Tag: 200-300

Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp³)-H bond functionalization was written by Mori, Keiji;Umehara, Nobuaki;Akiyama, Takahiko. And the article was included in Chemical Science in 2018.Name: 2-Bromo-4-fluorobenzylbromide This article mentions the following:

Bronsted acid-catalyzed double C(sp³)-H bond functionalization of alkyl phenethyl ether derivatives was described. In this process, a [1,5]-[1,5]-hydride shift occurred successively to afford tricyclic fused pyran derivatives in excellent chem. yields with excellent diastereoselectivities (up to >20 : 1). The key to achieve this reaction was the introduction of two Me groups at the benzylic position, which was effective in both hydride shift processes: (1) the Thorpe-Ingold effect for the first hydride shift and (2) conformational control in the second hydride shift. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0Name: 2-Bromo-4-fluorobenzylbromide).

2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Name: 2-Bromo-4-fluorobenzylbromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Hybrids consisting of the pharmacophores of salmeterol and roflumilast or phthalazinone: Dual β₂-adrenoceptor agonists-PDE4 inhibitors for the treatment of COPD was written by Liu, Anqiu;Huang, Ling;Wang, Zhiren;Luo, Zonghua;Mao, Fei;Shan, Wenjun;Xie, Jiaxing;Lai, Kefang;Li, Xingshu. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.SDS of cas: 954-81-4 This article mentions the following:

A novel class of dual pharmacol. bronchodilators I(n = 2, 3, 4, 5) and II(n = 1, 3, 4, 5) targeting both β₂-adrenoceptor and PDE4 was designed and synthesized by combining the pharmacophores of salmeterol and roflumilast or phthalazinone. All the compounds exhibited better β₂-adrenoceptor agonist activities (pEC₅₀ = 8.47-9.20) than the reference compound salmeterol (pEC₅₀ = 8.3) and good inhibitory activity on PDE4B2 (IC₅₀ = 0.235-1.093 μM). In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4SDS of cas: 954-81-4).

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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.SDS of cas: 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen was written by Wang, Yan-en;Li, Xueyan;Chen, Hua;Zhu, Mengyuan;Li, Xiaoliu. And the article was included in Chemical Research in Chinese Universities in 2018.Name: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane This article mentions the following:

The development of sensors that recognize Lewis oligosaccharides can help the diagnosis and early detection of cancer. Herein, authors reported the design and synthesis of a series of anthracene-based bisboronic acids (9a–9e) with different N-substituents near the boronic acid unit. Among them, compound 9a could recognize sialyl Lewis X(sLe^x) with selectivity over other Lewis sugars, and could significantly stain sLe^x-expressing HEPG2 cells with selectivity over the range of 0.1-10 μmol/L. Compound 9a possibly has two properly positioned boronic acids caused by the steric hindrance by the near N-benzyl substituent group, which empower its sLe^x selectivity and higher binding affinity. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1Name: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane).

2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1) 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.Name: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Parameters of the production of carboxin and its analogs was written by Dziedzic, Czeslaw;Eckstein, Zygmunt;Ejmocki, Zdzislaw;Miszczak, Kamila;Rusek, Dorota;Tippe, Andrzej. And the article was included in Przemysl Chemiczny in 1983.Application of 615-55-4 This article mentions the following:

Chlorinating MeCOCH₂CO₂Et (I) with SOCl₂ in C₆H₆ gave 98.1-9.9% MeCOCHClCO₂Et, which condensed with HSCH₂CH₂OH in the presence of NaHCO₃ to give the intermediate HOCH₂CH₂SCH(CO₂Et)COMe. Cyclocondensation of the latter in the presence of acid gave ester II (R = OEt), which was saponified to give 47.6-51.8% II (R = OH) (III), based on I. Treating III with SOCl₂ and then PhNH₂ and 34 other primary and secondary aromatic and heterocyclic amines yielded 21.0-98.8% II (R = substituted NH₂). The fungicidal activity of II (R = NHC₆H₄R¹; R¹ = C₁-C₅ alkoxy, F) exceeded that of II (R = NHPh). In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Application of 615-55-4).

3,4-Dibromoaniline (cas: 615-55-4) 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. 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.Application of 615-55-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Rhenium(I) complexation-dissociation strategy for synthesising fluorine-18 labelled pyridine bidentate radiotracers was written by Klenner, Mitchell A.;Zhang, Bo;Ciancaleoni, Gianluca;Howard, James K.;Maynard-Casely, Helen E.;Clegg, Jack K.;Massi, Massimiliano;Fraser, Benjamin H.;Pascali, Giancarlo. And the article was included in RSC Advances in 2020.Reference of 22426-14-8 This article mentions the following:

A novel fluorine-18 method employing rhenium(I) mediation is described herein. The method was found to afford moderate to high radiochem. yields of labeled rhenium(I) complexes. Subsequent thermal dissociation of the complexes enabled the radiosynthesis of fluorine-18 labeled pyridine bidentate structures which could not be radiofluorinated hitherto. This rhenium(I) complexation-dissociation strategy was further applied to the radiosynthesis of [¹⁸F]CABS13, an Alzheimer′s disease imaging agent, alongside other 2,2′-bipyridine, 1,10-phenanthroline and 8-hydroxyquinoline labeled radiotracers. Computational modeling of the reaction mechanism suggests that the efficiency of rhenium(I) activation may be attributed to both an electron withdrawal effect by the metal center and the formation of an acyl fluoride intermediate which anchors the fluoride subsequent to nucleophilic addition In the experiment, the researchers used many compounds, for example, 2-Bromo-1,10-phenanthroline (cas: 22426-14-8Reference of 22426-14-8).

2-Bromo-1,10-phenanthroline (cas: 22426-14-8) 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. 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.Reference of 22426-14-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes was written by Zhou, Lu;Zhu, Chuan;Bi, Peijia;Feng, Chao. And the article was included in Chemical Science in 2019.Application of 14425-64-0 This article mentions the following:

Nickel-catalyzed highly regio- and stereoselective migratory fluoro-alkenylation of unactivated alkyl bromides was reported. Catalytic cycle merged alkyl nickel chain-walking and defluorinative coupling enabled the introduction of a broad array of fluoroalkenyl moieties into carbon chains. Control experiments with other halogenated alkenes demonstrated the essential role of fluorine atoms in this reaction. The reaction proceeded under mild conditions and allowed for the synthesis of a variety of valuable monofluoroalkenes. 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–bromine 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 of 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Dehydrohalogenation of ethyl halides was written by Ahubelem, Nwakamma;Altarawneh, Mohammednoor;Dlugogorski, Bogdan Z.. And the article was included in Tetrahedron Letters in 2014.Synthetic Route of C9H11BrO This article mentions the following:

Unimol. decomposition kinetics of selected Et halides, phenethyl halides and methoxyphenethyl halides were studied using high level computational chem. methods. The phenethyl halides decompose faster than the Et halides due to a more electroneg. chlorine atom, induced by the chloroethyl functionality as an electron-withdrawing group. 1-Chloro-2-(methylthio)ethane exhibits faster dehydrochlorination than that of chloroethane/1-chloro-2-methoxyethane, owing to more polarizable C···H and C···Cl bonds in the transition structures. Calculations suggest that electronic factors rather than anchimeric assistance influence the dehydrochlorination reactions. 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. 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). 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.Synthetic Route of C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Using boronolectin in MALDI-MS imaging for the histological analysis of cancer tissue expressing the sialyl Lewis X antigen was written by Dai, Chaofeng;Cazares, Lisa H.;Wang, Lifang;Chu, Yong;Wang, Siming L.;Troyer, Dean A.;Semmes, O. John;Drake, Richard R.;Wang, Binghe. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2011.Synthetic Route of C12H16BBrO2 This article mentions the following:

Certain carbohydrate-based biomarkers are known to correlate with cancer formation and progression. By targeting sialyl Lewis X, the authors have developed the first boronolectin-MS tag conjugate, which allows for MALDI-based imaging of cancer based on its cell surface carbohydrate. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1Synthetic Route of C12H16BBrO2).

2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.Synthetic Route of C12H16BBrO2

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

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