cas 14140-15-9, 4-(2-Bromoethyl)phenol | Articles data

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Total synthesis of proposed structures of jiangrines C and D
On the basis of the proposed structures of jiangrines C and D, a synthetic strategy was initiated from D-glyceraldehyde acetonide, a readily available chiral material. Through a linear seven-step synthesis, the target molecules were accomplished. However, all characteristic data of the synthetic 3 and 4 were found to be different from those of natural jiangrines C and D. Accordingly, the molecular structures of jiangrines should be revised and a possible molecular skeleton for them was proposed.
Zhang, Zhijiang,Liu, Bo
p. 1205 - 1210
(2016)
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Preparation method 4 - (2 - bromoethyl) phenol
The invention discloses a preparation method of 4 - (2 - bromoethyl) phenol, which adopts relatively easily available cheap tyrosol and hydrobromic acid as a raw material, utilizes a bromination reaction of a bromine atom replacement alcohol hydroxyl group, and belongs to a substitution halogenation reaction of a classical organic reaction. The method has the technical effects of no polyhalogenation, high product purity, high yield and the like. The cheap and easily-manufactured hydrobromic acid is a brominating agent, and the reaction balance can be pushed to the direction of the generated product by proper excess use. The product yield can reach above 96%, the purity can reach 97.5% or more, the reaction liquid can be recycled after being subjected to distillation and concentration treatment, and a very good technical effect is obtained.
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Paragraph 0059-0069; 0075

(2021/11/26)

Inhibition of acetylcholinesterase by coumarin-linked amino acids synthetized via triazole associated with molecule partition coefficient
A previous study for the identification of acetylcholinesterase (AChE) inhibitors demonstrated that the hybrid between tyrosol, the 1,2,3-triazole nucleus, and the coumarin group, namely 7-({1-[2-(4-hydroxyphenyl)ethyl]-1H-1,2,3-triazol-4-yl}methoxy)-4-methyl-2H-chromen-2-one (10), has a high enzyme inhibitory activity. Here, we synthesized analogues of 10 via triazole with pharmacophoric groups represented by tyrosine, phenylalanine, tryptophan, and glycine in addition to evaluating the impact of coumarin-linked amino acids on AChE inhibition. We obtained eight triazoles, six of which are undescribed. In general, the presence of carboxylic acid decreased the inhibitory activity, while aromatic amino acids increased enzymatic inhibition compared to glycine. The derivative containing tyrosine, structurally most similar to 10, presented the lowest inhibition percentage, indicating that phenolic hydroxyl is not the preponderant factor for inhibition. Molecular docking was not enough to explain in vitro experiments. On the other hand, MlogP (logP calculated by the Moriguchi method) was related positively to enzymatic inhibition. To increase the hydrophobicity of the molecules, we tested the esterified triazole derivatives comparatively with the enzyme. The compound ethyl 2-(4-(((4-methyl-2-oxo-2H-chromen-7-yl)oxy)methyl)- 1H-1,2,3-triazol-1-yl)acetate (6) presented an increment of inhibitory activity of 46.97 ± 1.75% at 100 μmol L-1. We also associated the best activity with the lowest van der Waals volume and molar mass values.
De Sousa, Bianca L.,Leite, Jo?o P.V.,Mendes, Tiago A.O.,Varej?o, Eduardo V.V.,Chaves, Anna C.S.,da Silva, Júnio G.,Agrizzi, Ana P.,Ferreira, Priscila G.,Pilau, Eduardo J.,Silva, Evandro,dos Santos, Marcelo H.
p. 652 - 664
(2021/02/16)

Ni-Catalyzed Formal Cross-Electrophile Coupling of Alcohols with Aryl Halides
Direct coupling of unactivated alcohols remains a challenge in current synthetic chemistry. We herein demonstrate a strategy building upon in situ halogenation/reductive coupling of alcohols with aryl halides to forge Csp2-Csp3 bonds. The combination of 2-chloro-3-ethylbenzo[d]oxazol-3-ium salt (CEBO) and TBAB as the mild bromination reagents enables rapid transformation of a wide range of alcohols to their bromide counterparts within one to 5 min in CH3CN and DMF, which is compatible with the Ni-catalyzed cross-electrophile coupling conditions in the presence of a chemical reductant. The present method is suitable for arylation of a myriad of structurally complex alcohols with no need for prepreparation of alkyl halides. More importantly, the mild and kinetically rapid bromination process has shown good selectivity in the bromination/arylation of symmetric diols and less sterically hindered hydroxyl groups in polyols, thus offering promise for selective functionalization of diols and polyols without laborious protecting/deprotecting operations. The practicality of this work is also evident in the arylation of a number of carbohydrates, drug compounds, and naturally occurring alcohols.
Lin, Quan,Ma, Guobin,Gong, Hegui
p. 14102 - 14109
(2021/11/20)

Visible Light-Mediated Conversion of Alcohols to Bromides by a Benzothiadiazole-Containing Organic Photocatalyst
The search for metal-free, stable and high effective photocatalysts with sufficient photo-redox potentials remains a key challenge for organic chemists. Here, we present a benzothiadiazole-containing molecular organic photocatalyst with redox potentials of ?1.30 V and +1.64 V vs. SCE. The singlet state lifetime is 13 ns. Direct conversion from aliphatic alcohols to bromides has been conducted with the designed organic photocatalyst under visible light irradiation with high efficiency and selectivity. The catalytic efficiency of the novel benzothiadiazole-based photocatalyst is comparable with the state-of-art metal and non-metal catalysts. Furthermore, advanced photophysical studies including time-resolved photoluminescence and transient absorption spectroscopy offer a powerful support for photo-induced electron transfer from photocatalyst to the reactive substrates. Lastly, no photo-bleaching effect is observed, demonstrating the high stability and recyclable of the designed organic photocatalyst. (Figure presented.).
Li, Run,Gehrig, Dominik W.,Ramanan, Charusheela,Blom, Paul W. M.,Kohl, Fabien F.,Wagner, Manfred,Landfester, Katharina,Zhang, Kai A. I.
p. 3852 - 3859
(2019/07/15)

Site-Selective, Remote sp3 C?H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis
A photoinduced carboxylation of alkyl halides with CO2 at remote sp3 C?H sites enabled by the merger of photoredox and Ni catalysis is described. This protocol features a predictable reactivity and site selectivity that can be modulated by the ligand backbone. Preliminary studies reinforce a rationale based on a dynamic displacement of the catalyst throughout the alkyl side chain.
Sahoo, Basudev,Bellotti, Peter,Juliá-Hernández, Francisco,Meng, Qing-Yuan,Crespi, Stefano,K?nig, Burkhard,Martin, Ruben
supporting information
p. 9001 - 9005
(2019/06/24)

Synergistic Photo-Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides with Molecular Oxygen
Photoredox-mediated copper-catalyzed hydroxylation of (hetero)aryl halides (including chlorides, bromides, and iodides) with O2 at room temperature has been developed. Preliminary mechanistic studies indicate no arylcopper intermediate and that aryl radicals are involved in this procedure. 18O-labeling experiments confirm the hydroxyl oxygen atom originated from molecular oxygen.
Zhang, Xin,Wu, Ge,Gao, Wenxia,Ding, Jinchang,Huang, Xiaobo,Liu, Miaochang,Wu, Huayue
supporting information
p. 708 - 711
(2018/02/09)

EGFR PROTEOLYSIS TARGETING CHIMERIC MOLECULES AND ASSOCIATED METHODS OF USE
The present disclosure relates to bifunctional compounds, which find utility as modulators of receptor tyrosine kinase (RTK) proteins. In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a ligand which binds to an E3 ubiquitin ligase and on the other end a moiety which binds a target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effectuate ubiquitination, and therefore, degradation (and inhibition) of the target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.
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Paragraph 00954

(2018/07/29)

Indium(III)-catalyzed one-pot synthesis of alkyl cyanides from carboxylic Acids
The one-pot preparation of alkyl cyanides from carboxylic acids via alkyl iodides or alkyl bromides, which were in situ generated either by indium(III)-catalyzed reductive iodination or bromination of carboxylic acids, is described. Georg Thieme Verlag Stuttgart New York.
Moriya, Toshimitsu,Shoji, Kohei,Yoneda, Shinichiro,Ikeda, Reiko,Konakahara, Takeo,Sakai, Norio
p. 3233 - 3238
(2013/12/04)

Indium-catalyzed reductive bromination of carboxylic acids leading to alkyl bromides
The combination of 1,1,3,3-tetramethyldisiloxane (TMDS) and trimethylbromosilane (Me3SiBr) with a catalytic amount of indium bromide (InBr3) undertook direct bromination of carboxylic acids, which produced the corresponding alkyl bromides in good to excellent yields. The reducing system was tolerant to several functional groups.
Moriya, Toshimitsu,Yoneda, Shinichiro,Kawana, Keita,Ikeda, Reiko,Konakahara, Takeo,Sakai, Norio
supporting information
p. 4842 - 4845,4
(2020/09/16)

Bifunctional Aryloxylate Esters as potential oxidatively cleavable linkers
Selectively cleavable linkers are essential parts in environmentally responsive materials. Here, we introduce aryl oxalate esters (AOE) as one of the first examples for oxidatively cleavable linkers. To this end a series of novel AOEs was synthesized and explored regarding the H2O 2-dependent degradation. All AOEs were cleaved selectively at the oxalate group. The degradation rate was clearly dependent on the substituents. Further, it was found that the H2O2 based degradation undergoes an autocatalysis mechanism.
Czarnecki,Kampert,Barbe,Tiller
scheme or table
p. 3551 - 3554
(2011/07/29)

Thermolysis of 4-(ω-hydroxyalkyl)-2,6-di-tert-butylphenols
The process of thermolysis of tert-butylated hydroxyalkyl phenols includes de-tert-butylation, etherification, and fragmentation of the hydroxyalkyl group. On the basis of the proposed schemes of the mechanism of thermal de-tert-butylation the path of the search for catalysts for the synthesis of 4-hydroxyalkylphenols is defined and transformations of the by-products into biologically active substances were considered.
Krysin,Egorova,Vasil'Ev
experimental part
p. 275 - 283
(2010/07/15)

LTA4H modulators and uses thereof
Leukotriene A4 hydrolase (LTA4H) inhibitors, compositions containing them, and methods of use for the inhibition of LTA4H enzyme activity and the treatment, prevention or inhibition of inflammation and/or conditions associated with inflammation.
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Page/Page column 28

(2008/12/07)

Process for making galantamine
A novel process for the preparation of N-methyl-N-(2-[4-hydroxyphenyl]ethyl)-5-hydroxy-4-methoxy benzene carboxamide, which is useful as an intermediate in the synthesis of (?)-galantamine, comprises the reaction of a 5-hydroxy-4-methoxy benzoic acid derivative with N-methyl-N-(2-[4-hydroxyphenyl]ethyl)amine.
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Page/Page column 5

(2008/12/04)

Identification of a potent, selective, and orally active leukotriene A 4 hydrolase inhibitor with anti-inflammatory activity
LTA4H is a ubiquitously distributed 69 kDa zinc-containing cytosolic enzyme with both hydrolase and aminopeptidase activity. As a hydrolase, LTA4H stereospecifically catalyzes the transformation of the unstable epoxide LTA4 to the diol LTB4, a potent chemoattractant and activator of neutrophils and a chemoattractant of eosinophils, macrophages, mast cells, and T cells. Inhibiting the formation of LTB4 is expected to be beneficial in the treatment of inflammatory diseases such as inflammatory bowel disease (IBD), asthma, and atherosclerosis. We developed a pharmacophore model using a known inhibitor manually docked into the active site of LTA4H to identify a subset of compounds for screening. From this work we identified a series of benzoxazole, benzthiazole, and benzimidazole inhibitors. SAR studies resulted in the identification of several potent inhibitors with an appropriate cross-reactivity profile and excellent PK/PD properties. Our efforts focused on further profiling JNJ 27265732, which showed encouraging efficacy in a disease model relevant to IBD.
Grice, Cheryl A.,Tays, Kevin L.,Savall, Brad M.,Wei, Jianmei,Butler, Christopher R.,Axe, Frank U.,Bembenek, Scott D.,Fourie, Anne M.,Dunford, Paul J.,Lundeen, Katherine,Coles, Fawn,Xue, Xiaohua,Riley, Jason P.,Williams, Kacy N.,Karlsson, Lars,Edwards, James P.
experimental part
p. 4150 - 4169
(2009/07/19)

Interaction of functionally-substituted 4-alkyl-2,6-di-tert-butylphenols with hydrohalic acids
Reactions of 4-alkyl-2,6-di-tert-butylphenols containing OH, SH, COOH, and COOMe groups in their para substituents with hydrogen chloride and hydrohalic acids were studied. One-step transformations of 2,6-di-tert-butyl-4-(ω- hydroxyalkyl)phenols to the corresponding 4-(ω-halogenoalkyl)phenols, as well as of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid and its esters to phloretic acid were proposed. 4-(3-Mercaptopropyl)phenol upon heating with conc. HBr undergoes condensation to 3-(4-hydroxyphenyl)propyl 4-(3-mercaptopropyl)phenyl sulfide as the main product.
Prosenko,Skorobogatov,Dyubchenko,Pinko,Kandalintseva,Shakirov,Pokrovsky
p. 1119 - 1124
(2008/09/18)

Compounds for myocardial perfusion imaging
The present disclosure is directed to compounds comprising imaging moieties and their use for diagnosing certain disorders.
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Page/Page column 11

(2010/10/20)

Phenyl and pyridyl LTA4H modulators
Leukotriene A4 hydrolase (LTA4H) inhibitors, compositions containing them, and methods of use for the inhibition of LTA4H enzyme activity and the treatment, prevention or inhibition of inflammation and inflammatory conditions.
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Page/Page column 23

(2010/11/24)

USE OF INDAZOLE DERIVATIVES FOR THE TREATMENT OF NEUROPATHIC PAIN
Use of a compound of formula (I), wherein X is CH or N, and when X is CH, R is H, OH, a linear or branched alkyl chain having from 1 to 3 carbon atoms, a linear or branched alkoxy chain having from 1 to 3 carbon atoms, or a halogen atom, and when X is N, R is H, or an acid addition salt thereof with a pharmaceutically acceptable organic or inorganic acid, to prepare a pharmaceutical composition active in the treatment of neuropathic pain.
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Page/Page column 8; 9

(2008/06/13)

BENZIMIDAZOLE, BENZTHIAZOLE AND BENZOXAZOLE DERIVATIVES AND THEIR USE AS LTA4H MODULATORS
Leukotriene A4 hydrolase (LTA4H) inhibitors of formula I, compositions containing them, and their use for the inhibition of LTA4H enzyme activity and the treatment, prevention or inhibition of inflammation and/or conditions associated with inflammation, wherein X is selected from the group consisting of NR5, O, and S, with R5 being one of the H and CH3; Y is selected from the group consisting of CH2 and O; R4 is selected from the group consisting of H, OCH3, Cl, F, Br, I, OH, NH2, CN, CF3.
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Page/Page column 78

(2010/02/10)

PROPIONAMIDE DERIVATIVES USEFUL AS ANDROGEN RECEPTOR MODULATORS
Compounds of formula (I) wherein R1 to R4, X and A are as defined in the claims and pharmaceutically acceptable salts and esters thereof, are disclosed. The compounds of formula (I) possess utility as tissue-selective androgen receptor modulators (SARM) and are useful in hormonal therapy, e.g. in the treatment or prevention of male hypogonadism and age-related conditions such as andropause.
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Page 56

(2010/02/10)

PYRROLOPYRIMIDINE DERIVATIVES USEFUL AS MODULATORS OF MULTIDRUG RESISTANCE
A compound which is a pyrrolopyrimidine of formula (I) wherein: R1 is selected from R9 and halogen; R2 is NR6R7; R3 is selected from H, C1-C6 alkyl which is unsubstituted or substituted and -(CH2) nAr; R4 is selected from H, C1-C6 alkyl and -(CH2)? Ar; or R3 and R4 form, together with the N and C atoms to which they are attached, a fused five-, six-, seven- or eight-membered N-containing saturated ring which is unsubstituted or substituted; R5 is selected from CN, C02R9,C(O)NR10R11, -(CH2)nOH, -(CH2)nR10Rn, -C=CH, -C(S)NR10R11, -C(NH2)=NOR9, -C(R9)=NOR9, -C(NH2)NH, -C(O)R9 and an unsaturated 5- or 6-membered heterocyclic group which contains 1, 2 or 3 heteroatoms selected from N, O and S and which is unsubstituted or substituted; R6 and R7, which are the same or different, are selected from C1-C6 alkyl which is unsubstituted or substituted, -(CH2)nX and -(CH2)nAr; or R6 and R7 form, together with the nitrogen atom to which they are attached, a saturated five-, six-, seven- or eight-membered heterocyclic group which contains one nitrogen atom and 0 or from 1 to 3 additional heteroatoms selected from N, O and S, which is unsubstituted or substituted and which optionally contains one or two bridgehead atoms; R10and R11,which are the same or different, are selected from H, C1-C6 alkyl which is unsubstituted or substituted, -(CH2)nC3-C10 cycloalkyl and -(CH2)nAr; or R10 and R11 form, together with the nitrogen atom to which they are attached, a saturated five or six membered heterocyclic group which contains a nitrogen atom and 0 or from to 3 additional heteroatoms selected from O, S and N, which is unsubstituted or substituted and which is optionally fused to a benzene ring which is unsubstituted or substituted; n is the same or different when more than one is present within a given substituent group and is 0 or an integer of from 1 to 6; X is selected from -CN, -C02R9 and -NR10R11; R9 is the same or different when more than one is present within a given substituent group and is selected from -H, -QAr, -(CH2) nAr, C1-C6 alkyl which is unsubstituted or substituted and -(CH2) nC3-C10cycloalkyl, wherein the cycloalkyl moiety is optionally fused to a benzene ring which is unsubstituted or substituted; Q is C2-C6 alkenylene or alkynylene; and Ar is an unsaturated C6-C10 membered carbocyclic group or an unsaturated 5-11 membered heterocyclic group, which groups are unsubstituted or substituted; or a pharmaceutically acceptable salt thereof. These compounds have activity as inhibitors of MRP (multidrug resistant protein) and may thus be used to modulate multidrug resistance, for instance in potentiating the cytotoxicity of a chemotherapeutic agent.
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Page 48

(2010/02/07)

Total synthesis of the amaryllidaceae alkaloid (+)-plicamine and its unnatural enantiomer by using solid-supported reagents and scavengers in a multistep sequence of reactions
A sequence of polymer-supported reagents and scavengers was used to promote the synthetic transformations in the first total synthesis of (+)-plicamine (1), a member of the amaryllidaceae alkaloid family, starting from L-4-hydroxyphenylglycine (see scheme).
Baxendale, Ian R.,Ley, Steven V.,Piutti, Claudia
p. 2194 - 2197
(2007/10/03)

Total synthesis of the amaryllidaceae alkaloid (+)-plicamine using solid-supported reagents
In this report we describe in full the total synthesis of the amaryllidaceae alkaloid (+)-plicamine 1 including a model compound study. In both cases the compounds were prepared using solid-supported reagents and scavengers in multi-step sequences of reactions to give materials which required no conventional purification but could be carried on to the next synthetic step.
Baxendale, Ian R,Ley, Steven V,Nessi, Marcella,Piutti, Claudia
p. 6285 - 6304
(2007/10/03)

Structure-activity relationship for a series of 2-substituted 1,2,3,4- tetrahydro-9H-pyrido[3,4-b]indoles: Potent subtype-selective inhibitors of N- methyl-D-aspartate (NMDA) receptors
A series of 2-substituted 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indoles was synthesized as potential antagonists for the NR1(A)/2B subtype of N-methyl- D-aspartate (NMDA) receptors. Assayed by electrical recording under steady- state conditions, 7-hydroxy-2-(4-phenylbutyl)-1,2,3,4-tetrahydropyrido-[3,4- b]indole (30) was the most potent compound in the series having an IC50 value of 50 nM at the NR1(A)/2B receptors.
Tamiz, Amir P.,Whittemore, Edward R.,Woodward, Richard M.,Upasani, Ravindra B.,Keana, John F.W.
p. 1619 - 1624
(2007/10/03)

9-(Arylalkyl or aroylalkyl)-1-oxa-4,9-diazaspiro(5.5)undecan-3-ones
Compounds useful in the prevention and/or treatment of hypertension, congestive heart failure, arrhythmia, migraine, vasospastic disorders, and asthma are represented by the formula STR1 wherein: R1 is STR2 wherein X is hydrogen, lower alkyl, lower alkoxy, halo, carboxamido or hydroxy; m is 1, 2 or 3; and n is 1, 2 or 3; R2, R3 and R4 are independently hydrogen or lower alkyl; and the pharmaceutically acceptable acid addition salts thereof.
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(2008/06/13)