Synthesis of 4-Hydroxy-2-pyridinone Derivatives and Evaluation of Their Antioxidant/Anticancer Activities

被引:17
作者
Hamama, Wafaa S. [1 ]
Ghaith, Eslam A. [1 ]
Ibrahim, Mona E. [1 ]
Sawamura, Masaya [2 ]
Zoorob, Hanafi H. [1 ]
机构
[1] Mansoura Univ, Fac Sci, Dept Chem, Mansoura 35516, Egypt
[2] Hokkaido Univ, Inst Chem React Design & Discovery WPI ICReDD, Sapporo, Hokkaido 0010021, Japan
关键词
Antioxidants; Cytotoxic Activity; Dehydroacetic acid; Mechanisms; Molecular Modeling; Pyridinone; Reactions;
D O I
10.1002/slct.202004682
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple approach was applied for the regioselective synthesis of various pyridine-2-one derivatives or annulated pyridine as novel heterocyclic systems from the reaction of dehydroacetic acid (DHA) with mono- or bidentate nucleophile as with benzylamine and/or phenylenediamines in dichloromethane followed by transformation with different halo-compounds in refluxing 1,4-dioxane has been achieved in moderate to excellent yields (48-93 %). In addition, DFT studies of the key synthesized compounds were carried out for confirmed proposed mechanisms. The newly synthesized compounds were screened for their in-vitro inhibition activities against mammary gland breast cancer (MCF-7) and human prostate cancer (PC-3) using the MTT colorimetric method. Also, the target synthesized compounds were evaluated as antioxidant agents.
引用
收藏
页码:1430 / 1439
页数:10
相关论文
共 42 条
[11]   INFRARED SPECTRA OF COMPLEXES OF 4-PYRIDONES [J].
COOK, D .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1963, 41 (02) :515-&
[12]   1,3-N,O-Complexes of late transition metals. Ligands with flexible bonding modes and reaction profiles [J].
Drover, Marcus W. ;
Love, Jennifer A. ;
Schafer, Laurel L. .
CHEMICAL SOCIETY REVIEWS, 2017, 46 (10) :2913-2940
[13]   Design, Synthesis, Characterization, and Insecticidal Bioefficacy Screening of Some New Pyridine Derivatives [J].
El-Dean, Adel M. Kamal ;
Abd-Ella, Aly A. ;
Hassanien, Reda ;
El-Sayed, Mohamed E. A. ;
Abdel-Raheem, Shaban A. A. .
ACS OMEGA, 2019, 4 (05) :8406-8412
[14]   Pyridine-Ureas as Potential Anticancer Agents: Synthesis and In Vitro Biological Evaluation [J].
El-Naggar, Mohamed ;
Almahli, Hadia ;
Ibrahim, Hany S. ;
Eldehna, Wagdy M. ;
Abdel-Aziz, Hatem A. .
MOLECULES, 2018, 23 (06)
[15]   DEHYDROACETIC ACID, A BENZODIAZEPINE PRECURSOR [J].
ELABBASSI, M ;
DJERRARI, B ;
ESSASSI, EM ;
FIFANI, J .
TETRAHEDRON LETTERS, 1989, 30 (50) :7069-7070
[16]   Convenient Synthesis of Binary and Fused Pyrazole Ring Systems: Accredited by Molecular Modeling and Biological Evaluation [J].
Ghaith, Eslam A. ;
Zoorob, Hanafi H. ;
Ibrahim, Mona E. ;
Sawamura, Masaya ;
Hamama, Wafaa S. .
CHEMISTRYSELECT, 2020, 5 (47) :14917-14923
[17]   The Scope of 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (DHA) [J].
Ghaith, Eslam A. ;
Zoorob, Hanafi H. ;
Ibrahim, Mona E. ;
Sawamura, Masaya ;
Hamamai, Wafaa S. .
CURRENT ORGANIC CHEMISTRY, 2020, 24 (13) :1459-1490
[18]   Brexpiprazole: First Global Approval [J].
Greig, Sarah L. .
DRUGS, 2015, 75 (14) :1687-1697
[19]   8-Azapurines as new inhibitors of cyclin-dependent kinases [J].
Havlicek, L ;
Fuksova, K ;
Krystof, V ;
Orsag, M ;
Vojtesek, B ;
Strnad, M .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (18) :5399-5407
[20]   4-Hydroxy-2-pyridone alkaloids: Structures and synthetic approaches [J].
Jessen, Henning Jacob ;
Gademann, Karl .
NATURAL PRODUCT REPORTS, 2010, 27 (08) :1168-1185