Schiff bases and their amines: Synthesis and discovery of carbonic anhydrase and acetylcholinesterase enzymes inhibitors

Abstract

Three series of symmetrical Schiff bases were synthesized from 1,2-diaminoethane, 1,3-diaminopropane and 1,4-diaminobutane and substituted benzaldehydes, and reduced by sodium borohydride to the corresponding benzylic diamines 4-6. All of the compounds obtained were characterized using elemental analysis, FT-IR, H NMR, and C NMR spectroscopy. The enzyme inhibitory properties of these compounds were tested and the influence of the alkane chain length and the substituents on the phenyl group on the enzyme inhibition activity were examined. The novel Schiff bases and their amine derivatives (1a-d, 2a-d, 3b-d, 4a-c, 5a-c, 6a, 6c, 6d) were effective inhibitors of the cytosolic carbonic anhydrase I and II isoforms (hCA I and II), and acetylcholinesterase (AChE) with K values in the range of 159.43 ± 30.03 to 563.73 ± 115.30 nM for hCA I, 104.88 ± 18.44 to 524.32 ± 95.03 nM for hCA II, and 3.95 ± 0.74 to 30.83 ± 6.81 nM for AChE.

Synthesis, characterization, biological evaluation, and in silico studies of novel 1,3‐diaryltriazene‐substituted sulfathiazole derivatives

“…Furthermore, the K I values of novel ST1-11 and TAC are summarized in Table 1. As can be observed from the results recorded in [37,38] 2. (ACR), and miglitol compounds.…”

Synthesis and characterization of novel substituted thiophene derivatives and discovery of their carbonic anhydrase and acetylcholinesterase inhibition effects

“…Alzheimer’s disease (AD), a neurodegenerative, terminal disease, and incurable is the most popular form of dementia among aged people . Three out of the four drugs presently recorded for the therapy of AD are based on the inhibition act of acetylcholinesterase (AChE) enzyme; hence, their utility is still limited since the long‐term efficacy and safety are not exactly clear .…”

Inhibition profiles of Voriconazole against acetylcholinesterase, α‐glycosidase, and human carbonic anhydrase I and II isoenzymes

“…For determination of CA activity, both esterase and hydratase activities have been commonly employed; however, esterase activity has been used more often because its substrate is more easily adjusted than hydratase. Esterase activity was used for determining inhibition type and K i values of inhibitors . In this paper, AZA was employed.…”

“…Esterase activity was used for determining inhibition type and K i values of inhibitors. [79][80][81] In this paper, AZA was employed. AZA is used as a control for CA inhibitors (CAIs) and for the medical treatment of glaucoma, altitude sickness, epileptic seizure, dural ectasia, and idiopathic intracranial hypertension.…”