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Literature summary for 1.5.1.3 extracted from

  • Muddala, N.; White, J.; Nammalwar, B.; Pratt, I.; Thomas, L.; Bunce, R.; Berlin, K.; Bourne, C.
    Inhibitor design to target a unique feature in the folate pocket of Staphylococcus aureus dihydrofolate reductase (2020), Eur. J. Med. Chem., 200, 112412 .
    View publication on PubMed
Search for more literature for 1.5.1.3

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli Staphylococcus aureus

Inhibitors

Inhibitors Comment Organism Structure
(E)-1-(1-cyclopropyl-6,7-dimethoxyphthalazin-2(1H)-yl)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)prop-2-en-1-one
-
 Staphylococcus aureus
(E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(1-(4-methoxyphenyl)phthalazin-2(1H)-yl)prop-2-en-1-one
-
 Staphylococcus aureus
(E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(1-phenylphthalazin-2(1H)-yl)prop-2-en-1-one
-
 Staphylococcus aureus
(E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(1-propylphthalazin-2(1H)-yl)prop-2-en-1-one
-
 Staphylococcus aureus
(E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(6,7-dimethoxy-1-propylphthalazin-2(1H)-yl)prop-2-en-1-one
-
 Staphylococcus aureus
(E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(6,7-dimethyl-1-propylphthalazin-2(1H)-yl)prop-2-en-1-one
-
 Staphylococcus aureus
additional information synthesis of trimethoprim derivatives containing an acryloyl linker and a dihydophthalazine moiety. Structural data reveal accommodation of predominantly the S-enantiomer of the inhibitors within the folate-binding pocket. Longer modifications at the chiral carbon, such as p-methylbenzyl, protrude from the pocket into solvent and result in poorer Ki values, as do modifications with greater torsional freedom, such as 1-ethylpropyl Staphylococcus aureus

Organism

Organism UniProt Comment Textmining
Staphylococcus aureus A0A0M3KKX1
-
-
Staphylococcus aureus ET3-1 A0A0M3KKX1
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-

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0000007
-
 (E)-1-(1-cyclopropyl-6,7-dimethoxyphthalazin-2(1H)-yl)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)prop-2-en-1-one 30°C, pH not specified in the publication Staphylococcus aureus
0.0000011
-
 (E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(6,7-dimethoxy-1-propylphthalazin-2(1H)-yl)prop-2-en-1-one 30°C, pH not specified in the publication Staphylococcus aureus
0.0000012
-
 (E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(1-(4-methoxyphenyl)phthalazin-2(1H)-yl)prop-2-en-1-one 30°C, pH not specified in the publication Staphylococcus aureus
0.0000012
-
 (E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(1-phenylphthalazin-2(1H)-yl)prop-2-en-1-one 30°C, pH not specified in the publication Staphylococcus aureus
0.0000012
-
 (E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(1-propylphthalazin-2(1H)-yl)prop-2-en-1-one 30°C, pH not specified in the publication Staphylococcus aureus
0.0000012
-
 (E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(6,7-dimethyl-1-propylphthalazin-2(1H)-yl)prop-2-en-1-one 30°C, pH not specified in the publication Staphylococcus aureus