153168-05-9

Hazards Identification

Pictogram(s):

Signal:

Danger

GHS Hazard Statements:

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
H413 (100%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes:

P264, P270, P273, P301+P316, P321, P330, P405, and P501

Hazard Classes and Categories:

Acute Tox. 3 (100%)
Aquatic Chronic 4 (100%)

Usage

Uses

Used in Pharmaceutical Industry:
PLECONARIL is used as a control or reference compound for evaluating the antiviral activities of benzothiophene and other heteroaromatic derivatives against different human rhinoviruses (hRV-B14, hRV-A21, and hRV-A71). This application aids in the development of more effective antiviral agents.
Used in Antiviral Research:
As a picornavirus replication inhibitor, PLECONARIL is used in antiviral research to study and combat viral infections. Its role in inhibiting the replication of picornaviruses makes it a valuable tool in the development of new antiviral treatments.

Pharmaceutical Applications

An oxadiazole active against most enteroviruses and rhinoviruses. It binds to the hydrophobic pocket of the virus capsid protein VP1, inducing conformational changes that lead to altered receptor binding and viral uncoating. Concerns over safety and efficacy have constrained development of the drug.

Biochem/physiol Actions

Pleconaril is an effective drug against enteroviral infections. It can be used to treat chronic meningoencephalitis caused by echo virus 6.This can block viral replication by blocking the viral uncoating process and viral attachment to host cell receptors.

InChI:InChI=1/C18H18F3N3O3/c1-10-7-13(16-22-17(27-24-16)18(19,20)21)8-11(2)15(10)25-6-4-5-14-9-12(3)23-26-14/h7-9H,4-6H2,1-3H3

Upstream product

• 122372-40-1 2-(2,2,2-trifluoroethylidene)-1,3-dithiane 
• 153168-47-9 N-hydroxy-3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>benzenecarboxamide imine 
• 407-25-0 trifluoroacetic anhydride 

Relevant academic research and scientific papers

Picornavirus Inhibitors: Trifluoromethyl Substitution Provides a Global Protective Effect against Hepatic Metabolism

Several modifications of the oxazoline ring of WIN 54954, a broad spectrum antipicornavirus compound, have been prepared in order to address the acid lability and metabolic instability of this compound.We have previously shown that the oxadiazole analogue 3 displayed comparable activity against a variety of rhinoviruses and appeared to be stable to acid.A monkey liver microsomal assay was developed to examine the metabolic stability in vitro of both compounds, and it was determined that WIN 54954 displayed 18 metabolic products while 3 was converted to 8 products.Two major products of 3 were determined by LC-MS/MS to be monohydroxylated at each of the terminal methyl groups.Replacement of the methyl on the isoxazole ring with a trifluoromethyl group, while preventing hydroxylation at this position, did not reduce the sensitivity of the molecule to microsomal metabolism at other sites.However, the (trifluoromethyl)oxadiazole 9 not only prevented hydroxylation at this position but also provided protection at the isoxazole end of the molecule, resulting in only two minor products to the extent of 4percent.The major product was identified as the monohydroxylated compound 23.The global metabolic protective effect of trifluoromethyl group on the oxadiazole ring was further demonstrated by examining a variety of analogues including heterocyclic replacements of the isoxazole ring.In each case, the trifluoromethyl analogue displayed a protective effect when compared to the corresponding methyl analogue.

1,2,4-OXADIAZOLYL-PHENOXYALKYLISOXAZOLES AND THEIR USE AS ANTIVIRAL AGENTS

Compounds of the formula wherein: R1 is alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy, or cyanomethyl; Y is alkylene of 3 to 9 carbon atoms, R2 and R3 independently are hydrogen, alkyl, alkoxy, halo, cyano, trifluoromethyl and nitro; R4 is alkoxy, hydroxy, halomethyl, dihalomethyl, trihalomethyl, dihaloethyl, cycloalkyl, heterocyclyl, alkoxycarbonyl, hydroxyalkyl, alkoxyalkyl, alkanecarbonyloxyalkyl, cyano, halo, thioalkyl, alkylthioalkyl, alkylthio, thio, 2,2,2-trifluoro-ethyl, (4-methylphenyl)sulfonyloxymethyl, N=Q or CON=Q, where N=Q is amino, alkylamino or dialkylamino; R5 is hydrogen or halo or alkyl

1,2,4-oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral agents

Compounds of the formula STR1 wherein: R1 is alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, alkoxyalkyl or hydroxyalkoxy; Y is alkylene of 3 to 9 carbon atoms, R2 and R3 independently are hydrogen, alkyl, alkoxy, halo,