Author: Jessica.F

D′Agostino, Ilaria published the artcileAntibacterial alkylguanidino ureas: Molecular simplification approach, searching for membrane-based MoA, Recommanded Product: 1-Bromooctane, the publication is European Journal of Medicinal Chemistry (2022), 114158, database is CAplus and MEDLINE.

The ever-faster rise of antimicrobial resistance (AMR) represents a major global Public Health challenge. New chem. entities with innovative Modes of Action (MoAs) are thus desirable. We recently reported the development of a novel class of broad-spectrum bactericidal agents, the AlkylGuanidino Ureas (AGU). Due to their polycationic structure, they likely target bacterial membranes. In order to better understand their MoA, we synthesized a library of AGU derivatives by structural simplification of selected hit compounds and developed specific assays based on membrane models by means of both anal. and computational techniques. Cell-based assays provided exptl. evidence that AGUs disrupt bacterial membranes without showing hemolytic behavior. Hence, we herein report a thorough chem. and biol. characterization of a new series of AGUs obtained through mol. simplification, allowing the rational design of potent antibacterial compounds active on antibiotic-resistant strains.

European Journal of Medicinal Chemistry published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, Recommanded Product: 1-Bromooctane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Wu, Yulin published the artcileDiscovery of a Highly Potent, Nonabsorbable Apical Sodium-Dependent Bile Acid Transporter Inhibitor (GSK2330672) for Treatment of Type 2 Diabetes, SDS of cas: 55788-44-8, the publication is Journal of Medicinal Chemistry (2013), 56(12), 5094-5114, database is CAplus and MEDLINE.

The apical sodium-dependent bile acid transporter (ASBT) transports bile salts from the lumen of the gastrointestinal (GI) tract to the liver via the portal vein. Multiple pharmaceutical companies have exploited the physiol. link between ASBT and hepatic cholesterol metabolism, which led to the clin. investigation of ASBT inhibitors as lipid-lowering agents. While modest lipid effects were demonstrated, the potential utility of ASBT inhibitors for treatment of type 2 diabetes has been relatively unexplored. We initiated a lead optimization effort that focused on the identification of a potent, nonabsorbable ASBT inhibitor starting from the first-generation inhibitor 264W94 (1). Extensive SAR studies culminated in the discovery of GSK2330672 (56) as a highly potent, nonabsorbable ASBT inhibitor which lowers glucose in an animal model of type 2 diabetes and shows excellent developability properties for evaluating the potential therapeutic utility of a nonabsorbable ASBT inhibitor for treatment of patients with type 2 diabetes.

Journal of Medicinal Chemistry published new progress about 55788-44-8. 55788-44-8 belongs to bromides-buliding-blocks, auxiliary class Bromide,Salt,Aliphatic hydrocarbon chain,Aliphatic hydrocarbon chain, name is Sodium 3-bromopropane-1-sulfonate, and the molecular formula is C9H7NO2, SDS of cas: 55788-44-8.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Murakami, Yukito published the artcileTransition-metal complexes of pyrrole pigments. 16. Cobalt complexes of 1,19-dimethyldehydrocorrins as vitamin B₁₂ models, Name: 3-Bromo-2-methylpropanoic acid, the publication is Journal of the American Chemical Society (1980), 102(22), 6736-44, database is CAplus.

The Co complexes of 1,19-dimethyl-B,C-didehydrocorrin (BDHC) and its tetradehydro analog (TDHC), both having addnl. double bonds at peripheral positions and an addnl. angular Me group compared with the parent corrinoid, were investigated from the viewpoint of vitamin B₁₂ chem. The electronic effect of peripheral double bonds in TDHC is significant, and the TDHC complex is far from analogous to the corrinoid, whereas the BDHC complex is quite analogous to the corrinoid as far as the electronic properties are concerned on the basis of their spectroscopic, electrochem., and axial coordination behaviors. The angular Me groups in the BDHC complex exert an usually large steric effect in the bimol. reactions of Co^I(BDHC) with alkyl donors which result in the formation of an alkyl-Co bond. The steric interaction energies between an axial ligand and an angular Me and between an axial alkyl ligand and the macrocyclic skeleton are estimated from the kinetic and thermodn. data. The BDHC complex coordinated with a bulky alkyl ligand at its axial site undergoes a novel heterolytic C-Co bond cleavage in acidic media, giving Co(III) and a carbanionic intermediate under photolytic conditions and even in the dark. In reference to the electrochem. data for the BDHC complex and the related Co complexes, the significant steric pressure provided by BDHC on the bulky axial ligand is responsible for the heterolytic C-Co cleavage. Significance of the steric pressure effect is briefly discussed in connection with the mechanism for 1,2-rearrangement of substituents placed in the alkyl ligand. A synthetic usage of the BDHC complex as a catalyst for the selective reduction of a primary alkyl bromide is also described.

Journal of the American Chemical Society published new progress about 56970-78-6. 56970-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Carboxylic acid,Aliphatic hydrocarbon chain,Inhibitor, name is 3-Bromo-2-methylpropanoic acid, and the molecular formula is C4H7BrO2, Name: 3-Bromo-2-methylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Fuchibe, Kohei published the artcileCopper(I)-Catalyzed [4 + 1] Cycloaddition of Silyl Dienol Ethers with Sodium Bromodifluoroacetate: Access to β,β-Difluorocyclopentanone Derivatives, COA of Formula: C30H24BrCuN2P, the publication is Organic Letters (2016), 18(18), 4502-4505, database is CAplus and MEDLINE.

Silyl dienol ethers readily underwent copper(I)-catalyzed [4 + 1] cycloaddition with sodium bromodifluoroacetate to afford 4,4-difluorocyclopent-1-en-1-yl silyl ethers. On the basis of high-resolution mass spectroscopy anal., annulation presumably proceeded via a copper(I) difluorocarbene complex, which represents an unprecedented example of [4 + 1] cycloadditions promoted by a transition metal difluorocarbene complex.

Organic Letters published new progress about 25753-84-8. 25753-84-8 belongs to bromides-buliding-blocks, auxiliary class Copper, name is Bromo(1,10-phenanthroline)(triphenylphosphine)copper(I), and the molecular formula is C30H24BrCuN2P, COA of Formula: C30H24BrCuN2P.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Yagui, Javier published the artcileBenzodithiophene-based small molecules for vacuum-processed organic photovoltaic devices, Recommanded Product: 2-Bromo-3-(2-ethylhexyl)thiophene, the publication is Optical Materials (Amsterdam, Netherlands) (2020), 110354, database is CAplus.

Benzo[1,2-b:4,5-b’]dithiophene (BDT) derivatives were evaluated as donor materials for the first time in vacuum-processed organic photovoltaic (OPV) devices. Simple BDT derivatives coupled with thiophene, 3-methylthiophene, and 3-(2-ethylhexyl)thiophene, I [R = H, Me, CH₂CH(Et)(CH₂)₃Me], were synthesized and characterized as part of this evaluation study. Similar frontier MOs were determined for the three mols. by DFT calculations, optical, and electrochem. measurements. Therefore, the effect of the alkyl substituents on the film morphol. and mol. order was possible to evaluate as well. All mols. exhibited thermal stability for their co-evaporation with C60 to form bulk heterojunction layers in OPV devices. An increase in short-circuit c.d. was observed for devices with compound I [R = Me]. Microscopy images and hole-transport measurements suggested an induced mol. order by the Me group of compound I [R = Me] on the active layer. Although low photoconversion efficiency values were obtained (∼1.2%), this work demonstrates the feasibility to fabricate fully vacuum-processed OPV devices with BDT derivatives as donor materials. Devices with higher photoconversion efficiencies were expected for BDT derivatives with enhanced optoelectronic properties.

Optical Materials (Amsterdam, Netherlands) published new progress about 303734-52-3. 303734-52-3 belongs to bromides-buliding-blocks, auxiliary class Thiophene,Bromide, name is 2-Bromo-3-(2-ethylhexyl)thiophene, and the molecular formula is C24H20Ge, Recommanded Product: 2-Bromo-3-(2-ethylhexyl)thiophene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

La Monica, Girolamo published the artcileReactions of carbon dioxide with tetrahydroborato copper(I) complexes in moist solvents: synthesis and reactions of [(phen)₂Cu][(HO)₃B(O₂CH)] and (phen)(Ph₃P)Cu(O₂COH) (phen = 1,10-phenanthroline), Application In Synthesis of 25753-84-8, the publication is Inorganica Chimica Acta (1988), 143(2), 239-45, database is CAplus.

CO₂ reacts with Cu(phen)(PPh₃)(BH₄) (I; phen = 1,10-phenanthroline) in moist THF and in the presence of free phen affording [Cu(phen)₂][(HO)₃B(O₂CH)] (II). II can be obtained from I and aqueous HCO₂H in the presence of phen and from Cu(phen)₂(BH₄) and aqueous HCO₂H or CO₂ in moist THF. The reaction of I with CO₂ in moist MeOH gives Cu(phen)(PPh₃)(O₂COH) (III). The action of ROH on II gave [Cu(phen)₂](O₂CH), the B atom being eliminated as B(OR)₃. II reacts with an alc. Ph₃P solution giving Cu(phen)(PPh₃)(O₂CH). The reaction of II with PhCH₂Br gives HCO₂CH₂Ph. The reactivity of III toward neutral ligands such as phen and cyclohexylisocyanide (CyNC) was studied, [Cu(phen)₂](HCO₃) and [Cu(phen)(CNCy)₂](HCO₃), being obtained, resp.

Inorganica Chimica Acta published new progress about 25753-84-8. 25753-84-8 belongs to bromides-buliding-blocks, auxiliary class Copper, name is Bromo(1,10-phenanthroline)(triphenylphosphine)copper(I), and the molecular formula is C30H24BrCuN2P, Application In Synthesis of 25753-84-8.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Girvin, Zebediah C. published the artcileFoldamer-templated catalysis of macrocycle formation, Formula: C13H18BBrO3, the publication is Science (Washington, DC, United States) (2019), 366(6472), 1528-1531, database is CAplus and MEDLINE.

Macrocycles, compounds containing a ring of 12 or more atoms, find use in medicine, fragrances, and biol. ion sensing. The efficient preparation of macrocycles is a fundamental challenge in synthetic organic chem. because the high entropic cost of large-ring closure allows undesired intermol. reactions to compete. Here, we present a bioinspired strategy for macrocycle formation through carbon-carbon bond formation. The process relies on a catalytic oligomer containing α- and γ-amino acid residues to template the ring-closing process. The α/γ-peptide foldamer adopts a helical conformation that displays a catalytic primary amine-secondary amine diad in a specific three-dimensional arrangement. This catalyst promotes aldol reactions that form rings containing 14 to 22 atoms. Utility is demonstrated in the synthesis of the natural product robustol.

Science (Washington, DC, United States) published new progress about 401797-04-4. 401797-04-4 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronate Esters,Boronic acid and ester, name is 2-(3-Bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C13H18BBrO3, Formula: C13H18BBrO3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Chapman, Robert D. published the artcileSelective syntheses of mono- and bis(2-fluoro-2,2-dinitroethoxy)alkanes. Scope of the utility of triflate intermediates, Recommanded Product: 2,3-Dibromo-2,3-dimethylbutane, the publication is Journal of Organic Chemistry (1988), 53(16), 3771-5, database is CAplus.

Displacement of the bromide in BrCH₂CHMeOCH₂CF(NO₂)₂ (I) cannot be effected by AgO₃SCF₃ because of the electroneg. vicinal alkoxide’s deactivating inductive effect on the primary bromine; however substituents in the secondary position are more labile with respect to nucleophile displacement. The scope of the utility of nucleophilic substitutions using homologous α,ψ-dibromoalkanes, Br(CH₂)_nCHMeBr (n = 1,2,3) and a vicinal dibromoalkane, MeCHBrCHBrMe, is reported. This approach produced a variety of new fluorodinitroethyl ethers, including the novel (O₂N)₂CFCH₂OCH₂CHMeOCH₂CF(NO₂)₂, which possesses two electroneg. alkoxy substituents in a vicinal arrangement, from the fortuitous intermediate (O₂N)₂CFCH₂OCH₂CHBrMe (II) by way of anchimeric assistance in the reaction of BrCH₂CHBrMe, also yielding I, the regioisomer of II. Typically, α,ψ- and α,ω-dibromoalkanes are distinctly stepwise in their 2 possible S_N1Ag⁺ displacements of bromide by AgO₃SCF₃, a characteristic which allows selective incorporation of relatively nonnucleophilic alkoxy substituents via displacements of triflate intermediates.

Journal of Organic Chemistry published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C6H12Br2, Recommanded Product: 2,3-Dibromo-2,3-dimethylbutane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Bauer, Daniel published the artcileFunctionalisable acyclic cucurbiturils, Computed Properties of 55788-44-8, the publication is Organic Chemistry Frontiers (2019), 6(10), 1555-1560, database is CAplus.

Synthetic strategies were described to prepare acyclic cucurbituril derivatives with two different types of appended functional groups, one that mediates water solubility and another one that allows further functionalization. The synthesis started with the coupling of a 1,4-disubstituted naphthalene derivative containing one 2-chloroethoxy and one 3-sulfonatopropoxy group to a suitable tetrameric glycoluril-derived precursor. This reaction afforded two regioisomers, differing in the relative orientation of the peripheral substituents, which could be separated in a straightforward fashion and structurally characterized. Both isomers were then converted into the corresponding diazides and diamines that served to append further residues by, resp., copper(I)-catalyzed azide-alkyne cycloaddition or amide formation. Binding studies showed that the functionalized dianionic acyclic cucurbiturils thus obtained possess a notable cation affinity in water, albeit a lower one than an analog with four peripheral neg. charged substituents. This work constitutes the basis for the development of water-soluble acyclic cucurbiturils whose applications could potentially go beyond the use as receptors.

Organic Chemistry Frontiers published new progress about 55788-44-8. 55788-44-8 belongs to bromides-buliding-blocks, auxiliary class Bromide,Salt,Aliphatic hydrocarbon chain,Aliphatic hydrocarbon chain, name is Sodium 3-bromopropane-1-sulfonate, and the molecular formula is C3H6BrNaO3S, Computed Properties of 55788-44-8.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Nakayama, Yoshiki published the artcileKeto-Difluoromethylation of Aromatic Alkenes by Photoredox Catalysis: Step-Economical Synthesis of α-CF₂H-Substituted Ketones in Flow, SDS of cas: 111865-47-5, the publication is ACS Catalysis (2019), 9(7), 6555-6563, database is CAplus.

A step-economical method for synthesis of α-CF₂H-substituted ketones from readily available alkene feedstocks was developed. Radical difluoromethylation of aromatic alkenes combining DMSO oxidation and photoredox catalysis is a key to the successful transformation. Electrochem. anal., laser flash photolysis (LFP), and d. functional theory (DFT) calculations reveal that N-tosyl-S-difluoromethyl-S-phenylsulfoximine serves as the best CF₂H radical source among analogous sulfone-based CF₂H reagents. The present photocatalytic keto-difluoromethylation was applied to flow synthesis and easily scaled up to gram-scale synthesis within a reasonable reaction time. Furthermore, potentials of the α-CF₂H-substituted ketones for useful synthetic intermediates are shown; e.g., synthesis of the CF₂H-containing α-hydroxyamide with the same carbon skeleton as that of the anticonvulsant active CF₃-analog, is disclosed. Addnl., mechanistic studies are also discussed.

ACS Catalysis published new progress about 111865-47-5. 111865-47-5 belongs to bromides-buliding-blocks, auxiliary class Benzenes, name is Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, and the molecular formula is C10H16Br3N, SDS of cas: 111865-47-5.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary