Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 3.1.26.13 extracted from

  • Wang, L.; Tang, J.; Huber, A.D.; Casey, M.C.; Kirby, K.A.; Wilson, D.J.; Kankanala, J.; Parniak, M.A.; Sarafianos, S.G.; Wang, Z.
    6-Biphenylmethyl-3-hydroxypyrimidine-2,4-diones potently and selectively inhibited HIV reverse transcriptase-associated RNase H (2018), Eur. J. Med. Chem., 156, 680-691 .
    View publication on PubMedView publication on EuropePMC

Application

Application Comment Organism
drug development the HIV RT-associated RNase H is avaluable drug target Human immunodeficiency virus 1

Inhibitors

Inhibitors Comment Organism Structure
1,6-bis[(4-fluorophenyl)methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
1,6-dibenzyl-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
1-(ethoxymethyl)-3-hydroxy-6-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
1-(ethoxymethyl)-6-[(4-fluorophenyl)methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
1-benzyl-6-[(4-fluorophenyl)methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
1-[[(4-fluorophenyl)methoxy]methyl]-6-[(4-fluorophenyl)methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
3-hydroxy-6-((3'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methyl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
3-hydroxy-6-((3'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
3-hydroxy-6-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
4'-((3-(ethoxymethyl)-1-hydroxy-5-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)methyl)-[1,1'-biphenyl]-4-carbonitrile
-
Human immunodeficiency virus 1
5-benzyl-6-ethyl-1-(((4-fluorobenzyl)oxy)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
5-ethyl-1-(((4-fluorobenzyl)oxy)methyl)-6-(4-fluorophenyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-( (3'- fluoro-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((2',4'-bis(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((2',4'-dichloro-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((2',4'-difluoro-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((3',5'-dimethoxy-[1,1'-biphenyl]-4-yl)methyl)-1-(ethoxymethyl)-3-hydroxy-5-methylpyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((3'-chloro-5'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((3'-chloro-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((3'-chloro-[1,1'-biphenyl ] - 4 -yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((3'-chloro-[1,1'-biphenyl ]-3-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((3'-fluoro-4'-methoxy-[1,1'-biphenyl]-3-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((3'-fluoro-4'-methoxy-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((3'-fluoro-[1,1'-biphenyl]-3-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((4'-chloro-3'-fluoro-[1,1'-biphenyl]-4-yl)methyl)-1-(ethoxymethyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((4'-chloro-3'-fluoro-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((4'-chloro-[1,1'-biphenyl ]-3-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((4'-fluoro-3'-methyl-[1,1'-biphenyl]-3-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-((4'-fluoro-3'-methyl-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-(3-bromobenzyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-(4-bromobenzyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-([1,1'-biphenyl]-3-ylmethyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-([1,1'-biphenyl]-4-yl)-1-(ethoxymethyl)-3-hydroxy-5-methylpyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-([1,1'-biphenyl]-4-ylmethyl)-1-(ethoxymethyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-([1,1'-biphenyl]-4-ylmethyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-benzyl-1-(((4-fluorobenzyl)oxy)methyl)-5-isopropyl-3-methoxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-benzyl-1-(((4-fluorobenzyl)oxy)methyl)-5-isopropyl-3-methylpyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-benzyl-1-(ethoxymethyl)-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-benzyl-1-[(benzyloxy)methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-benzyl-1-[2-(4-fluorophenyl)ethyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-benzyl-1-[3-(4-fluorophenyl)propyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-benzyl-1-[4-(4-fluorophenyl)butyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-benzyl-1-[[(2,4-difluorophenyl)methoxy]methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-benzyl-1-[[(3-chloro-2-fluorophenyl)methoxy]methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-benzyl-1-[[(4-fluorophenyl)methoxy]methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-benzyl-1-[[3-(4-fluorophenyl)propoxy]methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-benzyl-1-[[4-(4-fluorophenyl)butoxy]methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-[(4'-chloro[1,1'-biphenyl]-3-yl)amino]-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
6-[([1,1'-biphenyl]-4-yl)amino]-3-hydroxypyrimidine-2,4(1H,3H)-dione
-
Human immunodeficiency virus 1
additional information 6-biphenylmethyl-3-hydroxypyrimidine-2,4-diones potently and selectively inhibit HIV reverse transcriptase-associated RNase H, overview. Design, synthesis, biochemical and antiviral evaluations of a 6-biphenylmethyl subtype of the 3-hydroxypyrimidine-2,4-dione (HPD) chemotype. The subtype potently inhibits RT RNase H in low nanomolar range without inhibiting RT polymerase (pol) or integrase strand transfer (INST) at the highest concentrations tested. A few analogues inhibit HIV in low micromolar range without cytotoxicity at concentrations up to 0.1 mM in cell-based assays. EC50 values and antiviral activity of the compounds, overview Human immunodeficiency virus 1

Organism

Organism UniProt Comment Textmining
Human immunodeficiency virus 1
-
HIV-1
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information RNA/DNA duplex substrate HTS-1 (RNA 5'-gaucugagccugggagcu-3'-fluorescein annealed to DNA 3'-CTAGACTCGGACCCTCGA-5'-dabsyl) is a high sensitivity duplex assessing non-specific internal cleavage Human immunodeficiency virus 1 ?
-
?

Synonyms

Synonyms Comment Organism
HIV reverse transcriptase-associated RNase H
-
Human immunodeficiency virus 1
HIV RT-associated RNase H
-
Human immunodeficiency virus 1
human immunodeficiency virus reverse transcriptase-associated RNase H
-
Human immunodeficiency virus 1
human immunodeficiency virus RT-associated RNase H
-
Human immunodeficiency virus 1
RT RNase H
-
Human immunodeficiency virus 1

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0000076
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((3'-fluoro-4'-methoxy-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.0000077
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((3'-fluoro-4'-methoxy-[1,1'-biphenyl]-3-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.0000088
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((4'-fluoro-3'-methyl-[1,1'-biphenyl]-3-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.0000092
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((2',4'-dichloro-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.0000094
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((4'-chloro-3'-fluoro-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000011
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((4'-fluoro-3'-methyl-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000011
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-(4-bromobenzyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000012
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((4'-chloro-[1,1'-biphenyl ]-3-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000013
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-(3-bromobenzyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000015
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((2',4'-difluoro-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000015
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((3'-chloro-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000016
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-([1,1'-biphenyl]-3-ylmethyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000016
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-([1,1'-biphenyl]-4-ylmethyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000016
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((3'-chloro-[1,1'-biphenyl ] - 4 -yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000018
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((3'-fluoro-[1,1'-biphenyl]-3-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.00002
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((3'-chloro-[1,1'-biphenyl ]-3-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000025
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 3-hydroxy-6-((3'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)pyrimidine-2,4(1H,3H)-dione
0.000028
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-( (3'- fluoro-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000037
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 3-hydroxy-6-((3'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methyl)pyrimidine-2,4(1H,3H)-dione
0.000038
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((3'-chloro-5'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.000047
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 3-hydroxy-6-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)pyrimidine-2,4(1H,3H)-dione
0.000085
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((2',4'-bis(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.00022
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-[(4'-chloro[1,1'-biphenyl]-3-yl)amino]-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.00025
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-[([1,1'-biphenyl]-4-yl)amino]-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.00043
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((4'-chloro-3'-fluoro-[1,1'-biphenyl]-4-yl)methyl)-1-(ethoxymethyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.0009
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-benzyl-1-[4-(4-fluorophenyl)butyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.0009
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-benzyl-1-[[(3-chloro-2-fluorophenyl)methoxy]methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.0018
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-benzyl-1-[[(2,4-difluorophenyl)methoxy]methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.0018
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-benzyl-1-[[4-(4-fluorophenyl)butoxy]methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.0021
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 1-(ethoxymethyl)-3-hydroxy-6-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)pyrimidine-2,4(1H,3H)-dione
0.0021
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-benzyl-1-[[(4-fluorophenyl)methoxy]methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.0025
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-benzyl-1-[(benzyloxy)methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.0028
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-benzyl-1-[[3-(4-fluorophenyl)propoxy]methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.0038
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-benzyl-1-[3-(4-fluorophenyl)propyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.005
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-([1,1'-biphenyl]-4-ylmethyl)-1-(ethoxymethyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.0052
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 4'-((3-(ethoxymethyl)-1-hydroxy-5-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)methyl)-[1,1'-biphenyl]-4-carbonitrile
0.0062
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 1-[[(4-fluorophenyl)methoxy]methyl]-6-[(4-fluorophenyl)methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.0062
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-([1,1'-biphenyl]-4-yl)-1-(ethoxymethyl)-3-hydroxy-5-methylpyrimidine-2,4(1H,3H)-dione
0.0066
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-benzyl-1-[2-(4-fluorophenyl)ethyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.0067
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-((3',5'-dimethoxy-[1,1'-biphenyl]-4-yl)methyl)-1-(ethoxymethyl)-3-hydroxy-5-methylpyrimidine-2,4(1H,3H)-dione
0.0068
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-benzyl-1-(ethoxymethyl)-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.007
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-benzyl-1-(((4-fluorobenzyl)oxy)methyl)-5-isopropyl-3-methylpyrimidine-2,4(1H,3H)-dione
0.01
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 1-benzyl-6-[(4-fluorophenyl)methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.011
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 6-benzyl-1-(((4-fluorobenzyl)oxy)methyl)-5-isopropyl-3-methoxypyrimidine-2,4(1H,3H)-dione
0.013
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 1,6-bis[(4-fluorophenyl)methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.015
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 1,6-dibenzyl-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
0.015
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 5-benzyl-6-ethyl-1-(((4-fluorobenzyl)oxy)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.017
-
pH and temperature not specified in the publication Human immunodeficiency virus 1 5-ethyl-1-(((4-fluorobenzyl)oxy)methyl)-6-(4-fluorophenyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
0.025
-
above, pH and temperature not specified in the publication Human immunodeficiency virus 1 1-(ethoxymethyl)-6-[(4-fluorophenyl)methyl]-3-hydroxy-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione