New vitamin K3 (menadione) analogues: synthesis, characterization, antioxidant and catalase inhibition activities
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Ó Indian Academy of Sciences Sadhana (0123456789().,-volV)FT3](0123456 789().,-volV)
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New vitamin K3 (menadione) analogues: synthesis, characterization, antioxidant and catalase inhibition activities NAHIDE GULSAH DENIZa , AESHA F SH ABDASSALAMa EMIN AHMET YESILc and CIGDEM SAYILa,*
, MUSTAFA OZYUREKb
,
a Engineering
Faculty, Department of Chemistry, Division of Organic Chemistry, Istanbul University-Cerrahpasa, 34320 Avcilar, Istanbul, Turkey b Engineering Faculty, Department of Chemistry, Division of Analytical Chemistry, Istanbul University-Cerrahpasa, 34320 Avcilar, Istanbul, Turkey c Vocational School, Polymer Technology Programme, Istanbul Gedik University, Pendik, Istanbul, Turkey E-mail: [email protected] MS received 13 January 2020; revised 21 July 2020; accepted 25 July 2020
Abstract. In this study, derivatives of new vitamin K3 were synthesized by the reactions of 2-methyl-1,4naphthoquinone 1 with some heterocyclic ring substituted nucleophiles: 1-piperonylpiperazine 2, 1-(2furoyl)piperazine 5, 1-(2-aminoethyl)piperidine 8, 1-(2-aminoethyl)pyrrolidine 10 and 2,6-dimethyl morpholine 12 in chloroform/triethylamine (TEA) or ethanol at room temperature. Their structures were characterized by Fourier transform infrared spectroscopy (FT-IR), 1H nuclear magnetic resonance (1H NMR), attached proton test nuclear magnetic resonance (APT-NMR) and mass spectrometry (MS). Newly synthesized vitamin K3 derivatives (3, 4, 6, 7, 9, 11, 13, 14) have shown catalase inhibition activity and compound 13 has displayed remarkable potency against catalase enzyme. These compounds were also tested for their antioxidant capacity in vitro by CUPRAC method. Keywords. Vitamin K3 (Menadione); heterocyclic ring; CUPRAC method; catalase inhibition activity.
1. Introduction The quinone compounds are colored compounds due to their conjugation system and are used as natural pigments. The quinone compounds have a wide range of biological activities, and their reactivity and chemical profile is an interesting field of research worldwide.1 A considerable number of natural and synthetic of quinones especially, 1,4-naphthoquinone derivatives have shown an interesting variety of biological properties, such as antimalarial,2–4 antifunantibacterial,9–12 antitumor,13,14 and gal,5–8 15,16 due to their redox antiallergic activities potentials.17 There are many known natural organic substances contained in the naphthoquinone in their main structure, especially vitamin K groups. Vitamins K, have a basic structure of 2-methyl-1,4-naphthoquinone and different side chain in (C-3) position. Generally,
vitamin K regulates blood clotting properties.18 Vitamin K is naturally found in two forms: Vitamin K1, K2. Vitamin K1 is called phylloquinone, its chemical is ‘‘2-methyl-3-suppository-1,4-naphthoquinone, green plants are rich in this vitamin, and vitamin K2 is a group of menaquinone compounds that can be made by bacteria inside the intestine. The chemical name is ‘‘2-methyl-3-difarnesyl-1,4-naphthoquinone.’’ There are also other na
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