2296-23-3

Usage

Uses

Used in Pharmaceutical Industry:
3-IODO-4-HYDROXYBENZONITRILE is used as an intermediate in the synthesis of various pharmaceuticals for its strong antibacterial and antifungal properties, contributing to the development of medicinal products that combat infections and diseases.
Used in Agrochemical Industry:
3-IODO-4-HYDROXYBENZONITRILE is used as an intermediate in the production of agrochemicals to leverage its antibacterial and antifungal properties, enhancing crop protection and yield by controlling harmful microorganisms in agricultural settings.
Used in Material Science:
3-IODO-4-HYDROXYBENZONITRILE is used in the development of novel polymers and heterocyclic compounds, showcasing its potential in advancing material science through the creation of innovative materials with unique properties and applications.

Upstream product

• 1689-83-4 Ioxynil 
• 60032-63-5 4-hydroxy-3-iodo-benzaldehyde 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 7487-88-9 magnesium sulfate 
• 3109-63-5 tert-butylammonium hexafluorophosphate(V) 
• 767-00-0 4-cyanophenol 

Downstream Products

• 360791-77-1 2-[2-(2-methoxyethoxymethoxy)biphenyl-3-yl]benzofuran-5-carbonitrile 
• 1026799-01-8 2-[2-(2-methoxy-ethoxymethoxy)-biphenyl-3-yl]-benzofuran-5-carboxamidine 
• 889884-75-7 C₃₅H₄₅NO₂Si₂ 
• 77084-12-9 2-(3-methoxyphenyl)benzofuran-5-carbonitrile 
• 1186301-59-6 2-(4-methoxyphenyl)benzofuran-5-carbonitrile 
• 82504-06-1 3-iodo-4-methoxybenzonitrile 
• 121045-40-7 2-phenyl-1-benzofuran-5-carbaldehyde 
• 1220973-39-6 3-iodo-4-isopropoxybenzonitrile 
• 1689-89-0 nitroxynil 

Relevant academic research and scientific papers

Synthesis and SAR of 5-amino- and 5-(aminomethyl)benzofuran histamine H3 receptor antagonists with improved potency

A new series of H3 receptor antagonists was discovered with nanomolar and subnanomolar affinities at human and rat H3 receptors. Starting from an earlier, more structurally limited series of benzofurans, the present series of compounds demonstrated increased structural variety and flexibility with greater in vitro potency. One compound in particular, {2-[2-(2-(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl}(5-nitropyridin-2-yl) amine (7h), gave the best binding potency (human Ki of 0.05 nM, rat Ki of 0.11 nM), which represented a 9-fold (in human) and an 11-fold (in rat) improvement over ABT-239 (compound 5), a compound previously reported to have excellent in vitro potency and in vivo efficacy. The synthesis, SAR of the H3 binding affinities, in vitro assay for phospholipidosis, and pharmacokinetic properties of the new compounds are described.

The autoprotonation in reduction mechanism of pesticide ioxynil

The reduction mechanism of ioxynil (3,5-diiodo-4-hydroxy-benzonitrile) was studied in dimethylsulfoxide using the electrochemical methods (tast polarography, cyclic voltammetry and controlled potential electrolysis) combined with GC/MS identification of products. The reduction is accompanied by the cleavage of iodide yielding 3-iodo-4-hydroxybenzonitrile. Surprisingly, this process requires only one electron for the exhaustive electrolysis of the starting compound. We showed that the apparent one electron reduction observed in the aprotic solvent is due to the autoprotonation by another molecule of ioxynil. The overall one electron reduction (uptake of two electrons per two molecules of ioxynil) is changed in the presence of a strong proton donor to a two electron process per one molecule.

Discovery of 5-(N-hydroxycarbamimidoyl) benzofuran derivatives as novel indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan dioxygenase (hTDO) are rate-limiting enzymes in the kynurenine pathway (KP) of L-tryptophan (L-Trp) metabolism and are becoming key drug targets in the combination therapy of checkpoint inhibitors in immunoncology. To discover a selective and potent IDO1 inhibitor, a structure–activity relationship (SAR) study of N-hydroxybenzofuran-5-carboximidamide as a novel scaffold was investigated in a systematic manner. Among the synthesized compounds, the N-3-bromophenyl derivative 19 showed the most potent inhibition, with an IC50 value of 0.44 μM for the enzyme and 1.1 μM in HeLa cells. The molecular modeling of 19 with the X-ray crystal structure of IDO1 indicated that dipole-ionic interactions with heme iron, halogen bonding with Cys129 and the two hydrophobic interactions were important for the high potency of 19.

A novel benzofuran derivatives and uses thereof

The present application relates to a novel benzofuran derivative and uses thereof. More specifically, the present invention provides: a compound represented by chemical formula I, a solvate, a stereoisomer, or a pharmaceutically acceptable salt thereof; a

Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source

A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.

Identification of novel GPR81 agonist lead series for target biology evaluation

GPR81 is a novel drug target that is implicated in the control of glucose and lipid metabolism. The lack of potent GPR81 modulators suitable for in vivo studies has limited the pharmacological characterization of this lactate sensing receptor. We performed a high throughput screen (HTS) and identified a GPR81 agonist chemical series containing a central acyl urea scaffold linker. During SAR exploration two additional new series were evolved, one containing cyclic acyl urea bioisosteres and another a central amide bond. These three series provide different selectivity and physicochemical properties suitable for in-vivo studies.

PHENOXYMETHYL DERIVATIVES

The invention provides novel compounds having the general formula (I), wherein RA, RB, RC, RC1 and W are as defined herein, compositions including the compounds and methods of using the compounds.

A General Copper Catalyst for Photoredox Transformations of Organic Halides

A broadly applicable copper catalyst for photoredox transformations of organic halides is reported. Upon visible light irradiation in the presence of catalytic amounts of [(DPEphos)(bcp)Cu]PF6 and an amine, a range of unactivated aryl and alkyl halides were shown to be smoothly activated through a rare Cu(I)/Cu(I)?/Cu(0) catalytic cycle. This complex efficiently catalyzes a series of radical processes, including reductions, cyclizations, and direct arylation of arenes.

ORGANIC COMPOUNDS

Novel benzofuran derivatives are disclosed. The derivatives have S1P1 receptor activity and/or disease modifying activity and find use in the treatment of conditions or diseases associated with the immune, vascular and nervous systems in animals and/or humans

Fused Thiazole Derivatives As Kinase Inhibitors

A series of 6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5H)-one derivatives, which are substituted in the 2-position by a substituted morpholin-4-yl moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.