Synthesis and Biological Evaluation of 3-Styrylchromone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

被引:24
作者
Takao, Koichi [1 ]
Ishikawa, Ryo [1 ]
Sugita, Yoshiaki [1 ]
机构
[1] Josai Univ, Fac Pharmaceut Sci, Dept Pharmaceut & Hlth Sci, Bioorgan Chem Lab, Sakado, Saitama 3500295, Japan
关键词
3-styrylchromone; alpha-glucosidase inhibitor; antioxidant; structure-activity relationship; 2-STYRYLCHROMONES; AGENTS; OXYGEN;
D O I
10.1248/cpb.c14-00351
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of 3-styrylchromone derivatives (4-20) were synthesized and the structure-activity relationships for alpha-glucosidase inhibition and antioxidant activities were analyzed. Among the synthesized compounds, compounds 15 and 20, which contain a catechol moiety, showed both potent 1,1-dipheny1-2-picrylhydrazyl (DPPH) free radical scavenging activity (15: EC50=17 mu m; 20: EC50=23 mu m) and alpha-glucosidase inhibitory activity (15: IC50=16 mu m; 20: IC50=10 mu m). Our data suggest that 3-styrylchromone derivatives are novel alpha-glucosidase inhibitors that have the potential to counteract diet-induced hyperglycemia in diabetes.
引用
收藏
页码:810 / 815
页数:6
相关论文
共 50 条
  • [41] 2,4-Dioxochroman Moiety Linked to 1,2,3-triazole Derivatives as Novel α-glucosidase Inhibitors: Synthesis, In vitro Biological Evaluation, and Docking Study
    Mollazadeh, Marjan
    Mohammadi-Khanaposhtani, Maryam
    Valizadeh, Yousef
    Zonouzi, Afsaneh
    Faramarzi, Mohammad Ali
    Hariri, Parsa
    Biglar, Mahmood
    Larijani, Bagher
    Hamedifar, Haleh
    Mahdavi, Mohammad
    Sepehri, Nima
    CURRENT ORGANIC CHEMISTRY, 2020, 24 (17) : 2019 - 2027
  • [42] Synthesis and biological evaluation of α-1-C-4′-carylbutyl-L-arabinoiminofuranoses, a new class of α-glucosidase inhibitors
    Natori, Yoshihiro
    Sakuma, Toshihiro
    Yoshimura, Yuichi
    Kinami, Kyoko
    Hirokami, Yuki
    Sato, Kasumi
    Adachi, Isao
    Kato, Atsushi
    Takahata, Hiroki
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (15) : 3298 - 3301
  • [43] Synthesis and evaluation of 2,3-indolotriterpenoids as new α-glucosidase inhibitors
    Khusnutdinova, Elmira F.
    Smirnova, Irina E.
    Kazakova, Oxana B.
    Petrova, Anastasiya V.
    Nguyen Thi Thu Ha
    Do Quoc Viet
    MEDICINAL CHEMISTRY RESEARCH, 2017, 26 (11) : 2737 - 2742
  • [44] Synthesis and biological evaluation of parthenolide derivatives with reduced toxicity as potential inhibitors of the NLRP3 inflammasome
    Ou, Yitao
    Sun, Ping
    Wu, Nannan
    Chen, Hao
    Wu, Dan
    Hu, Wenhui
    Yang, Zhongjin
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2020, 30 (17)
  • [45] Synthesis and biological evaluation of novel 3,4-diaryl lactam derivatives as triple reuptake inhibitors
    Park, Jung-eun
    Song, Chiman
    Choi, Keehyun
    Sim, Taebo
    Moon, Bongjin
    Roh, Eun Joo
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (20) : 5515 - 5518
  • [46] Bioassay-guided purification of α-amylase, α-glucosidase inhibitors and DPPH radical scavengers from roots of Rheum turkestanicum
    Dehghan, Hossein
    Salehi, Peyman
    Amiri, Mohammad Sadegh
    INDUSTRIAL CROPS AND PRODUCTS, 2018, 117 : 303 - 309
  • [47] Synthesis and biological evaluation of 2,5-disubstituted furan derivatives containing 1,3-thiazole moiety as potential α-glucosidase inhibitors
    He, Min
    Li, Yuan-Jing
    Shao, Jiang
    Li, Ya-Sheng
    Cui, Zi-Ning
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2023, 83
  • [48] Metal-free synthesis of functionalized tacrine derivatives and their evaluation for acetyl/butyrylcholinesterase and α-glucosidase inhibition
    Shirisha, Thangellapally
    Majhi, Subir
    Divakar, Kalivarathan
    Kashinath, Dhurke
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (04) : 790 - 804
  • [49] Synthesis of oxadiazoline and quinazolinone derivatives and their biological evaluation as nitric oxide synthase inhibitors
    Jose Pineda de las Infantas, M.
    Dora Carrion, M.
    Chayah, Mariem
    Lopez-Cara, Luisa C.
    Gallo, Miguel A.
    Acuna-Castroviejo, Dario
    Encarnacion Camacho, M.
    MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (06) : 1260 - 1273
  • [50] Synthesis and biological evaluation of benzyl styrylsulfonyl derivatives as potent anticancer mitotic inhibitors
    Chahrour, Osama
    Abdalla, Ashraf
    Lam, Frankie
    Midgley, Carol
    Wang, Shudong
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (10) : 3066 - 3069