Literature summary for 3.4.21.91 extracted from

Weng, Z.; Shao, X.; Graf, D.; Wang, C.; Klein, C.D.; Wang, J.; Zhou, G.C.
Identification of fused bicyclic derivatives of pyrrolidine and imidazolidinone as dengue virus-2 NS2B-NS3 protease inhibitors (2017), Eur. J. Med. Chem., 125, 751-759 .

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Inhibitors

Inhibitors	Comment	Organism
(3R,7aS)-2,3-bis(4-nitrophenyl)hexahydro-1H-pyrrolo-[1,2-c]imidazol-1-one	crystal structure analysis	Dengue virus type 2
(3R,7aS)-2-(4-nitrophenyl)-3-(4-(trifluoromethyl)-phenyl)-hexahydro-1H- pyrrolo[1,2-c]-imidazol-1-one	below 50% inhibition	Dengue virus type 2
(3R,7aS)-2-(4-nitrophenyl)-3-phenylhexahydro-1H-pyrrolo[1,2-c]imidazol-1-one	67% inhibition	Dengue virus type 2
(3R,7aS)-3-(3-nitrophenyl)-2-(4-nitrophenyl)hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one	below 50% inhibition	Dengue virus type 2
(3R,7aS)-3-(4-chlorophenyl)-2-(4-nitrophenyl)hexahydro-1H-pyrrolo[1,2-c]-imidazol-1-one	below 50% inhibition, crystal structure analysis	Dengue virus type 2
(3R,7aS)-3-(4-isopropylphenyl)-2-(4-nitrophenyl)-hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one	below 50% inhibition	Dengue virus type 2
(3R,7aS)-3-(4-methoxyphenyl)-2-(4-nitrophenyl)hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one	below 50% inhibition	Dengue virus type 2
(3R,7aS)-3-(4-nitrobenzyl)-2-(4-nitrophenyl)hexahydro-1Hpyrrolo[1,2-c]-imidaz-ol-1-one	below 50% inhibition	Dengue virus type 2
(3R,7aS)-3-benzyl-2-(4-nitrophenyl)hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one	42% inhibition	Dengue virus type 2
(3R,7aS)-3-ethyl-2-(4-nitrophenyl)hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one	60% inhibition	Dengue virus type 2
(3R,7aS)-3-isopropyl-2-(4-nitrophenyl)hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one	34% inhibition	Dengue virus type 2
(3R,7aS)-3-methyl-2-(4-nitrophenyl)hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one	42% inhibition	Dengue virus type 2
(3S,7aS)-2,3-bis(4-nitrophenyl)hexahydro-1H-pyrrolo-[1,2-c]imidazol-1-one	below 50% inhibition	Dengue virus type 2
(3S,7aS)-2-(4-nitrophenyl)-3-(4-(trifluoromethyl)-phenyl)hexahydro-1H- pyrrolo[1,2-c]-imidazol-1-one	below 50% inhibition	Dengue virus type 2
(3S,7aS)-3-(4-chlorophenyl)-2-(4-nitrophenyl)hexa-hydro-1H-pyrrolo[1,2-c]imidazol-1-one	below 50% inhibition	Dengue virus type 2
(S)-2-(4-nitrophenyl)hexahydro-1H-pyrrolo[1,2-c]imida-zol-1-one	39% inhibition	Dengue virus type 2
D-methionyl-N-(4-nitrobenzyl)-L-prolinamide	64% inhibition	Dengue virus type 2
D-methionyl-N-benzyl-L-prolinamide	42% inhibition	Dengue virus type 2
D-methionyl-N-phenyl-L-prolinamide	below 50% inhibition	Dengue virus type 2
L-methionyl-N-(4-nitrophenyl)-L-prolinamide	68% inhibition	Dengue virus type 2
additional information	identification of fused bicyclic derivatives of pyrrolidine and imidazolidinone as dengue virus-2 NS2B-NS3 protease inhibitors. The preliminary structure-activity relationship reveals that a substituent and its stereochemistry at C-3 position, substitution (X) at N-2 arene and a linker (Y) between C-3 position and its attached arene are important for the fused-ring scaffold of pyrrolidino [1,2-c]imidazolidinone to block the active site of NS2B-NS3 protease. The linear dipeptide L-methionyl-N-(4-nitrophenyl)-L-prolinamide) and the non-peptidic fused ring L-methionyl-N-(4-nitrophenyl)-L-prolinamide) show comparable activities against DENV-2 NS2B-NS3 protease and wild-type DENV-2 virus in a viral replication assay	Dengue virus type 2

Organism

Organism	UniProt	Comment	Textmining
Dengue virus type 2	-	DENV-2	-

Synonyms

Synonyms	Comment	Organism
DENV-2 NS2B-NS3 protease	-	Dengue virus type 2
NS2B-NS3 protease	-	Dengue virus type 2

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor	Structure
0.0012	-	pH and temperature not specified in the publication	Dengue virus type 2	(3R,7aS)-2,3-bis(4-nitrophenyl)hexahydro-1H-pyrrolo-[1,2-c]imidazol-1-one
0.0012	-	pH and temperature not specified in the publication	Dengue virus type 2	L-methionyl-N-(4-nitrophenyl)-L-prolinamide