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Literature summary extracted from

  • Grunewald, G.L.; Seim, M.R.; Regier, R.C.; Martin, J.L.; Gee, C.L.; Drinkwater, N.; Criscione, K.R.
    Comparison of the binding of 3-fluoromethyl-7-sulfonyl-1,2,3,4-tetrahydroisoquinolines with their isosteric sulfonamides to the active site of phenylethanolamine N-methyltransferase (2006), J. Med. Chem., 49, 5424-5433.
    View publication on PubMed

Application

EC Number Application Comment Organism
2.1.1.28 additional information a potent inhibitor of phenylethanolamine N-methyltransferase, which exhibits a minimal affinity for the alpha-adrenoceptor, would be a useful pharmacological tool for clearly defining the connection between central epinephrine concentrations and blood pressure. Homo sapiens

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.1.1.28 expressed in Escherichia coli Homo sapiens

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
2.1.1.28
-
 Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.1.1.28 3-fluoromethyl-7-(2,2,2-trifluoroethylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
 Homo sapiens
2.1.1.28 3-fluoromethyl-7-(3,3,3-trifluoropropylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
 Homo sapiens
2.1.1.28 3-fluoromethyl-7-(4,4,4-trifluorobutylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
 Homo sapiens
2.1.1.28 3-fluoromethyl-7-(4-chlorobenzylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
 Homo sapiens
2.1.1.28 3-fluoromethyl-7-propylsulfonyl-1,2,3,4-tetrahydroisoquinoline
-
 Homo sapiens
2.1.1.28 7-(3-methoxypropylsulfonyl)-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
 Homo sapiens
2.1.1.28 7-butylsulfonyl-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
 Homo sapiens
2.1.1.28 7-ethylsulfonyl-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
 Homo sapiens
2.1.1.28 additional information the series of 3-fluoromethyl-7-sulfonyl-1,2,3,4-tetrahydroisoquinolines is more lipophilic but less potent than the correspnding sulfonamides. The interaction of the human phenylethanolamnie N-methyltransferase main chain carbonyl oxygen of Asn39 with the sulfonamide -NH- is likely responsible for much of the enhanced inhibitory potency of the sulfonamides versus the sulfones. Homo sapiens

Organism

EC Number Organism UniProt Comment Textmining
2.1.1.28 Homo sapiens P11086
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.1.1.28
-
 Homo sapiens

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.1.1.28 0.0013
-
 3-fluoromethyl-7-(3,3,3-trifluoropropylsulfonyl)-1,2,3,4-tetrahydroisoquinoline inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate and three concentrations of inhibitor with a radiochemical assay. Homo sapiens
2.1.1.28 0.0014
-
 3-fluoromethyl-7-(2,2,2-trifluoroethylsulfonyl)-1,2,3,4-tetrahydroisoquinoline inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate and three concentrations of inhibitor with a radiochemical assay. Homo sapiens
2.1.1.28 0.0024
-
 3-fluoromethyl-7-propylsulfonyl-1,2,3,4-tetrahydroisoquinoline inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate and three concentrations of inhibitor with a radiochemical assay. Homo sapiens
2.1.1.28 0.014
-
 7-ethylsulfonyl-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline inhibition constants are determine using four concentrations of phenylethanolamnie as the variable substrate and three concentrations of inhibitor with a radiochemical assay. Homo sapiens
2.1.1.28 0.018
-
 7-butylsulfonyl-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate and three concentrations of inhibitor with a radiochemical assay. Homo sapiens
2.1.1.28 0.032
-
 3-fluoromethyl-7-(4-chlorobenzylsulfonyl)-1,2,3,4-tetrahydroisoquinoline inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate and three concentrations of inhibitor with a radiochemical assay. Homo sapiens
2.1.1.28 0.067
-
 3-fluoromethyl-7-(4,4,4-trifluorobutylsulfonyl)-1,2,3,4-tetrahydroisoquinoline inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate and three concentrations of inhibitor with a radiochemical assay. Homo sapiens
2.1.1.28 0.072
-
 7-(3-methoxypropylsulfonyl)-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline inhibition constants are determined using four concentrations of phenylethanolamnie as the variable substrate and three concentrations of inhibitor with a radiochemical assay. Homo sapiens