39859-36-4

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-BROMOBENZOPHENONE is used as a key intermediate for the synthesis of pharmaceutical compounds, playing a crucial role in the development of new drugs and medications. Its chemical structure allows for the creation of a diverse range of molecules with potential therapeutic applications.
Used in Chemical Research:
As a benzophenone derivative, 2-AMINO-5-BROMOBENZOPHENONE is also used in chemical research for studying the properties and reactions of similar compounds. This helps in understanding the behavior of benzophenones in various chemical processes and contributes to the advancement of chemical knowledge in this area.

InChI:InChI=1/C13H10BrNO/c14-10-6-7-12(15)11(8-10)13(16)9-4-2-1-3-5-9/h1-8H,15H2

Upstream product

• 98-88-4 benzoyl chloride 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 106-40-1 4-bromo-aniline 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 586-78-7 para-nitrophenyl bromide 
• 304858-65-9 2-amino-4-bromobenzonitrile 
• 100-58-3 phenylmagnesium bromide 
• 304854-54-4 2-amino-5-bromo-N-methoxy-N-methyl-benzamide 
• 108-86-1 bromobenzene 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 20357-20-4 5-bromo-2-nitrobenzaldehyde 
• 29124-57-0 2-amino-5-bromobenzaldehyde 
• 7141-05-1 (2-amino-5-bromophenyl)phenylmethanol 
• 39263-32-6 2-amino-5-bromobenzonitrile 

Downstream Products

• 102569-43-7 2-(6-Bromo-4-phenyl-quinolin-2-yl)-3-methyl-quinoxaline 
• 104542-53-2 2-(N-carbobenzoxyglycyl-glycyl)amido-5-bromobenzophenone 
• 104542-55-4 2-(N-carbobenzoxy-α-alanyl-glycyl)amido-5-bromobenzophenone 
• 136623-19-3 C₁₄H₁₄BrN₅*2ClH 
• 78259-16-2 6-Amino-hexanoic acid (2-benzoyl-4-bromo-phenyl)-amide; hydrochloride 
• 82221-44-1 5-bromo-2-(ε-aminocaproylamino)benzophenone 
• 102291-99-6 7-Bromo-5-phenyl-1,2-dihydro-3H-1,4-benzodiazepin-2-one-2-⁽¹⁴⁾C 
• 94579-32-5 2-N-Tosylamino-5-bromobenzophenone 
• 122438-77-1 C₂₀H₁₇BrN₄S 
• 39573-20-1 (5-bromo-2-(methylamino)phenyl)(phenyl)methanone 
• 92022-27-0 5-Bromo-2-aminobenzophenone-α-oxime 
• 91888-76-5 2-(6-Bromo-4-phenyl-quinolin-2-yl)-quinoxaline 
• 70890-58-3 5-Bromo-2-(chloroacetamido)benzophenone 
• 71858-13-4 6-bromo-2-(4-bromophenyl)-4-phenylquinoline 

Relevant academic research and scientific papers

Design, Synthesis, and in vitro Biological Evaluation of 3,5-Dimethylisoxazole Derivatives as BRD4 Inhibitors

BRD4 has been identified as a potential target for blocking proliferation in a variety of cancer cell lines. In this study, 3,5-dimethylisoxazole derivatives were designed and synthesized with excellent stability in liver microsomes as potent BRD4 inhibitors, and were evaluated for their BRD4 inhibitory activities in vitro. Gratifyingly, compound 11 h [3-((1-(2,4-difluorophenyl)-1H-1,2,3-triazol-4-yl)methyl)-6-(3,5-dimethylisoxazol-4-yl)-4-phenyl-3,4-dihydroquinazolin-2(1H)-one] exhibited robust potency for BRD4(1) and BRD4(2) inhibition with IC50 values of 27.0 and 180 nm, respectively. Docking studies were performed to illustrate the strategy of modification and analyze the conformation in detail. Furthermore, compound 11 h was found to potently inhibit cell proliferation in the BRD4-sensitive cell lines HL-60 and MV4-11, with IC50 values of 0.120 and 0.09 μm, respectively. Compound 11 h was further demonstrated to downregulate c-Myc levels in HL-60 cells. In summary, these results suggest that compound 11 h is most likely a potential BRD4 inhibitor and is a lead compound for further investigations.

Identification of 3,5-Dimethylisoxazole Derivatives as BRD4 Inhibitors for the Treatment of Colorectal Cancer

Bromodomain-containing protein 4 (Brd4) plays a critical regulatory role in gene transcription that has been recently recognized as a promising strategy for cancer therapy. Based on the BRD4 protein containing two tandem bromodomain structures, BD1 and BD2, we designed and synthesized a series of 3,5-dimethylisoxazole derivative dimers targeting both bromodomains simultaneously to enhance protein binding potency. Among them, compound 22 significantly inhibited the proliferation of colorectal cancer cells HCT116 (IC50= 162 nM), with a 20-fold increase in antiproliferative activity compared to inhibitor 14. The results of WesternBlot showed that compound 22 could down-regulate c-MYC protein levels and up-regulate HEXIM1 expression and modulate apoptosis through intrinsic pathways. In addition, compound 22 exhibited outstanding antitumor efficacy in the CT-26 tumor mouse model with a tumor suppression rate of 56.1%. Taken together, 3,5-dimethylisoxazole derivative dimer 22 has remarkable protein inhibitory effect and antitumor activity in vitro and in vivo. A protein binding model of compound 22 is being further analyzed, which will facilitate the development of bivalent BRD4 inhibitors and probe the biological function of BRD4.

Synthesis of substituted 2-pyridyl-4-phenylquinolines

The acid-catalyzed condensation of o-aminobenzophenones with aromatic acetyl derivatives, in a basic methanol/tetrahydrofuran medium, has been used to prepare a series of substituted 2-pyridyl-4-phenylquinolines. Derivatives having two aza binding sites can act as asymmetric bidendate ligands to complex transition metals such as ruthenium, osmium or iridium. All the compounds were characterized by elemental analysis, Ei or FAB (+) MS, 1H- and 13C-NMR spectroscopies. Complete assignments of the (1)H spectra were accomplished by using a combination of one- and two-dimensional NMR techniques.

Discovery of 3,5-dimethylisoxazole derivatives as novel, potent inhibitors for bromodomain and extraterminal domain (BET) family

Bromodomain and extra-terminal (BET) is a promising therapeutic target for various hematologic cancers. We used the BRD4 inhibitor compound 13 as a lead compound to develop a variety of compounds, and we introduced diverse groups into the position of the compound 13 orienting toward the ZA channel. A series of compounds (14–23, 38–41, 43, 47–49) bearing triazolopyridazine motif exhibited remarkable BRD4 protein inhibitory activities. Among them, compound 39 inhibited BRD4(BD1) protein with an IC50 of 0.003 μM was superior to lead compound 13. Meanwhile, compound 39 possess activity, IC50 = 2.1 μM, in antiproliferation activity against U266 cancer cells. On the other hand, compound 39 could arrest tumor cells into the G0/G1 phase and induce apoptosis, which was consistent with its results in inhibiting cell proliferation. Biological and biochemical data suggest that BRD4 protein might be a therapeutic target and that compound 39 is an excellent lead compound for further development.

NOVEL CELL METABOLISM MODULATING COMPOUNDS AND USES THEREOF

A class of compounds that bind to fatty acid binding protein (FABP4) and modulate adipocyte metabolism to drive enhanced glucose utilization, as well as pharmaceutical compositions comprising the class of compounds, in combination with a pharmaceutically acceptable diluent or carrier, and optionally, further in combination with a therapeutically active agent, and the use of these compounds in medicine and for the preparation of a medicament in the treatment of disorders acting on the FABP4.

IRIDIUM COMPLEX COMPOUND

An iridium complex compound represented by formula (5). Provided is an iridium complex compound that is useful as a material for a light-emitting layer of an organic electroluminescent element, has a narrow half-width of the emission spectrum thereof, has high solubility in a solvent, and has a short wavelength that is not too long and is suitable as a red-light-emitting material. where in formula (5), Ir represents an iridium atom. X represents a bidentate ligand. m represents an integer of 1 to 3. R1 to R22 each independently represent a hydrogen atom or a substituent. Adjacent substituents are optionally bonded together to form a ring. At least one of R13, R17, R18, and R22 represents a substituent other than a hydrogen atom.

Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles

Herein, an iridium(iii)-catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines is described. The developed method allows the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggest that the reaction proceeds through the electro-oxidation induced reductive elimination pathway.

Synthesis of 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides

The reaction of alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites furnishes 1-amino-2,2,2-trifluoroalkylphosphonates. The products were generated in moderate to good yields, and the scalability of this process was showcased. Partial hydrolysis of the phosphonate moiety was achieved. The cyclization is proposed to occur via formation of an imidoyl phosphonate intermediate that becomes susceptible to nucleophilic attack at nitrogen through the strong electron-withdrawing groups at the imidoyl carbon.

Structure-Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin

High-throughput screening has shown that Retro-1 inhibits ricin and Shiga toxins by diminishing their intracellular trafficking via the retrograde route, from early endosomes to the Golgi apparatus. To improve the activity of Retro-1, a structure-activity relationship (SAR) study was undertaken and yielded an analogue with a roughly 70-fold better half-maximal effective concentration (EC50) against Shiga toxin cytotoxicity measured in a cell protein synthesis assay.

Discovery of a new class of PROTAC BRD4 degraders based on a dihydroquinazolinone derivative and lenalidomide/pomalidomide

BRD4 has emerged as an attractive target for anticancer therapy. However, BRD4 inhibitors treatment leads to BRD4 protein accumulation, together with the reversible nature of inhibitors binding to BRD4, which may limit the efficacy of BRD4 inhibitors. To address these problems, a protein degradation strategy based on the proteolysis targeting chimera (PROTAC) technology has been developed to target BRD4 recently. Herein, we present our design, synthesis and biological evaluation of a new class of PROTAC BRD4 degraders, which were based on a potent dihydroquinazolinone-based BRD4 inhibitor compound 6 and lenalidomide/pomalidomide as ligand for E3 ligase cereblon. Gratifyingly, several compounds showed excellent inhibitory activity against BRD4, and high anti-proliferative potency against human monocyte lymphoma cell line THP-1. Especially, compound 21 (BRD4 BD1, IC50 = 41.8 nM) achieved a submicromolar IC50 value of 0.81 μM in inhibiting the growth of THP-1 cell line, and was 4 times more potent than compound 6. Moreover, the mechanism study established that 21 could effectively induce the degradation of BRD4 protein and suppression of c-Myc. All of these results suggested that 21 was an efficacious BRD4 degrader for further investigation.