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

被引：16

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

来源：

CHEMISTRYSELECT | 2021年 / 6卷 / 07期

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

页码：1430 / 1439

页数：10

共 42 条

[1] Al-Sehemi AG, 2014, INDIAN J CHEM B, V53, P1115
[2] Anam O., 2017, THERAP ADV GASTROENT, V10, P877
[3] Anticancer pyridines induce G2/M arrest and apoptosis via p53 and JNK upregulation in liver and breast cancer cells
Androustsopoulos, Vasilis P.
Spandidos, Demetrios A.
[J]. ONCOLOGY REPORTS, 2018, 39 (02) : 519 - 524
[4] Development of huperzine A and B for treatment of Alzheimer's disease
Bai, Donglu
[J]. PURE AND APPLIED CHEMISTRY, 2007, 79 (04) : 469 - 479
[5] Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid
Baldwin, Alex G.
Bevan, Jonathan
Brough, David
Ledder, Ruth
Freeman, Sally
[J]. MEDICINAL CHEMISTRY RESEARCH, 2018, 27 (03) : 884 - 889
[6] Novel milrinone analogs of pyridine-3-carbonitrile derivatives as promising cardiotonic agents
Bekhit, AA
Baraka, AM
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (12) : 1405 - 1413
[7] TTI-237:: A novel microtubule-active compound with in vivo antitumor activity
Beyer, Carl F.
Zhang, Nan
Hernandez, Richard
Vitale, Danielle
Lucas, Judy
Nguyen, Thai
Discafani, Carolyn
Ayral-Kaloustian, Semiramis
Gibbons, James J.
[J]. CANCER RESEARCH, 2008, 68 (07) : 2292 - 2300
[8] Synthesis and in vitro anti-proliferative effects of 3-(hetero)aryl substituted 3-[(prop-2-ynyloxy)(thiophen-2-yl)methyl]pyridine derivatives on various cancer cell lines
Chamakura, Upendar Reddy
Sailaja, E.
Dulla, Balakrishna
Kalle, Arunasree M.
Bhavani, S.
Rambabu, D.
Kapavarapu, Ravikumar
Rao, M. V. Basaveswara
Pal, Manojit
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (05) : 1366 - 1372
[9] Discovery of 2-aminopyridines bearing a pyridone moiety as potent ALK inhibitors to overcome the crizotinib-resistant mutants
Chen, Wenteng
Guo, Xiao
Zhang, Can
Ke, Di
Zhang, Guolin
Yu, Yongping
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 183
[10] Molecular and crystal structures of N,N′-propylene- and N,N′-phenylene-diylbis [3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione]
Cindric, M
Novak, TK
Uzarevic, K
[J]. JOURNAL OF MOLECULAR STRUCTURE, 2005, 750 (1-3) : 135 - 141

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