102170-56-9

Usage

Chemical Properties

yellow needles

InChI:InChI=1/C7H7BrN2O2/c1-4-2-5(10(11)12)3-6(8)7(4)9/h2-3H,9H2,1H3

Upstream product

• 99-52-5 2-methyl-4-nitro-benzenamine 
• 139291-81-9 2-methyl-4-nitroaniline hydrochloride 
• 10035-10-6 hydrogen bromide 
• 7722-84-1 dihydrogen peroxide 

Downstream Products

• 175610-68-1 1-bromo-2-fluoro-3-methyl-5-nitro-benzene 
• 685109-10-8 7-bromo-5-nitro-1H-indazole 
• 603-78-1 2,3-dibromobenzoic acid 
• 1263376-30-2 3,4-dibromo-5-methyl-aniline 
• 61563-25-5 2,3-dibromotoluene 
• 98590-25-1 chloro-acetic acid-(2-bromo-6-methyl-4-nitro-anilide) 
• 73557-64-9 2,3-dibromo-5-nitro-toluene 
• 52488-28-5 1-bromo-3-methyl-5-nitrobenzene 

Relevant academic research and scientific papers

Development of 2, 4-diaminoquinazoline derivatives as potent PAK4 inhibitors by the core refinement strategy

Upon analysis of the reported crystal structure of PAK4 inhibitor KY04031 (PAK4 IC50?=?0.790?μM) in the active site of PAK4, we investigated the possibility of changing the triazine core of KY04031 to a quinazoline. Using KY04031 as a starting

Synthesis, antimalarial activity, and molecular modeling of tebuquine analogues

Tebuquine (5) is a 4-aminoquinoline that is significantly more active than amodiaquine (2) and chloroquine (1) both in vitro and in vive. We have developed a novel more efficient synthetic route to tebuquine analogues which involves the use of a palladium-catalyzed Suzuki reaction to introduce the 4- chlorophenyl moiety into the 4-hydrexyaniline side chain. Using similar methodology, novel synthetic routes to fluorinated (7a,b) and a dehydroxylated (7c) analogue of tebuquine have also been developed. The novel analogues were subjected to testing against the chloroquine sensitive HB3 strain and the chloroquine resistant K1 strain of Plasmodium falciparum. Tebuquine was the most active compound tested against both strains of Plasmodia. Replacement of the 4-hydroxy function with either fluorine or hydrogen led to a decrease in antimalarial activity. Molecular modeling of the tebuquine analogues alongside amodiaquine and chloroquine reveals that the inter-nitrogen separation in this class of drugs ranges between 9.36 and 9.86 ? in their isolated diprotonated form and between 7.52 and 10.21 ? in the heme-drug complex. Further modeling studies on the interaction of 4- aminoquinolines with the proposed cellular receptor heme revealed favorable interaction energies for chloroquine, amodiaquine, and tebuquine analogues. Tebuquine, the most potent antimalarial in the series, had the most favorable interaction energy calculated in both the in vacuo and solvent-based simulation studies. Although fluorotebuquine (7a) had a similar interaction energy to tebuquine, this compound had significantly reduced potency when compared with (5). This disparity is possibly the result of the reduced cellular accumulation (CAR) of fluorotebuquine when compared with tebuquine within the parasite. Measurement of the cellular accumulation of the tebuquine analogues and seven related 4-aminoquinolines shows a significant relationship (r = 0.98) between the CAR of 4-aminoquinoline drugs and the reciprocal of drug IC50.

Structure-based design of highly selective 2,4,5-trisubstituted pyrimidine CDK9 inhibitors as anti-cancer agents

Cyclin-dependent kinases (CDKs) are a family of Ser/Thr kinases involved in cell cycle and transcriptional regulation. CDK9 regulates transcriptional elongation and this unique property has made it a potential target for several diseases. Due to the conserved ATP binding site, designing selective CDK9 inhibitors has been challenging. Here we report our continued efforts in the optimization of 2,4,5-tri-substituted pyrimidine compounds as potent and selective CDK9 inhibitors. The most selective compound 30m was >100-fold selective for CDK9 over CDK1 and CDK2. These compounds showed broad anti-proliferative activities in various solid tumour cell lines and patient-derived chronic lymphocytic leukaemia (CLL) cells. Decreased phosphorylation of the carboxyl terminal domain (CTD) of RNAPII at Ser-2 and down-regulation of anti-apoptotic protein Mcl-1 were confirmed in both the ovarian cancer model A2780 and patient-derived CLL cells.

AZABENZIMIDAZOLES AND THEIR USE AS AMPA RECEPTOR MODULATORS

Provided herein are compounds of Formula (I), and pharmaceutically acceptable salts, N-oxides, or solvates thereof, [formula (I) should be inserted here]. Also provided herein are pharmaceutical compositions comprising compounds of Formula (I) and methods

Halogenation Using Quaternary Ammonium Polyhalides. VI. Bromination of Aromatic Amines by Use of Benzyltrimethylammonium Tribromide

The reaction of aromatic amines with benzyltrimethylammonium tribromide in dichloromethane-methanol containing calcium carbonate powder for 0.5 h at room temperature gave bromo-substituted aromatic amines in good yields.