Category: 14425-64-0

New zileuton-hydroxycinnamic acid hybrids: synthesis and structure-activity relationship towards 5-lipoxygenase inhibition was written by Chiasson, Audrey Isabel;Robichaud, Samuel;Moutombi, Fanta J. Ndongou;Hebert, Mathieu P. A.;Mbarik, Maroua;Surette, Marc E.;Touaibia, Mohamed. And the article was included in Molecules in 2020.Quality Control of 1-(2-Bromoethyl)-4-methoxybenzene This article mentions the following:

A novel series of zileuton-hydroxycinnamic acid hybrids I (R¹ = H, OH, OMe; n = 0, 1, 2, 3), II (R² = C₆H₅, 4-OHC₆H₄, 2,6-(CH₃)₂C₆H₃, etc.) and III (R³ = H, OH, OMe; R⁴ = H, OH, OMe; R⁵ = H, OMe) were synthesized and screened as 5-lipoxygenase (5-LO) inhibitors in stimulated HEK293 cells and polymorphonuclear leukocytes (PMNL). Zileuton’s IV benzo[b]thiophene and hydroxyurea subunits combined with hydroxycinnamic acid esters’ ester linkage and phenolic acid moieties were investigated. Compound II (R² = 3,5-(OMe)₂-4-OHC₆H₂), bearing zileuton’s IV benzo[b]thiophene and sinapic acid phenethyl ester’s V 濞?濞?unsaturated phenolic acid moiety II (R² = 3,5-(OMe)₂-4-OHC₆H₂), was shown to be equipotent to zileuton IV, the only clin. approved 5-LO inhibitor, in stimulated HEK293 cells. Compound II (R² = 3,5-(OMe)₂-4-OHC₆H₂) was three times as active as zileuton IV for the inhibition of 5-LO in PMNL. Compound III (R³ = OMe, R⁴ = OH, R⁵ = OMe), bearing the same sinapic acid (3,5-dimethoxy-4-hydroxy substitution) moiety as II (R² = 3,5-(OMe)₂-4-OHC₆H₂), combined with zileuton’s IV hydroxyurea subunit was inactive. This result shows that the zileuton’s IV benzo[b]thiophene moiety is essential for the inhibition of 5-LO product biosynthesis with hydrids. Unlike zileuton IV, compound II (R² = 3,5-(OMe)₂-4-OHC₆H₂) formed two 闁?闁?interactions with Phe177 and Phe421 as predicted when docked into 5-LO. Compound II (R² = 3,5-(OMe)₂-4-OHC₆H₂) was the only docked ligand that showed a 闁?闁?interaction with Phe177 which may play a part in product specificity as reported. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Quality Control of 1-(2-Bromoethyl)-4-methoxybenzene).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Quality Control of 1-(2-Bromoethyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Structural Modifications to Tetrahydropyridine-3-carboxylate Esters en Route to the Discovery of M₅-Preferring Muscarinic Receptor Orthosteric Antagonists was written by Zheng, Guangrong;Smith, Andrew M.;Huang, Xiaoqin;Subramanian, Karunai L.;Siripurapu, Kiran B.;Deaciuc, Agripina;Zhan, Chang-Guo;Dwoskin, Linda P.. And the article was included in Journal of Medicinal Chemistry in 2013.Related Products of 14425-64-0 This article mentions the following:

The M₅ muscarinic acetylcholine receptor is suggested to be a potential pharmacotherapeutic target for the treatment of drug abuse. We describe herein the discovery of a series of M₅-preferring orthosteric antagonists based on the scaffold of 1,2,5,6-tetrahydropyridine-3-carboxylic acid. Compound 56, the most selective compound in this series, possesses an 11-fold selectivity for the M₅ over M₁ receptor and shows little activity at M₂-M₄. This compound, although exhibiting modest affinity (K_i = 2.24 婵炴挾鎷? for the [³H]N-methylscopolamine binding site on the M₅ receptor, is potent (IC₅₀ = 0.45 nM) in inhibiting oxotremorine-evoked [³H]DA release from rat striatal slices. Further, a homol. model of human M₅ receptor based on the crystal structure of the rat M₃ receptor was constructed, and docking studies of compounds 28 and 56 were performed in an attempt to understand the possible binding mode of these novel analogs to the receptor. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Related Products of 14425-64-0).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon闂佺偨鍎茶ぐ绲﹐mine bond is electrophilic, i.e. alkyl bromides are alkylating agents. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Related Products of 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Directing Group Enhanced Carbonylative Ring Expansions of Amino-Substituted Cyclopropanes: Rhodium-Catalyzed Multicomponent Synthesis of N-Heterobicyclic Enones was written by Shaw, Megan H.;Melikhova, Ekaterina Y.;Kloer, Daniel P.;Whittingham, William G.;Bower, John F.. And the article was included in Journal of the American Chemical Society in 2013.Application of 14425-64-0 This article mentions the following:

Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Application of 14425-64-0).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon闂佺偨鍎茶ぐ绲﹐mine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Application of 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

HCF₂Se/HCF₂S Installation by Tandem Substitutions from Alkyl Bromides was written by Zhang, Min;Lin, Jin-Hong;Xiao, Ji-Chang. And the article was included in Journal of Organic Chemistry in 2021.Synthetic Route of C9H11BrO This article mentions the following:

Herein authors describe an efficient construction of HCF₂Se and HCF₂S groups by tandem substitutions between alkyl bromides and a reagent system consisting of MSeCN (or MSCN) and Ph₃P+CF₂H Br-. The tandem process occurs via the first nucleophilic substitution of alkyl bromides by -SeCN (or -SCN) and the subsequent nucleophilic difluoromethylation. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Synthetic Route of C9H11BrO).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Synthetic Route of C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Enantioselective semireduction of allenes was written by Chen, Zhiwei;Dong, Vy M.. And the article was included in Nature Communications in 2017.Electric Literature of C9H11BrO This article mentions the following:

Herein, Rh-catalyzed regio- and enantioselective semiredn. of allenes to generate chiral benzylic motifs is reported. Rh-hydride catalysis solves a synthetic challenge by affording the enantioselective reduction of allenes, thereby yielding access to motifs commonly used in medicinal chem. A designer Josiphos ligand promotes the generation of chiral benzylic isomers, when combined with a Hantzsch ester as the reductant. This semiredn. proceeds chemoselectively in the presence of other functional groups, which are typically reduced using conventional hydrogenations. Isotopic labeling studies support a mechanism where the hydride is delivered to the branched position of a Rh-allyl intermediate. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Electric Literature of C9H11BrO).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Electric Literature of C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design, Synthesis, and Biological Activity of Substrate Competitive SMYD2 Inhibitors was written by Cowen, Scott D.;Russell, Daniel;Dakin, Leslie A.;Chen, Huawei;Larsen, Nicholas A.;Godin, Robert;Throner, Scott;Zheng, Xiaolan;Molina, Audrey;Wu, Jiaquan;Cheung, Tony;Howard, Tina;Garcia-Arenas, Renee;Keen, Nicholas;Pendleton, Christopher S.;Pietenpol, Jennifer A.;Ferguson, Andrew D.. And the article was included in Journal of Medicinal Chemistry in 2016.Application In Synthesis of 1-(2-Bromoethyl)-4-methoxybenzene This article mentions the following:

Protein lysine methyltransferases (KMTs) have emerged as important regulators of epigenetic signaling. These enzymes catalyze the transfer of donor Me groups from the cofactor S-adenosylmethionine to specific acceptor lysine residues on histones, leading to changes in chromatin structure and transcriptional regulation. These enzymes also methylate an array of non-histone proteins, suggesting addnl. mechanisms by which they influence cellular physiol. SMYD2 is reported to be an oncogenic methyltransferase that represses the functional activity of the tumor suppressor proteins p53 and RB. HTS screening led to identification of five distinct substrate-competitive chem. series, e.g., I (X = C, R¹ = H, CN, OMe; X = N, R¹ = H, OMe, NHMe). Determination of liganded crystal structures of SMYD2 contributed significantly to ‘hit-to-lead’ design efforts, culminating in the creation of potent and selective inhibitors that were used to understand the functional consequences of SMYD2 inhibition. Taken together these results have broad implications for inhibitor design against KMTs, and clearly demonstrate the potential for developing novel therapies against these enzymes. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Application In Synthesis of 1-(2-Bromoethyl)-4-methoxybenzene).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon闂佺偨鍎茶ぐ绲﹐mine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Application In Synthesis of 1-(2-Bromoethyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Electroreductive Nickel-Catalyzed Thiolation: Efficient Cross-Electrophile Coupling For C-S Formation was written by Ang, Nate W. J.;Ackermann, Lutz. And the article was included in Chemistry – A European Journal in 2021.Reference of 14425-64-0 This article mentions the following:

An efficient and mild electrochem. thiolation by cross-electrophile coupling of alkyl bromides with functionalized bench-stable thiosulfonates to access alkyl sulfides RSR¹ [R = (CH₂)₅Cl, Cy, (CH₂)₂Ph, etc.; R¹ = Cy, Ph, 2-thienyl, etc.] with excellent efficacy and broad functional group tolerance. Cyclic voltammetry and potentiostatic anal. were performed to elucidate mechanistic insights into this electrocatalytic thiolation reaction. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Reference of 14425-64-0).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Reference of 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols was written by Merad, Jeremy;Matyasovsky, Jan;Stopka, Tobias;Brutiu, Bogdan R.;Pinto, Alexandre;Drescher, Martina;Maulide, Nuno. And the article was included in Chemical Science in 2021.Product Details of 14425-64-0 This article mentions the following:

Isothiouronium salts N(CH₃)₂C(=N⁺(CH₃)₂)SR.X^– (R = prop-2-en-1-yl, 2-(4-methoxyphenyl)ethyl, 3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propyl, etc.; X = Br, I, SbF₆, BF₄, PF₆) are easily accessible and stable compounds Herein, their use as versatile deoxasulfenylating agents enabling a stereoselective, thiol-free protocol for synthesis of thioethers RSR¹ (R¹ = prop-2-yn-1-yl, 1-phenylethyl, 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl, etc.) from alcs. R¹OH was reported. The method is simple and scalable and tolerates a broad range of functional groups otherwise incompatible with other methods. Late-stage modification of several pharmaceuticals provides access to multiple analogs of biol. relevant mols. Performed experiments give insight into the reaction mechanism. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Product Details of 14425-64-0).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Product Details of 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and structure-activity relationships of novel arylpiperazines as potent antagonists of 浼?-adrenoceptor was written by Silva, Renata Oliveira;de Oliveira, Andressa Souza;Nunes Lemes, Lais Flavia;de Camargo Nascente, Luciana;Coelho do Nascimento Nogueira, Patricia;Silveira, Edilberto R.;Brand, Guilherme D.;Vistoli, Giulio;Cilia, Antonio;Poggesi, Elena;Buccioni, Michela;Marucci, Gabriella;Bolognesi, Maria Laura;Romeiro, Luiz Antonio Soares. And the article was included in European Journal of Medicinal Chemistry in 2016.Electric Literature of C9H11BrO This article mentions the following:

Arylpiperazines 2-11 were synthesized, and their biol. profiles at 浼?-adrenergic receptors (浼?-ARs) assessed by binding assays in CHO cells expressing human cloned subtypes and by functional experiments in isolated rat vas deferens (浼?A), spleen (浼?B), and aorta (浼?D). Modifications at the 1,3-benzodioxole and Ph phamacophoric units resulted in the identification of a number of potent compounds (moderately selective with respect to the 浼?b-AR), in binding experiments Notably, compound 7 (LDT451) showed a subnanomolar pK_i of 9.41 towards 浼?a-AR. An encouragingly lower 浼?B-potency was a general trend for all the series of compounds, which showed 浼?A/D over 浼?B selectivity in functional assays. If adequately optimized, such peculiar selectivity could have relevance for a potential LUTS/BPH therapeutic application. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Electric Literature of C9H11BrO).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Electric Literature of C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Improved Flavodoxin Inhibitors with Potential Therapeutic Effects against Helicobacter pylori Infection was written by Galano, Juan J.;Alias, Miriam;Perez, Reyes;Velazquez-Campoy, Adrian;Hoffman, Paul S.;Sancho, Javier. And the article was included in Journal of Medicinal Chemistry in 2013.Application of 14425-64-0 This article mentions the following:

A variety of electron-deficient chromenes and styrenes and nitrobenzooxadiazolyl thioethers and other compounds were tested (and in some cases prepared) as selective inhibitors of flavodoxin in Helicobacter pylori for potential use in the treatment of gastric ulcer and prevention of stomach cancer with fewer side effects and reduced susceptibilities to drug resistance; their inhibition of flavodoxin and of Helicobacter pylori and their cytotoxicities were determined For example, (E)-ArCH:CHNO₂ (Ar = 2-F-5-F₃CC₆H₃, 4-Cl-2,6-F₂C₆H₂) inhibited H. pylori with IC₅₀ values of 0.53 娓璏 and therapeutic indexes of 38 and 15, resp. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Application of 14425-64-0).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Application of 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary