Synthetic compound with high antioxidant properties

Abstract

The invention relates to a synthetic compound having high free radical scavenging activity and high antioxidant properties.

Description

[0001] SYNTHETIC COMPOUND WITH HIGH ANTIOXIDANT PROPERTIES Technical Field

[0002] The invention relates to a synthetic compound having high free radical scavenging activity and high antioxidant properties.

[0003] Prior Art

[0004] Antioxidants are essential for the survival of all living beings and are molecules that fight free radicals in the body. Antioxidants can prevent or slow down cell damage caused by free radicals, which are unstable molecules that the body produces in response to environmental and other pressures. It is harmful if the levels of free radicals in the body become too high. They are linked to many diseases, including diabetes, heart disease, and cancer. However, free radicals also serve important functions that are essential for health. For example, immune cells use free radicals to fight infections. Consequently, the body needs to maintain a certain balance between free radicals and antioxidants. The body has its own antioxidant defense to keep free radicals under control. When free radicals outnumber antioxidants, it can lead to a condition called oxidative stress. Prolonged oxidative stress can damage DNA and other important molecules in the body. Sometimes it even leads to cell death. Damage to DNA increases the risk of cancer. It is known that various lifestyle, stress, and environmental factors promote excessive free radical formation and oxidative stress.

[0005] However, antioxidants are also used as additives in the food, cosmetic, and pharmaceutical industries to prevent the oxidation of unstable compounds.

[0006] Antioxidants can be natural or synthetic. Natural antioxidants are also found in foods, particularly in fruits, vegetables, and other plant-based foods. Common supplement ingredients considered to have antioxidant effects include Vitamin E,beta-carotene, Vitamin C, selenium, and certain other compounds. Furthermore, there are also some synthetic antioxidants that inhibit oxidation, such as butylated hydroxytoluene (BHT), propyl gallate (PG), butylated hydroxyanisole (BHA), and tert-butylhydroquinone (TBHQ). In recent years, scientists have been making efforts not only to synthesize new chemical compounds but also to produce compounds that are targeted, economical, and potentially beneficial to humanity. Therefore, the investigation of compounds exhibiting antioxidant activity continues to be an important field for chemists today, as it was in the past. In this way, new antioxidant compounds are synthesized and their antioxidant activities are investigated day by day.

[0007] The concept of antioxidant capacity first emerged as a chemical concept and was subsequently adapted to fields such as medicine, biology, food, and epidemiology. It is quite important to know the antioxidant profiles of these products in order to prevent the loss of commercial and nutritional value during the processing and storage of foods and pharmaceutical products. Therefore, the determination of the potential antioxidant capacity of foods and pharmaceutical products necessitates the development of a rapid and simple method. Currently, there are many bioanalytical methods measuring the antioxidant effect. Among these, the l,l-diphenyl-2-picrylhydrazyl (DPPH) scavenging assay is the most standard, popular, and widely used method for determining antioxidant ability. In this context, many studies have been previously conducted involving attempts to adapt the DPPH radical scavenging method to different analytes, to investigate the highest antioxidant activity values, and to optimize the measurement method. Therefore, the introduction of measurements aiming to standardize the conditions of DPPH radical scavenging activity, including various reaction media suitable for this assay, is extremely important. This method is a simple analysis in which synthetic compounds or plant extracts are mixed with a DPPH solution and their absorbances are measured after a certain period of time. However, despite rapid advancements in instrumental techniques and analyses, this method has not undergone extreme alteration.The properties of the obtained new phosphazene derivatives vary depending on the attached substituents. There is a limited number of studies in the literature on the antioxidant activity of phosphazenes. When the free radical scavenging activities of these compounds are examined, it has been observed that cyclic phosphazene derivatives containing heterocyclic amine substituents such as pyrrolidine, piperidine, morpholine, and l,4-dioxa-8-azaspiro[4,5]decane exhibit higher activity compared to those containing chlorine substituents. Furthermore, it has been reported that the number of members in the spiro ring and groups such as methyl and ethyl located in the side chain affect the antioxidant activity.

[0008] In the document titled “Phosphorus-Nitrogen Compounds. Part 42. The comparative syntheses of 2-cis-4-ansa(N / O) and spiro(N / O) cyclotetraphosphazene derivatives: spectroscopic and crystallographic characterizations, anti tuberculosis and cytotoxic activity studies”, the comparative syntheses of 2-cis-4-ansa(N / O) and spiro(N / O) cyclotetraphosphazene derivatives: spectroscopic and crystallographic characterizations, and antituberculosis and cytotoxic activity studies are discussed.

[0009] Upon examination of the studies in the prior art, a need has arisen to develop the synthetic compound subject to the invention having high free radical scavenging activity and high antioxidant properties.

[0010] Object of the Invention

[0011] The object of the invention is to develop a synthetic compound having high free radical scavenging activity and high antioxidant properties.

[0012] Detailed Description of the Invention

[0013] The invention is the compound of Formula A having high free radical scavenging activity and high antioxidant properties, wherein;

[0014]

[0015] (Formula A)

[0016] X: N (nitrogen),

[0017] Y: FcCH2(ferrocenylmethyl).

[0018] Z: O (oxygen),

[0019] R: CH3(methyl),

[0020] R′: PipCH2(piperonylmethyl).

[0021] The IUPAC name and chemical structure of the compound subject to the invention are specified below.

[0022] Mono-ferrocenyl-spiro(N / O)-trispiro(N / N)-cyclotetraphosphazene

[0023]

[0024] The synthesis stages of the compound subject to the invention are explained below.

[0025] 3-{N-ferrocenylmethylimino)-1 -propanol

[0026] (1) 3-(N-fenocenylmethylarn!no)-1 -propanol

[0027]

[0028] (1i) Sodium 3-(N-ferrocenylmethylamino)-1-propoxide

[0029] The starting compound, mono-ferrocenyldiaminoalcohol (Fe(C5H5)2CH2N(CH2)3OH) (1), was obtained from the reduction of the Schiff base, formed as a result of reacting ferrocenecarboxaldehyde with 3 -amino- 1-propanol in a methanol medium, with NaBH4again in a methanol medium. The sodium salt (1i) was obtained by reacting the N / O donor mono-ferrocenyldiaminoalcohol compound with NaH in a tetrahydrofuran (THF) medium.

[0030]

[0031] The piperonyl bidentate diamine compound (2) used as a side group was obtained from the reduction of the Schiff base, formed as a result of reacting piperonal with 7V-methyl-l,3-propanediamine, with NaBH4again in a methanol medium.

[0032] Et3N dry THF

[0033] 04 } Ci

[0034]

[0035] Subsequently, spiro- (3) and 2,4-ansa-mono-ferrocenylcyclotetraphosphazene compounds were synthesized from the reaction of the sodium salt (li) of 3-(N-ferrocenylmethylamino)-1-propanol (1) with the tetramer in a 1:1 stoichiometric ratio in the presence of Et3N in THF solvent and under argon atmosphere at -10 °C. The solution was allowed to stir for 96 hours, filtered, and its solvent (THF) was removed in a rotary evaporator. Afterwards, the reaction solution was filtered, the solvent was removed by evaporating to dryness in a rotary evaporator, and the obtained mixture of mono-ferrocenyl derivatives in the solid state (ansa and spiro mixture) was dissolved in toluene and separated into its components with the aid of a silica gel filled column prepared again with toluene. The product mixture obtained from the column was dissolved in n-hexane(heptane): ethyl acetate (5:1) solvent mixture and applied to a silica gel filled column prepared with the solvent mixture in the same ratio, and mono-ferrocenyl spiro- (3) and 2,4-ansa-cyclotetraphosphazene products were isolated respectively.

[0036] Finally, the fully substituted cyclotetraphosphazene compound subject to the invention (4) was synthesized as a result of the reactions of the synthesized partially substituted mono-ferrocenyl-spiro-cyclotetraphosphazene compound (3) with excess N / N donor mono-piperonyldiamine (2) in the presence of triethylamine in adry THF medium under reflux under argon atmosphere. The reaction mixture was stirred under reflux for four days. The reaction solutions were filtered, and the solvent (THF) was removed in a rotary evaporator. The remaining mixture of products in the solid state was dissolved in a toluene-THF (1:5) solvent mixture and purified by column chromatography using a silica gel filled column prepared with the same solvent mixture.

[0037] Determination of the antioxidant activities of phosphazene compounds (DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging assay)

[0038] Initially, solutions of the compound subject to the invention (4) and positive controls (BHA and a-Tocopherol) having a concentration of 2500 pM were obtained by dissolving them in ethyl acetate. Subsequently, freshly prepared DPPH (0.1 mM) was added to these solutions, followed by allowing the mixtures to incubate in the dark at ambient temperature for 30 minutes. The maximum absorbance values of the obtained mixtures were measured using a UV-VIS spectrophotometer. After incubation, the maximum absorbance at 517 nm was measured. Equation 1 was used to evaluate the antioxidant activity of the samples.

[0039] % Radical scavenging activity = (ACOntroi - Asampie / ACOntroi) x 100 (Equation 1)

[0040] In this equation, ACOntroi represents the absorbance of the negative control (DPPH solution), while Asampie indicates the absorbance of the test compounds.

[0041] The results are specified in Table 1.

[0042] Compound DPPH radical scavenging activity (% inhibition) ± SEMa

[0043] Compound subject to the invention 91.3±0.2

[0044] BHAb94.0±0.3

[0045] a- Tocopherolb97.1±0.1

[0046]

[0047] Table 1: Free radical scavenging activity of the compound when DPPH is used at a concentration of 2500 pM (a) Standard mean error of three tests, (b) Standard antioxidant

Claims

CLAIMS1. A compound of Formula A having high free radical scavenging activity and high antioxidant properties, wherein;(Formula A)X: N (nitrogen),Y: FcCH2(ferrocenylmethyl).Z: O (oxygen),R: CH3(methyl),R′: PipCH2(piperonylmethyl).

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