Category: 76283-09-5

Cho, Young Shin published the artcileConformational Refinement of Hydroxamate-Based Histone Deacetylase Inhibitors and Exploration of 3-Piperidin-3-ylindole Analogues of Dacinostat (LAQ824), Application of 4-Bromo-1-(bromomethyl)-2-fluorobenzene, the publication is Journal of Medicinal Chemistry (2010), 53(7), 2952-2963, database is CAplus and MEDLINE.

A series of conformationally restrained HDAC inhibitors based on the hydroxamic acid dacinostat (LAQ824) was prepared Several scaffolds with improved biochem. and cellular potency, as well as attenuated hERG inhibition, were identified, suggesting that the introduction of mol. rigidity is a viable strategy to enhance HDAC binding and mitigate hERG liability. Further SAR studies around a 3-piperidin-3-ylindole moiety resulted in the discovery of compound I, for which a unique conformation was speculated to contribute to overcoming increased lipophilicity and attenuating hERG binding. Separation of racemic I afforded its R-enantiomer, which demonstrated improved potency in both enzyme and cellular assays compared to dacinostat.

Journal of Medicinal Chemistry published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Application of 4-Bromo-1-(bromomethyl)-2-fluorobenzene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Wu, Shaoxiang published the artcileA highly diastereoselective and enantioselective phase-transfer catalyzed epoxidation of β-trifluoromethyl-β,β-disubstituted enones with H₂O₂, Related Products of bromides-buliding-blocks, the publication is Iranian Journal of Chemistry & Chemical Engineering (2015), 34(4), 13-38, database is CAplus.

An efficient epoxidation of β-CF₃-β,β-disubstituted unsaturated ketones was developed with environmental benign hydrogen peroxide as the oxidant and F₅-substituted chiral quaternary ammonium salt derived from cinchona-alkaloid as the catalyst. Using 3 mol% of the catalyst, both enantiomers of (R,R) and (S,S) β-trifluoromethyl-α,β-epoxy ketones were obtained in excellent diastereoselectivities (up to 100:1 d.r.) and enantioselectivities (up to 99.7% ee). The effects of catalyst structure, catalyst loading, substrate structure, the nature of oxidant, and reaction conditions on the catalyst capacities were discussed in full length. The reaction mechanism was proposed to explain the origin of chiral induction. By subsequent reduction with zinc the epoxides were exhibited to be converted into trifluoromethylated quaternary alcs. without any loss in enantioselectivities. All new compounds were fully characterized by IR, NMR, elemental anal. and or high resolution mass spectrum.

Iranian Journal of Chemistry & Chemical Engineering published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C10H10CoF6P, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Cheng, Cang published the artcileEnantioselective synthesis of quaternary 3,4-dihydroisoquinolinones via Heck carbonylation reactions: development and application to the synthesis of Minalrestat analogues, Application In Synthesis of 76283-09-5, the publication is Chemical Science (2019), 10(42), 9853-9858, database is CAplus and MEDLINE.

Minalrestat and its analogs represent structurally novel aldose reductase inhibitors, and the asym. synthesis of such pharmaceutically privileged mols. has not been reported yet. We have developed a palladium-catalyzed enantioselective intramol. carbonylative Heck reaction by using formate esters as the source of CO, which represents the first enantioselective synthesis of quaternary 3,4-dihydroisoquinolines. The reaction provides a facile and efficient method for the synthesis of enantiopure nitrogen-containing heterocyclic compounds bearing an all-carbon quaternary stereocenter. The reaction has been successfully applied to the first asym. synthesis of Minalrestat analogs.

Chemical Science published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Application In Synthesis of 76283-09-5.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Goto, Shunsuke published the artcileThe Process Development of a Novel Aldose Reductase Inhibitor, FK366. Part 1. Improvement of Discovery Process and New Syntheses of 1-Substituted Quinazolinediones, Quality Control of 76283-09-5, the publication is Organic Process Research & Development (2003), 7(5), 700-706, database is CAplus.

The novel aldose reductase inhibitor FK366 I is prepared on multikilogram scale by an improved, practical and cost-effective process. Addition of base to a solution of 2-amino-4-chlorobenzoic acid followed by addition of sodium cyanate at pH 6-7 and a second treatment with aqueous sodium hydroxide yields the quinazoline II; the pH is carefully controlled in the cyanate addition step by addition of hydrochloric acid to the reaction mixture, preventing the decomposition of cyanate while allowing the cyclocondensation reaction to occur at a reasonable rate. Silylation of II with bis(trimethylsilyl)amide in the presence of sulfuric acid (with careful mixing of bis(trimethylsilyl)amide and sulfuric acid to avoid violent reaction) yields an intermediate bis(trimethylsilyloxy)quinazoline which undergoes regioselective alkylation in Et acetate to provide the intermediate III in good yield as a single regioisomer. Alkylation of the remaining free nitrogen of the quinazoline with 4-bromo-2-fluorobenzyl bromide followed by basic hydrolysis of the ethoxycarbonyl moiety yields I on 35 kg scale. The dibenzylated quinazoline IV, resulting from incomplete reaction of II in the regioselective alkylation reaction with Et bromoacetate followed by subsequent dibenzylation, acts as a initiator for the formation of an undesired polymorph of I which is difficult to filter and which forms thick slurries. Seeding solutions of I containing ≥1% of IV with either polymorph of I results in crystallization of the undesired polymorph of I from solution Solutions with 0.5% IV yield different polymorphs depending on the identity of the seed crystal; seeding the solution with a crystal of the undesired polymorph of I provides crystals of the undesired polymorph of I, while seeding the solution with a crystal of the desired polymorph of I results in crystallization of the desired polymorph of I. Monitoring of the initial silylation and regioselective alkylation step by HPLC is used to minimize the amount of IV present in the final product and thus to provide the desired polymorph of I upon recrystallization

Organic Process Research & Development published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Quality Control of 76283-09-5.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Schneider, Leon N. published the artcileStable and Storable N(CF₃)₂ Transfer Reagents, Formula: C7H5Br2F, the publication is Chemistry – A European Journal (2021), 27(42), 10973-10978, database is CAplus and MEDLINE.

Fluorinated groups are essential for drug design, agrochems., and materials science. The bis(trifluoromethyl)amino group is an example of a stable group that has a high potential. While the number of mols. containing perfluoroalkyl, perfluoroalkoxy, and other fluorinated groups is steadily increasing, examples with the N(CF₃)₂ group are rare. One reason is that transfer reagents are scarce and metal-based storable reagents are unknown. Herein, a set of Cu^I and Ag^I bis(trifluoromethyl)amido complexes stabilized by N- and P-donor ligands with unprecedented stability are presented. The complexes are stable solids that can even be manipulated in air for a short time. They are bis(trifluoromethyl)amination reagents as shown by nucleophilic substitution and Sandmeyer reactions. In addition to a series of benzylbis(trifluoromethyl)amines, 2-bis(trifluoromethyl)amino acetate was obtained, which, upon hydrolysis, gives the fluorinated amino acid-N,N-bis(trifluoromethyl)glycine.

Chemistry – A European Journal published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Formula: C7H5Br2F.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Milne, Kirsty published the artcileA fragment-like approach to PYCR1 inhibition, Related Products of bromides-buliding-blocks, the publication is Bioorganic & Medicinal Chemistry Letters (2019), 29(18), 2626-2631, database is CAplus and MEDLINE.

Pyrroline-5-carboxylate reductase 1 (PYCR1) is the final enzyme involved in the biosynthesis of proline and has been found to be upregulated in various forms of cancer. Due to the role of proline in maintaining the redox balance of cells and preventing apoptosis, PYCR1 is emerging as an attractive oncol. target. Previous PYCR1 knockout studies led to a reduction in tumor growth. Accordingly, a small mol. inhibitor of PYCR1 could lead to new treatments for cancer, and a focused screening effort identified pargyline as a fragment-like hit. Herein the design and synthesis of the first tool compounds as PYCR1 inhibitors, derived from pargyline, which were assayed to assess their ability to attenuate the production of proline, are reported. Structural activity studies have revealed the key determinants of activity, with the most potent compound, 4-bromobenzyl(propargyl)methylamine, showing improved activity in vitro in enzyme (IC₅₀ = 8.8μM) and pathway relevant effects in cell-based assays.

Bioorganic & Medicinal Chemistry Letters published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Xiang, Panjie published the artcileDirect benzylation reactions from benzyl halides enabled by transition-metal-free photocatalysis, SDS of cas: 76283-09-5, the publication is Chinese Chemical Letters (2022), 33(12), 5074-5079, database is CAplus.

An SN²-based photochem. strategy using dithiocarbamate anion as catalyst was developed for the activation of benzyl halides, which are extremely challenging to be applied as radical precursors in visible light photocatalysis. With this transition-metal-free and oxidant-free protocol, the benzylation (or cyanomethylation) of various heterocycles including quinoxalin-2(1H)-ones, coumarin, 2-phenyl-2H-indazole, 1-methyl-5-phenylpyrazin-2(1H)-one, 1-(fluoromethyl)cinnolin-4(1H)-one, and 2,4-dibenzyl-1,2,4-triazine-3,5(2H,4H)-dione could be realized (46 examples, up to 98% yield). Importantly, some biol. relevant 3-benzylquinoxalin-2(1H)-ones were also be synthesized under mild conditions.

Chinese Chemical Letters published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C13H18N2, SDS of cas: 76283-09-5.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Guelak, Samet published the artcileHighly chemoselective cobalt-catalyzed biaryl coupling reactions, Synthetic Route of 76283-09-5, the publication is Chemical Science (2013), 4(2), 776-784, database is CAplus.

A practical cobalt-catalyzed hetero-biaryl coupling reaction between aryl chlorides and arylmagnesium halides with unprecedented selectivity has been developed. The protocol utilizes 1 mol% of cheap Co(acac)₃ as pre-catalyst and effects clean reactions of deactivated chlorostyrenes with only 1.1 equivalent of the Grignard reagent under mild conditions (30°, 5-30 min). Highly chemoselective reactions were realized even in the presence of activated bromoarenes. The olefin substituent facilitates the activation of the C-Cl bond by coordination to the catalyst. Kinetic studies indicate the operation of an arylcobaltate(i) catalyst species. Catalyst formation during the induction period was studied in the presence of cobalt(iii), (i), and (-i) pre-catalysts.

Chemical Science published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Synthetic Route of 76283-09-5.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Hi, Jianxing published the artcileResearch on synthesis of chiral quinine quaternary ammonium ligand and its catalyzing activity for Darzens reaction, Name: 4-Bromo-1-(bromomethyl)-2-fluorobenzene, the publication is Guangdong Huagong (2013), 40(7), 27-29, 31, database is CAplus.

Through quaternization reaction of a series of halogenated hydrocarbons and quinine alkali, a series of chiral quinine quaternary ammonium salt ligands were generated with quinine as base matrix and its synthesized ligand structure was confirmed by ¹H-NMR, IR and MS. And catalytic performance of ligands in Darzens condensation reaction between 2-chloroacetophenone and benzaldehyde in the asym. catalytic condition was investigated, implying that the chiral catalytic properties were associated with the steric size of substituents. And the best enantioselectivity of 46% was obtained.

Guangdong Huagong published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Name: 4-Bromo-1-(bromomethyl)-2-fluorobenzene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Pokorny, Jan published the artcileSubstituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters, Application In Synthesis of 76283-09-5, the publication is European Journal of Medicinal Chemistry (2021), 113706, database is CAplus and MEDLINE.

A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Four compounds had IC₅₀ below 5μmol/L; I and II were selected for studies of the mechanism of action. Cell cycle anal. revealed an increase in the number of apoptotic cells at 5 x IC₅₀ concentration, where activation of irreversible changes leading to cell death can be expected. Both I and II led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 x IC₅₀ and almost complete inhibition at 5 x IC₅₀. Interestingly, compound II at 5 x IC₅₀ caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds I and II trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacol. parameters of derivative I were superior to II, therefore I was the finally selected candidate for the development of anticancer drug.

European Journal of Medicinal Chemistry published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Application In Synthesis of 76283-09-5.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary