90434-16-5

Usage

Uses

Used in Organic Synthesis:
1-(Bromomethyl)-2-methoxy-4-nitrobenzene is used as a reagent for the introduction of the bromomethyl group into other molecules. Its ability to facilitate the formation of new carbon-carbon bonds makes it a valuable tool in creating a variety of organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(Bromomethyl)-2-methoxy-4-nitrobenzene is utilized for the production of various drugs. Its unique structure allows for the development of molecules with specific therapeutic properties.
Used in Chemical Research:
Due to its potential mutagenicity and carcinogenicity, 1-(Bromomethyl)-2-methoxy-4-nitrobenzene is also used in chemical research to study the effects of nitro and bromo substituents on the biological activity of molecules. This research can contribute to the understanding of the mechanisms of mutagenicity and carcinogenicity, which is crucial for the development of safer chemicals and pharmaceuticals.
Caution:

Upstream product

• 13120-77-9 2-methyl-5-nitroanisole 
• 136507-14-7 (2-methoxy-4-nitrophenyl)methanol 
• 5428-54-6 2-methyl-5-nitrophenol 

Downstream Products

• 136507-13-6 acetic acid 2-methoxy-4-nitro-benzyl ester 
• 497851-46-4 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(1-oxidopyridin-2-yl)methyl]-3-methoxyphenyl}-1-(trifluoroacetyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide 
• 497854-60-1 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(pyridin-2-yl)methyl]-3-methoxyphenyl}-1-(trifluoroacetyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide 
• 497848-99-4 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(1-oxidopyridin-2-yl)methyl]-3-methoxyphenyl}-2,3-dihydro-1H-1-benzazepine-4-carboxamide 
• 497854-59-8 (4-amino-2-methoxyphenyl)(pyridin-2-yl)methanol 
• 497854-58-7 (2-methoxy-4-nitrophenyl)(pyridin-2-yl)methanol 
• 136507-14-7 (2-methoxy-4-nitrophenyl)methanol 
• 136507-15-8 4-nitro-2-methoxybenzaldehyde 

Relevant academic research and scientific papers

Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole -Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.

Discovery of Novel Resorcinol Dibenzyl Ethers Targeting the Programmed Cell Death-1/Programmed Cell Death-Ligand 1 Interaction as Potential Anticancer Agents

Novel small molecule compounds based on various scaffolds including chalcone, flavonoid, and resorcinol dibenzyl ether were designed and tested for their inhibitory activity against the Programmed Cell Death-1/Programmed Cell Death-Ligand 1 (PD-1/PD-L1) pathway. Among them, compound NP19 inhibited the human PD-1/PD-L1 interaction with IC50 values of 12.5 nM in homogeneous time-resolved fluorescence (HTRF) binding assays. In addition, NP19 dose-dependently elevated IFN-γproduction in a coculture model of Hep3B/OS-8/hPD-L1 and CD3 T cells. Furthermore, NP19 displayed significant in vivo antitumor efficacy in two different mouse models of cancer (a melanoma B16-F10 tumor model and an H22 hepatoma tumor model). Moreover, H&E staining and flow cytometry data suggested that NP19 activated the immune microenvironment in the tumor, which may contribute to its antitumor effects. This work shows NP19 is a promising lead compound for further development as a new generation of small molecule inhibitors targeting the PD-1/PD-L1 pathway.

Discovery and biological evaluation of vinylsulfonamide derivatives as highly potent, covalent TEAD autopalmitoylation inhibitors

Transcriptional enhancer associated domain family members (TEADs) are the most important downstream effectors that play the pivotal role in the development, regeneration and tissue homeostasis. Recent biochemical studies have demonstrated that TEADs could undergo autopalmitoylation that is indispensable for its function making the lipid-binding pocket an attractive target for chemical intervention. Herein, through structure-based virtual screen and rational medicinal chemistry optimization, we identified DC-TEADin02 as the most potent, selective, covalent TEAD autopalmitoylation inhibitor with the IC50 value of 197 ± 19 nM while it showed minimal effect on TEAD-YAP interaction. Further biochemical counter-screens demonstrate the specific thiol reactivity and selectivity of DC-TEADin02 over the kinase family, lipid-binding proteins and epigenetic targets. Notably, DC-TEADin02 inhibited TEADs transcription activity leading to downregulation of YAP-related downstream gene expression. Taken together, our findings proved the validity of modulating transcriptional output in the Hippo signaling pathway through irreversible chemical interventions of TEADs autopalmitoylation activity, which may serve as a qualified chemical tool for TEADs palmitoylation-related studies in the future.

COMPOUNDS FOR TREATMENT OF CARDIAC ARRHYTHMIAS AND HEART FAILURE

This disclosure concerns compounds and a method for modulating the activity of calcium ion channels, including Ca2+-induced (or Ca2+-activated) calcium release channels and conformationally coupled calcium release channels such as ryanodine receptors. Some of the compounds have a structure according to formula I, or a stereoisomer, tautomer, hydrate, solvate, prodrug, or pharmaceutically acceptable salt thereof.

Peroxisome proliferator-activated receptor agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related liver X receptor antagonists: Relationship between absolute configuration and subtype selectivity

Introduction of an alkylcarboxylic acid unit, which is a partial structure of endogenous peroxisome proliferator-activated receptor (PPAR) ligands, into a phenethylphenylphthalimide skeleton, which possesses liver X receptor (LXR) antagonistic activity, afforded novel PPAR ligands. The results of structure-activity relationship analysis and docking studies led us to the potent PPAR agonists 13c-e. The absolute configuration of 13c-e affects the PPAR subtype selectivity.

4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione inhibitors of the checkpoint kinase Wee1. structure-activity relationships for chromophore modification and phenyl ring substitution

High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors are based on a 4-phenylpyrrolo[3,4-c]-carbazole-1,3(2H,6H)- dione template and have been shown by X-ray crystallography to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-phenyl group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2′-position of the 4-phenyl ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogues of the pyrrolocarbazole lead with improved physical properties.

Nitroaryl phosphoramide compositions and methods for targeting and inhibiting undesirable cell growth or proliferation

The present invention relates to nitroaryl-substituted phosphoramide prodrug compounds and methods of producing the same for use in targeting and inhibiting undesirable cell growth or proliferation.

Orally active CCR5 antagonists as anti-HIV-1 agents 2: Synthesis and biological activities of anilide derivatives containing a pyridine N-oxide moiety

In order to develop orally active CCR5 antagonists, we investigated 1-benzoxepine derivatives containing new polar substituents, such as phosphonate, phosphine oxide or pyridine N-oxide moieties, as replacements for the previoiusly reported quaternary ammonium moiety. Among these compounds, the 2-(α-hydroxybenzyl)pyridine N-oxide 5e exhibited moderate CCR5 antagonistic activity and had an acceptable pharmacokinetic profile in rats. Subsequent chemical modification was performed and compound (S)-5f possessing the (S)-configuration hydroxy group was found to be more active than the (R)-isomer. Replacement of the 1-benzoxepine ring with a 4-methylphenyl group by a 1-benzazepine ring with a 4-[2-(butoxy)ethoxy]phenyl group enhanced the activity in the binding assay. In addition, introduction of a 3-trifluoromethyl group on the phenyl group of the anilide moiety led to greatly increased activity in the HIV-1 envelope-mediated membrane fusion assay. In particular, compound (S)-5s showed the most potent CCR5 antagonistic activity (IC 50=7.2 nM) and inhibitory effect (IC50=5.4 nM) in the fusion assay, together with good pharmacokinetic properties in rats.

1-benzyl-1,3-dihydro-2H-benzimidazol-2-one derivatives, their preparation and the pharmaceutical compositions containing them

The present invention relates to 1-benzyl-1,3-dihydro-2H-benzimidazol-2-one derivatives, of formula: STR1 and to the possible salts thereof, to a process for their preparation and to the pharmaceutical compositions containing them.These compounds have an