The Synthesis of 5-Functional 3-Hydroxypyridin-4-ones and Their Impact on the Chelating Properties of the Ligands

被引：4
|
作者：
Chen, Yu-Lin [1 ]
Chen, Jing [1 ]
Ma, Yongmin [1 ]
Hider, Robert C. [2 ]
机构：
[1] Zhejiang Chinese Med Univ, Coll Pharmaceut Sci, Hangzhou 310053, Zhejiang, Peoples R China
[2] Kings Coll London, Dept Pharm, London SE1 9NH, England
来源：
CHEMISTRY LETTERS | 2015年 / 44卷 / 04期
关键词：
ENHANCED PFE(3+) VALUES; ACTIVE IRON CHELATORS; PHYSICOCHEMICAL PROPERTIES; BIOLOGICAL EVALUATION; DESIGN; DEFERIPRONE; ARYL;
D O I：
10.1246/cl.141133
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The presence of the 5-functional group on 3-hydroxypyridin-4-ones (HPOs) can significantly change their chelating properties because the 5-position is adjacent to one of the chelating moieties. A 5-methoxy-substituted HPO has been successfully synthesized using a 5-bromo analogue with NaOMe in the presence of a copper(I) catalyst. The atomic charges and stability constants of the HPOs with either electron-donating or election-withdrawing groups on the 5-position were compared. The result showed that the 5-substituted HPOs possess lower stability constants, compared to those of the 5-unsubstituted analogue (deferiprone).
引用
收藏
页码：515 / 517
页数：3
相关论文
共 50 条
  • [41] SYNTHESIS AND PROPERTIES OF 5-METHYLENE-1,3-DIOXOLAN-4-ONES
    LIKHTEROV, VR
    ETLIS, VS
    TERNOSKOI, LA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1985, (10): : 1316 - 1318
  • [42] FUNCTIONAL POLYAMIDES .3. SYNTHESIS AND CHELATING PROPERTIES OF A NEW POLY(AMIDE THIOETHER)
    YAGCI, Y
    DENIZLIGIL, S
    BICAK, N
    ATAY, T
    ANGEWANDTE MAKROMOLEKULARE CHEMIE, 1992, 195 : 89 - 95
  • [43] SYNTHESIS OF 5-ARYL-3-HYDROXY-4H-PYRAN-4-ONES
    TAKAO, H
    ENDO, Y
    HORIE, T
    HETEROCYCLES, 1993, 36 (08) : 1803 - 1808
  • [44] Synthesis and anticancer activity evaluation of eta(5)-C-5(CH3)(4)R ruthenium complexes bearing chelating diphosphine ligands
    Rodriguez-Barzano, A.
    Lord, R. M.
    Basri, A. M.
    Phillips, R. M.
    Blacker, A. J.
    McGowan, P. C.
    DALTON TRANSACTIONS, 2015, 44 (07) : 3265 - 3270
  • [45] Synthesis, Characterization and Chelating Properties of 4-Butyrylsemicarbazone-1-phenyl-3-methyl-2-pyrazolin-5-one
    Patel, J. D.
    Shah, P. J.
    E-JOURNAL OF CHEMISTRY, 2010, 7 (02) : 357 - 362
  • [46] Synthesis of New Bis(3-hydroxy-4-pyridinone) Ligands as Chelating Agents for Uranyl Complexation
    Jin, Bo
    Zheng, Rongzong
    Peng, Rufang
    Chu, Shijin
    MOLECULES, 2016, 21 (03):
  • [47] Synthesis, iron(III)-binding affinity and in vitro evaluation of 3-hydroxypyridin-4-one hexadentate ligands as potential antimicrobial agents
    Xu, Bo
    Kong, Xiao-Le
    Zhou, Tao
    Qiu, Di-Hong
    Chen, Yu-Lin
    Liu, Mu-Song
    Yang, Rong-Hua
    Hider, Robert C.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (21) : 6376 - 6380
  • [48] Fast and Efficient Synthesis of 4-Arylidene-3-phenylisoxazol-5-ones
    Mirzazadeh, Maryam
    Mahdavinia, Gholam Hossein
    E-JOURNAL OF CHEMISTRY, 2012, 9 (01) : 425 - 429
  • [49] Synthesis and Biological Activities of 3-Substituent-5-aryloxazolidin-4-ones
    Yao Hong-Wei
    Li Huan-Huan
    Su Na-Na
    Wang Hong-Xue
    Liu Xing-Hai
    Wang Li-Zhong
    Zhang Xiao
    Li Zheng-Ming
    Zhao Wei-Guang
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2009, 30 (05): : 908 - 912
  • [50] Design, synthesis and biological evaluation of novel 3-hydroxypyridin-4 (1H)-ones based hybrids as Pseudomonas aeruginosa biofilm inhibitors
    Liu, Jun
    Meng, Ying
    Yang, Ming-Han
    Zhang, Xiao-Yi
    Zhao, Jian-Fu
    Sun, Ping-Hua
    Chen, Wei-Min
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2023, 259
12345