title: Synthesis of novel flavone derivatives possessing substituted benzamides and their biological evaluation against human cancer cells.
abstract: Baicalein is a well-known flavone derivative that possesses diverse biological properties, such as anticancer, antioxidant and anti-inflammatory activities. Numerous baicalein derivatives, including 5,6,7-trimethoxyflavone, have been synthesized with the aim of enhancing its inherent biological activities. In the present work, new flavones, possessing an N-aroylamine-substituent on the B-ring, were synthesized to improve the cytotoxicity of baicalein and 5,6,7-trimethoxyflavone against human cancer cell lines. The majority of the flavones synthesized exhibited greater cytotoxicity than baicalein and 5,6,7-trimethoxyflavone against HepG2 and MCF-7 cells. Among them, compounds 5n, possessing a 3-methoxybenzoylamino group, exhibited great cytotoxic effects on HepG2 (GI50=7.06μM) and MCF-7 (GI50=7.67μM) cells. In contrast, N-aroylamine-substituted 5-hydroxy-6,7-dimethoxyflavone derivatives showed greater cytotoxicity against MCF-7 than HepG2 cells, indicating that the replacement of a 5-methoxy group on the A-ring with a 5-hydroxy group has a marked influence on the cytotoxicity profile.
authors: Department of Life and Nanopharmaceutical Sciences, Kyung Hee University, 26 Kyungheedae-ro, Seoul 02447, Republic of Korea.
authors: Bo Hee
authors: BH
authors: Yun
authors: Department of Life and Nanopharmaceutical Sciences, Kyung Hee University, 26 Kyungheedae-ro, Seoul 02447, Republic of Korea.
authors: Young Hun
authors: YH
authors: Lee
authors: Department of Life and Nanopharmaceutical Sciences, Kyung Hee University, 26 Kyungheedae-ro, Seoul 02447, Republic of Korea.
authors: Kyung Tae
authors: KT
authors: Park
authors: Department of Life and Nanopharmaceutical Sciences, Kyung Hee University, 26 Kyungheedae-ro, Seoul 02447, Republic of Korea.
authors: Su Jin
authors: SJ
authors: Jung
authors: Department of Life and Nanopharmaceutical Sciences, Kyung Hee University, 26 Kyungheedae-ro, Seoul 02447, Republic of Korea; Medicinal Chemistry Laboratory, Department of Pharmacy, College of Pharmacy, Kyung Hee University, 26 Kyungheedae-ro, Seoul 02447, Republic of Korea. Electronic address: kyslee@khu.ac.kr.
authors: Yong Sup
authors: YS
authors: Lee
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D001549:Benzamides / Q000737:chemistry*; D002470:Cell Survival / Q000187:drug effects; D044950:Flavanones / Q000737:chemistry; D047309:Flavones / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D005419:Flavonoids / Q000737:chemistry / Q000633:toxicity; D056945:Hep G2 Cells; D006801:Humans; D061986:MCF-7 Cells; D009369:Neoplasms; D013329:Structure-Activity Relationship
chemical_list: C107364:5,6,7-trimethoxyflavone; D000970:Antineoplastic Agents; D001549:Benzamides; D044950:Flavanones; D047309:Flavones; D005419:Flavonoids; C006680:baicalein
keywords: 5,6,7-Trimethoxyflavone; Baicalein; Cytotoxicity; HepG2; MCF-7; N-Aroylamine-substituted