110301-23-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Amino-3,5-difluorobenzonitrile is used as a key intermediate in the synthesis of tricyclic AKR1C3 dependent KARS inhibitors. These inhibitors are designed to target and modulate the activity of the AKR1C3 dependent KARS enzyme, which plays a crucial role in the regulation of cellular processes and has been implicated in various diseases and disorders.
By developing tricyclic AKR1C3 dependent KARS inhibitors, researchers aim to create novel therapeutic agents that can effectively treat a range of conditions mediated by the AKR1C3 dependent KARS enzyme. This innovative approach has the potential to offer new treatment options for patients suffering from these diseases and disorders, ultimately improving their quality of life and overall health outcomes.

Upstream product

• 67567-26-4 4-bromo-2,6-difluoroaniline 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 141743-49-9 2,6-difluoro-4-iodoaniline 
• 544-92-3 copper(I) cyanide 
• 5509-65-9 2,6-difluoroaniline 

Downstream Products

• 886842-82-6 N-(4-cyano-2,6-difluoro-phenyl)-methanesulfonamide 
• 135564-22-6 4-bromo-3,5-difluorobenzaldehyde 
• 1415920-00-1 3,5-difluoro-4-aminobenzoic acid ethyl ester 
• 1415919-94-6 (E)-diethyl 4,4′-(2,2′,6,6′-tetrafluoro)azobenzenedicarboxylate 
• 1415919-99-1 diethyl (Z)-4,4'-(2,2',6,6'-tetrafluoro)azobenzenedicarboxylate 
• 956926-69-5 cyclopentyl (S)-2-[(4-amino-3,5-difluorobenzyl)-tert-butoxycarbonylamino]-4-methylpentanoate 
• 956926-71-9 cyclopentyl 2(S)-[(4-amino-3,5-difluorobenzyl)amino]-4-methylpentanoate 
• 500577-99-1 4‐amino-3,5-difluorobenzoic acid 

Relevant academic research and scientific papers

Chemical tuning of photoswitchable azobenzenes: A photopharmacological case study using nicotinic transmission

We have developed photochromic probes for the nicotinic acetylcholine receptor that exploit the unique chemical properties of the tetrafluoroazobenzene (4FAB) scaffold. Ultraviolet light switching and rapid thermal relaxation of the metastable cis configu

In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization

Photoswitchable oligonucleotides can determine specific biological outcomes by light-induced conformational changes. In particular, artificial probes activated by visible-light irradiation are highly desired in biological applications. Here, we report two novel types of visible-light photoswitchable peptide nucleic acids (PNAs) based on the molecular transducers: hemithioindigo and tetra-ortho-fluoroazobenzene. Our study reveals that the tetra-ortho-fluoroazobenzene–PNA conjugates have promising properties (fast reversible isomerization, exceptional thermal stability, high isomer conversions and sensitivity to visible-light irradiation) as reversible modulators to control oligonucleotide hybridization in biological contexts. Furthermore, we verified that this switchable modification delivers a slightly different hybridization behavior in the PNA. Thus, both melting experiments and strand-displacement assays showed that in all the cases the trans-isomer is the one with superior binding affinities. Alternative versions, inspired by our first compounds here reported, may find applications in different fields such as chemical biology, nanotechnology and materials science.

Fluorinated Azobenzenes Switchable with Red Light

Molecular photoswitches triggered with red or NIR light are optimal for photomodulation of complex biological systems, including efficient penetration of the human body for therapeutic purposes (“therapeutic window”). Yet, they are rarely reported, and ev

Active ester functionalized azobenzenes as versatile building blocks

Azobenzenes are important molecular switches that can still be difficult to functionalize selectively. A high yielding Pd-catalyzed cross-coupling method under mild conditions for the introduction of NHS esters to azobenzenes and diazocines has been established. Yields were consistently high with very few exceptions. The NHS functionalized azobenzenes react with primary amines quantitatively. These amines are ubiquitous in biological systems and in material science.

Red-shifted tetra-ortho-halo-azobenzenes for photo-regulated transmembrane anion transport

Photo-responsive synthetic ion transporters are of interest as tools for studying transmembrane transport processes and have potential applications as targeted therapeutics, due to the possibility of spatiotemporal control and wavelength-dependent function. Here we report the synthesis of novel symmetric and non-symmetric red-shifted tetra-ortho-chloro- and tetra-ortho-fluoro azobenzenes, bearing pendant amine functionality. Functionalisation of the photo-switchable scaffolds with squaramide hydrogen bond donors enabled the preparation of a family of anion receptors, which act as photo-regulated transmembrane chloride transporters in response to green or red light. The subtle effects of chlorine/fluorine substitution,meta/parapositioning of the anion receptors, and the use of more flexible linkers are explored. NMR titration experiments on the structurally diverse photo-switchable receptors reveal cooperative binding of chloride in theZ, but notEisomer, by the two squaramide binding sites. These results are supported by molecular dynamics simulations in explicit solvent and model membranes. We show that this intramolecular anion recognition leads to effective switching of transport activity in lipid bilayer membranes, in which optimalZisomer activity is achieved using a combination of fluorine substitution andpara-methylene spacer units.

Ortho -Fluoroazobenzene derivatives as DNA intercalators for photocontrol of DNA and nucleosome binding by visible light

We report a high-affinity photoswitchable DNA binder, which displays different nucleosome-binding capacities upon visible-light irradiation. Both photochemical and DNA-recognition properties were examined by UV-Vis, HPLC, CD spectroscopy, NMR, FID assays,

Bromofluoro polysubstituted benzaldehyde derivative and preparation method

The invention relates to a bromofluoro polysubstituted benzaldehyde derivative and a preparation method. The preparation method comprises the following steps: obtaining 2,6-difluoro-4-cyano phenylamine under nitrogen protection by using 2,6-difluoro-4-bro

Mechanistic Evaluation of Bioorthogonal Decaging with trans-Cyclooctene: The Effect of Fluorine Substituents on Aryl Azide Reactivity and Decaging from the 1,2,3-Triazoline

Bioorthogonal prodrug activation/decaging strategies need to be selective, rapid and release the drug from the masking group upon activation. The rates of the 1,3-dipolar cycloaddition between a trans-cyclooctene (TCO) and a series of fluorine-substituted

Linker Variation and Structure-Activity Relationship Analyses of Carboxylic Acid-based Small Molecule STAT3 Inhibitors

The molecular determinants for the activities of the reported benzoic acid (SH4-54), salicylic acid (BP-1-102), and benzohydroxamic acid (SH5-07)-based STAT3 inhibitors were investigated to design optimized analogues. All three leads are based on an N-met

2-ARYLSULFONAMIDO-N-ARYLACETAMIDE DERIVATIZED STAT3 INHIBITORS

The present disclosure provides pharmaceutical compositions comprising 2-arylsulfonamido-N-arylacetamide derivatized Stat3 inhibitors and certain pharmaceutically acceptable salts thereof, and methods of their use.