Synthesis and characterization of novel spiro-(2,2′-dioxybiphenyl)-cyclotriphosphazene derivatives bearing butylated oxyanisole groups and their antioxidant and antimicrobial activities

IF 2.4 3区化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Polyhedron Pub Date : 2024-10-11 DOI:10.1016/j.poly.2024.117252

Efe Bilal Sönmez , Şule Şahin Ün , Ceylan Mutlu Balcı , Devrim Atilla , Mine Gül Şeker , Hanife İbişoğlu

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Abstract

In this study, novel cyclotriphosphazene derivatives, {[N₃P₃(biph)(BA)₂] (6a/b), [N₃P₃(biph)(BA)₃] (7), [N₃P₃(biph)₂(BA)Cl (8) and [N₃P₃(biph)₂(BA)₂ (9)]}, (biph = 2′,2′′-dioxy-1′,1′′- biphenyl, BA = butylated oxyanisole}, were synthesized from the nucleophilic substitution reactions of butylated hydroxyanisole (BHA) (5) with [N₃P₃(biph)Cl₄] (3) and [N₃P₃(biph)₂Cl₂] (4), respectively. The structures of all the products (6a/b, 7, 8 and 9) were determined -using elemental analysis, mass and (¹H and ³¹P) NMR spectroscopic techniques. The molecular and crystal structure of compound 9 was also determined by single crystal X-ray crystallography. At the same time, the compounds (3, 4, 7, 8 and 9) were tested for their antimicrobial and antioxidant (free radical scavenging) activities. Of all, compounds 8 and 9 showed relatively significant antimicrobial activity against the control strains Bacillus cereus DSMZ 4312 (16,5 and 18,25 mm) and against Staphylococcus aureus ATCC 29213 (25 and 22,5 mm) compared to their positive controls. The MIC₅₀ values of compounds 8 and 9 against Bacillus cereus were determined at 125 µg/mL and < 325 µg/mL, respectively, and Staphylococcus aureus at 125 µg/ mL for both compounds. While the other compounds (3, 4 and 7) did not possess antimicrobial properties, they showed strong antioxidant activity. In the antioxidant assay based on the EC₅₀ value of BHA used as a control, compound 7 showed antioxidant activity even at low concentrations such as 9,37 µg/ mL (83 %), while compounds 3 and 4 showed antioxidant properties even at relatively low concentrations such as 18,75 µg/mL. Compounds 8 and 9, two antimicrobial compounds, did not exhibit antioxidant properties.

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带有丁基化氧杂茴香醚基团的新型螺-(2,2′-二氧联苯)-环三磷嗪衍生物的合成和表征及其抗氧化和抗菌活性

本研究中，新型环三唑烷衍生物{[N3P3(biph)(BA)2] (6a/b)、[N3P3(biph)(BA)3] (7)、[N3P3(biph)2(BA)Cl (8)和[N3P3(biph)2(BA)2 (9)]}，（biph = 2′,2′′-二氧-1′,1′′-联苯、BA = 丁基羟基苯甲醚}，分别由丁基羟基苯甲醚（BHA）（5）与[N3P3(biph)Cl4]（3）和[N3P3(biph)2Cl2]（4）的亲核取代反应合成。利用元素分析、质量和（1H 和 31P）核磁共振光谱技术确定了所有产物（6a/b、7、8 和 9）的结构。化合物 9 的分子和晶体结构也是通过单晶 X 射线晶体学确定的。同时，还测试了化合物（3、4、7、8 和 9）的抗菌和抗氧化（清除自由基）活性。与阳性对照相比，化合物 8 和 9 对对照菌株蜡样芽孢杆菌 DSMZ 4312（16.5 和 18.25 mm）和金黄色葡萄球菌 ATCC 29213（25 和 22.5 mm）具有相对显著的抗菌活性。化合物 8 和 9 对蜡样芽孢杆菌的 MIC50 值分别为 125 µg/mL 和 325 µg/mL，对金黄色葡萄球菌的 MIC50 值均为 125 µg/mL。虽然其他化合物（3、4 和 7）不具有抗菌特性，但它们具有很强的抗氧化活性。在以 BHA 的 EC50 值为对照的抗氧化试验中，化合物 7 即使在 9.37 µg/mL （83%）的低浓度下也显示出抗氧化活性，而化合物 3 和 4 即使在 18.75 µg/mL 的相对低浓度下也显示出抗氧化特性。化合物 8 和 9（两种抗菌化合物）没有表现出抗氧化特性。

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来源期刊

Polyhedron 化学-晶体学

CiteScore

4.90

自引率

7.70%

发文量

515

审稿时长

2 months

期刊介绍： Polyhedron publishes original, fundamental, experimental and theoretical work of the highest quality in all the major areas of inorganic chemistry. This includes synthetic chemistry, coordination chemistry, organometallic chemistry, bioinorganic chemistry, and solid-state and materials chemistry. Papers should be significant pieces of work, and all new compounds must be appropriately characterized. The inclusion of single-crystal X-ray structural data is strongly encouraged, but papers reporting only the X-ray structure determination of a single compound will usually not be considered. Papers on solid-state or materials chemistry will be expected to have a significant molecular chemistry component (such as the synthesis and characterization of the molecular precursors and/or a systematic study of the use of different precursors or reaction conditions) or demonstrate a cutting-edge application (for example inorganic materials for energy applications). Papers dealing only with stability constants are not considered.