59404-86-3

Usage

Uses

Used in Pharmaceutical Industry:
4-BENZYLOXY-3-CHLOROANILINE 96 is utilized as a key intermediate in the development and production of pharmaceuticals. Its unique structure allows it to serve as a building block for the synthesis of various drug molecules, contributing to the creation of new medications and therapies.
Used in Dye Industry:
In the dye industry, 4-BENZYLOXY-3-CHLOROANILINE 96 is employed as an intermediate for the synthesis of different types of dyes. Its chemical properties make it suitable for the production of a wide range of colorants used in various applications, such as textiles, plastics, and printing inks.
Used in Organic Compounds Synthesis:
Beyond its applications in pharmaceuticals and dyes, 4-BENZYLOXY-3-CHLOROANILINE 96 is also used as an intermediate in the synthesis of other organic compounds. Its versatility in chemical reactions enables it to be a valuable component in the production of a diverse array of organic substances.
Safety and Handling:

InChI:InChI=1/C13H12ClNO/c14-12-8-11(15)6-7-13(12)16-9-10-4-2-1-3-5-10/h1-8H,9,15H2

Upstream product

• 50508-54-8 2-chloro-4-nitro-1-(phenylmethoxy)benzene 
• 916336-30-6 (4-benzyloxy-3-chloro-phenyl)-carbamic acid tert-butyl ester 
• 911297-03-5 N-(3-chloro-4-hydroxyphenyl)carbamic acid tert-butyl ester 
• 95-57-8 2-monochlorophenol 
• 619-08-9 2-chloro-4-nitrophenol 
• 3964-52-1 2-chloro 4-aminophenol 
• 100-39-0 benzyl bromide 
• 38731-70-3 sodium salt of 2-chloro-4-nitrophenol 
• 100-44-7 benzyl chloride 
• 1643-19-2 tetrabutylammomium bromide 
• 1185221-12-8 C₁₃H₁₀ClN₃O 
• 100-51-6 benzyl alcohol 
• 350-30-1 3-chloro-4-fluoronitrobenzene 

Downstream Products

• 70338-98-6 1-Methyl-cyclopropanecarboxylic acid (4-benzyloxy-3-chloro-phenyl)-amide 
• 1600515-56-7 C₂₄H₁₈ClN₃O 
• 1430796-84-1 1-(benzyloxy)-2-chloro-4-isothiocyanatobenzene 

Relevant academic research and scientific papers

AGENTS FOR USE IN THE TREATMENT OF AMYLOIDOSIS

The present invention relates to compounds for stabilising the native tetrameric form of transthyretin and protecting it from proteolytic cleavage; compounds for use in the prevention and treatment of transthyretin amyloidosis; and agents and medicaments comprising such compounds. The compounds are based on a general structure A-L-B, wherein A is a group of formula (II) or of formula (III): or of formula (IV) or of formula (V) B is a group of formula (III), (IV), or (V), or a group of formula (VI) or a group of formula –R10Z, wherein: Z is selected from -CO2R', -CONR'R'', -SO2R' wherein R' and R'' are independently H or C1-C4 alkyl; and R10 is a C1-C4 alkylene or alkenylene group; and L represents a linker group which is a saturated or unsaturated chain of 5 to 13 carbon atoms.

Discovery of novel and potent safinamide-based derivatives as highly selective hMAO-B inhibitors for treatment of Parkinson's disease (PD): Design, synthesis, in vitro, in vivo and in silico biological studies

Up to date, the current clinical practice employs only symptomatic treatments for management of Parkinson's disease (PD) but unable to stop disease progression. The discovery of new chemical entities endowed with potent and selective human monoamine oxidase B (hMAO-B) inhibitory activity is a clinically relevant subject. Herein, a structural optimization strategy for safinamide (a well-known second generation hMAO-B inhibitor) afforded a series of thirty-six safinamide-derived new analogs (4aa–bj). Most compounds showed promising inhibitory activities against hMAO-B (>70% inhibition at a single dose concentration of 10 μM), with no apparent effect on hMAO-A at 100 μM. Moreover, while six compounds (4ak, 4as, 4az, 4be, 4bg, and 4bi) exhibited potent double-digit nanomolar activities over hMAO-B with IC50 values of 29.5, 42.2, 22.3, 18.8, 42.2, and 33.9 nM, respectively, three derivatives (4aq, 4at, and 4bf), possessing the same carboxamide moiety (2-pyrazinyl), showed the most potent single-digit nanomolar activities (IC50 = 9.7, 5.1, and 3.9 nM, respectively). Compound 4bf revealed an excellent selectivity index (SI > 25641) with a 29-fold increase compared to safinamide (SI > 892). A structure activity relationship along with molecular docking simulations provided insights into enzyme ? inhibitor interactions and a rational for the observed activity. In an in vivo MPTP-induced mouse model of PD, oral administration of compound 4bf significantly protected nigrostriatal dopaminergic neurons as revealed by tyrosine hydroxylase staining and prevented MPTP-induced Parkinsonism as revealed by motor behavioral assays. Accordingly, we present compound 4bf as a novel, highly potent, and selective hMAO-B inhibitor with an effective therapeutic profile for relieving PD.

Design and Synthesis of 4-Anilinothieno[2,3-d]pyrimidine-Based Compounds as Dual EGFR/HER-2 Inhibitors

Dual inhibition of the epidermal growth factor receptor (EGFR) and the human epidermal growth factor receptor 2 (HER-2) is an attractive cancer therapeutic approach. In this study, new series of 4-anilinothieno[2,3-d]pyrimidines were designed, synthesized, and tested as dual EGFR/HER-2 kinase inhibitors. Five compounds (8a, 8b, 8e–g) demonstrated low to submicromolar inhibition of both kinases with IC50 values of 1.2, 0.6, 0.3, 0.2, 0.4 μM and 8.2, 3.4, 1.3, 0.5, 2.7 μM for the EGFR and HER-2, respectively. Introduction of a 5,6-tetramethylene moiety into the thienopyrimidine core bearing a 4-(3-fluorobenzyloxy)-3-chloroaniline tail resulted in a favorable increase in both the EGFR and HER-2 inhibitory activities. Compound 8f (IC50 EGFR/HER-2: 0.2/0.5 μM) also exhibited significant cell growth inhibition on some specific NCI cell lines, especially ovarian, breast, non-small-cell lung cancer, and renal cancer cell lines.

Protozoan Parasite Growth Inhibitors Discovered by Cross-Screening Yield Potent Scaffolds for Lead Discovery

Tropical protozoal infections are a significant cause of morbidity and mortality worldwide; four in particular (human African trypanosomiasis (HAT), Chagas disease, cutaneous leishmaniasis, and malaria) have an estimated combined burden of over 87 million disability-adjusted life years. New drugs are needed for each of these diseases. Building on the previous identification of NEU-617 (1) as a potent and nontoxic inhibitor of proliferation for the HAT pathogen (Trypanosoma brucei), we have now tested this class of analogs against other protozoal species: T. cruzi (Chagas disease), Leishmania major (cutaneous leishmaniasis), and Plasmodium falciparum (malaria). Based on hits identified in this screening campaign, we describe the preparation of several replacements for the quinazoline scaffold and report these inhibitors' biological activities against these parasites. In doing this, we have identified several potent proliferation inhibitors for each pathogen, such as 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)quinoline-3-carbonitrile (NEU-924, 83) for T. cruzi and N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-7-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)cinnolin-4-amine (NEU-1017, 68) for L. major and P. falciparum.

PROTOZOAN PARASITE GROWTH INHIBITORS

Compounds and methods for inhibiting growth of a protozoan parasite. Methods of treating a protozoan parasite infection in a subject by administering a therapeutically effective amount of a compound as disclosed herein. The compounds and methods can be us

Design, synthesis, X-ray crystallographic analysis, and biological evaluation of thiazole derivatives as potent and selective inhibitors of human dihydroorotate dehydrogenase

Human dihydroorotate dehydrogenase (HsDHODH) is a flavin-dependent mitochondrial enzyme that has been certified as a potential therapeutic target for the treatment of rheumatoid arthritis and other autoimmune diseases. On the basis of lead compound 4, which was previously identified as potential HsDHODH inhibitor, a novel series of thiazole derivatives were designed and synthesized. The X-ray complex structures of the promising analogues 12 and 33 confirmed that these inhibitors bind at the putative ubiquinone binding tunnel and guided us to explore more potent inhibitors, such as compounds 44, 46, and 47 which showed double digit nanomolar activities of 26, 18, and 29 nM, respectively. Moreover, 44 presented considerable anti-inflammation effect in vivo and significantly alleviated foot swelling in a dose-dependent manner, which disclosed that thiazole-scaffold analogues can be developed into the drug candidates for the treatment of rheumatoid arthritis by suppressing the bioactivity of HsDHODH.

Bicyclic heteroaromatic compounds as protein tyrosine kinase inhibitors

A pharmaceutical formulation comprising the compound of formula

Chemoselective hydrogenation of functionalized nitroarenes and imines by using carbon nanofiber-supported iridium nanoparticles

The reaction of three types of carbon nanofibers (CNFs; platelet: CNF-P, tubular: CNF-T, herringbone: CNF-H) with Ir4(CO)12 in mesitylene at 165 °C provided the corresponding CNF-supported iridium nanoparticles, Ir/CNFs (Ir content=2.3-2.6 wt. %). Transmission electron microscopy (TEM) studies of these Ir/CNF samples revealed that size-controlled Ir nanoparticles (average particle size of 1.1-1.5 nm) existed on the CNFs. Among the three Ir/CNF samples, Ir/CNF-T showed an excellent catalytic activity and chemoselectivity towards hydrogenation of functionalized nitroarenes and imines; the corresponding aniline derivatives were obtained with high turnover numbers at ambient temperature under 10 atm of H2, and the catalyst is reusable. Ir/CNF-T was also effective for the reductive N-alkylation of anilines with carbonyl compounds.

Kinase scaffold repurposing for neglected disease drug discovery: Discovery of an efficacious, lapatanib-derived lead compound for trypanosomiasis

Human African trypanosomiasis (HAT) is a neglected tropical disease caused by the protozoan parasite Trypanosoma brucei. Because drugs in use against HAT are toxic and require intravenous dosing, new drugs are needed. Initiating lead discovery campaigns b

CYANOQUINOLINE DERIVATIVES

Disclosed is a compound of formula I, a stereoisomer thereof, a cis-trans-isomer thereof, a tautomer thereof, or a mixture thereof, or a pharmaceutically acceptable salt thereof, a solvate thereof or a prodrug thereof, wherein R1, R2, R3 and R4 are each as defined in the present application.