Tag: 200-300

Photochemical Synthesis of Phenanthridines: Exploring Fluoro and Protected Catechol Substitution was written by Linsenmeier, Anna M.;Williams, Craig M.;Brase, Stefan. And the article was included in European Journal of Organic Chemistry in 2013.Formula: C7H5Br2F This article mentions the following:

Substituted phenanthridines, such as the natural product trispheridine, have been accessed by the practical photochem. cyclization of N-benzylanilines. Functionalities, with a focus on fluoro substituents and protected catechols, are well tolerated on both the A and C rings. The phenanthridines were accessed in good to very good yields (up to 95 %) from iodinated substrates, whereas brominated substrates performed poorly in comparison (0-48 %). In the experiment, the researchers used many compounds, for example, 2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0Formula: C7H5Br2F).

2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0) 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. 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.Formula: C7H5Br2F

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Investigation on the synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones and their biological evaluation against cancer cells was written by Dago, Camille Deliko;Ambeu, Christelle N’ta;Coulibaly, Wacothon Karime;Bekro, Yves-Alain;Mamyrbekova-Bekro, Janat A.;Le Guevel, Remy;Corlu, Anne;Bazureau, Jean-Pierre. And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2017.Synthetic Route of C9H11BrO This article mentions the following:

The 5-step synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones I [X = (CH₂)_n; R = OMe, n = 2; R = H, n = 2; R = OMe, n = 1] without 5-arylidene fragments starting from tyramine was described. The construction involved protection with Boc₂O, regioselective O-alkylation, deprotection with 6 M HCl, neutralization, and finally reaction of bis(carboxymethyl)trithiocarbonate under microwave irradiation The intermediates and the N-substituted rhodanine have been also evaluated for their in vitro inhibition of cell proliferation (Huh7, Caco 2, MDA-MB231, HCT 116, PC3, NCI-H727, HaCat). Two compounds have shown a selective potent activity against HCT116 cell line. 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. 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. 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.Synthetic Route of C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The effect of catalyst granule size on the hydrogenation of benzene over a supported nickel catalyst was written by Burke, R. F.;Motard, R. L.;Canjar, L. N.;Beckmann, R. B.. And the article was included in Journal of Applied Chemistry in 1957.Electric Literature of C10H13BrO This article mentions the following:

For the hydrogenation of C₆H₆ to C₆H₁₂ over Ni on silica gel at 225-275° and 6.44-3.74 atm., the velocity constant was proportional to the particle size of the catalyst down to 80-100 mesh, beyond which it did not increase. The active Ni content was the same for all particle-size fractions of the catalyst. It was thought that the catalyst activity increased with decreasing particle size because the active sites in the pores of the larger particles were blocked by C₆H₆ condensation and that the catalyst activity leveled off after the particles had been sufficiently subdivided so that all the active Ni was on the surface of the particles. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Electric Literature of C10H13BrO).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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.Electric Literature of C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A cyanide-catalyzed imino-Stetter reaction enables the concise total syntheses of rucaparib was written by Park, Jinjae;Cheon, Cheol-Hong. And the article was included in RSC Advances in 2022.Synthetic Route of C9H7BrFNO4 This article mentions the following:

Two routes toward the synthesis of rucaparib, an FDA-approved drug used for the treatment of ovarian and prostate cancers, have been developed from com. available starting materials utilizing the cyanide-catalyzed imino-Stetter reaction as the key step for the construction of the indole motif bearing all the desired substituents in their correct positions. In the first-generation synthesis, meta-fluorobenzoate, the starting material currently used in the process chem. route of rucaparib, was converted into 4,6-disubstituted 2-aminocinnamic acid derivatives (ester or amide). The cyanide-catalyzed imino-Stetter reaction of aldimines derived from the resulting 2-aminocinnamic acid derivatives and a com. available aldehyde afforded the desired indole-3-acetic acid derivatives The final azepinone formation completed the total synthesis of rucaparib in 27% overall yield. To resolve the issues raised in the first-generation synthesis, we further developed a second-generation synthesis of rucaparib. The Heck reaction of a com. available ortho-iodoaniline derivative with acrylonitrile provided 4,6-disubstituted 2-aminocinnamonitrile, which was subjected to the imino-Stetter reaction with the same aldehyde to provide the desired indole-3-acetonitrile product. Subsequent construction of the azepinone scaffold completed the total synthesis of rucaparib in 59% overall yield over three separation operations. The synthetic strategy reported herein can provide a highly practical route to access rucaparib from com. available starting materials (5.2% overall yield in the current process chem. route vs. 59% overall yield in the second-generation synthesis). In the experiment, the researchers used many compounds, for example, Methyl 2-(bromomethyl)-5-fluoro-3-nitrobenzoate (cas: 850462-65-6Synthetic Route of C9H7BrFNO4).

Methyl 2-(bromomethyl)-5-fluoro-3-nitrobenzoate (cas: 850462-65-6) 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.Synthetic Route of C9H7BrFNO4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tricyclic pharmacophore-based molecules as novel integrin α_vβ₃ antagonists. Part IV: Preliminary control of α_vβ₃ selectivity by meta-oriented substitution was written by Kubota, Dai;Ishikawa, Minoru;Ishikawa, Midori;Yahata, Naokazu;Murakami, Shoichi;Fujishima, Kazuyuki;Kitakaze, Masafumi;Ajito, Keiichi. And the article was included in Bioorganic & Medicinal Chemistry in 2006.Application of 82702-31-6 This article mentions the following:

To establish the in vivo efficacy of α_vβ₃/α_IIbβ₃ dual antagonists possessing a tricyclic pharmacophore, a corresponding α_vβ₃-selective antagonist was required as a control. We initially took two synthetic approaches to obtain α_vβ₃-selective antagonists based on the RGD recognition pattern or on modification of the dihedral angle between the central benzene ring and the adjacent heterocycle, but both proved unsuccessful. However, synthesis of novel antagonists with meta-substitution of the central benzene ring generated weak selectivity for α_vβ₃ over α_IIbβ₃ for the first time in the family of compounds with the tricyclic pharmacophore. Optimization of meta-oriented antagonists furnished an α_vβ₃-selective antagonist exhibiting inhibitory activity not only in a receptor-binding assay, but also in a cell adhesion assay. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-4-fluorobenzoate (cas: 82702-31-6Application of 82702-31-6).

Methyl 3-bromo-4-fluorobenzoate (cas: 82702-31-6) 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). In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Application of 82702-31-6

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis, properties and antimicrobial activity of 5-trifluoromethyl-2-formylphenylboronic acid was written by Adamczyk-Wozniak, Agnieszka;Gozdalik, Jan T.;Wieczorek, Dorota;Madura, Izabela D.;Kaczorowska, Ewa;Brzezinska, Ewa;Sporzynski, Andrzej;Lipok, Jacek. And the article was included in Molecules in 2020.Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde This article mentions the following:

2-Formylphenylboronic acids display many interesting features, not only from synthetic but also from an application as well as structural points of view. 5-Trifluoromethyl-2-formyl phenylboronic acid has been synthesized and characterized in terms of its structure and properties. The presence of an electron-withdrawing substituent results in a considerable rise in the acidity in comparison with its analogs. Taking into account the probable mechanism of antifungal action of benzoxaboroles, which blocks the cytoplasmic leucyl-tRNA synthetase (LeuRS) of the microorganism, docking studies with the active site of the enzymes have been carried out. It showed possible binding of the cyclic isomer into the binding pocket of Candida albicans LeuRS, similar to that of the recently approved benzoxaborole antifungal drug (AN2690, Tavaborole, Kerydin). In case of Escherichia coli LeuRS, the opened isomer displays a much higher inhibition constant in comparison with the cyclic one. The antimicrobial activity of the title compound was also investigated in vitro, showing moderate action against Candida albicans. The compound reveals higher activity against Aspergillus niger as well as bacteria such as Escherichia coli and Bacillus cereus. In case of Bacillus cereus, the determined Min. Inhibitory Concentration (MIC) value is lower than that of AN2690 (Tavaborole). The results confirm potential of 2-formylphenylboronic acids as antibacterial agents and give a hint of their possible mechanism of action. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) 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.Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design, synthesis and structure of new potential electrochemically active boronic acid-based glucose sensors was written by Norrild, Jens Chr.;Sotofte, Inger. And the article was included in Journal of the Chemical Society, Perkin Transactions 2 in 2002.HPLC of Formula: 166821-88-1 This article mentions the following:

In the authors’ studies on new boronic acid based carbohydrate sensors three new boronic acids (2-FcCH₂NMeCH₂C₆H₄B(OH)₂ (3), 1,2-(2-(HO)₂BC₆H₄CH₂NMeCH₂)₂ferrocene (7) and 1,1′-(2-(HO)₂BC₆H₄CH₂NMeCH₂)₂ferrocene (11)) containing a ferrocene moiety were synthesized. Their design includes an intramol. B-N bonding motif to facilitate binding at physiol. pH. The authors report the synthesis of the compounds and studies on glucose complexation as studied by ¹³C NMR spectroscopy. The crystal structure of 2,4,6-tris[2-(N-ferrocenylmethyl-N-methylaminomethyl)phenyl]boroxin (13) (boroxin of boronic acid 3) (boroxin = cyclotriboroxane) was obtained and compared with structures obtained of 2,4,6-tris[2-(N,N-dimethylaminomethyl)phenyl]boroxin (14) and 2-(2-(dimethylaminomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (15). The structure of 13 shows the existence of intramol. B-N bonds in the solid phase. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1HPLC of Formula: 166821-88-1).

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. 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.HPLC of Formula: 166821-88-1

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

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

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