51317-87-4

Usage

InChI:InChI=1/C9H9BrO2/c1-6-2-3-8(11)7(4-6)9(12)5-10/h2-4,11H,5H2,1H3

Upstream product

• 106-44-5 p-cresol 
• 79-08-3 bromoacetic acid 
• 38829-10-6 Bromessigsaeure-(p-tolyl)ester 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 

Downstream Products

• 80930-54-7 1-(2-Hydroxy-5-methyl-phenyl)-2-imidazol-1-yl-ethanone 
• 129354-89-8 2-(5-methylbenzofuran-3-yl)acetic acid 
• 1422718-31-7 C₁₅H₁₁F₃N₂O 
• 1422718-30-6 5'-methyl-6-chloro-HPIP 
• 305834-65-5 2-azido-1-(2-hydroxy-5-methylphenyl)ethanone 
• 1207618-04-9 ethyl 1-[4-(2-hydroxy-5-methylphenyl)-1,3-thiazol-2-yl]-4-piperidinecarboxylate 
• 54120-66-0 5-methyl-benzofuran-3-one 
• 54450-39-4 4-methyl-2-quinoxalin-2-yl-phenol 
• 194226-50-1 2-hydroxy-3-bromo-5-methyl-α-bromoacetophenone 

Relevant academic research and scientific papers

Synthesis, characterization, reactivity, and catalytic studies of heterobimetallic vanadium(V) complexes containing hydrazone ligands

Six heterobimetallic alkali metal dioxidovanadium(V) coordination polymer complexes {[M6{VO(μ-O)}2(μ-OH)4(μ4-slox/nph)].n DMF}∞ where M = Na, K, and Cs; n = 1 for (1), 0 for (2)-(6) of two dihydrazone ligands, disalicylaldehydeoxaloyldihydrazone (H4slox) and bis(2-hydroxy-1-naphthaldehyde)oxaloyldihydrazone (H4nph) are reported. All the complexes have been characterized by various physicochemical techniques such as elemental analyses, molar conductance, IR, NMR, UV–vis, and cyclic voltammetry. The IR, 1HNMR, and 13CNMR spectral data suggest that the dihydrazones are coordinated through phenolate/naphtholate oxygen, enolate oxygen, and azine nitrogen atoms to the metal centres. The structure of complex {[Na6{VO(μ-O)}2(μ-OH)4(μ4-slox)].DMF}∞ (1) is also determined by single-crystal X-ray data, which revealed that the H4slox coordinated via all possible dative sites to metal centres as tetrabasic octadentate ligand. The vanadium metal centres adopted distorted square-pyramidal coordination geometries, and the sodium atoms are also in five coordination atmospheres. The electronic spectra of the complexes showed LMCT bands in addition to intra-ligand π → π* and n → π* transitions. As evident from the cyclic voltammetry, the complexes showed two metal-centred electron transfer reactions {[(VVVV(slox)2?/VVVIV(slox)3?] and [(VVVIV(slox)3?/VVVIV(slox)4?]}, in addition to the ligand centred electron transfer reactions. Further, bovine serum albumin (BSA interaction studies of the complexes {[Na6{VO(μ-O)}2(μ-OH)4(μ4-slox)].DMF}∞ (1) and [Na6{VO(μ-O)}2(μ-OH)4(μ4-nph)]∞ (4) revealed strong binding affinity. Moreover, the catalytic studies of the complexes (1) and (4) were found to be effective for the oxidation of alcohols into their corresponding aldehydes and ketones and bromination of some organic substrates in the presence of H2O2 as an oxidizing agent.

MeONH 2·hCl-Mediated α-Methylenation/Conjugate Addition of α-Sulfonylo-Hydroxyacetophenones with Methyl Sulfoxides: Route to 3-Sulfonylchroman-4-ones

A novel and efficient route for the synthesis of 3-sulfonylchroman-4-ones from α-sulfonyl o -hydroxyacetophenones with methyl sulfoxides via a MeONH 2·HCl-mediated sequential methylenation/ conjugate addition is described. Plausible reaction mechanisms are proposed and discussed. Various reaction conditions for this novel, one-pot, environmentally friendly conversion were investigated.

Synthesis, crystal structure and reactivity of homobimetallic vanadium(V) complexes derived from oxaloyldihydrazone ligands

Treatment of V2O5 with dihydrazone ligands (H4L) (disalicylaldehydeoxaloyldihydrazone (H4L1 = H4slox), bis(2-hydroxy-1-naphthaldehyde)oxaloyldihydrazone (H4L2 = H4nph) and bis(5-bromosalicylaldehyde)oxaloyldihydrazone (H4L3 = H4sloxBr)) in methanol leads to the formation of homobimetallic vanadium(V) complexes of the composition [(CH3)2NH2]2[(VO2)2(L)]·nH2O, where n = 2 (1, 2) and n = 4 (3). The reaction of complexes 1–3 with H2O2 results in the formation of bis(monooxidoperoxidovanadate(V)) complexes[{VO(O2)}2(L)]2? and the reaction with HCl leads to the formation of oxidohydroxido species of the composition [(VO(OH)(L)]2?. The complexes show great potential for the oxidation of alcohols and the oxidative bromination of some organic substrates.

Reactivity and Catalytic Activity of Homobimetallic Vanadium(V) Complex Derived from Bis(5-chlorosalicylaldehyde)oxaloyldihydrazone Ligand

Homobimetallic vanadium(V) complex of the composition [(CH3)2NH2+]2[(VO2)2(sloxCl)].4H2O was synthesized from the reaction of V2O5 with bis(5-chlorosalicylaldehyde)oxaloyldihydrazone ligand in a 1:1 molar ratio in methanol. The structure of the complex was established by X-ray crystallography. Reactivity of the complex with H2O2 leads to bis (monooxidoperoxidovanadate(V)) [{VO(O2)}2(sloxCl)]2? formation and with HCl, oxidohydroxido complex of composition [(VO (OH)(sloxCl)]2? was formed. Binding interaction of the complex was also investigated toward protein (BSA) and it was found to be 2.21 x 108?M?1. The catalytic activity of the complex in the oxidation of alcohols and oxidative bromination of some organic substrates was also studied, and it showed a great potent as a catalyst.

Discovery of clinical candidate (1 R,4 r)-4-((R)-2-((S)-6-Fluoro-5 H-imidazo[5,1-A[isoindol-5-yl)-1-hydroxyethyl)cyclohexan-1-ol (Navoximod), a potent and selective inhibitor of indoleamine 2,3-dioxygenase 1

A novel class of 5-substituted 5H-imidazo[5,1-a]isoindoles are described as potent inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1). A structure-based drug design approach was used to elaborate the 5H-imidazo[5,1-a]isoindole core and to improve potency and pharmacological properties. Suitably placed hydrophobic and polar functional groups in the lead molecule allowed improvement of IDO1 inhibitory activity while minimizing off-target liabilities. Structure-activity relationship studies focused on optimizing IDO1 inhibition potency and a pharmacokinetic profile amenable to oral dosing while controlling CYP450 and hERG inhibitory properties.

Pyridine-substituted thiazolylphenol derivatives: Synthesis, modeling studies, aromatase inhibition, and antiproliferative activity evaluation

Drugs used in breast cancer treatments target the suppression of estrogen biosynthesis. During this suppression, the main goal is to inhibit the aromatase enzyme that is responsible for the cyclization and structuring of estrogens either with steroid or non-steroidal-type inhibitors. Non-steroidal derivatives generally have a planar aromatic structure attached to the triazole ring system in their structures, which inhibits hydroxylation reactions during aromatization by coordinating the heme group. Bioisosteric replacement of the triazole ring system and development of aromatic/cyclic structures of the side chain can increase the selectivity for aromatase enzyme inhibition. In this study, pyridine-substituted thiazolylphenol derivatives, which are non-steroidal triazole bioisosteres, were synthesized using the Hantzsch method, and physical analysis and structural determination studies were performed. The IC50 values of the compounds were determined by a fluorescence-based aromatase inhibition assay. Then, their antiproliferative activities on the MCF7 and HEK 293 cell lines were evaluated with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Furthermore, the crystal structure of human placental aromatase was subjected to a series of docking experiments to identify the possible interactions between the most active structure and the active site. Lastly, an in silico technique was performed to analyze and predict the drug-likeness, molecular and ADME properties of the synthesized molecules.

Studies on non-steroidal inhibitors of aromatase enzyme; 4-(aryl/heteroaryl)-2-(pyrimidin-2-yl)thiazole derivatives

Steroidal and non-steroidal aromatase inhibitors target the suppression of estrogen biosynthesis in the treatment of breast cancer. Researchers have increasingly focused on developing non-steroidal derivatives for their potential clinical use avoiding steroidal side-effects. Non-steroidal derivatives generally have planar aromatic structures attached to the azole ring system. One part of this ring system comprises functional groups that inhibit aromatization through the coordination of the haem group of the aromatase enzyme. Replacement of the triazole ring system and development of aromatic/cyclic structures of the side chain can increase selectivity over aromatase enzyme inhibition. In this study, 4-(aryl/heteroaryl)-2-(pyrimidin-2-yl)thiazole derivatives were synthesized and physical analyses and structural determination studies were performed. The IC50 values were determined by a fluorescence-based aromatase inhibition assay and compound 1 (4-(2-hydroxyphenyl)-2-(pyrimidine-2-yl)thiazole) were found potent inhibitor of enzyme (IC50:0.42 nM). Then, their antiproliferative activity over MCF-7 and HEK-293 cell lines was evaluated using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Compounds 1, 7, 8, 13, 15, 18, 21 were active against MCF-7 breast cancer cells. Lastly, a series of docking experiments were undertaken to analyze the crystal structure of human placental aromatase and identify the possible interactions between the most active structure and the active site.

2-PHENYL OR 2-HETARYL IMIDAZOL[1,2-a]PYRIDINE DERIVATIVES

The invention relates to compounds of formulas I and II, formula I or formula II wherein R1 is hydrogen, lower alkyl, lower alkoxy, halogen, S-lower alkyl, lower alkoxy substituted by halogen, di-lower alkyl amino, C(O)O-lower alkyl, lower alky

Tuning of excited-state intramolecular proton transfer (ESIPT) fluorescence of imidazo[1,2-a]pyridine in rigid matrices by substitution effect

2-(2′-Hydroxyphenyl)imidazo[1,2-a]pyridine (HPIP, 1) and its derivatives are synthesized, and their fluorescence properties are studied. Although all the compounds show faint dual emission (Φ ≈ 0.01), which is assigned to the normal and excited-state intr

THIAZOLE COMPOUNDS AS ACTIVATORS OF SOLUBLE GUANYLATE CYCLASE

Disclosed are compounds of formula (I) wherein R1 and R2 are independently selected from hydrogen, halo, C1-4alkyl, C1-4alkoxy, CF3 and OCF3; -Y- represents formula (IA) R3 represents hydrogen, fluoro, chloro or C1-4alkyl; R4a and R4b each independently represent hydrogen, C1-4alkyl, C1-4alkoxy, CF3 or halo; and R5 represents a group Z-X; wherein Z is absent or represents (CH2)2 or O; and X represents formula (IB) wherein: J and L both represent CH, or one of J and L represents CH and the other represents N; when both J and L represent CH, R6 represents hydrogen, halo, CF3, C1-4alkyl or C1-4alkoxy in a meta or ortho position relative to the R7 substituent and R7 represents hydrogen, halo, CF3, OCF3, C1-4alkyl, C1-4alkoxy, CH2OH, CN, CONR8R9 or CO2H; or when one of J or L represents N, R6 represents hydrogen or halo in a meta or ortho position relative to the R7 substituent and R7 represents hydrogen, halo, CF3, C1-4alkyl, C1-4alkoxy, CH2OH, CN, CONR8R9 or CO2H; and R8 and R9 are independently selected from hydrogen and C1-4alkyl; or salts thereof which activate soluble guanylate cyclase (sGC), pharmaceutical compositions containing them, their use in medicine, and processes for their preparation.