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Mannich aminomethylation of flavonoids and anti-proliferative activity against breast cancer cell

T. Kim-Dung Hoang, T. Kim-Chi Huynh, T. Hong-Tuoi Do, and Thanh-Danh Nguyen

Graduate University of Science and Technology, Vietnam Academy of Science and Technology, Hanoi, Vietnam

 

E-mail: htkdung@ict.vast.vn

Abstract: We herein report Mannich aminomethylation of variously structural flavonoids and their biological evaluation against human breast cancer cell. Mannich reaction showed that substitution at C-6 position depends on amine basicity and C-ring feature of flavonoids. All five flavonoid substrates reacted with strong amine bases to afford the bis(6,8-aminomethyl) derivatives, while with weak amines, the different products were obtained dependently on structural characteristic of flavonoid. 3-OH and 3-O-substituted groups on the C-ring exhibited the deactivated aminomethylation at C-6 position, whereas substitution at this position was independent on bond feature at C-2 and C-3 on the C-ring. Screening anti-proliferative activity showed six flavonoids possessed activity against breast cancer cell, MDA-MB-231. Among them, the flavonoids, luteolin (2) and 3′,4′,5,7-tetrahydroxy-6,8-bis(pyrrolidin-1-ylmethyl)-3-rutinosylflavone (3a), displayed the highest anti-proliferative activity with the lowest IC50 values.

Keywords: Mannich aminomethylation ; Flavonoid ; Synthesis ; Anti-proliferative ; MDA-MB-231 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-018-0402-1

 

Chemical Papers 72 (6) 1399–1406 (2018)

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