Synthesis of kaempferide Mannich base derivatives and their antiproliferative activity on three human cancer cell lines

• Authors: Van-Son Nguyen , Ling Shi , Fang-Qian Luan , Qiu-An Wang
• Languages of publication: EN

Abstracts

EN

Kaempferide (3,5,7-trihydroxy-4'-methoxyflavone, 1), a naturally occurring flavonoid with potent anticancer activity in a number of human tumour cell lines, was first semisynthesized from naringin. Based on Mannich reaction of kaempferide with various secondary amines and formaldehyde, nine novel kaempferide Mannich base derivatives 2-10 were synthesized. The aminomethylation occurred preferentially in the position at C-6 and C-8 of the A-ring of kaempferide. All the synthetic compounds were tested for antiproliferative activity against three human cancer cell lines (Hela, HCC1954, SK-OV-3) by the standard MTT method. The results showed that compounds 1, 2 and 5-10 were more potent against Hela cells with IC50 values of 12.47-28.24 μM than the positive control cis-platin (IC50 41.25 μM), compounds 5, 6, 8 and 10 were more potent against HCC1954 cells with IC50 values of 8.82-14.97 μM than the positive control cis-platin (IC50 29.68 μM), and compounds 2, 3, 5, 6 and 10 were more potent against SK-OV-3 cells with IC50 values of 7.67-18.50 μM than the positive control cis-platin (IC50 21.27 μM).

Keywords

EN

kaempferide; flavonoids; Mannich base derivatives; synthesis; antiproliferative activity

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2015
• Volume: 62
• Issue: 3
• Pages: 547-552

Dates

published

2015

received

2015-02-13

revised

2015-04-18

accepted

2015-08-31

(unknown)

2015-09-08

Contributors

author

Van-Son Nguyen

• College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P R China
• Faculty of Chemical Engineering, Industry University of Hochiminh City, Vietnam

author

Ling Shi

• College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P R China

author

Fang-Qian Luan

• College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P R China

author

Qiu-An Wang

• College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P R China

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Identifiers

DOI

10.18388/abp.2015_992