313337-33-6

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole-7-carbonitrile,4-fluoro-(9CI) is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a promising candidate for drug discovery and development, particularly in the creation of new drugs with improved therapeutic effects.
Used in Medicinal Chemistry:
1H-Indole-7-carbonitrile,4-fluoro-(9CI) is used as a building block in medicinal chemistry for the design and synthesis of novel bioactive molecules. The presence of the nitrile group allows for further functionalization and synthesis of more complex compounds, expanding its potential applications in the development of new therapeutic agents.
Used in Chemical Industry:
1H-Indole-7-carbonitrile,4-fluoro-(9CI) is used as a versatile chemical intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable component in the development of new chemical products and materials.

InChI:InChI=1/C9H5FN2/c10-8-2-1-6(5-11)9-7(8)3-4-12-9/h1-4,12H

Upstream product

• 544-92-3 copper(I) cyanide 
• 292636-09-0 7-bromo-4-fluoro-1H-indole 
• 557-21-1 zinc(II) cyanide 
• 446-09-3 2-bromo-5-fluoronitrobenzene 

Downstream Products

• 313337-34-7 4-fluoroindole-7-carboxylic acid 
• 389629-41-8 1-(4-Benzoyl-piperazin-1-yl)-2-(4-fluoro-7-[1,2,4]oxadiazol-3-yl-1H-indol-3-yl)-ethane-1,2-dione 
• 389628-78-8 1-(4-Benzoyl-piperazin-1-yl)-2-[4-fluoro-7-(2H-tetrazol-5-yl)-1H-indol-3-yl]-ethane-1,2-dione 
• 389628-23-3 C₂₂H₁₇FN₄O₃ 
• 389628-85-7 C₂₂H₂₀FN₅O₄ 
• 389629-09-8 3-[2-(4-benzoyl-piperazin-1-yl)-2-oxo-acetyl]-4-fluoro-1H-indole-7-carboxylic acid methylamide 
• 389628-30-2 C₂₃H₂₀FN₃O₅ 
• 389628-31-3 C₂₂H₁₈FN₃O₅ 
• 13754-38-6 N-Benzoylpiperazine 
• 313337-35-8 methyl 4-fluoro-1H-indole-7-carboxylate 

Relevant academic research and scientific papers

Field-based affinity optimization of a novel azabicyclohexane scaffold HIV-1 entry inhibitor

Small-molecule HIV-1 entry inhibitors are an extremely attractive therapeutic modality. We have previously demonstrated that the entry inhibitor class can be optimized by using computational means to identify and extend the chemotypes available. Here we demonstrate unique and differential effects of previously published antiviral compounds on the gross structure of the HIV-1 Env complex, with an azabicyclohexane scaffolded inhibitor having a positive effect on glycoprotein thermostability. We demonstrate that modification of the methyltriazole-azaindole headgroup of these entry inhibitors directly effects the potency of the compounds, and substitution of the methyltriazole with an amine-oxadiazole increases the affinity of the compound 1000-fold over parental by improving the on-rate kinetic parameter. These findings support the continuing exploration of compounds that shift the conformational equilibrium of HIV-1 Env as a novel strategy to improve future inhibitor and vaccine design efforts.

Inhibitors of HIV-1 attachment. Part 7: Indole-7-carboxamides as potent and orally bioavailable antiviral agents

A series of substituted carboxamides at the indole C7 position of the previously described 4-fluoro-substituted indole HIV-1 attachment inhibitor 1 was synthesized and the SAR delineated. Heteroaryl carboxamide inhibitors that exhibited pM potency in the primary cell-based assay against a pseudotype virus expressing a JRFL envelope were identified. The simple methyl amide analog 4 displayed a promising in vitro profile, with its favorable HLM stability and membrane permeability translating into favorable pharmacokinetic properties in preclinical species.

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.

Inhibitors of HIV-1 attachment. Part 9: An assessment of oral prodrug approaches to improve the plasma exposure of a tetrazole-containing derivative

7-(2H-Tetrazol-5-yl)-1H-indole 3 was found to be a potent inhibitor of HIV-1 attachment but the compound lacked oral bioavailability in rats. The cause of the low exposure was believed to be poor absorption attributed to the acidic nature of the tetrazole moiety and, in an effort to address this liability, three more lipohilic tetrazole analogs, N-acetoxymethyl 4, N-pivaloyloxymethyl 5, and N-methyl 6, were evaluated as potential oral prodrugs in rats. Prodrug 5 was ineffective in improving the plasma concentration of 3 in vivo but compound 4 provided a 15-fold enhancement of the plasma concentration of 3. Most interestingly, oral dosing of analog 6 afforded a substantial increase in the plasma concentration of the parent in rats when compared to dosing of parent. This represents a novel example of a methyl tetrazole that acts as a prodrug for a free NH tetrazole-containing compound.

Indole, azaindole and related heterocyclic sulfonylureido 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 sulfonylureido piperazine derivatives of Formula I. 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. 1wherein: Z is 2Q is selected from the group consisting of: 3—W— is 4—represents a carbon-carbon bond or does not exist; and A is NR13R14.

INDOLE, AZAINDOLE AND RELATED HETEROCYCLIC UREIDO AND THIOUREIDO 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 ureido and thioureido piperazine derivatives of Formula (I). 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. The compounds of Formula (I) are Formula (I) wherein:Y is O or S;Z is Formula (II); Q is selected from the group consisting of Formula (A) and Formula (B); m is 2;A is NRR; and-W- is Formula (C).

Antiviral indoleoxoacetyl 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.