Author: Jessica.F

Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry was written by Kubota, Koji;Baba, Emiru;Seo, Tamae;Ishiyama, Tatsuo;Ito, Hajime. And the article was included in Beilstein Journal of Organic Chemistry in 2022.HPLC of Formula: 162258-89-1 This article mentions the following:

This study describes the solid-state palladium-catalyzed cross-coupling between aryl halides and bis(pinacolato)diboron using ball milling. The reactions were completed within 10 min for most aryl halides to afford a variety of synthetically useful arylboronates in high yields. Notably, all exptl. operations could be performed in air, and did not require the use of large amounts of dry and degassed organic solvents. The utility of this method was further demonstrated by gram-scale synthesis under solvent-free, mechanochem. conditions. In the experiment, the researchers used many compounds, for example, 4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1HPLC of Formula: 162258-89-1).

4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1) 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). When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.HPLC of Formula: 162258-89-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Efficient preparation of unsymmetrical disulfides by nickel-catalyzed reductive coupling strategy was written by Wang, Fei;Chen, Ying;Rao, Weidong;Ackermann, Lutz;Wang, Shun-Yi. And the article was included in Nature Communications in 2022.Quality Control of 1-(2-Bromoethyl)-4-methoxybenzene This article mentions the following:

Disulfides are widely found in natural products and find a wide range of applications in life sciences, materials chem. and other fields. The preparation of disulfides mainly rely on oxidative couplings of two sulfur containing compounds This strategy has many side reactions and other shortcomings. Herein, authors describe the reductive nickel-catalyzed cross-electrophile coupling of unactivated alkyl bromides with sym. alkyl- and aryltetrasulfides to form alkyl-alkyl and aryl-alkyl unsym. disulfides. This approach for disulfide synthesis is practical, relies on easily available, unfunctionalized substrates, and is scalable. Author investigated the mechanism of this transformation and found that the tetrasulfide compound does not selectively break the central S-S bond, but regio-selectively generates trisulfide intermediates. 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. 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.Quality Control of 1-(2-Bromoethyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A Responsive Magnetic Resonance Imaging Contrast Agent for Detection of Excess Copper(II) in the Liver In Vivo was written by Paranawithana, Namini N.;Martins, Andre F.;Clavijo Jordan, Veronica;Zhao, Piyu;Chirayil, Sara;Meloni, Gabriele;Sherry, A. Dean. And the article was included in Journal of the American Chemical Society in 2019.Application of 6515-58-8 This article mentions the following:

The design, synthesis, and properties of a new gadolinium-based copper-responsive magnetic resonance imaging (MRI) contrast agent is presented. The sensor (GdL₁) has high selectivity for copper ions and exhibits a 43% increase in r₁ relaxivity (20 MHz) upon binding to 1 equiv of Cu²⁺ in aqueous buffer. Interestingly, in the presence of physiol. levels of human serum albumin (HSA), the r₁ relaxivity is amplified further up to 270%. Addnl. spectroscopic and X-ray absorption spectroscopy (XAS) studies show that Cu²⁺ is coordinated by two carboxylic acid groups and the single amine group on an appended side chain of GdL₁ and forms a ternary complex with HSA (GdL₁-Cu²⁺-HSA). T₁-weighted in vivo imaging demonstrates that GdL₁ can detect basal, endogenous labile copper(II) ions in living mice. This offers a unique opportunity to explore the role of copper ions in the development and progression of neurol. diseases such as Wilson’s disease. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Application of 6515-58-8).

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Application of 6515-58-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of oligo-6-bromo-6-deoxy-β-cyclodextrins was written by Kurochkina, G. I.;Trushkin, I. Yu.;Grachev, M. K.;Nifant’ev, E. E.. And the article was included in Russian Journal of General Chemistry in 2004.Safety of Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin This article mentions the following:

Two methods of synthesis of oligo-6-bromo-6-deoxy-β-cyclodextrins, with use of the Vilsmeier-Haack reagent and via tosyl derivatives of β-cyclodextrin, were compared. The second method holds more promise, since it allows a desired number of bromine atoms to be introduced into the β-cyclodextrin mol. instead of hydroxy groups. A correlation between the decomposition onset points of oligo-6-bromo-6-deoxy-β-cyclodextrins and the number of bromine substituents in them was revealed. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Safety of Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Safety of Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Behavior of mixed halogenated phenols in the Zincke method of nitration was written by Raiford, L. Chas.;Miller, Glen R.. And the article was included in Journal of the American Chemical Society in 1933.Category: bromides-buliding-blocks This article mentions the following:

In the nitration of mixed halogenated phenols and cresols it is shown that when Br occupies both the o- and p-positions, isomeric mono-NO₂ compounds may be formed; a phenol having H in 1 o-position and Br in the other may undergo nitration at both positions in the same experiment Cl is not replaceable by the NO₂ group under the conditions studied. Further evidence is reported to support the view that, in general, only 1 Ac-Bz derivative can be prepared from an o-aminophenol, regardless of the order of the introduction of the acyl radicals. o-ClC₆H₄OH and Br in CCl₄ give 87% of the 4-Br derivative, m. 48-9°; p-ClC₆H₄OH gives 62% of the 2-Br derivative, m. 121-3° (Bz derivative, m. 99-100°). 2-Bromo-6-chloro-p-cresol, b₃ 127-8°, m. 30° (69% yield); 2,3-di-Br derivative, pale brown, m. 80-1°; 2,3,5-tri-Br derivative, m. 197-8°. 2,4-BrClC₆H₃OH gives 34% of the 6-NO₂ derivative, m. 112°; 2,4-ClBrC₆H₃OH gives a mixture of the 6-NO₂ derivative and 2,4-Cl(O₂N)C₆H₃OH; 2,4,6-BrCl₂C₆H₂OH gives 4,6,2-Cl₂(O₂N)C₆H₃OH, while 2,6,4-Cl₂BrC₆H₂OH gives 2,6,4-Cl₂(O₂N)C₆H₂OH. 2,6,4-Br₂ClC₆H₂OH gives 2,4,6-BrCl(O₂N)C₆H₂OH, while 4,6,2-Br₂ClC₆H₂OH gives a mixture of 2,6,4- and 2,4,6-ClBr(O₂N)C₆H₂OH. 2,3,4,5,6-MeBr₃ClC₆OH gives 2,3,5,6,4-MeBr₂Cl(O₂N)C₆OH, m. 182-3° (91% yield); the isomeric 2,3,5,6,4-MeBr₃ClC₆OH gives 87% of 2-methyl-3,5-dibromo-4-chloro-6-nitrophenol, yellow, m. 149-50° (Bz derivative, m. 131-2°). 3,4,6-MeClBrC₆H₂OH gives 25% of 3-methyl-4-chloro-6-nitrophenol (I), yellow, m. 133-4°, and also 2-nitro-3-methyl-4-chloro-6-bromophenol, yellow, m. 103-4°. 3,4,2,6-MeClBr₂C₆HOH gives nearly quant. 2-bromo-3-methyl-4-chloro-6-nitrophenol, yellow, m. 87°, also formed by bromination of I. 2,3,4,5-Br₂MeClC₆HOH gives 2-nitro-3-bromo-4-methyl-6-chlorophenol, yellow, m. 109-10°; 2,3,5,4,6-Br₃MeClC₆OH gives 2-nitro-3,5-dibromo-4-methyl-6-chlorophenol, pale yellow, m. 157-8°. 4-Chloro-6-amino-o-cresol, gray, m. 107°; N,O-di-Ac derivative, pink, m. 195-6°; acetylamino derivative, brown, m. 110°; N-Bz-O-Ac derivative, m. 159°; benzoylamino derivative, brown, m. 203°. 2-Amino-4-chloro-6-bromo-m-cresol, brown, m. 131-2°; N,O-di-Ac derivative, m. 215°; N-Ac derivative, brown, m. 184-5°; N-Bz-O-Ac derivative, m. 166-7°; N-Bz derivative, m. 247°. 2-Bromo-4-chloro-6-amino-m-cresol, pale brown, m. 111-2°; N,O-di-Ac derivative, m. 220°; N-Ac derivative, pale brown, m. 180° (decomposition); N-Bz-O-Ac derivative, pink, m. 189°; N-Bz derivative, brownish, m. 192-3°; N,O-di-Bz derivative, m. 191°. 2-Amino-3-bromo-6-chloro-p-cresol, brownish, m. 146-7°; N,O-di-Ac derivative, m. 194-5°; N-Ac derivative, brown, m. 149-9.5°; N-Bz-O-Ac derivative, m. 220-1°; N-Bz derivative, pale brown, m. 178°. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-chloro-6-nitrophenol (cas: 58349-01-2Category: bromides-buliding-blocks).

4-Bromo-2-chloro-6-nitrophenol (cas: 58349-01-2) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Free energy perturbation (FEP)-guided scaffold hopping was written by Wu, Deyan;Zheng, Xuehua;Liu, Runduo;Li, Zhe;Jiang, Zan;Zhou, Qian;Huang, Yue;Wu, Xu-Nian;Zhang, Chen;Huang, Yi-You;Luo, Hai-Bin. And the article was included in Acta Pharmaceutica Sinica B in 2022.SDS of cas: 4457-67-4 This article mentions the following:

Scaffold hopping refers to computer-aided screening for active compounds with different structures against the same receptor to enrich privileged scaffolds, which is a topic of high interest in organic and medicinal chem. However, most approaches cannot efficiently predict the potency level of candidates after scaffold hopping. Herein, we identified potent PDE5 inhibitors with a novel scaffold via a free energy perturbation (FEP)-guided scaffold-hopping strategy, and FEP shows great advantages to precisely predict the theor. binding potencies ΔGFEP between ligands and their target, which were more consistent with the exptl. binding potencies ΔGEXP (the mean absolute deviations |ΔGFEP – ΔGEXP| < 2 kcal/mol) than those ΔGMM-PBSA or ΔGMM-GBSA predicted by the MM-PBSA or MM-GBSA method. Lead L12 had an IC50 of 8.7 nmol/L and exhibited a different binding pattern in its crystal structure with PDE5 from the famous starting drug tadalafil. Our work provides the first report via the FEP-guided scaffold hopping strategy for potent inhibitor discovery with a novel scaffold, implying that it will have a variety of future applications in rational mol. design and drug discovery. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4SDS of cas: 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.SDS of cas: 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of highly active juvenile hormone analogs, juvocimene I and II, from the oil of sweet basil, Ocimum basilicum L was written by Nishida, Ritsuo;Bowers, William S.;Evans, Philip H.. And the article was included in Journal of Chemical Ecology in 1984.Safety of 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

Juvocimene I and II (I, R = CH:CMe₂, 3,3-dimethyl-2-oxiranyl, resp.) were isolated from the oil of O. basilicum and their structures determined by synthesis from p-MeOC₆H₄(CH₂)₃Br and Me₂C:CHCH(OAc)CH₂CHMeEt. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Safety of 1-(3-Bromopropyl)-4-methoxybenzene).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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.Safety of 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Steering Siglec-sialic acid interactions on living cells using bioorthogonal chemistry was written by Buell, Christian;Heise, Torben;van Hilten, Niek;Pijnenborg, Johan F. A.;Bloemendal, Victor;Gerrits, Lotte;Kers-Rebel, Esther D.;Ritschel, Tina;den Brok, Martijn H.;Adema, Gosse J.;Boltje, Thomas J.. And the article was included in Angewandte Chemie, International Edition in 2017.Formula: C8H7BrO2 This article mentions the following:

Sialic acid sugars that terminate cell-surface glycans form the ligands for the sialic acid binding Ig-like lectin (Siglec) family, which are immunomodulatory receptors expressed by immune cells. Interactions between sialic acid and Siglecs regulate the immune system, and aberrations contribute to pathologies like autoimmunity and cancer. Sialic acid/Siglec interactions between living cells are difficult to study owing to a lack of specific tools. Here, we report a glycoengineering approach to remodel the sialic acids of living cells and their binding to Siglecs. Using bioorthogonal chem., a library of cells with more than sixty different sialic acid modifications was generated that showed dramatically increased binding toward the different Siglec family members. Rational design reduced cross-reactivity and led to the discovery of three selective Siglec-5/14 ligands. Furthermore, glycoengineered cells carrying sialic acid ligands for Siglec-3 dampened the activation of Siglec-3⁺ monocytic cells through the NF-κB and IRF pathways. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Formula: C8H7BrO2).

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) 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. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Formula: C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Characteristics of metabolic stability and the cell permeability of 2-pyrimidinyl-piperazinyl-alkyl derivatives of 1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione with antidepressant- and anxiolytic-like activities was written by Zagorska, Agnieszka;Partyka, Anna;Bucki, Adam;Kolaczkowski, Marcin;Jastrzebska-Wiesek, Magdalena;Czopek, Anna;Siwek, Agata;Gluch-Lutwin, Monika;Bednarski, Marek;Bajda, Marek;Jonczyk, Jakub;Piska, Kamil;Koczurkiewicz, Paulina;Wesolowska, Anna;Pawlowski, Maciej. And the article was included in Chemical Biology & Drug Design in 2019.Synthetic Route of C13H14BrNO2 This article mentions the following:

A series of 2-pyrimidinyl-piperazinyl-alkyl derivatives of 1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione has been synthesized in an attempt to discover a new class of psychotropic agents. Compounds were evaluated for their in vitro affinity for serotonin 5-HT_1A, 5-HT₇, and phosphodiesterases PDE4 and PDE10. The most potent compound 2-pyrimidinyl-1-piperazinyl-butyl-imidazo[2,1-f]purine-2,4-dione (4b) behaved as strong and selective antagonist of 5-HT_1A. Mol. modeling studies revealed differences in binding mode between compound 4b and buspirone, which might reflect variation of the ligands’ affinity and potency in the 5-HT_1A receptor. Compound 4b in silico models demonstrated drug-likeness properties and, contrary to buspirone, showed a metabolic stability in mouse liver microsomes system. Exptl. obtained value of apparent permeability coefficient P_app for 4b in parallel artificial permeability assay indicates the possibility of binding weakly to plasma proteins and high intestinal absorption fraction. Evaluation of the antidepressant- and anxiolytic-like activities of 4b revealed both activities at the same dose of 1.25 mg/kg and seemed to be specific. The antidepressant and/or anxiolytic properties of 4b may be related to its first-pass effect. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Synthetic Route of C13H14BrNO2).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Synthetic Route of C13H14BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and Biological Evaluation of Quinoxaline Derivatives for PET Imaging of the NMDA Receptor was written by Milicevic Sephton, Selena;Vetterli, Peter T.;Pedani, Valentina;Cermak, Stjepko;Chiotellis, Aristeidis;Roscales, Sylvia;Mueller Herde, Adrienne;Schibli, Roger;Auberson, Yves P.;Ametamey, Simon M.. And the article was included in Helvetica Chimica Acta in 2017.Synthetic Route of C7H6BrF This article mentions the following:

Due to the biol. complexity of the N-methyl-D-aspartate receptor (NMDAR), the development of a positron emission tomog. radiotracer for the imaging of NMDAR has met with limited success. Recent studies have established the presence of GluN2A subunit of the NMDAR in the heart and its role in the regulation of intracellular calcium levels. In our efforts to develop an imaging agent for the GluN2A subunit, we designed three new compounds based on a quinoxaline scaffold. The synthesis of the analogs was based on a two-step Kabachnik-Fields reaction in sequence with Suzuki cross-coupling and acid hydrolysis. They exhibited comparable high binding affinity values below 5 nM. A two-step radiolabeling procedure was successfully developed for the synthesis of [¹⁸F]I. [¹⁸F]I was obtained in a modest overall radiochem. yield of 5.5 ± 4.2%, a good specific radioactivity of 254 ± 158 GBq/μmol, and a radiochem. purity > 99%. While two compounds showed comparable binding affinity towards NMDAR, sluggish radiolabeling, prevented their further evaluation. For [¹⁸F]I, in vitro autoradiog. on rat heart slices demonstrated heterogeneous but unspecific accumulation, whereas for the brain a high in vitro specificity towards NMDAR, could be demonstrated. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-fluorotoluene (cas: 452-62-0Synthetic Route of C7H6BrF).

3-Bromo-4-fluorotoluene (cas: 452-62-0) 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. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Synthetic Route of C7H6BrF

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary