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RN-18

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Category Human immunodeficiency Virus (HIV)
CAS 431980-38-0
Description RN-18, a selective inhibitor of virion infectivity factor (Vif) APOBEC interactions and HIV-1 replication (IC50= 6 μM in nonpermissive H9 cells), antagonizes Vif function and inhibits HIV-1 replication only in the presence of A3G.
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Product Information

Synonyms RN-18; RN 18; RN18; N-(2-methoxyphenyl)-2-(4-nitrophenyl)sulfanylbenzamide; 2-(4-Nitrophenylthio)-N-(2-methoxyphenyl)benzamide; AC1LQ42R; Ambcb6776439
IUPAC Name N-(2-methoxyphenyl)-2-(4-nitrophenyl)sulfanylbenzamide
Molecular Weight 380.42
Molecular Formula C20H16N2O4S
Canonical SMILES COC1=CC=CC=C1NC(=O)C2=CC=CC=C2SC3=CC=C(C=C3)[N+](=O)[O-]
InChI 1S/C20H16N2O4S/c1-26-18-8-4-3-7-17(18)21-20(23)16-6-2-5-9-19(16)27-15-12-10-14(11-13-15)22(24)25/h2-13H,1H3,(H,21,23)
InChIKey JKNUDHUHXMELIJ-UHFFFAOYSA-N
Boiling Point 493.6±40.0 °C at 760 Torr
Purity 99.37%
Density 1.36±0.1 g/cm3
Solubility DMSO: 10 mM
Appearance Light yellow to yellow (Solid)
Storage Store in a cool and dry place (or refer to the Certificate of Analysis).
Complexity 505
Exact Mass 380.08307817
In Vitro RN-18 and RN-19 exhibits potent antiviral activity in the nonpermissive H9 and CEM cells but not in MT4 or CEM-SS cells, confirming that the antiviral activity was Vif specific. RN-18 shows the greater potency (IC50=4.5 μM in CEM cells) and specificity (IC50>100 μM in MT4 cells) among the two compounds. In the presence of the inhibitor, RN-18, reverse transcriptase activity in the nonpermissive H9 and CEM cells decreases substantially and in a dose-dependent manner. RN-18 also exhibits antiviral activity in CEM-SS modified to stably express A3G but does not exhibit antiviral activity in the parental CEM-SS cell line. RN-18 antagonizes Vif function and inhibits HIV-1 replication only in the presence of A3G. RN-18 increases cellular A3G levels in a Vif-dependent manner and increases A3G incorporation into virions without inhibiting general proteasome-mediated protein degradation. RN-18 enhances Vif degradation only in the presence of A3G, reduces viral infectivity by increasing A3G incorporation into virions and enhances cytidine deamination of the viral genome.
PSA 112.94000
Target HIV
XLogP3-AA 4.6

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