Design and Bioevaluation of Novel Hydrazide-Hydrazones Derived from 4-Acetyl- N -Substituted Benzenesulfonamide
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esign and Bioevaluation of Novel Hydrazide-Hydrazones Derived from 4-Acetyl-N-Substituted Benzenesulfonamide E. Bozkurta, Y. Sıcakb, E. E. Oruç-Emrea, 1, A. Karaküçük Iyidoğana, and M. Öztürkc aDepartment
of Chemistry, Faculty of Arts and Sciences, Gaziantep University, Gaziantep, 27410 Turkey of Medicinal and Aromatic Plants, Köyceğiz Vocational School, Muğla Sıtkı Koçman University, Muğla, 48800 Turkey cDepartment of Chemistry, Faculty of Sciences, Muğla Sıtkı Koçman University, Muğla, 48800 Turkey
bDepartment
Received January 1, 2020; revised March 18, 2020; accepted March 22, 2020
Abstract—In this research, a series of hydrazine-hydrazone derivatives (Ia–g), (IIa–h) were synthesized to discover new antioxidant and anticholinesterase agents. The structures of synthesized compounds were characterized by spectroscopic data using UV, IR, 1H, 13C NMR, mass spectroscopy, and elemental analysis. The bio-evaluation of the synthesized compounds (Ia–g), (IIa–h) were evaluated according to in vitro activity assays. The results of β-carotene/linoleic acid assay showed that among the synthesized compounds, the (Ib), (Ie), (IIb–IIe), and (IIh) compound exhibited higher activity for the lipid peroxidation inhibitory activity. In the DPPH free scavenging activity and the cation radical scavenging activity in ABTS•+ activity, compound (IIb) was found to be more active. In the CUPRAC reduced power assay, the A0.5 values of all synthesized compounds were better than α-TOC. In AChE assay, compound (IIb) exhibited the most activity with IC50 = 11.12 ± 0.74 μM, while the compounds (Ib–g) and (IIb–h), exhibited excellent activity than the positive standard galantamine (IC50 = 46.06 ± 0.10 μM) in the BChE assay. Keywords: sulfonamide, hydrazone, antioxidant activity, anticholinesterase inhibitory activity, Lipinski’s rules DOI: 10.1134/S1068162020050052
INTRODUCTION Sulfonamides (sulfa drugs) are significant bioactive synthetic medicines. Over the last decades, many sulfa drugs have been developed and began using in the treatment. [1]. The brinzolamide, which is a carbonic anhydrase inhibitor, has been used to reduce intraocular pressure in patients with open-angle glaucoma or ocular hypertension [2]. An anti-glaucoma agent, dorzolamide, is used to decrease the production of aqueous humor [3]. Another sulfonamide drug sultiame having anticonvulsant activity is reported for the cure of West syndrome and epilepsy [4]. Besides, studies have shown that sulfonamides exhibit antioxidant and anticholinesterase activities [5–9]. Another essential organic compound class, hydrazones (–CONHN=CH–) are formed by the reaction of hydrazine and ketones/aldehydes [10]. Hydrazones can be used as intermediates to synthesize coupling products using the active hydrogen of the azomethine group. Besides, they are very effective organic compounds and used as drugs in the treatment such as iso1 Corresponding
author: phone: + (903) 423-17-29-98; fax: + (903) 423-60-10-32; e-mail: [email protected].
niazid (antimicrobial), nifuroxazide (intestinal antisep
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