Synthesis and biological evaluation of some novel resveratrol amide derivatives as potential anti-tumor agents

被引：21

作者：

Yao, Ri-Sheng ^{[1
]}

Lu, Xiao-Qin ^{[1
]}

Guan, Qiu-Xiang ^{[1
]}

Zheng, Lei ^{[2
]}

Lu, Xiang ^{[3
]}

Ruan, Ban-Feng ^{[1
]}

机构：

[1] Hefei Univ Technol, Sch Med Engn, Hefei, Peoples R China

[2] Hefei Univ Technol, Sch Biol & Food Engn, Hefei, Peoples R China

[3] Nanjing Univ, State Key Lab Pharmaceut Biotechnol, Nanjing, Jiangsu, Peoples R China

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 62卷

关键词：

Resveratrol derivatives; COX-2; inhibitor; Anti-tumor; Molecular docking; SELECTIVE INHIBITORS; CANCER-CHEMOTHERAPY; CYCLOOXYGENASE-2; COX-2; EXPRESSION; ANALOGS; DESIGN;

D O I：

10.1016/j.ejmech.2012.11.021

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Three series of novel resveratrol amide derivatives (1a-q, 2a-h, 3a-I) were synthesized and evaluated for their biological activities. All compounds were characterized by H-1 NMR, C-13 NMR, MS and elemental analysis. Furthermore, compound 3e was also characterized by X-ray crystallography. All the compounds were evaluated for their anti-tumor activity against MCF-7, A549 and B16-F10 tumor cell lines as well as cyclooxygenase-2 (COX-2)-derived prostaglandin E2 (PGE(2)) inhibitory activity of murine macrophage RAW 264.7 cell line. Among them, compounds 1c, 1g and 3e displayed the most potent COX-2 inhibitory activity with the IC50 values of 1.02, 1.27 and 1.98 mu M, respectively. Molecular docking studies were performed to position compounds 1c and 3e into the active site of COX-2 to determine the probable binding modes. (C) 2012 Elsevier Masson SAS. All rights reserved.

引用

页码：222 / 231

页数：10

共 22 条

[1] Anti-inflammatory profile of some synthesized heterocyclic pyridone and pyridine derivatives fused with steroidal structure [J].

Amr, Abdel-Galil E. ;

Abdulla, Mohamed M. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (13) :4341-4352

[2]

Attiga FA, 2000, CANCER RES, V60, P4629

[3] Antimitotic and antiproliferative activities of chalcones: Forward structure-activity relationship [J].

Boumendjel, Ahcene ;

Boccard, Juien ;

Carrupt, Pierre-Alain ;

Nicolle, Edwige ;

Blanc, Madeleine ;

Geze, Annabelle ;

Choisnard, Luc ;

Wouessidjewe, Denis ;

Matera, Eva-Laure ;

Dumontet, Charles .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (07) :2307-2310

[4] Potential anti-inflammatory phenolic glycosides from the medicinal plant Moringa oleifera fruits [J].

Cheenpracha, Sarot ;

Park, Eun-Jung ;

Yoshida, Wesley Y. ;

Barit, Chaz ;

Wall, Marisa ;

Pezzuto, John M. ;

Chang, Leng Chee .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (17) :6598-6602

[5]

Davies NM, 2004, J PHARM PHARM SCI, V7, P332

[6] Cyclooxygenase-2: a novel target for cancer chemotherapy? [J].

Dempke, W ;

Rie, C ;

Grothey, A ;

Schmoll, HJ .

JOURNAL OF CANCER RESEARCH AND CLINICAL ONCOLOGY, 2001, 127 (07) :411-417

[7] Design and synthesis of new anticancer pyrimidines with multiple-kinase inhibitory effect [J].

El-Deeb, Ibrahim Mustafa ;

Lee, So Ha .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (11) :3860-3874

[8] Synthesis, biological evaluation, and docking studies of novel heterocyclic diaryl compounds as selective COX-2 inhibitors [J].

Eren, Goekcen ;

Unlu, Serdar ;

Nunez, Maria-Teresa ;

Labeaga, Luis ;

Ledo, Francisco ;

Entrena, Antonio ;

Banoglu, Erden ;

Costantino, Gabriele ;

Sahin, M. Fethi .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (17) :6367-6376

[9] Prostaglandins and leukotrienes: Advances in eicosanoid biology [J].

Funk, CD .

SCIENCE, 2001, 294 (5548) :1871-1875

[10] Synthesis and crystal structure of 4,6-dihydroxy-2-[2-(4-hydroxy-phenyl)-vinyl]-benzene-1,3-dicarbaldehyde [J].

Huang, Xian-Feng ;

Shi, Lei ;

Li, Huan-Qiu ;

Zhu, Hai-Liang .

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2007, 37 (11) :739-742

← 1 2 3 →