Synthesis and Urease Inhibitory Activity of Some 5-aminomethylene Barbituric/Thiobarbituric Acid Derivatives

被引：8
作者：
Asadi, Mehdi [1 ]
Mahdavi, Mohammad [2 ]
Mahernia, Shabnam [1 ]
Rezaei, Zahra [1 ]
Safavi, Maliheh [3 ]
Saeedi, Mina [4 ,5 ]
Amanlou, Massoud [1 ]
机构：
[1] Univ Tehran Med Sci, Fac Pharm & Pharmaceut Sci, Dept Med Chem, Res Ctr, Tehran, Iran
[2] Univ Tehran Med Sci, Endocrinol & Metab Res Inst, Endocrinol & Metab Res Ctr, Tehran, Iran
[3] Iranian Res Org Sci & Technol, Dept Biotechnol, POB 3353-5111, Tehran, Iran
[4] Univ Tehran Med Sci, Med Plants Res Ctr, Fac Pharm, Tehran, Iran
[5] Univ Tehran Med Sci, Persian Med & Pharm Res Ctr, Tehran, Iran
来源：
LETTERS IN DRUG DESIGN & DISCOVERY | 2018年 / 15卷 / 04期
关键词：
Barbituric acid; thiobarbituric acid; isocyanides; urease inhibitory activity; docking study; (THIO)BARBITURIC ACID; DESIGN; ANTIBACTERIAL; PERMEABILITY; BARBITURATE; SOLUBILITY; CHEMISTRY; AGENTS;
D O I：
10.2174/1570180814666170727142928
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Background: In this work, a wide spectrum of 5-aminomethylene barbituric/thiobarbituric acid derivatives was synthesized and evaluated for their Jack bean urease inhibitory activity. Methods: Among the synthesized compounds, 5-cyclohexylaminomethylene barbituric acid (3a) showed the most potent activity (IC50 = 25.8 mu M), 4 times more potent than hydroxyurea (IC50 = 100.0 mu M) and a similar activity to thiourea (IC50 = 22.0 mu M), both being as the reference drugs. Results and Conclusion: Also, results from docking studies were in good agreement with those obtained in in vitro assay.
引用
收藏
页码：428 / 436
页数：9
相关论文
共 30 条
  • [1] Chemistry and mechanism of urease inhibition
    Amtul, Z
    Atta-ur-Rahman
    Siddiqui, RA
    Choudhary, MI
    [J]. CURRENT MEDICINAL CHEMISTRY, 2002, 9 (14) : 1323 - 1348
  • [2] Large-scale virtual screening for the identification of new Helicobacter pylori urease inhibitor scaffolds
    Azizian, Homa
    Nabati, Farzaneh
    Sharifi, Amirhossein
    Siavoshi, Farideh
    Mahdavi, Mohammad
    Amanlou, Massoud
    [J]. JOURNAL OF MOLECULAR MODELING, 2012, 18 (07) : 2917 - 2927
  • [3] SYNTHESIS AND ANTIBACTERIAL PROPERTIES OF SUBSTITUTED DECYLBARBITURIC ACIDS
    BERES, JA
    COONS, TL
    KAELIN, MJ
    [J]. JOURNAL OF PHARMACEUTICAL SCIENCES, 1974, 63 (03) : 469 - 471
  • [4] Design and synthesis of novel nucleobase-based barbiturate derivatives as potential anticancer agents
    Dhorajiya, Bhaveshkumar D.
    Ibrahim, Ahmed S.
    Badria, Farid A.
    Dholakiya, Bharatkumar Z.
    [J]. MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (02) : 839 - 847
  • [5] Helicobacter pylori
    Dunn, BE
    Cohen, H
    Blaser, MJ
    [J]. CLINICAL MICROBIOLOGY REVIEWS, 1997, 10 (04) : 720 - +
  • [6] Elbayaa RY, 2014, MED CHEM, V10, P66
  • [7] EFFECTS OF A SEDATIVE AND A CONVULSANT BARBITURATE ON SYNAPTOSOMAL CALCIUM-TRANSPORT
    HARRIS, RA
    STOKES, JA
    [J]. BRAIN RESEARCH, 1982, 242 (01) : 157 - 163
  • [8] CONTRIBUTION OF PROTEUS-MIRABILIS UREASE TO PERSISTENCE, UROLITHIASIS, AND ACUTE PYELONEPHRITIS IN A MOUSE MODEL OF ASCENDING URINARY-TRACT INFECTION
    JOHNSON, DE
    RUSSELL, RG
    LOCKATELL, CV
    ZULTY, JC
    WARREN, JW
    MOBLEY, HLT
    [J]. INFECTION AND IMMUNITY, 1993, 61 (07) : 2748 - 2754
  • [9] Synthesis and structure-activity relationship of thiobarbituric acid derivatives as potent inhibitors of urease
    Khan, Khalid Mohammed
    Rahim, Fazal
    Khan, Ajmal
    Shabeer, Muhammad
    Hussain, Shafqat
    Rehman, Wajid
    Taha, Muhammad
    Khan, Momin
    Perveen, Shahnaz
    Choudhary, M. Iqbal
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (15) : 4119 - 4123
  • [10] Molecular modeling-based antioxidant arylidene barbiturates as urease inhibitors
    Khan, Khalid Mohammed
    Ali, Muhammad
    Wadood, Abdul
    ul-Haq, Zaheer
    Khan, Momin
    Lodhi, Muhammad Arif
    Perveen, Shahnaz
    Choudhary, Muhammad Iqbal
    Voelter, Wolfgang
    [J]. JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2011, 30 : 153 - 156
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