An empirical relationship between antidiabetic and antioxidant properties of molecules using protocatechuic acid (PcA) as a test compound has been found.
Tryptanthrin is a potent natural alkaloid with good in vitro pharmacological properties. Herein, we report the synthesis of the compound via a new method involving the reduction of isatin with solid-state-supported sodium borohydride under microwave irradiation. The title compound has been tested for its analgesic and antiinflammatory activity. The results showed that tryptanthrin dose dependently inhibits oedema and pain formation in all the models used. The agent also exhibited significant higher effects in its anti-inflammatory and analgesic activities better than positive drugs (aspirin and indomethacin) being currently used in the treatment and in the management of acute and chronic forms of pain and inflammatory disorders. The inhibitory potential of the compound was investigated by molecular docking using the software AutoDock Vina. The docking results were used to better rationalize the action and prediction of the binding affinity of tryptanthrin. Density Functional Theory (DFT) calculations at the B3LYP/6-311þþG (2df, 2pd) level of theory showed that compared to ascorbic acid, tryptanthrin shows higher antioxidant activity which may be improved upon by functionalizing the aromatic core to enhance its solubility in polar solvents. The calculated electronic and thermodynamic properties obtained for tryptanthrin compete well with the standard ascorbic acid.
ÖzetBu çalışmada periferal olmayan konumlarında tetra sübstitüe karboksilik asit uçları içeren, suda çözünür, dört yeni ftalosiyanin türevi sentezlenmiştir. Bunun için öncelikle 3-nitroftalonitril ile 4-merkaptobenzoikasit tepkimeye sokularak yeni bir ftalonitril türevi (1) elde edilmiştir. Bu yeni ftalonitril türevi FTIR, 1 H NMR ve MS gibi spektroskopik teknikler ile elementel analiz kullanılarak karakterize edilmiştir. 1 bileşiğinden çıkılarak metalsiz (2a), çinko (2b), kobalt (2c) ve nikel (2d) metalli dört farklı ve suda çözünür ftalosiyanin türevi sentezlenmiştir. Bu türevler arasındaki metalsiz ve çinko ftalosiyaninlerin fotofiziksel ve fotokimyasal özellikleri incelenmiştir. Fotofiziksel özellik olarak bileşiklerin (2a ve 2b) floresans emisyon ve uyarılma spektrumları alınmış, floresans kuantum verimleri ile floresans ömürleri hesaplanmıştır. Fotokimyasal çalışma olarak ise bileşiklerin (2a ve 2b) singlet oksijen kuantum verimleri hesaplanmıştır. Elde edilen sonuçlar ışığında özellikle 2b bileşiği, atık sulardaki organik kirleticilerin foto bozunmasında kullanılmak üzere önerilebilir.
Synthesis of Water-Soluble New Phthalocyanines and Investigation of Their PhotophysicochemicalPropertiesKeywords "Waste water";"Organic pollutant";"Phthalocyanines";"Singlet oxygen";"Photodegradation"
AbstractIn this work, four new phthalocyanine derivatives containing tetra-substituted carboxylic acid moieties at nanperipheral position and water soluble have been synthesized. First of all for this, a new phthalonitrile derivative (1) was obtained from the reaction of 3-nitrophthalonitrile and 4-mercapto benzoic acid. This phthalonitrile derivative (1) was characterized by spectroscopic techniques such as FTIR, 1 H NMR, MS and as well as elemental analysis. Four different (2a, 2b, 2c and 2d) and water-soluble phthalocyanine derivatives were synthesized by cyclotrimerization reaction of compound 1. Among these phthalocyanines the photophysical and photochemical properties of metal-free (2a) and zinc (2b) derivatives have been examined. The fluorescence emission and excitation spectra of the compounds (2a and 2b) were examined, fluorescence quantum yields and fluorescence lifetimes were calculated as photophysical properties. Singlet oxygen quantum yields of the compounds (2a and 2b) were calculated as a photochemical study. The results obtained show that in particular the compound 2bmay be suggested to be used for photodegradation of organic pollutants in the waste water.
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