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Synthesis, Structure-activity Relationship Analysis And Kinetics Study Of Reductive Derivatives Of Flavonoids As Helicobacter Pylori Urease Inhibitors.

Zhu-Ping Xiao, Zhi-Yun Peng, Jing-Jun Dong, Juan He, H. Ouyang, Yu-ting Feng, Chun-Lei Lu, W. Lin, Jin-Xiang Wang, Yin-Ping Xiang, Hai-Liang Zhu
Published 2013 · Chemistry, Medicine

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In a continuing study for discovering urease inhibitors based on flavonoids, nineteen reductive derivatives of flavonoids were synthesized and evaluated against Helicobacter pylori urease. Analysis of structure-activity relationship disclosed that 4-deoxy analogues are more potent than other reductive products. Out of them, 4',7,8-trihydroxyl-2-isoflavene (13) was found to be the most active with IC50 of 0.85 μM, being over 20-fold more potent than the commercial available urease inhibitor, acetohydroxamic acid (AHA). Kinetics study revealed that 13 is a competitive inhibitor of H. pylori urease with a Ki value of 0.641 μM, which is well matched with the results of molecular docking. Biological evaluation and mechanism study of 13 suggest that it is a good candidate for discovering novel anti-gastritis and anti-gastric ulcer agent.
This paper references
10.1016/0006-3002(62)91067-3
Specific inhibition of urease by hydroxamic acids.
Kyoichi Kobashi (1962)
10.1021/AC60252A045
Phenol-hypochlorite reaction for determination of ammonia
M. Weatherburn (1967)
10.1021/JO00365A034
Reductive deoxygenation of aryl aldehydes and ketones and benzylic, allylic, and tertiary alcohols by zinc iodide-sodium cyanoborohydride
C. Lau (1986)
10.1080/00397918908050959
Catalytic Transfer Hydrogenation, A Facile Conversion of Hydroxyflavanones Into Hydroxydihydrochalcones
H. Krishnamurty (1989)
10.1016/S0955-2863(95)00168-9
Flavonoids—Chemistry, metabolism, cardioprotective effects, and dietary sources
N. Cook (1996)
10.1039/A904946K
Synthesis of α-methyldeoxybenzoins
A. Salakka (1999)
10.1080/14756360127569
Inhibition of Jack Bean Urease by N-(n-butyl)thiophosphorictriamide and N-(n-butyl)phosphorictriamide: Determination of the Inhibition Mechanism
M. Kot (2001)
10.1055/S-2001-11499
In vitro anti-Helicobacter pylori activity of irisolidone isolated from the flowers and rhizomes of Pueraria thunbergiana.
E. Bae (2001)
10.2174/0929867023369853
Chemistry and mechanism of urease inhibition.
Z. Amtul (2002)
10.1021/NP030096L
Natural products as sources of new drugs over the period 1981-2002.
D. Newman (2003)
10.1021/JO0301200
Experimental and DFT 1H NMR study of conformational equilibria in trans-4',7-dihydroxyisoflavan-4-ol and trans-isoflavan-4-ol.
K. Pihlaja (2003)
10.1016/J.BBRC.2003.09.066
Suppression of Helicobacter pylori-induced gastritis by green tea extract in Mongolian gerbils.
S. Matsubara (2003)
10.1038/nrd1657
The evolving role of natural products in drug discovery
F. Koehn (2005)
10.1002/ANIE.200600350
Antibacterial natural products in medicinal chemistry--exodus or revival?
Franz von Nussbaum (2006)
10.1021/JF0712503
Onions: a source of unique dietary flavonoids.
R. Slimestad (2007)
10.1016/J.BMC.2007.03.045
Polyphenols based on isoflavones as inhibitors of Helicobacter pylori urease.
Zhu-Ping Xiao (2007)
10.1021/jf072901y
Design, synthesis, and biological evaluation of phosphoramide derivatives as urease inhibitors.
M. J. Domínguez (2008)
10.1080/14756360701536513
Urease inhibitor from Datisca cannabina linn
M. Ahmad (2008)
10.1016/J.MOLCATB.2009.01.003
Ureases I. Functional, catalytic and kinetic properties: A review
B. Krajewska (2009)
10.1016/j.ejmech.2008.06.001
Amines and oximes derived from deoxybenzoins as Helicobacter pylori urease inhibitors.
H. Li (2009)
10.1016/j.ejmech.2010.08.015
The synthesis, structure and activity evaluation of pyrogallol and catechol derivatives as Helicobacter pylori urease inhibitors.
Zhu-Ping Xiao (2010)
10.1271/bbb.90895
Inhibitory Activity against Urease of Quercetin Glycosides Isolated from Allium cepa and Psidium guajava
S. Shabana (2010)
10.2174/138955711794519546
Flavonoids health benefits and their molecular mechanism.
Z-P Xiao (2011)
10.1080/10286020.2011.593171
Antioxidant and urease inhibitory C-glycosylflavonoids from Celtis africana
S. Perveen (2011)
Structures of 1-(3,4-Dihydroxyphenyl)-2-(3,4-dimethoxyphenyl) ethanone and Its Hydrate Complex
Xiao (2011)
10.1007/s00726-011-0920-4
N-substituted aminomethanephosphonic and aminomethane-P-methylphosphinic acids as inhibitors of ureases
Łukasz Berlicki (2011)
10.1016/j.ejmech.2011.09.009
Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors.
M. Aslam (2011)
10.1007/s00044-011-9762-6
Molecular simulations of bergenin as a new urease inhibitor
Mohammad Arfan (2011)
10.1007/s12272-012-0702-x
Ophiamides A-B, new potent urease inhibitory sphingolipids from Heliotropium ophioglossum
S. Firdous (2012)
10.1016/j.fitote.2011.10.014
Chemical constituents of Stereospermum acuminatissimum and their urease and α-chymotrypsin inhibitions.
K. Ramsay (2012)
10.1021/jf303393n
Molecular docking, kinetics study, and structure-activity relationship analysis of quercetin and its analogous as Helicobacter pylori urease inhibitors.
Zhu-Ping Xiao (2012)
10.1021/jm201121b
Amine linked flavonoid dimers as modulators for P-glycoprotein-based multidrug resistance: structure-activity relationship and mechanism of modulation.
Kin-Fai Chan (2012)
10.1016/J.ICA.2011.11.039
Synthesis, structures, and urease inhibitory activities of oxovanadium(V) complexes with Schiff bases
Z. You (2012)
10.1016/J.CPLETT.2012.07.078
A kinetic study of jack-bean urease denaturation by a new dithiocarbamate bismuth compound
D. C. Menezes (2012)
10.1007/s12272-012-0305-6
Biologically active C-alkylated flavonoids from Dodonaea viscosa
A. Muhammad (2012)
10.1007/s00775-012-0926-8
Temperature- and pressure-dependent stopped-flow kinetic studies of jack bean urease. Implications for the catalytic mechanism
B. Krajewska (2012)
10.3109/14756366.2012.719025
Urease inhibitory isoflavonoids from different parts of Calopogonium mucunoides (Fabaceae)
Brigitte Ndemangou (2013)



This paper is referenced by
10.1039/d1cc01872h
Iridium-catalysed branched-selective hydroacylation of 1,3-dienes with salicylaldehydes.
Yang Yang (2021)
10.1007/978-981-16-0223-8_12
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S. A. Rasool (2021)
10.1080/14756366.2021.1943378
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Guangcheng Wang (2021)
10.1080/14756366.2019.1706503
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Wei-yi Li (2020)
10.3390/ijms21176006
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Zhenyu Zhang (2020)
10.1021/acs.orglett.0c03106
Synthesis of Functionalized Benzopyran/Coumarin-Derived Aryne Precursors and Their Applications.
Yuka Nakamura (2020)
10.4155/fmc-2020-0048
N-monosubstituted thiosemicarbazide as novel Ure inhibitors: synthesis, biological evaluation and molecular docking.
Wei-Wei Ni (2020)
10.1016/j.molstruc.2020.127958
Structures, kinetic and synergistic mechanisms studies of urease inhibition of copper(II) complex based on MOSs
W. Duan (2020)
10.1186/s13065-019-0556-0
In-silico design, synthesis, ADMET studies and biological evaluation of novel derivatives of Chlorogenic acid against Urease protein and H. Pylori bacterium
Ritu Kataria (2019)
10.1016/j.bioorg.2018.10.018
Synthesis of novel N-(1,3-thiazol-2-yl)benzamide clubbed oxadiazole scaffolds: Urease inhibition, Lipinski rule and molecular docking analyses.
Muhammad Athar Abbasi (2019)
10.2174/1389203720666190320170215
Lead Molecules for Targeted Urease Inhibition: An Updated Review From 2010 -2018.
Ritu Kataria (2019)
10.2174/0929867326666190301143549
Insights into the design of inhibitors of the urease enzyme - a major target for the treatment of Helicobacter pylori infections.
Ana Thereza Fiori-Duarte (2019)
10.1002/ptr.6208
Antibacterial activity of flavonoids and their structure–activity relationship: An update review
F. Farhadi (2019)
10.18540/jcecvl5iss5pp0482-0493
QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP AND MOLECULAR DOCKING STUDIES OF HYDROXAMIC ACID DERIVATIVES AS NOVEL CLASS INHIBITORS AGAINST HELICOBACTER PYLORI UREASE
I. T. Ibrahim (2019)
10.1186/s13065-019-0562-2
Molecular docking, synthesis, kinetics study, structure–activity relationship and ADMET analysis of morin analogous as Helicobacter pylori urease inhibitors
Ritu Kataria (2019)
10.1038/s41598-019-44853-5
Structure-Activity Relationships of Baicalein and its Analogs as Novel TSLP Inhibitors
B. B. Park (2019)
10.1186/s13756-019-0559-6
Review on plant antimicrobials: a mechanistic viewpoint
B. Khameneh (2019)
10.2174/1568026619666191114123452
In-silico designing, ADMET Analysis, synthesis and biological evaluation of novel derivatives of diosmin against urease protein and Helicobactor Pylori bacterium.
Ritu Kataria (2019)
10.1039/C8RA01606B
A concise synthesis of (±)-7-O-galloyltricetiflavan
W. Zhang (2018)
10.1016/j.bmc.2018.06.005
Synthesis, in vitro and in silico studies of novel potent urease inhibitors: N-[4-({5-[(3-Un/substituted-anilino-3-oxopropyl)sulfanyl]-1,3,4-oxadiazol-2-yl}methyl)-1,3-thiazol-2-yl]benzamides.
M. Abbasi (2018)
10.1016/j.bmc.2018.07.003
The synthesis and evaluation of phenoxyacylhydroxamic acids as potential agents for Helicobacter pylori infections.
Wei-Wei Ni (2018)
10.1016/j.jare.2018.01.007
Recent advances in design of new urease inhibitors: A review
P. Kafarski (2018)
10.1016/j.bmcl.2018.08.025
Developing potential Helicobacter pylori urease inhibitors from novel oxoindoline derivatives: Synthesis, biological evaluation and in silico study.
Yushun Yang (2018)
10.1016/j.ejmech.2018.06.065
Arylamino containing hydroxamic acids as potent urease inhibitors for the treatment of Helicobacter pylori infection.
Q. Liu (2018)
10.1111/cbdd.12998
An expedient synthesis of N‐(1‐(5‐mercapto‐4‐((substituted benzylidene)amino)‐4H‐1,2,4‐triazol‐3‐yl)‐2‐phenylethyl)benzamides as jack bean urease inhibitors and free radical scavengers: Kinetic mechanism and molecular docking studies
A. Saeed (2017)
10.1021/acs.orglett.7b02341
Iridium-Catalyzed Asymmetric Hydrogenation of 2H-Chromenes: A Highly Enantioselective Approach to Isoflavan Derivatives.
Jingzhao Xia (2017)
10.1080/13543776.2017.1338687
Novel benzopyran derivatives and their therapeutic applications: a patent review (2009–2016)
Cheng Xiu (2017)
10.1021/acs.orglett.7b00088
Asymmetric Synthesis of 4-Aryl-3,4-dihydrocoumarins by N-Heterocyclic Carbene Catalyzed Annulation of Phenols with Enals.
Guotai Li (2017)
10.1016/J.MOLSTRUC.2016.03.084
Synthesis, crystal structures, molecular docking, and in vitro biological activities evaluation of transition metal complexes with 4-(3,4-dichlorophenyl) piperazine-1-carboxylic acid
Zhi-jian Chen (2016)
10.1016/j.bmcl.2016.05.003
Synthesis and biological evaluation of 5,7-dihydroxyflavanone derivatives as antimicrobial agents.
X. Zhang (2016)
A New Phenolic Compound Isolated from Semen Celosia cristata L
.. Li (2016)
Bioassay- guided Isolation of New Urease Inhibitory Constituents from Monotheca buxifolia (Falc.) Fruit and Their Molecular Docking Studies
A. Wadood (2016)
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