6307-87-5

Usage

Uses

Used in Organic Synthesis:
Methyl 3-bromo-5-nitrobenzoate is utilized as a key building block in organic synthesis, serving as a precursor for the creation of a diverse array of chemical compounds. Its unique structure and reactivity contribute to the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, methyl 3-bromo-5-nitrobenzoate is employed as a precursor for the synthesis of pharmaceuticals. Its properties allow for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
Methyl 3-bromo-5-nitrobenzoate also finds application in the production of agrochemicals, where it acts as a starting material for the synthesis of various agricultural chemicals, contributing to crop protection and enhancement.
Used in Dye and Pigment Manufacturing:
Methyl 3-bromo-5-nitrobenzoate is used as an intermediate in the production of dyes and pigments, where its chemical properties are leveraged to create a wide range of colorants for different industries.
Used in the Production of Fine Chemicals:
Methyl 3-bromo-5-nitrobenzoate is also valuable in the manufacturing of fine chemicals, where its distinctive attributes are harnessed to produce high-quality specialty chemicals for specific applications.

InChI:InChI=1/C8H6BrNO4/c1-14-8(11)5-2-6(9)4-7(3-5)10(12)13/h2-4H,1H3

Upstream product

• 67-56-1 methanol 
• 6307-83-1 3-bromo-5-nitro-benzoic acid 
• 74-88-4 methyl iodide 
• 121-92-6 3-nitrobenzoic acid 
• 618-89-3 methyl 3-bromobenzoate 
• 1025718-78-8 methyl 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 618-95-1 methyl 3-nitrobenzoate 

Downstream Products

• 6307-83-1 3-bromo-5-nitro-benzoic acid 
• 706791-83-5 3-amino-5-bromobenzoic acid methyl ester 
• 102153-77-5 3-(dihydroxyphosphoryl)-5-nitrobenzoic acid 
• 1426520-50-4 methyl 3-amino-5-(diethoxyphosphoryl)benzoate 
• 1068437-86-4 3-amino-5-(dihydroxyphosphoryl)benzoic acid 
• 1426520-49-1 methyl 3-(diisopropyloxyphosphoryl)-5-nitrobenzoate 
• 1610566-96-5 methyl 3-(2,7-diphenylheptylamino)-5-nitrobenzoate 
• 1610566-94-3 methyl 3-(4-(hexyloxycarbonyl)phenylamino)-5-nitrobenzoate 
• 1639866-71-9 3-ethynyl-5-nitrobenzoic acid 
• 1639866-72-0 3-amino-5-ethynylbenzoic acid 
• 60912-61-0 methyl 3-bromo-5-acetylaminobenzoate 

Relevant academic research and scientific papers

POLYIMIDE-POLYARYLENE POLYMERS

Disclosed is a bis-imide compound comprising two or more aryl moieties substituted with ethynyl moieties and the two or more aryl moieties each having one or more polar substituents. Further disclosed is a polymer composition comprising a copolymer polymerized from a monomer mixture of (a) one or more first monomers comprising a bis-imide compound comprising two or more aryl moieties substituted with ethynyl moieties and the two or more aryl moieties each having one or more polar substituents; and (b) one or more second monomers comprising two or more cyclopentadienone moieties. The polymer compositions exhibit favorable properties for use in electronics and displays applications.

A small molecule inhibitor of PCSK9 that antagonizes LDL receptor binding via interaction with a cryptic PCSK9 binding groove

Proprotein convertase (PC) subtilisin kexin type 9 (PCSK9) inhibits the clearance of low density lipoprotein (LDL) cholesterol from plasma by directly interacting with the LDL receptor (LDLR). As the interaction promotes elevated plasma LDL cholesterol levels and a predisposition to cardiovascular disease (CVD), it has attracted much interest as a therapeutic target. While anti-PCSK9 monoclonal antibodies have been successful in the treatment of hypercholesteremia by decreasing CVD risk, their high cost and a requirement for injection have prohibited widespread use. The advent of an orally bioavailable small molecule inhibitor of the PCSK9-LDLR interaction is an attractive alternative, however efforts have been tempered as the binding interface is unfavourable for binding by small organic molecules. Despite its challenging nature, we report herein the discovery of compound 3f as a small molecule inhibitor of PCSK9. The kinase inhibitor nilotinib emerged from a computational screen that was applied to identify compounds that may bind to a cryptic groove within PCSK9 and proximal to the LDLR-binding interface. A subsequent in vitro PCSK9-LDLR binding assay established that nilotinib was a bona fide but modest inhibitor of the interaction (IC50 = 9.8 μM). Through multiple rounds of medicinal chemistry, 3f emerged as a lead-like molecule by demonstrating disruption of the PCSK9-LDLR interaction at nanomolar levels in vitro (IC50 = 537 nM) with no inhibitory activity (IC50 > 10 μM) against a small panel of kinases. Compound 3f restored LDL uptake by liver cells at sub-micromolar levels and demonstrated excellent bioavailability when delivered subcutaneously in mice. Most significantly, compound 3f lowered total cholesterol levels in the plasma of wild-type mice, thereby providing proof-of-concept that the notion of a small molecule inhibitor against PCSK9 is therapeutically viable.

PROTEIN KINASE INHIBITORS FOR PROMOTING LIVER REGENERATION OR REDUCING OR PREVENTING HEPATOCYTE DEATH

The invention relates to compounds of formula (I) which are inhibitors of MKK4 (mitogen-activated protein kinase kinase 4) and their use in promoting liver regeneration or reducing or preventing hepatocyte death. The compounds selectively inhibit protein kinase MKK4 over protein kinases JNK and MKK7. (I), wherein R x, R y , R z and R zz are selected from: a) R x and R y are F and R z and R zz are H; b) R x, R y and R zz are independently halogen and R z is H; c) R x R z and R zz are independently halogen and R y is H; and d) R x R y and R z are independently halogen and R zz is H

Regioselective synthesis of carboxylic and fluoromethyl tetrazoles enabled by silver-catalyzed cycloaddition of diazoacetates and aryl diazonium salts

Here we present a dipolar [3 + 2] cycloaddition transformation of diazoacetates with arenediazonium salts under silver catalysis, thus offering a straightforward approach for the regioselective construction of carboxylic tetrazoles. Several merits are accompanied with this reaction including readily available starting reagents, broad coupling scope, high yields, and friendly reaction conditions. The synthetic value is further showcased by one-pot conversion of commercially available primary arylamines to tetrazoles and successful transformations of the cycloadducts into valuable 5-fluoromethyltetrazoles and an analogue of P2X3 receptor antagonist.

Catalytic Direct Construction of Cyano-tetrazoles

Cyano-tetrazole is the first reported compound that bears four nitrogen atoms in a single five-membered ring. This unique molecular scaffold has long been ignored after its discovery in 1885, mainly attributed to the scarcity of available synthetic methods. Indeed, the most popular approach to tetrazoles (that is the cycloaddition reaction between nitriles and azides) has inevitably excluded the possibility of introducing valuable cyano groups to decorate the final heterocyclic cores. Here, we describe a completely different disconnection strategy to the long time-pursued cyano-tetrazoles via a simple, direct, and practical cycloaddition transformation between readily accessible aryl diazonium salts and diazoacetonitrile. This method provides both regioisomers of disubstituted tetrazoles from the same set of starting materials in a metal cation controlled fashion.

meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation

Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.

Construction of Difluoromethylated Tetrazoles via Silver-Catalyzed Regioselective [3 + 2] Cycloadditions of Aryl Diazonium Salts

A silver-catalyzed regioselective [3 + 2] cycloaddition reaction of PhSO2CF2CHN2 with aryl diazonium salts is described. This protocol enables the straightforward construction of a novel class of difluoromethylated tetrazoles under mild conditions, tolerates a broad spectrum of functionalities, and is applicable to one-pot operation from commercially available aniline derivatives. The synthetic merit of this method is further demonstrated by the facile preparation of versatile difluoromethylated azoles, including a valuable HCF2-analogue of P2X3 receptor antagonist.

HETEROCYCLIC INHIBITORS OF PCSK9

This application relates to chemical compounds which may act as inhibitors of, or which may otherwise modulate the activity of, PCSK9, or a pharmaceutically acceptable salt, solvate, prodrug or polymorph thereof, and to compositions and formulations comprising such compounds, and methods of using and making such compounds. Compounds include compounds of Formula (I): (I) wherein A, D and Q are described herein.

3-acylamino benzoic acid derivatives as well as preparation method and medical application thereof

The invention belongs to the field of medicinal chemistry and relates to 3-acylamino benzoic acid derivatives, pharmaceutical composition containing the compounds, a preparation method of the derivatives and an application of the derivatives as a therapeutic agent in the aspect of medical treatment, in particular to a medical application of the derivatives as a P2Y14 receptor antagonist.

The Importance of Being Me: Magic Methyls, Methyltransferase Inhibitors, and the Discovery of Tazemetostat

Posttranslational methylation of histones plays a critical role in gene regulation. Misregulation of histone methylation can lead to oncogenic transformation. Enhancer of Zeste homologue 2 (EZH2) methylates histone 3 at lysine 27 (H3K27) and abnormal methylation of this site is found in many cancers. Tazemetostat, an EHZ2 inhibitor in clinical development, has shown activity in both preclinical models of cancer as well as in patients with lymphoma or INI1-deficient solid tumors. Herein we report the structure-activity relationships from identification of an initial hit in a high-throughput screen through selection of tazemetostat for clinical development. The importance of several methyl groups to the potency of the inhibitors is highlighted as well as the importance of balancing pharmacokinetic properties with potency.