6307-83-1

Usage

Chemical Properties

white to slightly yellow crystalline needles

InChI:InChI=1/C7H4BrNO4/c8-5-1-4(7(10)11)2-6(3-5)9(12)13/h1-3H,(H,10,11)/p-1

Upstream product

• 355134-13-3 3-bromo-5-nitrobenzaldehyde 
• 6307-87-5 methyl 3-bromo-5-nitrobenzoate 
• 136649-26-8 3-bromo-5-nitro-biphenyl 
• 64-19-7 acetic acid 
• 121-92-6 3-nitrobenzoic acid 
• 128-08-5 N-Bromosuccinimide 
• 610-29-7 2-nitroterephthalic acid 
• 618-95-1 methyl 3-nitrobenzoate 
• 99-61-6 3-nitro-benzaldehyde 
• 618-84-8 3-amino-5-nitro-benzoic acid 

Downstream Products

• 42237-85-4 3-amino-5-bromobenzoic acid 
• 51339-40-3 3-bromo-5-nitrobenzoyl chloride 
• 139194-79-9 (3-bromo-5-nitrophenyl)methanol 
• 51339-45-8 3-Brom-5-nitro-4'-methoxy-benzophenon 
• 51339-36-7 3-Bromo-5-nitro-4'-methoxybenzhydrol 
• 51339-39-0 (3-bromo-5-nitrophenyl)(phenyl)methanone 
• 51339-15-2 3-Brom-5-nitro-benzhydrylbromid 
• 51339-29-8 3-Bromo-5-nitrobenzhydrol 
• 51339-21-0 3-Bromo-5-nitro-4'-methoxybenzhydrylbromid 
• 632627-69-1 3-morpholin-4-yl-5-nitro-benzoic acid 
• 26090-60-8 3-nitro-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid 
• 6307-87-5 methyl 3-bromo-5-nitrobenzoate 
• 90050-52-5 3-bromo-N-methyl-5-nitrobenzamide 
• 1041114-84-4 3-(6-methoxy-2-naphthyl)-5-nitrobenzoic acid 

Relevant academic research and scientific papers

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.

Pd-Catalyzed Decarboxylative Ortho-Halogenation of Aryl Carboxylic Acids with Sodium Halide NaX Using Carboxyl as a Traceless Directing Group

A highly regioselective Pd-catalyzed carboxyl directed decarboxylative ortho-C-H halogenation of cheap o-nitrobenzoic acids with NaX (X = I, Br) under aerobic conditions has been established. The utility of the method has been demonstrated by the gram-scale reaction and derivatization of the product. Experimental results have confirmed Pd and Bi played critical roles in the transformation and indicated the transformation might proceed via 2-halo-6-nitrobenzoic acid derivative intermediate.

PYRIMIDINE COMPOUND AND PHARMACEUTICAL USE THEREOF

Provided are a pyrimidine compound represented by Formula 1, a method of preparing the same, and a pharmaceutical use of the pyrimidine compound for the prevention or treatment of cancer.

Pyrimidine compounds and pharmaceutical composition for preventing or treating cancers comprising the same

The present invention relates to a pyrimidine compound having excellent FLT3 inhibitory activity, and a pharmaceutical composition for preventing or treating a cancer, including the same. The pyrimidine compound is represented by chemical formula 14, wherein the pyrimidine compound is selected from a stereoisomer, a tautomer, a solvate, and a pharmaceutically acceptable salt thereof. In the chemical formula 14, E^a is hydrogen, hydroxy or C_(1-4) alkoxy, and E^b is hydrogen, halogen, C_(1-4) alkyl or C_(1-4) fluoroalkyl.COPYRIGHT KIPO 2019

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.

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.

A Critical Cross-Catalytic Relationship Determines the Outcome of Competition in a Replicator Network

A network of two synthetic replicators exhibits a critical unidirectional cross-catalytic relationship that directs competing replication processes. In this network, nitrone N bearing a 6-methylamidopyridine recognition site can participate in 1,3-dipolar cycloaddition reactions with two maleimides that differ in the relative position of their carboxylic acid recognition site: either para (Mp) or meta (Mm) relative to the maleimide ring. These cycloaddition reactions create replicators trans-Tp and trans-Tm. In isolation, trans-Tp templates its own formation with an efficiency that is markedly greater than that of trans-Tm. Kinetic fitting and simulations reveal that this efficiency arises from a higher template-mediated rate constant for the cycloaddition and lower stability of the trans-Tp template duplex, compared to trans-Tm. By contrast, in a situation where Mp and Mm compete for a limited quantity of N, the normally less efficient trans-Tm outcompetes trans-Tp. Through a series of comprehensive kinetic 19F{1H} NMR spectroscopy experiments, this system-level outcome is traced to a critical cross-catalytic pathway, whereby the presence of trans-Tp templates the formation of trans-Tm, but not vice versa. Replicator trans-Tm also reduces the efficiency of its competitor trans-Tp by sequestering trans-Tp in a heteroduplex that is more stable than homoduplex [Tp·Tp]. The addition of different templates as instructions reveals that, while the outcome of competition between replicators can be altered selectively, it is limited by the reaction environment employed. These results represent a conceptual and practical framework for the examination of selectivity in replication networks operating outside well-stirred batch reactor conditions.

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.

A reactive nitrone-based organogel that self-assembles from its constituents in chloroform

The reversible reaction of an aldehyde with a hydroxylamine affords a nitrone which is capable of forming a stiff gel with chloroform at concentrations as low as 0.20 wt% (6 mM). The gelator forms dynamically from its constituents and the gel assembly can be degraded in a controlled manner through a recognition-mediated reaction that targets the nitrone component of the gel network.