Month: January 2023

Structure-activity relationship studies of acridones as potential antipsoriatic agents. 2. Synthesis and antiproliferative activity of 10-substituted hydroxy-10H-acridin-9-ones against human keratinocyte growth was written by Putic, Aleksandar;Stecher, Lambert;Prinz, Helge;Mueller, Klaus. And the article was included in European Journal of Medicinal Chemistry in 2010.COA of Formula: C9H11BrO This article mentions the following:

A series of 10-substituted hydroxy-10H-acridin-9-ones were synthesized and studied as potential antipsoriatic agents. The antiproliferative activity of the novel derivatives, which can be considered as aza-analogs of the antipsoriatic drug anthralin, was determined using the human keratinocyte cell line HaCaT. Structure-activity relationships with respect to the nature of the N-substituent at the acridone scaffold were delineated. Release of lactate dehydrogenase (LDH) was used to exclude non-specific cytotoxic effects. As compared to anthralin, N-substitution of the acridone scaffold in the target compounds provided agents devoid of radical producing properties, which was documented by their ineffectiveness to interact with the free radical 2,2-diphenyl-1-picrylhydrazyl. This was in excellent agreement with the data obtained from the LDH assay in which the novel compounds did not induce membrane damage. Benzyl substitution at the 10-position yielded keratinocyte growth inhibitory activity in the low micromolar range. The most potent inhibitor of keratinocyte hyperproliferation was I having an N-Me group and a 1,3-dihydroxy arrangement at the acridone scaffold, with an IC₅₀ value comparable to that of anthralin. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0COA of Formula: 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.COA of Formula: C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Target-Selective Fluorescence Imaging and Photocytotoxicity against H₂O₂ High-Expressing Cancer Cells Using a Photoactivatable Theranostic Agent was written by Takagi, Ryoma;Takeda, Ayano;Takahashi, Daisuke;Toshima, Kazunobu. And the article was included in Chemistry – An Asian Journal in 2017.Synthetic Route of C7H7BrO2 This article mentions the following:

A purpose-designed and synthesized H₂O₂-reactive and photoactivatable theranostic agent I consisting of 1) an arylboronic acid moiety, 2) pro-fluorophore moiety, and 3) photoactivatable moiety (photosensitizer), selectively and effectively reacted with H₂O₂ while simultaneously releasing resorufin for fluorescence detection under neutral aqueous conditions. In addition, I was cell-permeable, and exhibited effective photocytotoxicity against fluorescently visualized cells only upon photoirradiation The results also showed that I produced a selective fluorescence response to H₂O₂, even in living cultured cells. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-(hydroxymethyl)phenol (cas: 170434-11-4Synthetic Route of C7H7BrO2).

5-Bromo-2-(hydroxymethyl)phenol (cas: 170434-11-4) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Synthetic Route of C7H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of a series of brominated 1-phenyl-2-pyridylethenes as inhibitors of the protein-tyrosine kinase p56^lck was written by He, Hu-Ming;Geahlen, Robert L.;Cushman, Mark. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1994.Product Details of 108940-96-1 This article mentions the following:

A series of brominated 1-phenyl-2-pyridylethenes was prepared and tested for inhibition of p56^lck, a protein-tyrosine kinase of the src family which is overexpressed in several lymphomas. The most potent compound of the series proved to be 2-(3,5-dibromo-4-hydroxybenzylidene)-2-(2-pyridyl)acetonitrile. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Product Details of 108940-96-1).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Product Details of 108940-96-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mild conversion of β-diketone and β-ketoesters to carboxylic acids was written by Zhang, Yang;Jiao, Jingliang;Flowers, Robert A. II. And the article was included in Journal of Organic Chemistry in 2006.Recommanded Product: 1-Bromo-6-methoxyhexane This article mentions the following:

A mild protocol for the conversion of β-ketoesters and β-diketone to carboxylic acids with use of CAN in CH₃CN was described. The method was compatible with a number of functional groups, and could generate carboxylic acids under neutral conditions at room temperature The reaction was fast and general, providing an alternative method to the commonly used malonic ester acid preparation Initial mechanistic studies showed that initial oxidation of the enol form of the β-dicarbonyl initiated the reaction. The presence of nitrate as an oxidant ligand or as an additive was critical for success of the reaction. In the experiment, the researchers used many compounds, for example, 1-Bromo-6-methoxyhexane (cas: 50592-87-5Recommanded Product: 1-Bromo-6-methoxyhexane).

1-Bromo-6-methoxyhexane (cas: 50592-87-5) 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.Recommanded Product: 1-Bromo-6-methoxyhexane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Toward Optimization of the Linker Substructure Common to Transthyretin Amyloidogenesis Inhibitors Using Biochemical and Structural Studies was written by Johnson, Steven M.;Connelly, Stephen;Wilson, Ian A.;Kelly, Jeffery W.. And the article was included in Journal of Medicinal Chemistry in 2008.Computed Properties of C8H6Br2O2 This article mentions the following:

To develop potent and highly selective transthyretin (TTR) amyloidogenesis inhibitors, it is useful to systematically optimize the three substructural elements that compose a typical TTR kinetic stabilizer: the two aryl rings and the linker joining them. Herein, the authors evaluated 40 bisaryl mols. based on 10 unique linker substructures to determine how these linkages influence inhibitor potency and selectivity. These linkers connect one unsubstituted aromatic ring to either a 3,5-X₂ or a 3,5-X₂-4-OH Ph substructure (X = Br or CH₃). Consideration of amyloid inhibition and ex vivo plasma TTR binding selectivity data reveal that direct connection of the two aryls or linkage through nonpolar E-olefin or -CH₂CH₂– substructures generates the most potent and selective TTR amyloidogenesis inhibitors exhibiting minimal undesirable binding to the thyroid hormone nuclear receptor or the COX-1 enzyme. Five high-resolution TTR·inhibitor crystal structures (1.4-1.8 Å) provide insight into why such linkers afford inhibitors with greater potency and selectivity. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Computed Properties of C8H6Br2O2).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) 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.Computed Properties of C8H6Br2O2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Carbonylative Suzuki-Miyaura couplings of sterically hindered aryl halides: synthesis of 2-aroylbenzoate derivatives was written by Ismael, Aya;Skrydstrup, Troels;Bayer, Annette. And the article was included in Organic & Biomolecular Chemistry in 2020.HPLC of Formula: 653-92-9 This article mentions the following:

A carbonylative approach to the synthesis of diversely substituted 2-aroylbenzoate esters ArC(O)R¹ (Ar = 2-methoxyphenyl, thiophen-2-yl, 2-naphthyl, etc.; R¹ = 2-methoxycarbonyl-6-methylphenyl, 2-methoxycarbonylphenyl, 2-methoxycarbonyl-4,5-dimethoxyphenyl, etc.) featuring a new protocol for the carbonylative coupling of aryl bromides R¹Br with boronic acids ArB(OH)₂ and a new strategy to favor carbonylative over non-carbonylative reactions were developed. Two different synthetic pathways – (i) the alkoxycarbonylation of 2-bromo benzophenones R²C₆H₄C(O)(2-BrC₆H₅) (R² = 2-F, 4-F, 3-OMe, 4-OMe) and (ii) the carbonylative Suzuki-Miyaura coupling of 2-bromobenzoate esters – were evaluated. The latter approach provided a broader substrate tolerance, and thus it was the preferred pathway. Here observed that 2-substituted aryl bromides were challenging substrates for carbonylative chem. favoring the non-carbonylative pathway. However, it is found that carbonylative Suzuki-Miyaura couplings can be improved by slow addition of the boronic acid, suppressing the unwanted direct Suzuki coupling and, thus increasing the yield of the carbonylative reaction. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9HPLC of Formula: 653-92-9).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) 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.HPLC of Formula: 653-92-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Fluorescence sensing of a ribonucleoside 5′-triphosphate was written by Patterson, Steven;Smith, Bradley D.;Taylor, Richard E.. And the article was included in Tetrahedron Letters in 1997.Name: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane This article mentions the following:

Conjugation of a fluorescent saccharide sensor to poly(allylamine) produces a sensing compound with selectivity for ribonucleoside 5′-triphosphate. An association constant (log K_a) of 5.6 was determined for UTP in pH 7.3 phosphate solution (15 mM, 298 K), whereas log K_a was less than 2 for uridine, UMP, and UDP. 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. 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. 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.Name: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of the four stereoisomers of 22,23-dimethylcholesterol was written by Gebreyesus, Tarekegn;Djerassi, Carl. And the article was included in Journal of Organic Chemistry in 1985.SDS of cas: 28322-40-9 This article mentions the following:

The 4 diastereoisomers of 22,23-dimethylcholesterol I were prepared from cyclodinorcholanal II and characterized by NMR spectroscopy and HPLC. Thus, Grignard reaction of Me iodide with II and subsequent Jones oxidation gave cyclonorcholenone III (Z = O), which underwent Wittig condensation with Me₂CHCH₂CH₂P⁺Ph₃ Br^– to give III (Z = Me₂CHCH₂CH:). Hydroboration-oxidation of the latter and then Jones oxidation gave methylcyclocholestanones IV (Z¹ = O), which underwent Wittig reaction with MeP⁺Ph₃ Br^– to give IV (Z¹ = CH₂🙂 (V). Hydrogenation of (22R)-V and subsequent hydrolysis gave (22S,23R)- and (22S,23S)-I. Hydroboration-oxidation of (22S)-V gave diastereoisomeric IV (Z¹ = H, HOCH₂), which underwent successive mesylation, LiAlH₄ reduction, and hydrolysis to give (22R,23R)- and (22R,23S)-I. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9SDS of cas: 28322-40-9).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) 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.SDS of cas: 28322-40-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

TCDA: Practical Synthesis and Application in the Trifluoromethylation of Arenes and Heteroarenes was written by Wang, Jian;Zhang, Xiaomin;Wan, Zehong;Ren, Feng. And the article was included in Organic Process Research & Development in 2016.SDS of cas: 4457-67-4 This article mentions the following:

A practical synthesis of the reagent trimethylsilyl chlorodifluoroacetate (TCDA) is reported on a 50 g scale. The trifluoromethylation with TCDA was optimized, and the reaction shows very broad scope with respect to electron-deficient, -neutral, -rich aryl/heteroaryl iodides, as well as excellent functional group tolerability, such as ester, amide, aldehyde, hydroxyl, and carboxylic acid. The reagent was also applied to the late-stage trifluoromethylation of three medicinally relevant compounds Addnl., the building block trifluoromethylpyridine and one drug related mol. Boc-Fluoxetin were synthesized in 10 g scale by this method, demonstrating its practical applications in process chem. 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. 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.SDS of cas: 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Coupling N-H Deprotonation, C-H Activation, and Oxidation: Metal-Free C(sp³)-H Aminations with Unprotected Anilines was written by Evoniuk, Christopher J.;Gomes, Gabriel dos Passos;Hill, Sean P.;Fujita, Satoshi;Hanson, Kenneth;Alabugin, Igor V.. And the article was included in Journal of the American Chemical Society in 2017.Related Products of 14425-64-0 This article mentions the following:

An intramol. oxidative C(sp³)-H amination from unprotected anilines and C(sp³)-H bonds readily occurs under mild conditions using t-BuOK, mol. oxygen and N,N-dimethylformamide (DMF). Success of this process, which requires mildly acidic N-H bonds and an activated C(sp³)-H bond (BDE < 85 kcal/mol), stems from synergy between basic, radical, and oxidizing species working together to promote a coordinated sequence of deprotonation: H atom transfer and oxidation that forges a new C-N bond. This process is applicable for the synthesis of a wide variety of N-heterocycles, ranging from small mols. to extended aromatics without the need for transition metals or strong oxidants. Computational results reveal the mechanistic details and energy landscape for the sequence of individual steps that comprise this reaction cascade. The importance of base in this process stems from the much greater acidity of transition state and product for the 2c,3e C-N bond formation relative to the reactant. In this scenario, selective deprotonation provides the driving force for the process. 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–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.Related Products of 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary