Category: bromides-buliding-blocks

Improved Flavodoxin Inhibitors with Potential Therapeutic Effects against Helicobacter pylori Infection was written by Galano, Juan J.;Alias, Miriam;Perez, Reyes;Velazquez-Campoy, Adrian;Hoffman, Paul S.;Sancho, Javier. And the article was included in Journal of Medicinal Chemistry in 2013.Application In Synthesis of 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

A variety of electron-deficient chromenes and styrenes and nitrobenzooxadiazolyl thioethers and other compounds were tested (and in some cases prepared) as selective inhibitors of flavodoxin in Helicobacter pylori for potential use in the treatment of gastric ulcer and prevention of stomach cancer with fewer side effects and reduced susceptibilities to drug resistance; their inhibition of flavodoxin and of Helicobacter pylori and their cytotoxicities were determined For example, (E)-ArCH:CHNO₂ (Ar = 2-F-5-F₃CC₆H₃, 4-Cl-2,6-F₂C₆H₂) inhibited H. pylori with IC₅₀ values of 0.53 μM and therapeutic indexes of 38 and 15, resp. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Application In Synthesis of 1-(3-Bromopropyl)-4-methoxybenzene).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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). 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.Application In Synthesis of 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of unsymmetrical dihydro triazine-2,4-diones by the N-N bond fragmentation of urazoles followed by intramolecular cyclization was written by Panga, Subhaskar R.;Hall, Roger G.;Samant, Rashmi V.;Montgomery, Mark;Shyadligeri, Ashok S.. And the article was included in Tetrahedron Letters in 2022.Application In Synthesis of 1-Bromopyrrolidine-2,5-dione This article mentions the following:

A new synthesis of unsym. dihydro triazine-2,4-diones I (R¹ = Ph, 3-ClC₆H₄, 4-MeOC₆H₄, 1-phenyl-3-trifluoromethylpyrazol-5-yl, etc., R² = H, R³ = Me; R¹ = 4-ClC₆H₄, R² = H, Me, R³ = Me, Et, i-Pr) has been accomplished through the strategy of a base-induced fragmentation of urazole derivatives II followed by an intramol. cyclization. Treating substituted urazole derivativesII with LDA resulted in fragmentation of the N-N bond generating an imine, which was trapped in an intramol. fashion to give products I in good to excellent yields. Features of this transformation include atom economy and a broad tolerance of aryl substituents. Where differentially substituted urazole derivatives were employed, only one dihydrotriazine-2,4-dione isomer was obtained. The transformation of the formed dihydrotriazine-2,4-diones into triazine-2,4-diones and triazine-2,4,6-triones has been demonstrated, enlarging the scope of this approach. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Application In Synthesis of 1-Bromopyrrolidine-2,5-dione).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and Radiosynthesis of Prospective 2-Nitroimidazole Hypoxia PET Tracers via Thiazolidine Ligation with 5-Fluorodeoxyribose (FDR) was written by Musolino, M.;Dall’Angelo, S.;Zanda, M.. And the article was included in SynOpen in 2017.Quality Control of N-(5-Bromopentyl)phthalimide This article mentions the following:

The first prospective fluorinated PET tracers for imaging hypoxia obtained via thiazolidine-ligation are reported. Three 1,2-thiol-amine linkers were combined with four different 2-nitroimidazole spacers via amide or urea bond formation. The resulting compounds, e.g., I were submitted to thiazolidine-ring-forming ligation reaction with the fluorinated carbohydrate L-5-fluoro-5-deoxy-ribose (FDR), affording the desired candidate PET tracers, e.g., II in variable yields. The same ligation reactions performed on L-ribose – a byproduct of [18F]FDR radiosynthesis – under conditions mimicking a radiochem. production and showed that the fluorinated adducts can be efficiently purified and isolated by HPLC. Finally, one of the prospective hypoxia tracers was successfully produced in radiolabeled form in 29.2% radiochem. yield from [18F]FDR. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Quality Control of N-(5-Bromopentyl)phthalimide).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Quality Control of N-(5-Bromopentyl)phthalimide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Two bicyclic dinuclear complexes generated from 3,3′-[1,3,4-thiadiazole-2,5-diyldi(thiomethylene)]dibenzoic acid (L) and dimethylformamide (DMF): [Cu(L)(DMF)]₂ and [Zn(L)(DMF)]₂ was written by Wang, Ping;Ma, Jian-Ping;Li, Xiao-Yan;Huang, Ru-Qi;Dong, Yu-Bin. And the article was included in Acta Crystallographica, Section C: Crystal Structure Communications in 2009.Category: bromides-buliding-blocks This article mentions the following:

A new 1,3,4-thiadiazole bridging ligand, 3,3′-[1,3,4-thiadiazole-2,5-diyldi(thiomethylene)]dibenzoic acid (L), was used to create the novel isomorphous complexes bis{μ-3,3′-[1,3,4-thiadiazole-2,5-diyldi(thiomethylene)]dibenzoato}bis[(DMF)copper(II)], [Cu₂(C₁₈H₁₂N₂O₄S₃)₂(C₃H₇NO)₂], (I), and bis{μ-3,3′-[1,3,4-thiadiazole-2,5-diyldi(thiomethylene)]dibenzoato}bis[(DMF)zinc(II)], [Zn₂(C₁₈H₁₂N₂O₄S₃)₂(C₃H₇NO)₂], (II). Crystallog. data are given. Both exist as centrosym. bicyclic dimers constructed through the syn-syn bidentate bridging mode of the carboxylate groups. The two rings share a metal-metal bond and each of the metal atoms possesses a square-pyramidal geometry capped by the DMF mol. The 1,3,4-thiadiazole rings play a critical role in the formation of a π-π stacking system that expands the dimensionality of the structure from zero to one. The TGA of (I) indicates decomposition of the coordinated ligands on heating. Compared with the fluorescence of L in the solid state, the fluorescence intensity of (II) is relatively enhanced with a slight red shift, while that of (I) is quenched. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Category: bromides-buliding-blocks).

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) 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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Polythiophenes with unusual electrical and optical properties based on donor acceptor alternance strategy was written by Gallazzi, Maria C.;Toscano, Francesca;Paganuzzi, Daniela;Bertarelli, Chiara;Farina, Alessandra;Zotti, Gianni. And the article was included in Macromolecular Chemistry and Physics in 2001.Safety of 5-Bromothiophene-3-carbaldehyde This article mentions the following:

The strategy of donor-acceptor alternation was adopted to reduce the energy gap in substituted polythiophenes; energy gaps down to 1.2 eV were obtained, which is a very low value in the class of polythiophenes. Alkoxy groups and dicyanoethenyl groups were used to prepare electron-rich and electron-poor thiophene units. The copolymers were obtained by coupling reaction methods (Suzuki) and by oxidative chem. and electrochem. polymerization of an opportunely designed substituted terthiophene. X-ray studies and spectroscopic data on the copolymers evidenced that the dicyanoethenyl group as substituent was rather steric demanding and susceptible of side reactions also preventing the n-doping of the material. The conductivity behavior was unusual but compatible with localized charge carriers. In the experiment, the researchers used many compounds, for example, 5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2Safety of 5-Bromothiophene-3-carbaldehyde).

5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2) 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.Safety of 5-Bromothiophene-3-carbaldehyde

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

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

Podands with 10-ethyl-3,7-dithienyl-10H-phenothiazine core: synthesis and structural analysis was written by Petran, Anca;Bogdan, Elena;Terec, Anamaria;Grosu, Ion. And the article was included in Revue Roumaine de Chimie in 2012.Quality Control of 5-Bromothiophene-3-carbaldehyde This article mentions the following:

New podands showing substituted thiophene groups connected to positions 3 and 7 of a central 10-ethyl-10H-phenothiazine unit were obtained in good yield by cross-coupling reaction strategy. The thiophene rings are substituted either with formyl or hydroxymethyl groups, either at position 4′ or at position 5′. These podands can participate by various reactions to the enclosure of macrocyclic compounds and the reported compounds are versatile precursors for host mols. embedding thiophene and phenothiazine moieties. The structure of the podands was investigated by NMR and MS spectra. The title compounds thus formed included a dimethanol (I) and alc. regioisomer analog (II). The synthesis of the target compounds was achieved using 10-ethyl-3,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenothiazine, 3,7-dibromo-10-ethyl-10H-phenothiazine as starting materials. In the experiment, the researchers used many compounds, for example, 5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2Quality Control of 5-Bromothiophene-3-carbaldehyde).

5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2) 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.Quality Control of 5-Bromothiophene-3-carbaldehyde

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