Month: December 2022

Structure-Activity Relationship Studies of New Sinapic Acid Phenethyl Ester Analogues Targeting the Biosynthesis of 5-Lipoxygenase Products: The Role of Phenolic Moiety, Ester Function, and Bioisosterism was written by Touaibia, Mohamed;Faye, Diene Codou;Doiron, Jeremie A.;Chiasson, Audrey Isabel;Blanchard, Sebastien;Roy, Pierre-Philippe;Surette, Marc E.. And the article was included in Journal of Natural Products in 2022.Computed Properties of C9H11BrO This article mentions the following:

Sinapic acid is found in many edible plants and fruits, such as rapeseed, where it is the predominant phenolic compound New sinapic acid phenethyl ester (SAPE) analogs were synthesized and screened as inhibitors of the biosynthesis of 5-lipoxygenase (5-LO) in stimulated HEK293 cells and polymorphonuclear leukocytes (PMNL). Inhibition of leukotriene biosynthesis catalyzed by 5-LO is a validated therapeutic strategy against certain inflammatory diseases and allergies. Unfortunately, the only inhibitor approved to date has limited clin. use because of its poor pharmacokinetic profile and liver toxicity. With the new analogs synthesized in this study, the role of the phenolic moiety, ester function, and bioisosterism was investigated. Several of the 34 compounds inhibited the biosynthesis of 5-LO products, and 20 compounds were 2-11 times more potent than zileuton in PMNL, which are important producers of 5-LO products. Compounds 5i (I)(IC₅₀: 0.20 μM), 5l (II) (IC₅₀: 0.20 μM), and 5o (III)(IC₅₀: 0.21 μM) bearing 4-trifluoromethyl, Me, or methoxy substituent at meta-position of the phenethyl moiety were 1.5 and 11.5 times more potent than SAPE (IC₅₀: 0.30 μM) and zileuton (IC₅₀: 2.31 μM), resp. Addnl., compound 9 (IC₅₀: 0.27 μM), which was obtained after acetylation of the 4-hydroxyl of SAPE, was equivalent to SAPE and 8 times more active than zileuton. Furthermore, compound 20b (IV) (IC₅₀: 0.27 μM) obtained after the bioisosteric replacement of the ester function of SAPE by the 1,2,4-oxadiazole heterocycle was equivalent to SAPE and 8 times more active than zileuton. Thus, this study provides a basis for the rational design of new mols. that could be developed further as anti 5-LO therapeutics. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Computed Properties 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.Computed Properties of C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Air-Stable Pd^I Dimer Enabled Remote Functionalization: Access to Fluorinated 1,1-Diaryl Alkanes with Unprecedented Speed was written by Kundu, Gourab;Opincal, Filip;Sperger, Theresa;Schoenebeck, Franziska. And the article was included in Angewandte Chemie, International Edition in 2022.Category: bromides-buliding-blocks This article mentions the following:

This work features a remote arylation in less than 10 min reaction time at room temperature over a distance of up to 11 carbons. The unprecedented speed was enabled by the air-stable Pd^I dimer [Pd(μ-I)(PCy₂t-Bu)]₂, which in contrast to its PtBu₃ counterpart does not trigger direct coupling at the initiation site, but regioconvergent and chemoselective remote functionalization to yield valuable fluorinated 1,1-diaryl alkanes. This study combined exptl. and computational studies rationalize the origins of switchability, which were primarily due to differences in dispersion interactions. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Category: bromides-buliding-blocks).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery of Novel Pterostilbene-Based Derivatives as Potent and Orally Active NLRP3 Inflammasome Inhibitors with Inflammatory Activity for Colitis was written by Chen, Liu Zeng;Zhang, Xing Xing;Liu, Ming Ming;Wu, Jing;Ma, Duo;Diao, Liang Zhuo;Li, Qingshan;Huang, Yan Shuang;Zhang, Rui;Ruan, Ban Feng;Liu, Xin Hua. And the article was included in Journal of Medicinal Chemistry in 2021.Product Details of 4457-67-4 This article mentions the following:

Studies have shown that the abnormal activation of the NLRP3 inflammasome is involved in a variety of inflammatory-based diseases. In this study, a high content screening model targeting the activation of inflammasome was first established and pterostilbene was discovered as the active scaffold. Based on this finding, total of 50 pterostilbene derivatives were then designed and synthesized. Among them, compound 47 was found to be the best one for inhibiting cell pyroptosis [inhibitory rate (IR) = 73.09% at 10μM], showing low toxicity and high efficiency [against interleukin-1β (IL-1β): half-maximal inhibitory concentration (IC₅₀) = 0.56μM]. Further studies showed that compound 47 affected the assembly of the NLRP3 inflammasomes by targeting NLRP3. The in vivo biol. activity showed that this compound significantly alleviated dextran sodium sulfate (DSS)-induced colitis in mice. In general, our study provided a novel lead compound directly targeting the NLRP3 protein, which is worthy of further research and structural optimization. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Product Details of 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) 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.Product Details of 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tetracationic Bis-Triarylborane 1,3-Butadiyne as a Combined Fluorimetric and Raman Probe for Simultaneous and Selective Sensing of Various DNA, RNA, and Proteins was written by Amini, Hashem;Ban, Zeljka;Ferger, Matthias;Lorenzen, Sabine;Rauch, Florian;Friedrich, Alexandra;Crnolatac, Ivo;Kendel, Adriana;Miljanic, Snezana;Piantanida, Ivo;Marder, Todd B.. And the article was included in Chemistry – A European Journal in 2020.HPLC of Formula: 100189-84-2 This article mentions the following:

A bis-triarylborane tetracation (4-Ar₂B-3,5-Me₂C₆H₂)-C C-C C-(3,5-Me₂C₆H₂-4-BAr₂ [Ar = (2,6-Me₂-4-NMe₃-C₆H₂)⁺] (2⁴⁺)) shows distinctly different behavior in its fluorometric response than that of the authors′ recently published bis-triarylborane 5-(4-Ar₂B-3,5-Me₂C₆H₂)-2,2′-(C₄H₂S)₂-5′-(3,5-Me₂C₆H₂-4-BAr₂) (3⁴⁺). Single-crystal x-ray diffraction data on the neutral bis-triarylborane precursor 2 N confirm its rod-like dumbbell structure, which is important for DNA/RNA targeting and also for BSA protein binding. Fluorometric titrations with DNA/RNA/BSA revealed the very strong affinity of 2⁴⁺ and indicated the importance of the properties of the linker connecting the two triarylboranes. Using the butadiyne rather than a bithiophene linker resulted in an opposite emission effect (quenching vs. enhancement), and 2⁴⁺ bound to BSA 100 times stronger than 3⁴⁺. Moreover, 2⁴⁺ interacted strongly with ss-RNA, and CD results suggest ss-RNA chain-wrapping around the rod-like bis-triarylborane dumbbell structure like a thread around a spindle, a very unusual mode of binding of ss-RNA with small mols. Furthermore, 2⁴⁺ yielded strong Raman/SERS signals, allowing DNA or protein detection at ∼10 nM concentrations The above observations, combined with low cytotoxicity, efficient human cell uptake and organelle-selective accumulation make such compounds intriguing novel lead structures for bio-oriented, dual fluorescence/Raman-based applications. In the experiment, the researchers used many compounds, for example, 2,5-Dibromo-1,3-dimethylbenzene (cas: 100189-84-2HPLC of Formula: 100189-84-2).

2,5-Dibromo-1,3-dimethylbenzene (cas: 100189-84-2) 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. 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: 100189-84-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Molecular Recognition of Sialic Acid by Lanthanide(III) Complexes through Cooperative Two-Site Binding was written by Regueiro-Figueroa, Martin;Djanashvili, Kristina;Esteban-Gomez, David;Chauvin, Thomas;Toth, Eva;de Blas, Andres;Rodriguez-Blas, Teresa;Platas-Iglesias, Carlos. And the article was included in Inorganic Chemistry in 2010.Recommanded Product: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane This article mentions the following:

Herein the authors report two new ligands, 1,4,7-tris(carboxymethyl)-10-[2-(dihydroxyboranyl)benzyl]-1,4,7,10-tetraazacyclododecane (L¹) and 1,4,7-tris(carboxymethyl)-10-[3-(dihydroxyboranyl)benzyl]-1,4,7,10-tetraazacyclododecane (L²), which contain a phenylboronic acid (PBA) function and a 1,4,7,10-tetraazacyclododecane-1,4,7-triacetate cage for complexation of lanthanide ions in an aqueous solution The pK_a of the PBA function amounts to 4.6 in [Gd(L¹)] and 8.9 in [Gd(L²)], with the value of the L² analog being very similar to that of PBA (8.8). These results are explained by the coordination of the PBA function of L¹ to the Gd^III ion, which results in a dramatic lowering of its pK_a. As a consequence, [Gd(L¹)] does not bind to saccharides at physiol. pH. The nuclear magnetic relaxation dispersion profiles recorded for [Gd(L¹)] and [Gd(L²)] confirm that the phenylboronate function is coordinated to the metal ion in the L¹ derivative, which results in a q = 0 complex. The interaction of the [Gd(L²)] complex with 5-acetylneuraminic acid (Neu5Ac) and 2-α-O-methyl-5-acetylneuraminic acid (MeNeu5Ac) was studied by spectrophotometric titrations in an aqueous solution (pH 7.4, 0.1M 3-(N-morpholino)propanesulfonic acid buffer). Also, the authors have also studied the binding of these receptors with competing monosaccharides such as D-(+)-glucose, D-fructose, D-mannose, D-galactose, Me α-D-galactoside, and Me α-D-mannoside. The binding constants obtained indicate an important selectivity of [Gd(L²)] for Neu5Ac (K_eq = 151) over D-(+)-glucose (K_eq = 12.3), D-mannose (K_eq = 21.9), and D-galactose (K_eq = 24.5). Also, a very weak binding affinity was observed in the case of Me α-D-galactoside and Me α-D-mannoside. An 8-fold increase of the binding constant of [Gd(L²)] with Neu5Ac is observed when compared to that of PBA determined under the same conditions (K_eq = 19). ¹³C NMR spectroscopy and d. functional theory calculations performed at the B3LYP/6-31G(d) level show that this is due to a cooperative two-site binding of Neu5Ac through (1) ester formation by interaction on the PBA function of the receptor and (2) coordination of the carboxylate group of Neu5Ac to the Gd^III ion. The emission lifetime of the ⁵D₄ level of Tb^III in [Tb(L²)] increases upon Neu5Ac binding, in line with the displacement of inner-sphere water mols. due to coordination of Neu5Ac to the metal ion. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1Recommanded Product: 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. 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. 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.Recommanded Product: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Arenesulfonyl Fluoride Synthesis via Copper-Catalyzed Fluorosulfonylation of Arenediazonium Salts was written by Liu, Yongan;Yu, Donghai;Guo, Yong;Xiao, Ji-Chang;Chen, Qing-Yun;Liu, Chao. And the article was included in Organic Letters in 2020.Application of 454-65-9 This article mentions the following:

We report herein a general and practical copper-catalyzed fluorosulfonylation reaction of a wide range of abundant arenediazonium salts to smoothly prepare various arenesulfonyl fluorides using the 1,4-diazabicyclo[2.2.2]octane-bis(sulfur dioxide) adduct as a convenient sulfonyl source in combination with KHF₂ as an ideal fluorine source and without the need for addnl. oxidants. Interestingly, the electronic character of the arene ring in the starting arenediazonium salts has a significant impact on the reaction mechanistic pathway. In the experiment, the researchers used many compounds, for example, 3-Bromobenzene-1-sulfonyl fluoride (cas: 454-65-9Application of 454-65-9).

3-Bromobenzene-1-sulfonyl fluoride (cas: 454-65-9) 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. 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 454-65-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Optimum difunctionality in a 2-(2-pyridyl-2-ol)-1,10-phenanthroline based ruthenium complex for transfer hydrogenation of ketones and nitriles: impact of the number of 2-hydroxypyridine fragments was written by Paul, Bhaskar;Chakrabarti, Kaushik;Kundu, Sabuj. And the article was included in Dalton Transactions in 2016.Related Products of 22426-14-8 This article mentions the following:

Considerable differences in reactivity and selectivity for 2-hydroxypyridine (2-HP) derived ruthenium complexes in transfer hydrogenation are described. Bifunctional Ru(II)-(phenpy-OH) [phenpy-OH: 2-(2-pyridyl-2-ol)-1,10-phenanthroline] complex (I: 2) exhibited excellent catalytic activity in transfer hydrogenation (TH) of ketones and nitriles. Notably, in comparison with all the reported 2-hydroxypyridine (2-HP) derived ruthenium complexes in transfer hydrogenation, complex 2 displayed significantly higher activity. Addnl., exploiting the metal-ligand cooperativity in complex 2, chemoselective TH of ketones was achieved and sterically demanding ketones were readily reduced. An outer-sphere mechanism is proposed for this system as exogenous PPh₃ has no significant effect on the rate of this reaction. This is a rare example of a highly active bifunctional Ru(II) catalyst bearing only one 2-HP unit. In the experiment, the researchers used many compounds, for example, 2-Bromo-1,10-phenanthroline (cas: 22426-14-8Related Products of 22426-14-8).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Silver-Mediated Trifluoromethoxylation of (Hetero)aryldiazonium Tetrafluoroborates was written by Yang, Yu-Ming;Yao, Jian-Fei;Yan, Wei;Luo, Zhuangzhu;Tang, Zhen-Yu. And the article was included in Organic Letters in 2019.Formula: C6H5BrClN This article mentions the following:

Here we report a silver-mediated trifluoromethoxylation of (hetero)aryldiazonium tetrafluoroborates by converting an aromatic amino group into an OCF₃ group. This method, which can be considered to be a trifluoromethoxylation variation of the classic Sandmeyer-type reaction, uses readily available aryl and heteroaromatic amines as starting materials and AgOCF₃ as trifluoromethoxylating reagents. The broad substrate scope and simple, mild reaction condition made this transformation a valuable method in constructing aryl-OCF₃ bonds. In the experiment, the researchers used many compounds, for example, 3-Bromo-5-chlorophenylamine (cas: 96558-78-0Formula: C6H5BrClN).

3-Bromo-5-chlorophenylamine (cas: 96558-78-0) 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.Formula: C6H5BrClN

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Ortho effect in hydrolysis of phenyl esters was written by Nishioka, Takaaki;Fujita, Toshio;Kitamura, Koji;Nakajima, Minoru. And the article was included in Journal of Organic Chemistry in 1975.Recommanded Product: 35065-86-2 This article mentions the following:

The kinetics of the alk. hydrolysis of substituted phenyl esters of acetic acid, N,N-dimethylcarbamic acid, di-Et phosphate, and N-methylcarbamic acid were studied using uv spectroscopy. The logarithmic value of the second-order rate constant was correlated using log k = ρσo,m,p + δEs + fF + c, where Es and F are the Taft-Kutter-Hansch steric and the Swain-Lupton-Hansch field effect constants of ortho substituents, resp. By means of the resp. susceptibility constants, ρ δ, and f, the role of ortho substituents in the hydrolysis reaction course was analyzed quant. In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2Recommanded Product: 35065-86-2).

3-Bromophenyl acetate (cas: 35065-86-2) 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. 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.Recommanded Product: 35065-86-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Investigation of the Adsorption of Gaseous Aromatic Compounds at Surfaces Coated with Heptakis(6-thio-6-deoxy)-β-cyclodextrin by Surface-Enhanced Raman Scattering was written by Hill, Wieland;Fallourd, Valerie;Klockow, Dieter. And the article was included in Journal of Physical Chemistry B in 1999.Application of 53784-83-1 This article mentions the following:

Heptakis(6-thio-6-deoxy)-β-cyclodextrin (TCD) was prepared and chemisorbed at the surface of rough silver substrates for surface-enhanced Raman scattering (SERS). The enhanced adsorption of methyl orange and the stability of its azo form at the TCD-coated substrates proved the capability of the immobilized TCD to form inclusion complexes with organic guest mols. This complexation was used for the detection of aromatics in the gas phase. Toluene, ethylbenzene, m-xylene, chlorobenzene, and m-dichlorobenzene were strongly adsorbed at the TCD-coated substrates, thus making possible the detection of low concentrations, as for example 15 ppm of m-dichlorobenzene. Benzene was weakly adsorbed and detectable in high concentrations only. Since the strongly adsorbed aromatics desorb very slowly, TCD-coated substrates may be applicable for the detection of slowly changing concentrations or as integrating sensors in the surveillance of chem. exposures. The capability of immobilized TCD to adsorb also polycyclic aromatic hydrocarbons was demonstrated using naphthalene. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Application of 53784-83-1).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) 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 53784-83-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary