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(2R)-3-[4-(hydroxymethyl)-4-[[4-(hydroxymethyl)phenyl]methyl]piperidin-1-yl]propane-1,2-diol
-
-
(2R)-3-[4-[2-[(cyclohexa-2,4-dien-1-yl)oxy]ethyl]-4-(hydroxymethyl)piperidin-1-yl]propane-1,2-diol
-
-
(2R)-3-[[[1-butyl-2-(cyclobutylmethanesulfonyl)-1H-imidazol-5-yl]methyl](methyl)amino]propane-1,2-diol
-
-
(3R)-1-(2,2-dimethylpropyl)-3-hydroxy-3-([[(5-methyl-4H-1,2,4-triazol-3-yl)methyl]amino]methyl)piperidin-2-one
-
-
(3S)-1-(cyclopropylmethyl)-3-([[(4,5-dimethyl-1,3-thiazol-2-yl)methyl]amino]methyl)-3-hydroxypiperidin-2-one
-
-
(3S,4R)-3-((2S)-1-(6,7-dimethoxy-4-(pyrrolidin-1-yl)-1,7,8,8a-tetrahydroquinazolin-2-yl)-4-hydroxybutan-2-yl)-4-hydroxytetrahydrothiophene 1,1-dioxide
-
-
(4-chloro-2-[[1-(2,3-dihydroxypropyl)piperidin-4-yl]oxy]phenyl)(piperidin-1-yl)methanone
-
-
(5R)-5-[1-[(2R)-2,3-dihydroxypropyl]piperidin-4-yl]-5-(3-phenylpropyl)imidazolidine-2,4-dione
-
-
([[acetyl(hydroxy)amino]methoxy]methyl)phosphonic acid
-
-
([[formyl(hydroxy)amino]methoxy]methyl)phosphonic acid
-
-
1-[(2S)-2,3-dihydroxypropyl]-N-[3-(furan-2-yl)phenyl]piperidine-4-carboxamide
-
-
3,3-dimethyl-11-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one
-
4-(1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-methylpropyl)-5-methyl-2-(4-nitrophenyl)-1,2-dihydro-3H-pyrazol-3-one
-
-
4-butyl-6-[4-([[(2R)-2,3-dihydroxypropyl](methyl)amino]methyl)phenyl]pyridin-2(1H)-one
-
-
diethyl [2-(3-hydroxyanilino)-2-oxoethyl]phosphonate
45.2% inhibition at 0.25 mM
diethyl [2-[3-(hydroxymethyl)anilino]-2-oxoethyl]phosphonate
40.7% inhibition at 0.25 mM
-
ethyl 1-[(2R)-2,3-dihydroxypropyl]-4-(2-phenoxyethyl)piperidine-4-carboxylate
-
-
ethyl 1-[(2R)-2,3-dihydroxypropyl]-4-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxylate
-
-
ethyl 2-(2-ethoxy-2-oxoethyl)-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate
-
methyl N-([(3S)-1-[(2,3-difluorophenyl)methyl]-3-hydroxy-2-oxopiperidin-3-yl]methyl)glycinate
-
-
[(3,4-dichlorophenyl)([2-[hydroxy(methyl)amino]-2-oxoethyl]sulfanyl)methyl]phosphonic acid
-
-
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
inhibition of strain D2d
[2-([1-[(2R)-2,3-dihydroxypropyl]piperidin-4-yl]oxy)phenyl](piperidin-1-yl)methanone
-
-
[3-[acetyl(hydroxy)amino]-1-(1,4-dihydropyridin-4-yl)propyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
inhibition of strain D2d
[4-(2-acetylanilino)-4-oxobutyl]phosphonic acid
-
-
[4-(2-fluoroanilino)-4-oxobutyl]phosphonic acid
-
-
[4-[2-(methanesulfonyl)anilino]-4-oxobutyl]phosphonic acid
-
-
(4-[[3-(hydroxymethyl)phenyl]amino]-4-oxobutyl)phosphonic acid
-
-
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid
-
-
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid
-
-
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid
-
-
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid
-
-
diethyl (2-[[3-(hydroxymethyl)phenyl]amino]-2-oxoethyl)phosphonate
-
-
diethyl [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonate
-
-
diethyl [2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonate
-
-
FR-900098
-
fosmidomycin homologue
[2-[(3-bromophenyl)amino]-2-oxoethyl]phosphonic acid
-
-
[2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonic acid
-
-
[2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
[4-[(3-bromophenyl)amino]-4-oxobutyl]phosphonic acid
-
-
[4-[(3-hydroxyphenyl)amino]-4-oxobutyl]phosphonic acid
-
-
3,3-dimethyl-11-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one
-
-
3,3-dimethyl-11-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one
the inhibitor is believed to hamper the captivating step of the synthetic pathway, as a result of which inadequacy of IPP pool will definitely foster the endurance of parasite in the intraerythrocytic stage
-
ethyl 2-(2-ethoxy-2-oxoethyl)-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate
-
-
ethyl 2-(2-ethoxy-2-oxoethyl)-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate
the inhibitor is believed to hamper the captivating step of the synthetic pathway, as a result of which inadequacy of IPP pool will definitely foster the endurance of parasite in the intraerythrocytic stage
-
fosmidomycin
a natural product, which forms a chelate with the active site divalent metal ion (Mg2+/Mn2+) through its hydroxamate metal-binding group. Competitive versus 1-deoxy-D-xylulose 5-phosphate, uncompetitive versus NADPH. No or poor inhibition by diethyl [3-[3-(hydroxymethyl)anilino]-3-oxopropyl]phosphonate, diethyl [3-(3-hydroxyanilino)-3-oxopropyl]phosphonate, and [3-(3-methoxyanilino)-3-oxopropyl]phosphonic acid
fosmidomycin
the DXR inhibitor shows safety as well as efficacy against Plasmodium falciparum malaria in clinical trials
fosmidomycin
-
-
fosmidomycin
a natural antibiotic from Streptomyces lavendulae, a specific, mixed type inhibitor, the N-formyl-N-hydroxy amino headgroup of fosmidomycin coordinates Mg2+ ion forming an octahedral complex with active site residues Asp157, Glu159, and Glu241 and a critical binding site water molecule, residue His219 is essential for placing fosmidomycin in the active site for optimal catalysis, mechanism, overview, NADPH has a vital role in tight binding of the inhibitor within the enzyme active site
fosmidomycin
analysis of parasite growth in infected cultured erythrocytes. 50% growth inhibition at about 301 nM
fosmidomycin
-
a natural product isolated from Streptomyces lavendulae
FR900098
-
FR900098
analysis of parasite growth in infected cultured erythrocytes. 50% growth inhibition at about 118 nM
FR900098
-
an acetyl analogue of fosmidomycin
additional information
computational design of potent inhibitors for deoxyxylulose 5-phosphate reductoisomerase and prediction of pharmacokinetics and pharmacodynamics, active site binding, molecular docking, and complex-based pharmacophore modeling, binding structures, overview
-
additional information
-
computational design of potent inhibitors for deoxyxylulose 5-phosphate reductoisomerase and prediction of pharmacokinetics and pharmacodynamics, active site binding, molecular docking, and complex-based pharmacophore modeling, binding structures, overview
-
additional information
in silico identification and biological evaluation of inhibitors targeting 1-deoxy-D-xylulose-5-phosphate reductoisomerase, structure-based computational approach and biological evaluation, docking and binding mode estimation and molecular dynamics simulation, overview. Inhibitor screening in different database sources such as ZINC, NCI, ChemDB, PubChem, and Drugbank
-
additional information
non-hydroxamate inhibitors of 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), docking study, structure-activity analysis, overview
-
additional information
design and development of inhibitors, structure and docking modeling, overview
-
additional information
-
design and development of inhibitors, structure and docking modeling, overview
-
additional information
-
inhibitory potencies of a series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts as analogues of the potent DXR inhibitor fosmidomycin, effects of the carboxamide N-substituents and the length of the methylene linker, in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays, overview. Molecular modelling and simulated docking studies. No or poor inhibition by diethyl [3-[(3-hydroxyphenyl)amino]-3-oxopropyl]phosphonate, diethyl [2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonate, diethyl [3-[(3-methoxyphenyl)amino]-3-oxopropyl]phosphonate, diethyl [2-[(3-bromophenyl)amino]-2-oxoethyl]phosphonate, diethyl (3-[[3-(hydroxymethyl)phenyl]amino]-3-oxopropyl)phosphonate, [4-[(3-methoxyphenyl)amino]-4-oxobutyl]phosphonic acid, and [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonic acid
-
additional information
pyridine-containing fosmidomycin derivative inhibitor design and development using quantitative structure?activity relationship and crystallographic studies, synthesis, overview
-
additional information
-
pyridine-containing fosmidomycin derivative inhibitor design and development using quantitative structure?activity relationship and crystallographic studies, synthesis, overview
-
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0.00036
([[acetyl(hydroxy)amino]methoxy]methyl)phosphonic acid
Plasmodium falciparum
pH and temperature not specified in the publication
-
0.0049
([[formyl(hydroxy)amino]methoxy]methyl)phosphonic acid
Plasmodium falciparum
pH and temperature not specified in the publication
-
0.00312 - 0.125
3,3-dimethyl-11-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one
-
0.1
4-(1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-methylpropyl)-5-methyl-2-(4-nitrophenyl)-1,2-dihydro-3H-pyrazol-3-one
Plasmodium falciparum
pH 7.5, 22°C
-
0.04 - 0.125
ethyl 2-(2-ethoxy-2-oxoethyl)-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate
-
0.000036
fosmidomycin
Plasmodium falciparum
pH and temperature not specified in the publication
0.000018
FR-900098
Plasmodium falciparum
pH and temperature not specified in the publication
0.0000045
[(3,4-dichlorophenyl)([2-[hydroxy(methyl)amino]-2-oxoethyl]sulfanyl)methyl]phosphonic acid
Plasmodium falciparum
pH and temperature not specified in the publication
-
0.000028
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
Plasmodium falciparum
pH and temperature not specified in the publication
0.00009
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
Plasmodium falciparum
pH and temperature not specified in the publication
0.064
[4-(2-acetylanilino)-4-oxobutyl]phosphonic acid, [4-(2-fluoroanilino)-4-oxobutyl]phosphonic acid, [4-[2-(methanesulfonyl)anilino]-4-oxobutyl]phosphonic acid
Plasmodium falciparum
above, pH and temperature not specified in the publication
-
0.0093
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
Plasmodium falciparum
-
-
0.0096
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid
Plasmodium falciparum
-
-
0.0004
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid
Plasmodium falciparum
-
-
0.02
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
Plasmodium falciparum
-
-
0.012
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid
Plasmodium falciparum
-
-
0.0033
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid
Plasmodium falciparum
-
-
0.0029
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid
Plasmodium falciparum
-
-
0.0066
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid
Plasmodium falciparum
-
-
0.000032 - 0.00117
fosmidomycin
0.000018
FR-900098
Plasmodium falciparum
-
-
0.118
FR900098
Plasmodium falciparum
-
0.00031 - 0.00044
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.00046 - 0.00063
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.0017 - 0.0035
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
0.00018 - 0.00034
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.00017 - 0.00018
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.00312
3,3-dimethyl-11-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one
Plasmodium falciparum
pH 7.5, 22°C
-
0.125
3,3-dimethyl-11-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one
Plasmodium falciparum
pH 7.5, 22°C
-
0.04
ethyl 2-(2-ethoxy-2-oxoethyl)-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate
Plasmodium falciparum
pH 7.5, 22°C
-
0.125
ethyl 2-(2-ethoxy-2-oxoethyl)-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate
Plasmodium falciparum
pH 7.5, 22°C
-
0.000032
fosmidomycin
Plasmodium falciparum
-
-
0.000301
fosmidomycin
Plasmodium falciparum
-
0.00044
fosmidomycin
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00117
fosmidomycin
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.00031
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00044
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.00046
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00063
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.0017
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.0035
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.00018
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00034
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.00017
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00018
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
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Wiesner, J.; Hintz, M.; Altincicek, B.; Sanderbrand, S.; Weidemeyer, C.; Beck, E.; Jomaa, H.
Plasmodium falciparum: Detection of the deoxyxylulose 5-phosphate reductoisomerase activity
Exp. Parasitol.
96
182-186
2000
Plasmodium falciparum
brenda
Singh, N.; Cheve, G.; Avery, M.A.; McCurdy, C.R.
Comparative protein modeling of 1-deoxy-D-xylulose-5-phosphate reductoisomerase enzyme from Plasmodium falciparum: a potential target for antimalarial drug discovery
J. Chem. Inf. Model.
46
1360-1370
2006
Plasmodium falciparum (O96693), Plasmodium falciparum
brenda
Tahar, R.; Basco, L.K.
Molecular epidemiology of malaria in Cameroon. XXV. In vitro activity of fosmidomycin and its derivatives against fresh clinical isolates of Plasmodium falciparum and sequence analysis of 1-deoxy-D-xylulose 5-phosphate reductoisomerase
Am. J. Trop. Med. Hyg.
77
214-220
2007
Plasmodium falciparum (O96693), Plasmodium falciparum
brenda
Giessmann, D.; Heidler, P.; Haemers, T.; Van Calenbergh, S.; Reichenberg, A.; Jomaa, H.; Weidemeyer, C.; Sanderbrand, S.; Wiesner, J.; Link, A.
Towards new antimalarial drugs: synthesis of non-hydrolyzable phosphate mimics as feed for a predictive QSAR study on 1-deoxy-D-xylulose-5-phosphate reductoisomerase inhibitors
Chem. Biodivers.
5
643-656
2008
Escherichia coli, Plasmodium falciparum
brenda
Umeda, T.; Tanaka, N.; Kusakabe, Y.; Nakanishi, M.; Kitade, Y.; Nakamura, K.T.
Crystallization and preliminary X-ray crystallographic study of 1-deoxy-D-xylulose 5-phosphate reductoisomerase from Plasmodium falciparum
Acta Crystallogr. Sect. F
66
330-332
2010
Plasmodium falciparum
brenda
Goble, J.L.; Adendorff, M.R.; de Beer, T.A.; Stephens, L.L.; Blatch, G.L.
The malarial drug target Plasmodium falciparum 1-deoxy-D-xylulose-5-phosphate reductoisomerase (PfDXR): development of a 3-D model for identification of novel, structural and functional features and for inhibitor screening
Protein Pept. Lett.
17
109-120
2010
Plasmodium falciparum (Q8IKG4), Plasmodium falciparum
brenda
Xue, J.; Diao, J.; Cai, G.; Deng, L.; Zheng, B.; Yao, Y.; Song, Y.
Antimalarial and structural studies of pyridine-containing inhibitors of 1-deoxyxylulose-5-phosphate reductoisomerase
ACS Med. Chem. Lett.
4
278-282
2013
Escherichia coli, Plasmodium falciparum (O96693), Plasmodium falciparum
brenda
Bodill, T.; Conibear, A.C.; Mutorwa, M.K.; Goble, J.L.; Blatch, G.L.; Lobb, K.A.; Klein, R.; Kaye, P.T.
Exploring DOXP-reductoisomerase binding limits using phosphonated N-aryl and N-heteroarylcarboxamides as DXR inhibitors
Bioorg. Med. Chem.
21
4332-4341
2013
Escherichia coli, Plasmodium falciparum
brenda
Kesharwani, S.; Sundriyal, S.
Non-hydroxamate inhibitors of 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR) a critical review and future perspective
Eur. J. Med. Chem.
213
113055
2021
Escherichia coli (P45568), Mycobacterium tuberculosis (P9WNS1), Plasmodium falciparum (Q8IKG4), Mycobacterium tuberculosis H37Rv (P9WNS1), Mycobacterium tuberculosis ATCC 25618 (P9WNS1)
brenda
Sharma, D.; Dada, R.; Tejavath, K.; Rai, P.; Soni, R.; Yaragorla, S.; Bhatt, T.
A paradigm towards the antimalarial quest in silico identification and biological evaluation of novel inhibitors targeting 1-deoxy-D-xylulose-5-phosphate reductoisomerase
J. Biomol. Struct. Dyn.
38
295-301
2020
Plasmodium falciparum (Q8IKG4)
brenda
Wadood, A.; Ghufran, M.; Hassan, S.; Khan, H.; Azam, S.; Rashid, U.
In silico identification of promiscuous scaffolds as potential inhibitors of 1-deoxy-D-xylulose 5-phosphate reductoisomerase for treatment of falciparum malaria
Pharm. Biol.
55
19-32
2017
Plasmodium falciparum (Q8IKG4), Plasmodium falciparum
brenda