Month: February 2023

Design, synthesis and structure-activity relationships of novel biarylamine-based Met kinase inhibitors was written by Williams, David K.;Chen, Xiao-Tao;Tarby, Christine;Kaltenbach, Robert;Cai, Zhen-Wei;Tokarski, John S.;An, Yongmi;Sack, John S.;Wautlet, Barri;Gullo-Brown, Johnni;Henley, Benjamin J.;Jeyaseelan, Robert;Kellar, Kristen;Manne, Veeraswamy;Trainor, George L.;Lombardo, Louis J.;Fargnoli, Joseph;Borzilleri, Robert M.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Reference of 29241-66-5 This article mentions the following:

Aminopyridinyloxy- or azaindolyloxy phenylamino heteroarylcarboxamides such as I are prepared and tested for their inhibition of Met kinase and for their inhibition of a human gastric cancer cell line. X-ray crystallog. of an aminopyridinyloxyphenylamino pyridinecarboxamide bound to Met kinase reveals that these compounds adopt a bioactive conformation, in the kinase domain, consistent with that seen for a 2-pyridone-based Met kinase inhibitor. I demonstrated potent in vivo antitumor activity in the GTL-16 human tumor xenograft model; its selectivity against various kinases is determined In the experiment, the researchers used many compounds, for example, 5-Bromo-2-fluoronicotinic acid (cas: 29241-66-5Reference of 29241-66-5).

5-Bromo-2-fluoronicotinic acid (cas: 29241-66-5) 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 principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Reference of 29241-66-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Substituted caffeic and ferulic acid phenethyl esters: synthesis, leukotrienes biosynthesis inhibition and cytotoxic activity was written by Morin, Pier Jr.;St-Coeur, Patrick-Denis;Doiron, Jeremie A.;Cormier, Marc;Poitras, Julie J.;Surette, Marc E.;Touaibia, Mohamed. And the article was included in Molecules in 2017.Electric Literature of C9H11BrO This article mentions the following:

A series of caffeic and ferulic acid esters bearing addnl. oxygens moieties (OH or OCH₃) were designed and synthesized. Polyphenolic compounds, including caffeic acid phenethyl ester (CAPE) was investigated for their anticancer properties in several types of cancer while ferulic acid phenethyl ester (FAPE) displayed substantial cytotoxicity against two glioma cell lines. Some selected compounds derived from both (CAPE) and (FAPE) also displayed cytotoxicity. All CAPE-derived compounds were able to significantly inhibit 5-lipoxygenase (5-LO), however FAPE-derived compounds were largely ineffective 5-LO inhibitors. Mol. docking revealed new hydrogen bonds and π-π interactions between the enzyme and some of the investigated compounds Overall, this work highlighted the relevance of exploring polyphenolic compounds in cancer models and provides addnl. led in the development of novel therapeutic strategies in gliomas. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Electric Literature 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. 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.Electric Literature of C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Condensation of tertiary aliphatic alcohols with aromatic compounds in the presence of aluminum chloride. IV. Tertiary dimethylamylcarbinols with phenol was written by Huston, R. C.;Guile, R. L.. And the article was included in Journal of the American Chemical Society in 1939.SDS of cas: 35065-86-2 This article mentions the following:

The Grignard reagent from 2-methyl-3-bromobutane with AcCl gives 9.3% of 3,4-dimethylpentan-2-one, b₇₄₄ 135-40°; with MeI this yields 58% of 2,3,4-trimethylpentan-2-ol, b₇₅₂ 155-7°, n_D¹³ 1.4400, d₂₀²⁰ 0.8095, γ²⁰ 27.48 dynes. Condensations were carried out by adding dropwise (2 h.) 32 g. of the alc. and 28 g. PhOH in 100 cc. petr. ether to 17 g. AlCl₃ in petr. ether at 25-30° and after standing overnight decomposing with dilute HCl. The following compounds were thus prepared: 2-methyl-2-p-hydroxyphenylheptane (I), b₂ 114-17°, b₇₄₁ 293.5°, d₂₀²⁰ 0.95053, n_D¹⁶ 1.5102, γ²⁸ 32.31, 69.5% yield; 2,3-dimethyl-2-p-hydroxyphenylhexane (II), b₂ 111-14°, b₇₄₁ 293°, d. 0.96836, n 1.5191, γ 33.74, 35.5%; 2,4-di-Me isomer (III), b₂ 113-16°, b₇₄₁ 290.5°, d. 0.95427, n 1.5121, γ 32.00, 58.5%; 2,5-di-Me isomer (IV), b₂ 105-7°, b₇₄₁ 288°, d. 0.95183, n 1.5110, γ 31.69, 64.6%; 2-methyl-3-ethyl-2-p-hydroxyphenylpentane (V), b₂ 109-11°, b₇₄₁ 293°, d. 0.96845, n 1.5190, γ 33.80, 28.3%; 2,4,4-tri-Me isomer (VI), b₇₄₁ 289°, m. 83°, 64.6%; 2,3,4-tri-Me isomer (VII), m. 74°, 23.1% yield; 2,3,3-tri-Me isomer, b₇₄₁ 325° (decomposition), m. 160°, 2.1%. Bz esters; I m. 27-23° (?), II m. 54.2-5.2°, III m. 37-8°, IV m. 46-7°, V m. 69-70°, VI m. 73-4°, VII m. 47-8°. α-Naphthylurethanes: I m. 120-1°, II m. 105-5.5°, III m. 119.5-20.5°, IV m. 132.5-33.5°, V m. 109.5-10.5°, VI m. 102-3°, VII m. 114.5-15.5°. p-Nitro- and p-amino-tert-octylbenzenes were prepared in establishing the structures of I-VI; 2-methyl-2-p-nitrophenylheptane, b₂ 148-50°; p-NH₂ derivative, b₂ 108-11°; 2,3-dimethyl-2-p-nitrophenylhexane, b₂ 133-5°; 2,4-di-Me isomer, b₂ 135-7°; 2,5-di-Me isomer, b₂ 129-31°; the corresponding p-NH₂ derivatives b₄ 115-19°, b₂ 99-101° and b₂ 99-102°; 2-methyl-3-ethyl-2-p-nitrophenylpentane, b₄ 127-30°; 2,4,-4-tri-Me isomer, b₄ 108-10°; the corresponding p-NH₂ derivatives b₂ 103-6° and b₅ 112-15°. In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2SDS of cas: 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. 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: 35065-86-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

An improved preparation of (S)-N-(Boc)-cyclohexylalaninal. The Moffat-Swern oxidation of α-amino alcohols was written by Krysan, D. J.;Haight, A. R.;Lallaman, J. E.;Langridge, D. C.;Menzia, J. A.;Narayanan, B. A.;Pariza, R. J.;Reno, D. S.;Rockway, T. W.. And the article was included in Organic Preparations and Procedures International in 1993.Formula: C23H26BrP This article mentions the following:

Moffat-Swern oxidation of protected alc. (S)-BocNHCH(CH₂R)CH₂OH (I; Boc = Me₃CO₂C; R = cyclohexyl) with DMSO/(COCl)₂/EtN(CHMe₂)₂ or DMSO/pyridine-SO₃/Et₃N gave the title compound (S)-BocNHCH(CH₂R)CHO (II) in >95% enantiomeric excess. The chem. efficiency of this oxidation os demonstrated in the 2-step conversion of I to (S,Z)-BocNHCH(CH₂R)CH:CHCH₂CHMe₂ in 60% yield via subsequent olefination of intermediate II with Ph₂P⁺CH₂CH₂CHMe₂ Br^–. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Formula: C23H26BrP).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) 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. 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: C23H26BrP

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Deoxofluorination of (Hetero)aromatic Acids was written by Trofymchuk, Serhii;Bugera, Maksym Ya.;Klipkov, Anton A.;Razhyk, Bohdan;Semenov, Sergey;Tarasenko, Karen;Starova, Viktoriia S.;Zaporozhets, Olga A.;Tananaiko, Oksana Yu.;Alekseenko, Anatoliy N.;Pustovit, Yurii;Kiriakov, Oleksandr;Gerus, Igor I.;Tolmachev, Andrei A.;Mykhailiuk, Pavel K.. And the article was included in Journal of Organic Chemistry in 2020.Reference of 29241-66-5 This article mentions the following:

Diverse trifluoromethyl-substituted compounds were synthesized by deoxofluorination of cinnamic and (hetero)aromatic carboxylic acids with sulfur tetrafluoride. The obtained products were used as starting materials in the preparation of novel fluorinated amino acids, anilines, and aliphatic amines – valuable building blocks for medicinal chem. and agrochem. Of note, sulfur tetrafluoride (SF4) and hydrogen fluoride (HF) are toxic, therefore, safety and addnl. tech. training must be taken before working with them. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-fluoronicotinic acid (cas: 29241-66-5Reference of 29241-66-5).

5-Bromo-2-fluoronicotinic acid (cas: 29241-66-5) 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. 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.Reference of 29241-66-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tetrasubstituted naphthalene diimide ligands with selectivity for telomeric G-quadruplexes and cancer cells was written by Hampel, Sonja M.;Sidibe, Assitan;Gunaratnam, Mekala;Riou, Jean-Francois;Neidle, Stephen. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.COA of Formula: C13H14BrNO2 This article mentions the following:

A series of tetrasubstituted naphthalene diimide compounds I (n = 2-4) with N-methylpiperazine end groups has been synthesized and evaluated as G-quadruplex ligands. They have high affinity and selectivity for telomeric G-quadruplex DNA over duplex DNA. CD studies show that they induce formation of a parallel G-quadruplex topol. They inhibit the binding of hPOT1 and topoisomerase IIIα to telomeric DNA and inhibit telomerase activity in MCF7 cells. I has potent activity in a panel of cancer cell lines, with typical IC₅₀ values of âˆ?.1 μM, and up to 100-fold lower toxicity in a normal human fibroblast cell line. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4COA of Formula: 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. 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.COA of Formula: C13H14BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Constructing Soluble Anthracene-Based Blue Emitters Free of Electrically Inert Alkyl Chains for Efficient Evaporation- and Solution-Based OLEDs was written by Noda, Taito;Sasabe, Hisahiro;Owada, Tsukasa;Sugiyama, Ryo;Arai, Ayato;Kumada, Kengo;Tsuneyama, Hisaki;Saito, Yu;Kido, Junji. And the article was included in ChemPlusChem in 2022.Application of 128-08-5 This article mentions the following:

Anthracene derivatives are one of the most promising blue emitters employed in organic light-emitting devices (OLEDs) because of their electrochem. and thermal stabilities. However, their high crystallinity owing to their large π-planar structures severely impedes the progress in the development of solution-based systems. In this work, we developed two types of highly soluble multifunctional anthracene derivatives terminated with ortho-biphenyl and triphenylamine moieties and showed high solubility in general organic solvents such as toluene, THF, and cyclohexanone at high concentrations (>10 mg mL-1), and showed blue emission with a peak wavelength of âˆ?65 nm and a high photoluminescence quantum yield that ranges up to 81 %. Notably, these emitters are suitable for fabricating both evaporation- and solution-based systems. The evaporation-based system OLED achieved a high external quantum efficiency (EQE) of 5.4 %. While the solution-processed system realized 4.8 %, exhibiting the best performance among the anthracene-based solution-processed OLEDs so far. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Application of 128-08-5).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) 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. 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.Application of 128-08-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Structure-Activity Relationship Studies and Molecular Modeling of Naphthalene-Based Sphingosine Kinase 2 Inhibitors was written by Congdon, Molly D.;Kharel, Yugesh;Brown, Anne M.;Lewis, Stephanie N.;Bevan, David R.;Lynch, Kevin R.;Santos, Webster L.. And the article was included in ACS Medicinal Chemistry Letters in 2016.Name: 1-Bromo-4-methoxybutane This article mentions the following:

The two isoforms of sphingosine kinase (SphK1 and SphK2) are the only enzymes that phosphorylate sphingosine to sphingosine-1-phosphate (S1P), which is a pleiotropic lipid mediator involved in a broad range of cellular processes including migration, proliferation, and inflammation. SphKs are targets for various diseases such as cancer, fibrosis, and Alzheimer’s and sickle cell disease. Herein, the authors disclose the structure-activity profile of naphthalene-containing SphK inhibitors, e.g. I, and mol. modeling studies that reveal a key mol. switch that controls SphK selectivity. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Name: 1-Bromo-4-methoxybutane).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Glycerol-Based Bicontinuous Cubic Lyotropic Liquid Crystal Monomer System for the Fabrication of Thin-Film Membranes with Uniform Nanopores was written by Carter, Blaine M.;Wiesenauer, Brian R.;Hatakeyama, Evan S.;Barton, John L.;Noble, Richard D.;Gin, Douglas L.. And the article was included in Chemistry of Materials in 2012.Formula: C15H29BrO2 This article mentions the following:

This article present a new imidazolium-based gemini Lyotropic liquid crystal (LLC) monomer that forms a cross-linkable Q₁-phase with the low volatility and environmentally benign solvent, glycerol, instead of water. In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Formula: C15H29BrO2).

15-Bromopentadecanoic acid (cas: 56523-59-2) 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. 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.Formula: C15H29BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Analytical chemistry of the platinum metals. VIII. Application of phosphonium and arsonium salts to the gravimetric determination of osmium was written by Neeb, R.. And the article was included in Fresenius’ Zeitschrift fuer Analytische Chemie in 1960.Electric Literature of C23H26BrP This article mentions the following:

Solubility determinations are reported of halo-osmates of substituted phosphonium and arsonium compounds, and several are investigated for determining Os. Those recommended are tetraphenylarsonium chloride and benzyltriphenylphosphonium chloride in HCl solution, and tetraphenylarsonium and tetraphenylphosphonium chlorides in HBr solution In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Electric Literature of C23H26BrP).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) 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.Electric Literature of C23H26BrP

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary