Synthesis of some new isoxazole compounds and their biological tyrosinase and antioxidant activities

被引:0
作者
Fandakli, Seda [1 ]
机构
[1] Avrasya Univ, Dept Nutr & Dietet, Fac Hlth Sci, Trabzon, Turkey
关键词
Isoxazole; tyrosinase inhibition; antioxidant activity; ANTIMICROBIAL ACTIVITY; IN-VITRO; INHIBITION; EXTRACT;
D O I
10.3906/kim-2110-39
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this study, 7 new isoxazole compounds (8-14) were synthesized from the cyclization of chalcone compounds (1-7) containing different functional groups with hydroxylamine hydrochloride in alkaline medium. Tyrosinase and antioxidant properties of 8-14 were investigated. IC50 values for the tyrosinase enzyme inhibition of compounds 8, 11, 12, and 13 were varied between 61.47 +/- 3.46 and 188.52 +/- 5.85, while compounds 9, 10 and 14 did not show any inhibition effect. The antioxidant properties of 8-14 were investigated by DPPH and CUPRAC methods. Compound 12 showed the best DPPH radical scavenging activity (SC50: 40.21 +/- 2.71), while 12 and 13 had shown the greatest Cupric ion reducing effect as 1.233 +/- 0.015 and 1.245 +/- 0.019 mg TEAC/mg, respectively. As a result, the change of functional groups in the synthesized compounds caused a significant difference in the biological properties of 8-14.
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页数:22
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共 43 条
[1]   Design and synthesis of (3,5-disubstituted isoxazole)-linked [1,5]-benzodiazepine conjugates: evaluation of their antimicrobial and anti-tyrosinase activities [J].
Abdallah, Wejdane ;
Daami-Remadi, Mejda ;
Znati, Mansour ;
Ben Jannet, Hichem ;
Gharbi, Rafik .
JOURNAL OF CHEMICAL RESEARCH, 2017, (01) :12-17
[2]   4-Hydroxyphenylpyruvate Dioxygenase Inhibitors in Combination with Safeners: Solutions for Modern and Sustainable Agriculture [J].
Ahrens, Hartmut ;
Lange, Gudrun ;
Mueller, Thomas ;
Rosinger, Chris ;
Willms, Lothar ;
van Almsick, Andreas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (36) :9388-9398
[3]   Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides [J].
Albay, Canan ;
Kahriman, Nuran ;
Iskender, Nagihan Yilmaz ;
Karaoglu, Sengul Alpay ;
Yayli, Nurettin .
TURKISH JOURNAL OF CHEMISTRY, 2011, 35 (03) :441-454
[4]   Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine:: CUPRAC method [J].
Apak, R ;
Güçlu, K ;
Özyürek, M ;
Karademir, SE .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (26) :7970-7981
[5]   Potent Tyrosinase Inhibitory Activity of Curcuminoid Analogues and Inhibition Kinetics Studies [J].
Athipornchai, Anan ;
Niyomtham, Nattisa ;
Pabuprapap, Wachirachai ;
Ajavakom, Vachiraporn ;
Duca, Maria ;
Azoulay, Stephane ;
Suksamrarn, Apichart .
COSMETICS, 2021, 8 (02)
[6]   A NEW SYNTHESIS OF ISOXAZOLES FROM 1,4 DIANIONS OF OXIMES HAVING AN ALPHA HYDROGEN - MASS SPECTROMETRY [J].
BEAM, CF ;
DYER, MCD ;
SCHWARZ, RA ;
HAUSER, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) :1806-+
[7]   Green multicomponent synthesis, antimicrobial and antioxidant evaluation of novel 5-amino-isoxazole-4-carbonitriles [J].
Beyzaei, Hamid ;
Deljoo, Mahboubeh Kamali ;
Aryan, Reza ;
Ghasemi, Behzad ;
Zahedi, Mohammad Mehdi ;
Moghaddam-Manesh, Mohammadreza .
CHEMISTRY CENTRAL JOURNAL, 2018, 12
[8]  
BRAND-WILLIAMS W, 1995, FOOD SCI TECHNOL-LEB, V28, P25
[9]   Final Report of the Safety Assessment of Kojic Acid as Used in Cosmetics [J].
Burnett, Christina L. ;
Bergfeld, Wilma F. ;
Belsito, Donald V. ;
Hill, Ronald A. ;
Klaassen, Curtis D. ;
Liebler, Daniel C. ;
Marks, James G., Jr. ;
Shank, Ronald C. ;
Slaga, Thomas J. ;
Snyder, Paul W. ;
Andersen, F. Alan .
INTERNATIONAL JOURNAL OF TOXICOLOGY, 2010, 29 :244S-273S
[10]   Natural Melanogenesis Inhibitors Acting Through the Down-Regulation of Tyrosinase Activity [J].
Chang, Te-Sheng .
MATERIALS, 2012, 5 (09) :1661-1685