389629-41-8

Basic information

• Product Name: Piperazine, 1-benzoyl-4-[[4-fluoro-7-(1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]oxoacetyl]-
• CAS NO: 389629-41-8
• Molecular Formula: C23H18FN5O4
• Mol File: 389629-41-8.mol

Chemical Properties

• CAS DataBase Reference: Piperazine, 1-benzoyl-4-[[4-fluoro-7-(1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]oxoacetyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperazine, 1-benzoyl-4-[[4-fluoro-7-(1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]oxoacetyl]-(389629-41-8)
• EPA Substance Registry System: Piperazine, 1-benzoyl-4-[[4-fluoro-7-(1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]oxoacetyl]-(389629-41-8)

Safety Data

• Hazardous Substances Data: 389629-41-8(Hazardous Substances Data)

Upstream product

• 389628-85-7 C₂₂H₂₀FN₅O₄ 
• 122-51-0 orthoformic acid triethyl ester 
• 389628-22-2 C₁₁H₄ClFN₂O₂ 
• 313337-33-6 4-fluoro-1H-indole-7-carbonitrile 
• 292636-09-0 7-bromo-4-fluoro-1H-indole 

Relevant articles and documents

Inhibitors of HIV-1 attachment. Part 8: The effect of C7-heteroaryl substitution on the potency, and in vitro and in vivo profiles of indole-based inhibitors

As part of the SAR profiling of the indole-oxoacetic piperazinyl benzamide class of HIV-1 attachment inhibitors, substitution at the C7 position of the lead 4-fluoroindole 2 with various 5- and 6-membered heteroaryl moieties was explored. Highly potent (picomolar) inhibitors of pseudotyped HIV-1 in a primary, cell-based assay were identified and select examples were shown to possess nanomolar inhibitory activity against M- and T-tropic viruses in cell culture. These C7-heteroaryl-indole analogs maintained the ligand efficiency (LE) of 2 and were also lipophilic efficient as measured by LLE and LELP. Pharmacokinetic studies of this class of inhibitor in rats showed that several possessed substantially improved IV clearance and half-lives compared to 2. Oral exposure in the rat correlated with membrane permeability as measured in a Caco-2 assay where the highly permeable 1,2,4-oxadiazole analog 13 exhibited the highest exposure.

Composition and antiviral activity of substituted indoleoxoacetic piperazine derivatives

This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with indoleoxoacetyl piperazine derivatives. These compounds possess unique antiviral activity, whether used alone or in combination with other antivirals, antiinfectives, immunomodulators or HIV entry inhibitors. More particularly, the present invention relates to the treatment of HIV and AIDS.

Composition and antiviral activity of substituted indoleoxoacetic piperazine derivatives

The invention comprises substituted indoleoxoacetic piperazine derivatives of general Formula I, compositions thereof and their use as antiviral agents, and particularly for treating HIV infection.