All Photos(1)
Synonym(s):
2-(3,4-Dichlorophenoxy)-5-nitrobenzonitrile
Empirical Formula (Hill Notation):
C13H6Cl2N2O3
Recommended Products
Assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
2-8°C
SMILES string
ClC1=CC=C(OC2=CC=C([N+]([O-])=O)C=C2C#N)C=C1Cl
InChI
1S/C13H6Cl2N2O3/c14-11-3-2-10(6-12(11)15)20-13-4-1-9(17(18)19)5-8(13)7-16/h1-6H
InChI key
QAYKDRUKUZJJSO-UHFFFAOYSA-N
Biochem/physiol Actions
MDL-860 is a 5-nitro-2-phenoxybenzonitrile that exerts broad-spectrum antipicornaviral activity (MIC50 from 0.1-1.5 μg/mL in HeLa cultures) by acting as an irreversible inhibitor against host phosphatidylinositol-4 kinase beta (PI4KB; PtdIns 4-kinase beta; PI4Kbeta; NPIK; PI4K92) via covalent modification of Cys646 located at the bottom of a surface pocket apart from the PI4KB active site. MCL-860 (MIC50 from 0.1-1.5 μg/mL in HeLa cultures). A pleconaril/MDL-860/oxoglaucine consecutive alternating administration (CAA), but not simultaneous daily treatment, is reported to be effective against coxsackievirus B1 infection without the development of drug resistance in newborn mice (75 mg/kg MDL-860 via s.c. every third day on the day following pleconaril and prior to oxoglaucine).
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Oral
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Antiviral activity and mechanism of action of 2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile (MDL-860).
H L Torney et al.
Antimicrobial agents and chemotherapy, 22(4), 635-638 (1982-10-01)
A nitrobenzene derivative, MDL-860, was found to inhibit plaque formation, cytopathic effect, or both in 11 of 12 picornaviruses at concentrations which did not affect cell growth. The compound did not directly inactivate the virus. MDL-860 inhibited actinomycin D-resistant [3H]uridine
R D Powers et al.
Antimicrobial agents and chemotherapy, 22(4), 639-642 (1982-10-01)
The newly synthesized compound 2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile (MDL-860) has been found to inhibit picornavirus replication. In multiple growth cycle experiments, 1 microgram of MDL-860 per ml caused a reduction in virus yield of at least 1.0 log10 50% tissue culture infectious doses
Georgi M Dobrikov et al.
Bioorganic & medicinal chemistry letters, 27(19), 4540-4543 (2017-09-06)
A series of twelve novel compounds, analogues of antiviral agent MDL-860 were synthesized and their antiviral activity was evaluated in vitro against enteroviruses poliovirus 1 (PV1), Coxsackieviruses B1 (CVB1) and Coxsackieviruses B3 (CVB3). Compounds 14, 24 and 25 manifested strong
Minetaro Arita et al.
ACS infectious diseases, 3(8), 585-594 (2017-06-13)
MDL-860 is a broad-spectrum antipicornavirus compound discovered in 1982 and one of the few promising candidates effective in in vivo virus infection. Despite the effectiveness, the target and the mechanism of action of MDL-860 remain unknown. Here, we have characterized
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