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Literature summary for 3.1.26.13 extracted from

  • Murelli, R.P.; D'Erasmo, M.P.; Hirsch, D.R.; Meck, C.; Masaoka, T.; Wilson, J.A.; Zhang, B.; Pal, R.K.; Gallicchio, E.; Beutler, J.A.; Le Grice, S.F.
    Synthetic alpha-hydroxytropolones as inhibitors of HIV reverse transcriptase ribonuclease H activity (2016), MedChemComm, 7, 1783-1788 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 3.1.26.13

Inhibitors

Inhibitors Comment Organism Structure
2,7-dihydroxy-4-methyl-5-(2-methylbutanoyl)cyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
2,7-dihydroxy-4-methyl-5-(4-nitrophenyl)cyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
2,7-dihydroxy-4-methyl-5-(naphthalen-1-yl)cyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
2,7-dihydroxy-4-methyl-5-(naphthalen-2-yl)cyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
2,7-dihydroxy-4-methyl-5-phenylcyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
2,7-dihydroxy-4-methyl-5-[4-(trifluoromethyl)phenyl]cyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
4-(3-bromophenyl)-2,7-dihydroxy-5-methylcyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
4-(4-bromophenyl)-2,7-dihydroxy-5-methylcyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
4-(4-chlorophenyl)-2,7-dihydroxy-5-methylcyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
4-(cyclohexanecarbonyl)-2,7-dihydroxy-5-methylcyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
4-(cyclohexylacetyl)-2,7-dihydroxy-5-methylcyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
4-([1,1'-biphenyl]-4-carbonyl)-2,7-dihydroxy-5-methylcyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
4-([1,1'-biphenyl]-4-yl)-2,7-dihydroxy-5-methylcyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
4-acetyl-2,7-dihydroxy-5-methylcyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
4-benzoyl-2,7-dihydroxy-5-methylcyclohepta-2,4,6-trien-1-one
-
 Human immunodeficiency virus 1
beta-thujaplicinol a non-competitive inhibitor of RNase H Human immunodeficiency virus 1
dimethyl 3-(chloromethyl)-5,7-dihydroxy-6-oxocyclohepta-2,4,7-triene-1,2-dicarboxylate
-
 Human immunodeficiency virus 1
dimethyl 5,7-dihydroxy-3-(methoxymethyl)-6-oxocyclohepta-2,4,7-triene-1,2-dicarboxylate
-
 Human immunodeficiency virus 1
dimethyl 5,7-dihydroxy-3-methyl-6-oxocyclohepta-2,4,7-triene-1,2-dicarboxylate
-
 Human immunodeficiency virus 1
ethyl 4,6-dihydroxy-2,7-dimethyl-5-oxocyclohepta-1,3,6-triene-1-carboxylate
-
 Human immunodeficiency virus 1
ethyl 4,6-dihydroxy-2-methyl-5-oxocyclohepta-1,3,6-triene-1-carboxylate
-
 Human immunodeficiency virus 1
manicol source of manicol is the root bark of a rare Guyanan tree, Dulacia guianeinsis Human immunodeficiency virus 1
methyl 4,6-dihydroxy-2-methyl-5-oxocyclohepta-1,3,6-triene-1-carboxylate
-
 Human immunodeficiency virus 1
methyl 7-bromo-4,6-dihydroxy-2-methyl-5-oxocyclohepta-1,3,6-triene-1-carboxylate
-
 Human immunodeficiency virus 1
additional information library screening of alpha-hydroxytropolones synthesized through a convenient oxidopyrylium cycloaddition/ring-opening sequence, synthetic alpha-hydroxytropolones act as inhibitors of HIV reverse transcriptase ribonuclease H activity, structure-function analysis, overview. Homology model of substrate- and inhibitor-bound HIV-1 RNase H, molecular docking. beta-Thujaplicinol and manicol share a rare alpha-hydroxytropolone moiety that crystal-structure analysis reveals to be a key for the potent inhibition of the enzyme. Unfortunately, both of these natural products display cytotoxicity in cell-based antiviral assays that precludes cellular antiviral activity. The slight steric change from a methyl to chloromethylene to methoxymethylene decreases the inhibitory potency by close to a full order of magnitude. Enzyme residue Tyr501, which is predicted computationally to be involved in interactions with the side chain, is blocked by the substrate. HIV-1 cytopathicity assays are performed, cytotoxicity of synthetic alpha-hydroxytropolones and beta-thujaplicinol against CEM-SS cells Human immunodeficiency virus 1

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required Human immunodeficiency virus 1

Organism

Organism UniProt Comment Textmining
Human immunodeficiency virus 1 P05959 HIV-1
-
Human immunodeficiency virus 1 RF P05959 HIV-1
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information a 18-nucleotide 3'-fluorescein-labeled RNA is annealed to a complementary 18-nucleotide 5'-dabsyl-labeled DNA. Cleavage of the HIV-1 polypurine tract (PPT) primer is performed with a 29 nt Cy5-labeled RNA (5'-Cy5-UUU UAA AAG AAA AGGGGG G*AC UGG AAG GG-3', where * represents the PPT 3' terminus) hybridized to a 40 nt DNA (5'-ATT AGCCCT TCC AGT CCC CCC TTT TCT TTT AAA AAG TGG C-3'). For cytopathicity assays, HIV-1 virus strain RF is used to infect CEM-SS cells Human immunodeficiency virus 1 ?
-
 ?
additional information a 18-nucleotide 3'-fluorescein-labeled RNA is annealed to a complementary 18-nucleotide 5'-dabsyl-labeled DNA. Cleavage of the HIV-1 polypurine tract (PPT) primer is performed with a 29 nt Cy5-labeled RNA (5'-Cy5-UUU UAA AAG AAA AGGGGG G*AC UGG AAG GG-3', where * represents the PPT 3' terminus) hybridized to a 40 nt DNA (5'-ATT AGCCCT TCC AGT CCC CCC TTT TCT TTT AAA AAG TGG C-3'). For cytopathicity assays, HIV-1 virus strain RF is used to infect CEM-SS cells Human immunodeficiency virus 1 RF ?
-
 ?

Synonyms

Synonyms Comment Organism
HIV reverse transcriptase ribonuclease H
-
 Human immunodeficiency virus 1
HIV RT RNaseH
-
 Human immunodeficiency virus 1
RNaseH
-
 Human immunodeficiency virus 1

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Human immunodeficiency virus 1

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
 assay at Human immunodeficiency virus 1

General Information

General Information Comment Organism
additional information homology model of substrate- and inhibitor-bound HIV-1 RNase H, molecular docking, overview Human immunodeficiency virus 1