Reaktion #1946229

ord-97e4c5341f154b538ffd8ba29af57b97

Reaktionsgleichung

Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)[O-])C(=O)O)cc1)CN2
dihydrofolate
COc1cc(NCc2ccc3nc(N)nc(N)c3c2C)cc(OC)c1OC.Cc1nc(N)nc(N)c1-c1ccc(Cl)c(Cl)c1
2,4-diamino,5-(3',4'-dichlorophenyl),6-methylpyrimidine trimetrexate
Nc1nc(N)c2nc(CNc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cnc2n1
aminopterin
CCc1nc(N)nc(N)c1-c1ccc(Cl)cc1
pyrimethamine
Nc1nc(=O)c2c([nH]1)NCC(CCc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)C2
5,10-dideazatetrahydrofolate
CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1
methotrexate
→
Nc1nc2nccnc2c(=O)[nH]1
pterin

Edukte

Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)[O-])C(=O)O)cc1)CN2
dihydrofolate
COc1cc(NCc2ccc3nc(N)nc(N)c3c2C)cc(OC)c1OC.Cc1nc(N)nc(N)c1-c1ccc(Cl)c(Cl)c1
2,4-diamino,5-(3',4'-dichlorophenyl),6-methylpyrimidine trimetrexate
Nc1nc(N)c2nc(CNc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cnc2n1
aminopterin
—
10-propargyl-5,8-dideazafolate
CCc1nc(N)nc(N)c1-c1ccc(Cl)cc1
pyrimethamine
Nc1nc(=O)c2c([nH]1)NCC(CCc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)C2
5,10-dideazatetrahydrofolate
—
10-ethyl,10-deaza-aminopterin
CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1
methotrexate

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

When in the above examples, other dihydrofolate reductase inhibitors replace methotrexate, e.g. aminopterin or 10-propargyl-5,8-dideazafolate or 2,4-diamino,5-(3',4'-dichlorophenyl),6-methylpyrimidine trimetrexate, or pyrimethamine or trimethorprim or pyritrexim 5,10-dideazatetrahydrofolate or 10-ethyl,10-deaza-aminopterin, similar results of pterin salvage pathway blocking are obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06153615uspto-grants-2000_11