210992-28-2

Usage

Uses

Used in Pharmaceutical Industry:
5-Amino-3-fluorobenzonitrile is utilized as a key intermediate in the synthesis of various antiviral and anticancer drugs. Its unique structure allows for the development of compounds that can target specific biological pathways, contributing to the treatment and management of viral infections and cancer.
Used in Agrochemical Production:
In the agrochemical sector, 5-Amino-3-fluorobenzonitrile serves as an essential intermediate for the production of herbicides and insecticides. Its incorporation in these products aids in the control of weeds and pests, thereby enhancing crop protection and contributing to increased agricultural productivity.
Used in Organic Chemical Synthesis:
5-Amino-3-fluorobenzonitrile is also employed as a versatile building block in the synthesis of a variety of organic chemicals. Its presence in these syntheses is crucial for the creation of new compounds with potential applications in various industries, including but not limited to pharmaceuticals, materials science, and specialty chemicals.

InChI:InChI=1/C8H6BrF3S/c9-5-6-1-3-7(4-2-6)13-8(10,11)12/h1-4H,5H2

Upstream product

• 64248-63-1 3,5-difluorobenzonitrile 
• 557-21-1 dicyanozinc 
• 134168-97-1 3-bromo-5-fluoroaniline 
• 110882-60-5 3-fluoro-5-nitrobenzonitrile 
• 1435-51-4 1,3-dibromo-5-fluorobenzene 
• 807620-95-7 N-(3-bromo-5-fluorophenyl)acetamide 
• 3819-88-3 1-fluoro-3-iodo-5-nitrobenzene 

Downstream Products

• 507269-27-4 3-fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile 
• 1026751-11-0 3-fluoro-5-{4-[3-(5-methyl-1-pyrimidin-2-yl-1H-pyrazol-4-yl)-3-oxo-propyl]-piperazin-1-yl}-benzonitrile 
• 1167055-08-4 N-(3-cyano-5-fluorophenyl)-6-[3-(hydroxymethyl)phenyl]imidazo[1,2-a]pyridine-2-carboxamide 

Relevant academic research and scientific papers

Synthesis and antitumor activity of novel pyrimidinyl pyrazole derivatives. III. Synthesis and antitumor activity of 3-phenylpiperazinyl-1-trans-propenes

A series of novel 3-[4-phenyl-1-piperazinyl]-1-[5-methyl-1-(2-pyrimidinyl)- 4-pyrazolyl]-1-trans-propenes and related compounds were synthesized and evaluated by their cytotoxic activity against several tumor cell lines in vitro and in vivo antitumor acti

5-FLUORO-, CHLORO- AND CYANO-PYRIDIN-2-YL-TETRAZOLES AS LIGANDS OF THE METABOTROPIC GLUTAMATE RECEPTOR-5

The present invention relates to new compounds of formula I, wherein Z, Q, X1, X2, R1 and R2, are as defined as in formula I, or salts, solvates or solvated salts thereof, processes for their preparation, pharmaceutical formulations containing said compounds and to the use of said compounds in therapy.

3-[Substituted]-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitriles: Identification of highly potent and selective metabotropic glutamate subtype 5 receptor antagonists

Structure-activity relationship studies on the phenyl ring of 3-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile 2 led to the discovery that small, non-hydrogen bond donor substituents at the 3-position led to a substantial increase in in vitro potency. In particular, 3-fluoro-5-(5-pyridin- 2-yl-2H-tetrazol-2-yl)benzonitrile (7) is a highly potent and selective mGlu5 receptor antagonist with good rat pharmacokinetics, brain penetration, and in vivo receptor occupancy.

3-[3-Fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)phenyl]-4-methylpyridine: A highly potent and orally bioavailable metabotropic glutamate subtype 5 (mGlu5) receptor antagonist

Structure-activity relationship studies performed around 3-fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile for the purposes of developing novel mGlu5 receptor antagonists are described. Synthesis of a series of four-ring tetrazoles led to the discovery of 3-[3-fluoro-5-(5-pyridin-2-yl- 2H-tetrazol-2-yl)phenyl]-4-methylpyridine (26), a highly potent, brain penetrant, tetrazole-based mGlu5 receptor antagonist. Structure-activity relationship studies performed around 3-fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2- yl)benzonitrile for the purpose of developing novel mGlu5 receptor antagonists are described. Synthesis of a series of four-ring tetrazoles led to the discovery of 3-[3-fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)phenyl]-4- methylpyridine, a highly potent, brain penetrant, azole-based mGlu5 receptor antagonist.

Discovery of novel heteroarylazoles that are metabotropic glutamate subtype 5 receptor antagonists with anxiolytic activity

The highly potent, selective, and brain-penetrant metabotropic glutamate subtype 5 (mGlu5) receptor antagonists 3-(5-pyridin-2-yl-2H-tetrazol-2-yl) benzonitrile (47) and 3-fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile (48) are reported. Compound 47 is active in the rat fear-potentiated startle (FPS) model of anxiety with ED50 = 5.4 mg/kg (po) when dosed acutely. In this model the anxiolytic effects of 47 rapidly tolerate on repeated dosing.

Pyrazole derivatives

The present invention relates to cis- and trans-forms of pyrazole derivatives, salts thereof, or agents containing the same, and represented by the general formula (I): wherein G represents a nitrogen containing saturated heterocyclic structure represented by the following formula: These compounds exhibit anti-tumor activity on 5-FU-resistant tumors and effects on P glycoprotein expressing, multiple-drug resistant tumors. An example of a pyrazole derivative which demonstrates 50% inhibition of tumor cell growth is 3-[4-(3-chloro-5-fluorophenyl)-1 piperazinyl]-1-[1-(3-chloro-2-pyridyl)-5-methyl-4-pyrazolyl)-1-trans-propene hydrochloride. Synthesis of the compounds represented by formula (I) can be prepared by any one of various routes such as a Mannich reaction, a Wittig reaction, reductive amination or substitution by allylation.