4452-06-6

Usage

Uses

Used in Pharmaceutical Industry:
ZM 449829 is used as a research compound for studying the role of JAK3 in various cellular processes and diseases. Its ability to inhibit JAK3 activity makes it a potential therapeutic agent for conditions involving abnormal immune response or cell proliferation, such as autoimmune disorders and certain types of cancer.
Used in Immunology Research:
ZM 449829 is used as a research tool in immunology to investigate the role of JAK3 in immune cell signaling and function. By inhibiting JAK3, researchers can gain insights into the underlying mechanisms of immune response and identify potential targets for therapeutic intervention.
Used in Cancer Research:
ZM 449829 is used as a research compound in cancer research to explore its potential as an anticancer agent. Its ability to inhibit JAK3, STAT-5 phosphorylation, and T-cell proliferation suggests that it may have therapeutic applications in the treatment of certain types of cancer, particularly those involving abnormal JAK3 activity.
Used in Drug Development:
ZM 449829 serves as a lead compound in the development of new drugs targeting JAK3 and related pathways. Its potent and selective inhibition of JAK3 makes it a valuable starting point for the design and synthesis of novel therapeutic agents with improved efficacy and selectivity.

InChI:InChI=1/C13H10O/c1-2-13(14)12-8-7-10-5-3-4-6-11(10)9-12/h2-9H,1H2

Upstream product

• 22422-70-4 3-chloro-1-(naphthalen-2-yl)propan-1-one 
• 1590-22-3 4-(2-naphthyl)-4-oxobutyric acid 
• 1826-67-1 vinyl magnesium bromide 
• 113443-62-2 N-methoxy-N-methylnaphthalene-2-carboxamide 
• 76635-88-6 vinyl-2-naphthylcarbinol 
• 2243-83-6 2-naphthaloyl chloride 
• 50-00-0 formaldehyd 
• 893-33-4 4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedione 
• 66-99-9 β-naphthaldehyde 
• 93-08-3 methyl 2-naphthyl ketone 
• 127-19-5 N,N-dimethyl acetamide 
• 67-68-5 dimethyl sulfoxide 
• 67-56-1 methanol 

Downstream Products

• 1218988-68-1 (R)-1-(3-(naphthalen-2-yl)-3-oxopropyl)-2-oxocyclohexanecarbonitrile 
• 1146191-81-2 C₂₃H₂₇NO 
• 1146191-80-1 C₂₃H₂₇NO 

Relevant academic research and scientific papers

Silver oxide(I) promoted Conia-ene/radical cyclization for a straightforward access to furan derivatives

A novel access to fused furan cores using silver oxide(I) has been developed. Mechanistic investigations indicate the involvement of a Conia-ene reaction/radical cyclization for an expedient path to complex furan derivatives. The reaction is broad in scop

Generation of α-Boryl Radicals and Their Conjugate Addition to Enones: Transition-Metal-Free Alkylation of gem-Diborylalkanes

A transition-metal-free method for the alkylation of gem-diborylalkanes with α,β-unsaturated ketones has been developed. It is demonstrated that the α-boryl radicals can be generated efficiently from gem-diborylalkanes with the aid of catechol and oxidants. The α-boryl radicals formed through such process can be engaged in conjugate addition reaction with α,β-unsaturated ketones. This transformation is a straightforward method for the synthesis of γ-borylketones.

Enantioselective Copper-Catalyzed Electrophilic Sulfenylation of Cyclic Imino Esters

Herein we report an enantioselective sulfenylation of cyclic imino esters with the efficient and versatile sulfenylation reagent S-alkyl 4-methylbenzenesulfonothioates. By utilizing the Cu/tBu-Phosferrox catalytic system, we can assemble diverse S-alkyl groups into the cyclic imino esters under mild conditions in good yields and with excellent enantioselectivities. Remarkably, this method demonstrates a high tolerance of diverse functional groups and proves to be applicable in the late-stage functionalization of pharmaceuticals.

Design and synthesis of Mannich base-type derivatives containing imidazole and benzimidazole as lead compounds for drug discovery in Chagas Disease

The protozoan parasite Trypanosoma cruzi is the causative agent of Chagas disease, the most important parasitic infection in Latin America. The only treatments currently available are nitro-derivative drugs that are characterised by high toxicity and limited efficacy. Therefore, there is an urgent need for more effective, less toxic therapeutic agents. We have previously identified the potential for Mannich base derivatives as novel inhibitors of this parasite. To further explore this family of compounds, we synthesised a panel of 69 new analogues, based on multi-parametric structure-activity relationships, which allowed optimization of both anti-parasitic activity, physicochemical parameters and ADME properties. Additionally, we optimized our in vitro screening approaches against all three developmental forms of the parasite, allowing us to discard the least effective and trypanostatic derivatives at an early stage. We ultimately identified derivative 3c, which demonstrated excellent trypanocidal properties, and a synergistic mode of action against trypomastigotes in combination with the reference drug benznidazole. Both its druggability and low-cost production make this derivative a promising candidate for the preclinical, in vivo assays of the Chagas disease drug-discovery pipeline.

Nickel-Catalyzed C(sp3)-H Functionalization of Benzyl Nitriles: Direct Michael Addition to Terminal Vinyl Ketones

An efficient nickel(0)-catalyzed addition of benzyl nitriles to terminal vinyl ketones via C(sp3)-H functionalization has been developed. The reaction provides a novel and efficient protocol for the synthesis of α-functionalized benzyl nitriles with a wide range of structural diversity under mild reaction conditions while obviating the use of a strong base. The work might be potentially useful toward the development of an enantioselective variant using chiral nitrogen ligands.

Nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane

Herein we describe a nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane. A range ofZ-silyl enol ethers are obtained as major isomers due to the process of nickel triggered alkene isomerization. Notably, some specific

Copper-Catalyzed Asymmetric Hydrosilylation of β-Nitroethyl Aryl Ketones

A copper-catalyzed asymmetric hydrosilylation of β-nitroethyl aryl ketones has been disclosed, and the corresponding chiral alcohols could be obtained in high yields (up to 99% yield) and excellent enantioselectivities (up to 96% ee). Moreover, the reaction worked well on a gram scale with 0.3 mol % of ligand loading, indicating that our protocol has potential applications in the synthesis of important pharmaceuticals such as Tranylcypromine and Ticagrelor.

Photocatalytic C(sp3)?H Activation towards α-methylenation of Ketones using MeOH as 1 C Source Steering Reagent

Unprecedented direct access to terminal enones via α-methylenation of aryl ketones to form C=C bond is achieved under visible-light conditions using methanol as one carbon source substrate and solvent as well. The reaction involves Cu@g-C3N4-catalysed in situ oxidation of methanol into formaldehyde followed by dehydrative cross aldol type reaction. Various aryl ketones react efficiently with MeOH, producing α,β-unsaturated carbonyl compounds only in 4–8 h at room temperature in excellent yield (84–97%). Operational simplicity, wide substrate scope, ambient reaction conditions, visible-light photocatalysis and novel application of MeOH as methylene donor substrate are the salient features making the envisaged protocol mild, efficient and green alternative to the existing methods for synthesis of such fine chemicals. (Figure presented.).

Rh-Catalyzed Decarbonylative Addition of Salicylaldehydes with Vinyl Ketones: Synthesis of Taccabulins A–E

A rhodium-catalyzed decarbonylative addition of salicylaldehydes with vinyl ketones was developed to synthesize o-hydroxydihydrochalcones (2-hydroxyphenethyl ketones). These decarbonylative addition reactions afforded various functionalized o-hydroxydihydrochalcones in moderate to good yields with broad functional group tolerance and selectivity. This method was also applied further in the divergent synthesis of dihydrochalcone derived taccabulins A–E.

Manganese-Catalyzed Ring-Opening Coupling Reactions of Cyclopropanols with Enones

A manganese-catalyzed ring-opening coupling reaction of cyclopropanols with enones for the facile and efficient preparation of 1,6-diketones is described. A wide array of synthetically important 1,6-diketones bearing manifold functional groups are obtained with up to 93% yield. These reactions feature broad substrate scopes, environmentally benign conditions, inexpensive catalyst, and operational simplicity.