51012-63-6

Usage

InChI:InChI=1/C10H11BrO2/c1-2-13-9-5-3-8(4-6-9)10(12)7-11/h3-6H,2,7H2,1H3

Upstream product

• 1676-63-7 4'-ethoxyacetophenone 
• 186581-53-3 diazomethane 
• 16331-46-7 4-ethoxybenzoylchloride 
• 619-86-3 4-(ethoxy)benzoic acid 
• 99-93-4 4-Hydroxyacetophenone 

Downstream Products

• 202202-62-8 2-(4-ethoxy-phenyl)-imidazo[1,2-a]pyridine 
• 56921-71-2 7-chloro-2-(4-ethoxy-phenyl)-benzo[d]imidazo[2,1-b]thiazole 
• 56921-62-1 6-(4-ethoxy-phenyl)-3-thiophen-2-yl-imidazo[2,1-b]thiazole 
• 56921-81-4 9-(4-ethoxy-phenyl)-naphtho[2,1-d]imidazo[2,1-b]thiazole 
• 88675-32-5 2-Azepan-1-yl-1-(4-ethoxy-phenyl)-ethanone 
• 193208-30-9 2-Thiomorpholino-5-(4-ethoxyphenyl)-6H-1,3,4-thiadiazine, hydrobromide 
• 1104526-81-9 C₁₈H₁₄Cl₂N₂O₃S 
• 1016833-60-5 C₁₃H₁₂N₂OS 
• 260415-85-8 3-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-(4-ethoxyphenyl)butan-1-one 
• 1622931-23-0 4-(4-(4-ethoxyphenyl)thiazol-2-ylamino)phenol 
• 1590402-78-0 ethyl 1-benzoyl-2-methylindolizine-3-carboxylate 
• 1590402-80-4 ethyl 2-methyl-1-(3-phenylpropanoyl)indolizine-3-carboxylate 
• 26367-92-0 C₁₇H₁₄O₃ 

Relevant academic research and scientific papers

Rhodium-Catalyzed Annulation of Phenacyl Ammonium Salts with Propargylic Alcohols via a Sequential Dual C-H and a C-C Bond Activation: Modular Entry to Diverse Isochromenones

Given their omnipresence in natural products and pharmaceuticals, isochromenone congeners are one of the most privileged scaffolds to synthetic chemists. Disclosed herein is a dual (ortho/meta) C-H and C-C activation of phenacyl ammonium salts (acylammonium as traceless directing group) toward annulation with propargylic alcohols to accomplish rapid access for novel isochromenones by means of rhodium catalysis from readily available starting materials. This operationally simple protocol features broad substrate scope and wide functional group tolerance. Importantly, the protocol circumvents the need of any stoichiometric metal oxidants and proceeds under aerobic conditions.

NOVEL COMPOUND AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME

Disclosed are compounds of formula (I) below and pharmaceutically acceptable salts thereof: Formula (I), in which each of variables L, R3, R4, Y, Z1, Z2 and Z3 is defined herein. Also disclosed is a method for treating a cancer with a compound of formula (I) or a salt thereof and a pharmaceutical composition containing same.

Identification of Anti-Mycobacterial Biofilm Agents Based on the 2-Aminoimidazole Scaffold

Tuberculosis (TB) remains a significant global health problem for which new therapeutic options are sorely needed. The ability of the causative agent, Mycobacterium tuberculosis, to reside within host macrophages and form biofilm-like communities contributes to the persistent and drug-tolerant nature of the disease. Compounds that can prevent or reverse the biofilm-like phenotype have the potential to serve alongside TB antibiotics to overcome this tolerance, and decrease treatment duration. Using Mycobacterium smegmatis as a surrogate organism, we report the identification of two new 2-aminoimidazole compounds that inhibit and disperse mycobacterial biofilms, work synergistically with isoniazid and rifampicin to eradicate preformed M. smegmatis biofilms in vitro, are nontoxic toward Galleria mellonella, and exhibit stability in mouse plasma.

Molecular modeling study, synthesis and biological evaluation of combretastatin A-4 analogues as anticancer agents and tubulin inhibitors

As the major structural component of microtubules, tubulin is an interesting target for the development of anticancer agents. In this study, 64 tubulin polymerization inhibitors of five-membered heterocycle-based combretastatin A-4 analogues were studied by a combination of molecular modeling techniques including 3D-QSAR, molecular docking, and molecular dynamics (MD) simulation. The CoMFA (comparative molecular field analysis) and CoMSIA (comparative molecular similarity indices analysis) models were established with desirable statistical parameters and excellent predictive ability. 20 ns MD simulations were successfully performed to confirm the detailed binding mode and validate the rationality of docking results. Combining the binding free energy calculations and 3D-QSAR results, some new heterocycle-based combretastatin A-4 analogues were designed. Three of them were synthesized and biologically evaluated. Compound 13a displayed potent antiproliferative activity (IC50 value of 1.31 M against HepG2 cells, IC50 value of 1.37 M against A549 cells) and inhibition of tubulin polymerization activity (IC50 value of 0.86 M). Compound 13b also presented good activity against HepG2 cells (IC50 value of 4.75 μM). The experimental results demonstrated that the built models were effective for the development of novel anticancer agents and tubulin inhibitors.

Aq HBr–NaNO2–KI/air: a new catalytic system for α-monobromination of ketones

An efficient approach for α-bromination of aryl alkyl ketones, utilizing a system consisting of aqueous hydrobromic acid as bromine source, sodium nitrite–KI as catalyst, and air as terminal oxidant, has been developed. The method offers advantages of selective monobromination, mild reaction conditions, broad substrate scope, and good yield. The use of air as the terminal oxidant makes the reaction very attractive from both economical and environmental viewpoints.

In(OTf)3/acid co-catalyzed hydration of 1-haloalkynes to α-halomethyl ketones

A novel and efficient In(OTf)3and HOAc cooperatively catalyzed hydration of 1-haloalkynes is described. This method provides ready access to α-chloromethyl ketones, α-bromomethyl ketones and α-iodomethyl ketones in moderate to high yields from simple, inexpensive starting materials. A broad substrate scope is achieved, and the reaction is compatible with various functional groups, including alkoxy, trifluoromethyl, halide, hydroxyl, cyclohexyl, and heterocyclic groups.

2-((Benzimidazol-2-yl)thio)-1-arylethan-1-ones: Synthesis, crystal study and cancer stem cells CD133 targeting potential

In order to develop a potent anti-tumor agent that can target both cancer stem cells and the bulk of tumor cells, a series of 2-((benzimidazol-2-yl)thio)-1-arylethan-1-ones 5a-o was synthesized. All compounds were evaluated for their anti-proliferative activity towards colon HT-29 cancer cell line. In addition, their inhibitory effect against cell surface expression of CD133, a potent cancer stem cells (CSCs) marker, in the same cells was evaluated by flow cytometry at 10 μM. Compound 5l emerged as the most active anti-proliferative analog against HT-29 (IC50 Combining double low line 18.83 ± 1.37 μM), that almost equipotent as 5-fluorouracil (IC50 Combining double low line 15.83 ± 1.63 μM) with 50.11 ± 4.05% inhibition effect on CD133 expression, suggested dual targeted effect. Also, compounds 5h, 5j, 5k and 5m-o inhibited the expression of CD133 with more than 50%. The SAR study pointed out the significance of substitution of the pendent phenyl group with lipophilic electron-donating groups or replacing it by 2-thienyl or 2-furyl groups.

Multi-dimensional target profiling of N,4-diaryl-1,3-thiazole-2-amines as potent inhibitors of eicosanoid metabolism

Eicosanoids like leukotrienes and prostaglandins play a considerable role in inflammation. Produced within the arachidonic acid (AA) cascade, these lipid mediators are involved in the pathogenesis of pain as well as acute and chronic inflammatory diseases like rheumatoid arthritis and asthma. With regard to the lipid cross-talk within the AA pathway, a promising approach for an effective anti-inflammatory therapy is the development of inhibitors targeting more than one enzyme of this cascade. Within this study, thirty N-4-diaryl-1,3-thiazole-2- amine based compounds with different substitution patterns were synthesized and tested in various cell-based assays to investigate their activity and selectivity profile concerning five key enzymes involved in eicosanoid metabolism (5-, 12-, 15-lipoxygenase (LO), cyclooxygenase-1 and -2 (COX-1/-2)). With compound 7, 2-(4-phenyl)thiazol-2-ylamino)phenol (ST-1355), a multi-target ligand targeting all tested enzymes is presented, whereas compound 9, 2-(4-(4-chlorophenyl)thiazol-2-ylamino)phenol (ST-1705), represents a potent and selective 5-LO and COX-2 inhibitor with an IC50 value of 0.9 ± 0.2 μM (5-LO) and a residual activity of 9.1 ± 1.1% at 10 μM (COX-2 product formation). The promising characteristics and the additional non-cytotoxic profile of both compounds reveal new lead structures for the treatment of eicosanoid-mediated diseases.

Palladium-catalyzed asymmetric hydrogenation of α-acyloxy-1- arylethanones

First hand: The first example of a palladium-catalyzed asymmetric hydrogenation of α-acyloxy ketones (1) was accomplished to give the hydrogenated products 2 with by far the highest catalytic efficiency in up to quantitative conversions and excellent enantioselectivities. The hydrogenated products could serve as important intermediates for the preparation of many drug candidates. TFE=2,2,2-trifluoroethanol. Copyright

Novel Ethanediamone Hepcidine Antagonists

The present invention relates to novel hepcidin antagonists of formula (I), pharmaceutical compositions comprising them and the use thereof as medicaments, in particular for treatment of disorders in iron metabolism, such as, in particular, iron deficiency diseases and anaemias, in particular anaemias in connection with chronic inflammatory diseases (ACD: anaemia of chronic disease and AI: anaemia of inflammation).