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Literature summary for 1.5.1.3 extracted from

  • Gangjee, A.; Adair, O.O.; Pagley, M.; Queener, S.F.
    N9-substituted 2,4-diaminoquinazolines: synthesis and biological evaluation of lipophilic inhibitors of Pneumocystis carinii and Toxoplasma gondii dihydrofolate reductase (2008), J. Med. Chem., 51, 6195-6200.
    View publication on PubMedView publication on EuropePMC

Application

Application Comment Organism
drug development the enzyme is a target for drug development since the organism causes the opportunistic infection Pneumocystis pneumonia, a major cause of mortality in acquired immunodeficiency syndrome, AIDS, patients Pneumocystis carinii
drug development the enzyme is a target for drug development since the organism causes the opportunistic infection toxoplasmosis, a major cause of mortality in acquired immunodeficiency syndrome, AIDS, patients Toxoplasma gondii

Inhibitors

Inhibitors Comment Organism Structure
2,4-diamino-6-[N-(2,3,5-trichlorobenzyl)-N-ethylamino]quinazoline
-
Pneumocystis carinii
2,4-diamino-6-[N-(2,3,5-trichlorobenzyl)-N-ethylamino]quinazoline
-
Toxoplasma gondii
2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-cyclopropyl methylamino]quinazoline
-
Pneumocystis carinii
2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-cyclopropyl methylamino]quinazoline
-
Toxoplasma gondii
2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-ethylamino]quinazoline
-
Pneumocystis carinii
2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-ethylamino]quinazoline
-
Toxoplasma gondii
2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-propylamino]quinazoline
-
Pneumocystis carinii
2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-propylamino]quinazoline
-
Toxoplasma gondii
2,4-diamino-6-[N-(alpha-naphthyl)-N-ethylamino]quinazoline
-
Pneumocystis carinii
2,4-diamino-6-[N-(alpha-naphthyl)-N-ethylamino]quinazoline
-
Toxoplasma gondii
2,4-diamino-6-[N-(benzyl)-N-ethylamino]quinazoline
-
Pneumocystis carinii
2,4-diamino-6-[N-(benzyl)-N-ethylamino]quinazoline
-
Toxoplasma gondii
2,4-diamino-6-[N-(beta-naphthyl)-N-cyclopropyl methylamino]-quinazoline
-
Pneumocystis carinii
2,4-diamino-6-[N-(beta-naphthyl)-N-cyclopropyl methylamino]-quinazoline
-
Toxoplasma gondii
2,4-diamino-6-[N-(beta-naphthyl)-N-ethylamino]quinazoline
-
Pneumocystis carinii
2,4-diamino-6-[N-(beta-naphthyl)-N-ethylamino]quinazoline
-
Toxoplasma gondii
2,4-diamino-6-[N-(beta-naphthyl)-N-propylamino]quinazoline
-
Pneumocystis carinii
2,4-diamino-6-[N-(beta-naphthyl)-N-propylamino]quinazoline
-
Toxoplasma gondii
additional information inhibitor design and synthesis, overview Pneumocystis carinii
additional information inhibitor design and synthesis, overview Toxoplasma gondii
N6-(2,5-dimethoxybenzyl)-N6-methylpyrido[2,3-d]pyrimidine-2,4,6-triamine
-
Pneumocystis carinii
N6-(2,5-dimethoxybenzyl)-N6-methylpyrido[2,3-d]pyrimidine-2,4,6-triamine
-
Toxoplasma gondii
N6-(2,5-dimethoxybenzyl)-N6-methylquinazoline-2,4,6-triamine
-
Pneumocystis carinii
N6-(2,5-dimethoxybenzyl)-N6-methylquinazoline-2,4,6-triamine
-
Toxoplasma gondii
N6-(2,5-dimethoxybenzyl)pyrido[2,3-d]pyrimidine-2,4,6-triamine
-
Pneumocystis carinii
N6-(2,5-dimethoxybenzyl)pyrido[2,3-d]pyrimidine-2,4,6-triamine
-
Toxoplasma gondii
N6-(2,5-dimethoxybenzyl)quinazoline-2,4,6-triamine
-
Pneumocystis carinii
N6-(2,5-dimethoxybenzyl)quinazoline-2,4,6-triamine
-
Toxoplasma gondii
trimethoprim
-
Pneumocystis carinii
trimethoprim
-
Toxoplasma gondii
trimetrexate
-
Pneumocystis carinii
trimetrexate
-
Toxoplasma gondii

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
7,8-dihydrofolate + NADPH + H+ Pneumocystis carinii
-
5,6,7,8-tetrahydrofolate + NADP+
-
?
7,8-dihydrofolate + NADPH + H+ Toxoplasma gondii
-
5,6,7,8-tetrahydrofolate + NADP+
-
?

Organism

Organism UniProt Comment Textmining
Pneumocystis carinii
-
-
-
Toxoplasma gondii
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
7,8-dihydrofolate + NADPH + H+
-
Pneumocystis carinii 5,6,7,8-tetrahydrofolate + NADP+
-
?
7,8-dihydrofolate + NADPH + H+
-
Toxoplasma gondii 5,6,7,8-tetrahydrofolate + NADP+
-
?

Synonyms

Synonyms Comment Organism
DHFR
-
Pneumocystis carinii
DHFR
-
Toxoplasma gondii

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Pneumocystis carinii
37
-
assay at Toxoplasma gondii

Cofactor

Cofactor Comment Organism Structure
NADPH
-
Pneumocystis carinii
NADPH
-
Toxoplasma gondii

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0000025
-
-
Pneumocystis carinii 2,4-diamino-6-[N-(alpha-naphthyl)-N-ethylamino]quinazoline
0.0000036
-
-
Toxoplasma gondii 2,4-diamino-6-[N-(benzyl)-N-ethylamino]quinazoline
0.0000037
-
-
Toxoplasma gondii 2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-ethylamino]quinazoline
0.0000063
-
-
Toxoplasma gondii N6-(2,5-dimethoxybenzyl)-N6-methylpyrido[2,3-d]pyrimidine-2,4,6-triamine
0.0000069
-
-
Pneumocystis carinii 2,4-diamino-6-[N-(2,3,5-trichlorobenzyl)-N-ethylamino]quinazoline
0.0000072
-
-
Pneumocystis carinii 2,4-diamino-6-[N-(beta-naphthyl)-N-ethylamino]quinazoline
0.0000073
-
-
Toxoplasma gondii 2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-cyclopropyl methylamino]quinazoline
0.0000078
-
-
Toxoplasma gondii 2,4-diamino-6-[N-(alpha-naphthyl)-N-ethylamino]quinazoline
0.0000095
-
-
Toxoplasma gondii 2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-propylamino]quinazoline
0.0000099
-
-
Pneumocystis carinii 2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-ethylamino]quinazoline
0.000012
-
-
Toxoplasma gondii 2,4-diamino-6-[N-(beta-naphthyl)-N-ethylamino]quinazoline
0.000019
-
-
Toxoplasma gondii 2,4-diamino-6-[N-(2,3,5-trichlorobenzyl)-N-ethylamino]quinazoline
0.000019
-
-
Toxoplasma gondii 2,4-diamino-6-[N-(beta-naphthyl)-N-propylamino]quinazoline
0.000021
-
-
Pneumocystis carinii 2,4-diamino-6-[N-(benzyl)-N-ethylamino]quinazoline
0.000025
-
-
Pneumocystis carinii 2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-cyclopropyl methylamino]quinazoline
0.000025
-
-
Toxoplasma gondii 2,4-diamino-6-[N-(beta-naphthyl)-N-cyclopropyl methylamino]-quinazoline
0.000027
-
-
Pneumocystis carinii 2,4-diamino-6-[N-(beta-naphthyl)-N-propylamino]quinazoline
0.00003
-
-
Toxoplasma gondii N6-(2,5-dimethoxybenzyl)-N6-methylquinazoline-2,4,6-triamine
0.000038
-
-
Pneumocystis carinii 2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-propylamino]quinazoline
0.000042
-
-
Pneumocystis carinii 2,4-diamino-6-[N-(beta-naphthyl)-N-cyclopropyl methylamino]-quinazoline
0.000084
-
-
Pneumocystis carinii N6-(2,5-dimethoxybenzyl)-N6-methylpyrido[2,3-d]pyrimidine-2,4,6-triamine
0.000087
-
-
Pneumocystis carinii N6-(2,5-dimethoxybenzyl)-N6-methylquinazoline-2,4,6-triamine
0.00016
-
-
Toxoplasma gondii N6-(2,5-dimethoxybenzyl)quinazoline-2,4,6-triamine
0.00031
-
-
Toxoplasma gondii N6-(2,5-dimethoxybenzyl)pyrido[2,3-d]pyrimidine-2,4,6-triamine
0.0038
-
-
Pneumocystis carinii N6-(2,5-dimethoxybenzyl)pyrido[2,3-d]pyrimidine-2,4,6-triamine
0.0046
-
-
Pneumocystis carinii N6-(2,5-dimethoxybenzyl)quinazoline-2,4,6-triamine