Synthesis of triazole Schiff bases: Novel inhibitors of nucleotide pyrophosphatase/phosphodiesterase-1

被引:39
|
作者
Khan, Khalid Mohammed [1 ]
Siddiqui, Salman [1 ]
Saleem, Muhammad [1 ]
Taha, Muhammad [1 ,2 ]
Saad, Syed Muhammad [1 ]
Perveen, Shahnaz [3 ]
Choudhary, M. Iqbal [1 ,4 ]
机构
[1] Univ Karachi, HEJ Res Inst Chem, Int Ctr Chem & Biol Sci, Karachi 75270, Pakistan
[2] Univ Teknol MARA UiTM, Atta ur Rahman Inst Nat Prod Discovery, Bandar Puncak Alam 42300, Selangor, Malaysia
[3] Shahrah e Dr Salimuzzaman Siddiqui, PCSIR Labs Complex, Karachi 75280, Pakistan
[4] King Abdulaziz Univ, Fac Sci, Dept Biochem, Jeddah 21412, Saudi Arabia
关键词
Nucleotide pyrophosphatase/phosphodiesterase-1; Schiff bases of triazoles; PC3 cell lines; Chondrocalcinosis; DERIVATIVES; PHOSPHODIESTERASE; ANTICANCER; GLYCOSIDES; DRUGS;
D O I
10.1016/j.bmc.2014.08.032
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of Schiff base triazoles 1-25 was synthesized and evaluated for their nucleotide pyrophosphatase/ phosphodiesterase-1 inhibitory activities. Among twenty-five compounds, three compounds 10 (IC50 = 132.20 +/- 2.89 mu M), 13 (IC50 = 152.83 +/- 2.39 mu M), and 22 (IC50 = 251.0 +/- 6.64 mu M) were identified as potent inhibitors with superior activities than the standard EDTA (IC50 = 277.69 +/- 2.52 mu M). The newly identified inhibitors may open a new avenue for the development of treatment of phosphodiesterase-I related disorders. These compounds were also evaluated for carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase inhibitory potential and were found to be inactive. The compounds showed non-toxic effect towards PC3 cell lines. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6509 / 6514
页数:6
相关论文
共 50 条
  • [1] Phenolic glycosides, a new class of human recombinant nucleotide pyrophosphatase phosphodiesterase-1 inhibitors
    Choudhary, MI
    Fatima, N
    Abbasi, MA
    Jalil, S
    Ahmad, VU
    Atta-ur-Rahman
    BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (22) : 5793 - 5798
  • [2] Synthesis of biphenyl oxazole derivatives via Suzuki coupling and biological evaluations as nucleotide pyrophosphatase/phosphodiesterase-1 and-3 inhibitors
    Ahmad, Haseen
    Ullah, Saif
    Rahman, Fouzia
    Saeed, Aamer
    Pelletier, Julie
    Sevigny, Jean
    Hassan, Abbas
    Iqbal, Jamshed
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 208
  • [3] Synthesis of new sulphonate derivatives containing adamantane and 4-chlorophenyl moieties as nucleotide pyrophosphatase/phosphodiesterase-1 and-3 inhibitors
    Ullah, Saif
    Hamid, Kiran
    Batool, Amna
    Pelletier, Julie
    Sevigny, Jean
    Khan, Abdul Rehman
    Langer, Peter
    Iqbal, Jamshed
    JOURNAL OF MOLECULAR STRUCTURE, 2023, 1274
  • [4] Synthesis and Biological Evaluation of Arylamide Sulphonate Derivatives as Ectonucleotide Pyrophosphatase/Phosphodiesterase-1 and-3 Inhibitors
    Ullah, Saif
    Pelletier, Julie
    Sevigny, Jean
    Iqbal, Jamshed
    ACS OMEGA, 2022, 7 (30): : 26905 - 26918
  • [5] Proteoliposomes Carrying Alkaline Phosphatase and Nucleotide Pyrophosphatase/Phosphodiesterase-1 as Matrix Vesicle Mimetics
    Ciancaglini, P.
    Siniao, A. M. S.
    Yadav, M. C.
    Narisawa, S.
    Hoylaerts, M. F.
    Millan, J. L.
    JOURNAL OF BONE AND MINERAL RESEARCH, 2008, 23 : S146 - S146
  • [6] ECTO-NUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE-1 IS EXPRESSED BY OSTEOCLASTS BUT DOES NOT AFFECT OSTEOCLAST FUNCTION
    Hajjawi, Mark
    Orriss, Isabel
    Arnett, Timothy
    OSTEOPOROSIS INTERNATIONAL, 2012, 23 : S535 - S535
  • [7] Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1) and its inhibitors
    Lee, Sang-Yong
    Mueller, Christa E.
    MEDCHEMCOMM, 2017, 8 (05) : 823 - 840
  • [8] Synthesis, in vitro, and in silico studies of morpholine-based thiosemicarbazones as ectonucleotide pyrophosphatase/ phosphodiesterase-1 and-3 inhibitors
    Tasleem, Mussarat
    Pelletier, Julie
    Sevigny, Jean
    Hussain, Zahid
    Khan, Ajmal
    Al-Harrasi, Ahmed
    El-kott, Attalla F.
    Taslimi, Parham
    Negm, Sally
    Shafiq, Zahid
    Iqbal, Jamshed
    INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2024, 266
  • [9] PHOSPHODIESTERASE-1 INHIBITORS AS NOVEL THERAPEUTICS FOR ENHANCEMENT OF COGNITION IN SCHIZOPHRENIA
    Wennogle, Lawrence Paul
    Hendrick, J. P.
    Snyder, G. L.
    Li, P.
    Vanover, K. E.
    Davis, R. E.
    Prickaerts, J.
    Fienberg, A. A.
    Mates, S.
    SCHIZOPHRENIA BULLETIN, 2011, 37 : 233 - 234
  • [10] Development of Novel Ecto-Nucleotide Pyrophosphatase/Phosphodiesterase 1 (ENPP1) Inhibitors for Tumor Immunotherapy
    Wang, Xiang
    Lu, Xing
    Yan, Daojing
    Zhou, Yajun
    Tan, Xiangshi
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2022, 23 (13)