthesized hydrazones towards cathepsin Е and(or) elastase of human neutrophils has been determined.

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

“…The hydrazide-hydrazones which had phenyl or alkyl group near the salicylic hydroxy group caused a weak bathochromic effect. The spectroscopic data were consistent with the data published in the literature [46][47][48][50][51][52][53]. The geometry of the imine CH=N double bond of the aroyl hydrazones has an E configuration, which was proved by crystallographic studies of the imine derivatives of 4-hydroxybenzhydrazide with aldehydes such as 2,3-dimethoxybenzaldehyde [50], 5-bromosalicylaldehyde (2d) [53] and vanillic aldehyde (2g) [52].…”

“…Purity and homogeneity of known compounds were confirmed by measuring their m.p. for 1a [44], 1c [46], 1e [47], 1f [48], 1g [49], 1h-j [50], 2d [49], 2g [51], 4b [89], 4c [90], 6a [60], 6d [91], 6e [57], 6f [92], 7a [93], 7b [56], 7d [61], 7f [62], 8b [94], and 8c [95], or boiling points for 6b [96], 7e [97], FT-IR spectra for 1a [51], 1g [52], 1h-i [50], 2g [51], 1 H-and 13 C-NMR spectra for 1c [46], 1e [47], 1f [48], 1g [46], 1h-j [50], 2c [48], 2d [53] and/or HRMS for 2c [48], and comparing them with literature data. All new hydrazide-hydrazones 1b, 1d, 2a-b, 2e-f, 2h, 3a-g, were fully characterized.…”

Synthesis of a novel hydrazone-based compound applied as a fluorescence turn-on chemosensor for iron(iii) and a colorimetric sensor for copper(ii) with antimicrobial, DFT and molecular docking studies

“…Due to various medicinal properties such as antibacterial, antiviral, antifungal, anticancer and anti-inammatory activities, such compounds have attracted substantial interest over many years in the design of novel chemical compounds. [1][2][3][4][5][6][7] Moussa and co-workers reported a series of organic compounds containing the hydrazone moiety, which demonstrated high antioxidant activity against tyrosinase and cholinesterase. 8 Rahim et al designed and synthesized an aromatic hydrazidebased Schiff base targeting Alzheimer's disease that was shown to signicantly inhibit acetylcholinesterase and butyrylcholinesterase compared to the standard physostigmine.…”

Preparation and biological assessment of some aromatic hydrazones derived from hydrazides of phenolic acids and aromatic aldehydes

“…XO inhibitors are prospective agents for treatment of chronic heart failure and cardiovascular disease. The anti-inflammatory effect of derivatives of N -arylidene hydrazones has also been investigated in vitro as well as in inhibiting the activities of the proteolytic enzymes cathepsin Е and human neutrophil elastase which play important role in the development of autoimmune diseases ( Nurkenov et al., 2017 ).…”