Month: February 2023

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

Halide Perovskite Cluster Precursors: A Paradigm for Obtaining Structure- and Color-Tunable Light-Emitting Nanocrystals was written by Dutta, Sumit Kumar;Peng, Lucheng;Hudait, Biswajit;Xie, Renguo;Pradhan, Narayan. And the article was included in ACS Energy Letters in 2022.SDS of cas: 128-08-5 This article mentions the following:

The compositions of precursors during the syntheses of CsPbX₃ nanocrystals typically determine the resulting crystal phase and stability. Different precursors providing single or multiple constituent ions have already been developed for tuning the reaction pathways for architecting different sizes and shapes of such nanocrystals. Among these, the CsPbBr₃ clusters, composed of Cs, Pb, and Br, as well as limited ligands, employed as single-source precursors, provide an ideal pathway for obtaining a wide window of size/shape-tunable CsPbBr₃ nanocrystals. Recent reports also revealed that this pathway can lead to the epitaxial growth of non-perovskite nanostructures on perovskite nanocrystals. Further, the limited ligands here helped in shape modulation by opening different facets and also triggering facet directed connections of the nanocrystals. Keeping those in mind, the importance of these unique cluster precursors for the development of halide perovskite nanocrystals and their heterostructures is discussed, and possibilities for their utilization in different unexplored areas of research are proposed in this Perspective. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5SDS of cas: 128-08-5).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of a metabolically stable modified long-chain fatty acid salt and its photolabile derivative was written by Stoll, G. H.;Voges, R.;Gerok, W.;Kurz, G.. And the article was included in Journal of Lipid Research in 1991.Recommanded Product: 15-Bromopentadecanoic acid This article mentions the following:

An analog of the long-chain fatty acid salt, sodium stearate, was synthesized in which the H atoms at carbons 2, 3, and 18 were replaced by fluorine. The key step in the synthesis was the addition of 3-iodo-2,2,3,3-tetrafluoropropanoic acid amide to 15,15,15-trifluoro-1-pentadecene. Radioactivity was introduced by catalytic reduction of 2,2,3,3,18,18,18-heptafluoro-4-octadecenoic acid amide with carrier-free tritium gas yielding a product with the specific radioactivity of 2.63 TBq/mmol. The resulting 2,2,3,3,18,18,18-heptafluoro-4-octadecenoic acid has a pK_a of about 0.5 and is completely dissociated under normal physiol. conditions. The fluorinated fatty acid salt analog is readily taken up into hepatocytes and proved to be metabolically inert. In an approach to the identification of proteins involved in long-chain fatty acid salt transport across membranes and intracellular compartments, the photolabile derivative 11,11-azo-2,2,3,3,18,18,18-heptafluoro[G–³H]octadecanoic acid sodium salt was synthesized with a specific radioactivity of 2.63 TBq/mmol. Photolysis of the photolabile derivative, using a light source with a maximum emission at 350 nm, occurred with a half-life of 1.5 min. The generated carbene reacted with ¹⁴C-labeled MeOH and MeCN with covalent bond formation of 6-13%. Its efficacy for photoaffinity labeling was demonstrated by incorporation into serum albumin, the extracellular fatty acid salt-binding protein, as well as into the intracellular fatty acid salt-binding protein (FABP) of rat liver with mol. weight of 14,000. In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Recommanded Product: 15-Bromopentadecanoic acid).

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. 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: 15-Bromopentadecanoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Characterization of a chemosensory protein (ASP3c) from honeybee (Apis mellifera L.) as a brood pheromone carrier was written by Briand, Loic;Swasdipan, Nicharat;Nespoulous, Claude;Bezirard, Valerie;Blon, Florence;Huet, Jean-Claude;Ebert, Paul;Pernollet, Jean-Claude. And the article was included in European Journal of Biochemistry in 2002.Synthetic Route of C15H29BrO2 This article mentions the following:

We report the cloning of a honeybee chemosensory proteins (CSP) gene called ASP3c, as well as the structural and functional characterization of the encoded protein. The protein was heterologously secreted by the yeast Pichia pastoris using the native signal peptide. ASP3c disulfide bonds were assigned after trypsinolysis followed by chromatog. and mass spectrometry combined with microsequencing. The pairing (Cys(I)-Cys(II), Cys(III)-Cys(IV)) was found to be identical to that of Schistocerca gregaria CSPs, suggesting that this pattern occurs commonly throughout the insect CSPs. CD measurements revealed that ASP3c mainly consists of α-helixes, like other insect CSPs. Gel filtration anal. showed that ASP3c is monomeric at neutral pH. Using ASA, a fluorescent fatty acid anthroyloxy analog as a probe, ASP3c was shown to bind specifically to large fatty acids and ester derivatives, which are brood pheromone components, in the micromolar range. It was unable to bind tested general odorants and other tested pheromones (sexual and nonsexual). This is the 1st report on a natural pheromonal ligand bound by a recombinant CSP with a measured affinity constant In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Synthetic Route of C15H29BrO2).

15-Bromopentadecanoic acid (cas: 56523-59-2) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Synthetic Route of C15H29BrO2

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

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

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

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

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

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