title: Design and synthesis of azaisoflavone analogs as phytoestrogen mimetics.
abstract: A series of azaisoflavone analogs were designed and synthesized and their transactivation activities and binding affinities for ERα and ERβ were investigated. Among these compounds, 2b and 3a were the most potent with 6.5 and 1.1 μM of EC50, respectively. Molecular modeling study showed putative binding modes of the compound 3a in the active site of ERα and ERβ, which were similar with that of genistein and provided insight of the effect of N-alkyl substitution of azaisoflavones on ERβ activity. Also, a biphasic effect of azaisoflavone analogs on MCF-7 cell growth depending on their concentrations was investigated.
authors: Research Center for Cell Fate Control, College of Pharmacy, Sookmyung Women's University, 52 Hyochangwon-Gil, Yongsan-Ku, Seoul 140-742, Republic of Korea.
authors: Hyo Jin
authors: HJ
authors: Gim
authors: Research Center for Cell Fate Control, College of Pharmacy, Sookmyung Women's University, 52 Hyochangwon-Gil, Yongsan-Ku, Seoul 140-742, Republic of Korea.
authors: Hua
authors: H
authors: Li
authors: Research Center for Cell Fate Control, College of Pharmacy, Sookmyung Women's University, 52 Hyochangwon-Gil, Yongsan-Ku, Seoul 140-742, Republic of Korea.
authors: So Ra
authors: SR
authors: Jung
authors: School of Pharmacy, Sungkyunkwan University, 2066, Seobu-ro, Jangan-gu, Suwon-si, Gyeonggi-do, Republic of Korea.
authors: Yong Joo
authors: YJ
authors: Park
authors: Research Center for Cell Fate Control, College of Pharmacy, Sookmyung Women's University, 52 Hyochangwon-Gil, Yongsan-Ku, Seoul 140-742, Republic of Korea.
authors: Jae-Ha
authors: JH
authors: Ryu
authors: School of Pharmacy, Sungkyunkwan University, 2066, Seobu-ro, Jangan-gu, Suwon-si, Gyeonggi-do, Republic of Korea.
authors: Kyu Hyuck
authors: KH
authors: Chung
authors: Research Center for Cell Fate Control, College of Pharmacy, Sookmyung Women's University, 52 Hyochangwon-Gil, Yongsan-Ku, Seoul 140-742, Republic of Korea. Electronic address: rjeon@sookmyung.ac.kr.
authors: Raok
authors: R
authors: Jeon
mesh_terms: D020134:Catalytic Domain; D049109:Cell Proliferation / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D047628:Estrogen Receptor alpha / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D047629:Estrogen Receptor beta / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D047309:Flavones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D006801:Humans; D061986:MCF-7 Cells; D062105:Molecular Docking Simulation; D048789:Phytoestrogens / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D015533:Transcriptional Activation / Q000187:drug effects
chemical_list: D047628:Estrogen Receptor alpha; D047629:Estrogen Receptor beta; D047309:Flavones; D048789:Phytoestrogens; D015363:Quinolones
keywords: Azaisoflavones; ER agonist; Estrogen receptor; Proliferation