99548-54-6

Usage

Uses

3-Bromo-2-methylbenzoic Acid Methyl Ester is a compound useful in organic synthesis.

Chemical Properties

White Solid

Upstream product

• 67-56-1 methanol 
• 21900-48-1 3-bromo-2-methylbenzoic acid chloride 
• 76006-33-2 3-bromo-2-methylbenzoic acid 
• 79669-49-1 5-bromo-2-methylbenzoic acid 
• 74-88-4 methyl iodide 
• 118-90-1 ortho-methylbenzoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 337536-14-8 methyl 3-bromo-2-(bromomethyl)benzoate 
• 102308-43-0 4-bromoisobenzofuran-1(3H)-one 
• 573692-58-7 methyl 6-amino-3-bromo-2-methylbenzoate 
• 885519-05-1 methyl 3-bromo-2-methyl-5-nitrobenzoate 
• 894351-65-6 methyl 3-bromo-2-methyl-6-nitrobenzoate 
• 93340-09-1 methyl 3-cyano-2-methylbenzoate 
• 79670-17-0 methyl 2-bromomethyl-5-bromobenzoate 
• 1149379-00-9 methyl 2,2',6'-trimethylbiphenyl-3-carboxylate 
• 914220-72-7 C₉H₈BrClO₂ 
• 83647-43-2 3-bromo-2-methylbenzyl alcohol 
• 1361938-20-6 C₁₆H₁₄O₃ 
• 329222-89-1 C₁₅H₁₂O₃ 
• 1329496-87-8 methyl 2-methyl-[1,1’-biphenyl]-3-carboxylate 
• 169045-01-6 7-amino-4-bromoisoindolin-1-one 

Relevant academic research and scientific papers

COMPOUNDS MODULATING PROTEIN RECRUITMENT AND/OR DEGRADATION

The invention provides cereblon binders for the degradation of proteins by the ubiquitin proteasome pathway for therapeutic applications.

Novel biphenyl derivative as well as preparation method and medical application thereof

The invention relates to the field of medicinal chemistry, and discloses biphenyl derivatives with PD-1/PD-L1 inhibitory activity as well as a preparation method and application of the biphenyl derivatives. The invention further discloses a composition containing the biphenyl derivative with the PD-1/PD-L1 inhibitory activity or the pharmaceutically acceptable salt of the biphenyl derivative and a pharmaceutically acceptable carrier of the biphenyl derivative, and application of the biphenyl derivative in preparation of a PD-1/PD-L1 inhibitor. The compound can be used for treating tumors.

Design, synthesis, evaluation, and SAR of 4-phenylindoline derivatives, a novel class of small-molecule inhibitors of the programmed cell death-1/ programmed cell death-ligand 1 (PD-1/PD-L1) interaction

The blockade of the PD-1/PD-L1 immune checkpoint pathway with small molecules is an emerging immunotherapeutic approach. A novel series of 4-phenylindoline derivatives were synthesized, and their inhibitory activity against the PD-1/PD-L1 protein-protein interaction (PPI) was evaluated through a homogenous time-resolved fluorescence (HTRF) assay. Among them, A20 and A22 exhibited potent activity with IC50 values of 17 nM and 12 nM, respectively. Furthermore, A20 showed the promising inhibitory activity against the PD-1/PD-L1 interaction with the EC50 value of 0.43 μM in a co-culture model of PD-L1/TCR Activator-expressing CHO cells and PD-1-expressing Jurkat cells. Besides, the structure?activity relationships (SAR) of the novel synthesized 4-phenylindoline derivatives was concluded, and the binding mode of A22 with the PD-L1 dimer was analyzed by molecular simulation and docking, demonstrating that the N-atom in the side chain of indoline fragment could interact with the amino acid residue of the PD-L1 protein to lead to the potent inhibitory activity. This study provided a new insight for further drug design.

Palladium-Catalyzed Tandem Carbonylative Diels-Alder Reaction for Construction of Bridged Polycyclic Skeletons

A palladium-catalyzed tandem carbonylative lactonization and Diels-Alder cycloaddition reaction between aldehyde-tethered benzylhalides and alkenes has been developed. A range of alkenes and aldehyde-tethered benzylhalides bearing different substituents can be successfully transformed into the corresponding bridged polycyclic compounds in good yields. This strategy provides a unique approach to complex lactone-containing bridged polycyclic compounds.

New Series of Potent Allosteric Inhibitors of Deoxyhypusine Synthase

Deoxyhypusine synthase (DHPS) is the primary enzyme responsible for the hypusine modification and, thereby, activation of the eukaryotic translation initiation factor 5A (eIF5A), which is key in regulating the protein translation processes associated with tumor proliferation. Although DHPS inhibitors could be a promising therapeutic option for treating cancer, only a few studies reported druglike compounds with this inhibition property. Thus, in this work, we designed and synthesized a new chemical series possessing fused ring scaffolds designed from high-throughput screening hit compounds, discovering a 5,6-dihydrothieno[2,3-c]pyridine derivative (26d) with potent inhibitory activity; furthermore, the X-ray crystallographic analysis of the DHPS complex with 26d demonstrated a distinct allosteric binding mode compared to a previously reported inhibitor. These findings could be significantly useful in the functional analysis of conformational changes in DHPS as well as the structure-based design of allosteric inhibitors.

Biphenyl compound as well as preparation method and medical application thereof

The invention discloses a biphenyl compound as well as a preparation method and medical application thereof, the structure of the biphenyl compound is shown as a formula (I) or a formula (II), and thebiphenyl compound or pharmaceutically acceptable salt, tautomer, meso-isomer, raceme, stereoisomer, metabolite, metabolite precursor, prodrug or solvate thereof is a PD-L1 inhibitor. The compound hasa remarkable inhibiting effect on the interaction of PD-1 and PD-L1 protein, so that the compound can be applied to the preparation of PD-L1 inhibitors and immunomodulator drugs for preventing or treating tumors, autoimmune diseases, organ transplant rejection, infectious diseases and inflammatory diseases.

SMALL MOLECULE MDM2 PROTEIN DEGRADERS

The present disclosure provides compounds represented by Formula I: wherein R1a, R1b, R2a, R2b, R3a, R3b, R4, A, L, X, Y, and Z are as defined as set forth in the specification. The present disclosure also provides compounds of Formula I for use to treat cancer or any other disease, condition, or disorder that is responsive to degradation of MDM2 protein.

Efficient C-H Amination Catalysis Using Nickel-Dipyrrin Complexes

A dipyrrin-supported nickel catalyst (AdFL)Ni(py) (AdFL: 1,9-di(1-adamantyl)-5-perfluorophenyldipyrrin; py: pyridine) displays productive intramolecular C-H bond amination to afford N-heterocyclic products using aliphatic azide substrates. The catalytic amination conditions are mild, requiring 0.1-2 mol% catalyst loading and operational at room temperature. The scope of C-H bond substrates was explored and benzylic, tertiary, secondary, and primary C-H bonds are successfully aminated. The amination chemoselectivity was examined using substrates featuring multiple activatable C-H bonds. Uniformly, the catalyst showcases high chemoselectivity favoring C-H bonds with lower bond dissociation energy as well as a wide range of functional group tolerance (e.g., ethers, halides, thioetheres, esters, etc.). Sequential cyclization of substrates with ester groups could be achieved, providing facile preparation of an indolizidine framework commonly found in a variety of alkaloids. The amination cyclization reaction mechanism was examined employing nuclear magnetic resonance (NMR) spectroscopy to determine the reaction kinetic profile. A large, primary intermolecular kinetic isotope effect (KIE = 31.9 ± 1.0) suggests H-atom abstraction (HAA) is the rate-determining step, indicative of H-atom tunneling being operative. The reaction rate has first order dependence in the catalyst and zeroth order in substrate, consistent with the resting state of the catalyst as the corresponding nickel iminyl radical. The presence of the nickel iminyl was determined by multinuclear NMR spectroscopy observed during catalysis. The activation parameters (ΔH? = 13.4 ± 0.5 kcal/mol; ΔS?= -24.3 ± 1.7 cal/mol·K) were measured using Eyring analysis, implying a highly ordered transition state during the HAA step. The proposed mechanism of rapid iminyl formation, rate-determining HAA, and subsequent radical recombination was corroborated by intramolecular isotope labeling experiments and theoretical calculations.

Benzoxadiazole compound and preparation method and medical use thereof

The invention discloses a benzoxadiazole compound and a preparation method and medical use thereof. The benzoxadiazole compound has the general structure shown in formula (I). The compound or pharmaceutically acceptable salts, tautomers, mesomers, racemates, stereoisomers, metabolites, metabolic precursors, prodrugs or solvates of the benzoxadiazole compound have an obvious inhibiting effect on PD-1/PD-L1 protein-protein interaction, so that the benzoxadiazole compound shown in the description can be applied to the preparation of an inhibitor with a PD-1/ PD-L1 inhibitory activity and the immunotherapy of tumors as an immunocheckpoint inhibitor.

Fused ring compound and application thereof (by machine translation)

The invention discloses a fused ring compound and application. The invention provides a compound, a pharmaceutically acceptable salt, a hydrate, a solvate, a metabolite, a stereoisomer, a tautomer or a prodrug. The compound I, provided by the invention, has the advantages of high activity, high bioavailability, stable medicine, oral administration, and the like. (by machine translation)