Category: bromides-buliding-blocks

Formula: C8H7BrO2In 2016 ,《Property Focused Structure-Based Optimization of Small Molecule Inhibitors of the Protein-Protein Interaction between Menin and Mixed Lineage Leukemia (MLL)》 appeared in Journal of Medicinal Chemistry. The author of the article were Borkin, Dmitry; Pollock, Jonathan; Kempinska, Katarzyna; Purohit, Trupta; Li, Xiaoqin; Wen, Bo; Zhao, Ting; Miao, Hongzhi; Shukla, Shirish; He, Miao; Sun, Duxin; Cierpicki, Tomasz; Grembecka, Jolanta. The article conveys some information:

Development of potent small mol. inhibitors of protein-protein interactions with optimized druglike properties represents a challenging task in lead optimization process. Here, we report synthesis and structure-based optimization of new thienopyrimidine class of compounds, which block the protein-protein interaction between menin and MLL fusion proteins that plays an important role in acute leukemias with MLL translocations. We performed simultaneous optimization of both activity and druglike properties through systematic exploration of substituents introduced to the indole ring of lead compound 1 (MI-136) to identify compounds suitable for in vivo studies in mice. This work resulted in the identification of compound 27 (MI-538), which showed significantly increased activity, selectivity, polarity, and pharmacokinetic profile over 1 and demonstrated a pronounced effect in a mouse model of MLL leukemia. This study, which reports detailed structure-activity and structure-property relationships for the menin-MLL inhibitors, demonstrates challenges in optimizing inhibitors of protein-protein interactions for potential therapeutic applications. After reading the article, we found that the author used 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Formula: C8H7BrO2)

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) belongs to organobromine compounds.Organobromine chemicals are produced naturally by an array of biological and other chemical processes in our environment. Some of these compounds are identical to man-made organobromine compounds, such as methyl bromide, bromoform, and bromophenols, but many others are entirely new moleclar entities, often possessing extraordinary and important biological properties. Formula: C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Computed Properties of C9H11BrO3In 2021 ,《Tuning the Molecular Packing of Self-Assembled Amphiphilic PtII Complexes by Varying the Hydrophilic Side-Chain Length》 appeared in Chemistry – A European Journal. The author of the article were Herkert, Lorena; Selter, Philipp; Daniliuc, Constantin G.; Baeumer, Nils; Palakkal, Jasnamol P.; Fernandez, Gustavo; Hansen, Michael Ryan. The article conveys some information:

Understanding the relation between mol. design and packing modes constitutes one of the major challenges in self-assembly and is essential for the preparation of functional materials. Herein, the authors have achieved high precision control over the supramol. packing of amphiphilic PtII complexes by systematic variation of the hydrophilic side-chain length. A novel approach of general applicability based on complementary x-ray diffraction and solid-state NMR spectroscopy has allowed the authors to establish a clear correlation between mol. features and supramol. ordering. Systematically increasing the side-chain length gradually increases the steric demand and reduces the extent of aromatic interactions, thereby inducing a gradual shift in the mol. packing from parallel to a long-slipped organization. Notably, the authors’ findings highlight the necessity of advanced solid-state NMR techniques to gain structural information for supramol. systems where single-crystal growth is not possible. The authors’ work further demonstrates a new mol. design strategy to modulate aromatic interaction strengths and packing arrangements that could be useful for the engineering of functional materials based on PtII and aromatic mols. In the experiment, the researchers used many compounds, for example, 1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8Computed Properties of C9H11BrO3)

1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8) is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.Computed Properties of C9H11BrO31-Bromo-3,4,5-trimethoxybenzene can be used to synthesize analogs of HA14-1, which shows promising anticancer properties.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Safety of Bromopentacarbonylmanganese(I)In 2022 ,《Synthesis and properties of a new nine-membered triphospha-macrocyclic complex via a manganese(I) tricarbonyl template》 appeared in Journal of Molecular Structure. The author of the article were Zhang, Wenjian; Levason, William; Reid, Gillian. The article conveys some information:

Reaction of the primary diphosphine H2P(CH2)2PH2 with [MnBr(CO)5], followed by removal of the bromide by treatment with AgOTf (OTf = CF3SO3) and addition of PAr3 (Ar = o-C6H4F), gives the acyclic precursor complex, fac-[Mn(CO)3{H2P(CH2)2PH2}(PAr3)][OTf], thus positioning the primary phosphine functions adjacent to the o-fluorophenyl substituents. The identity of this species was confirmed by multinuclear NMR (1H, 19F{1H}, 31P{1H} and 55Mn) and IR spectroscopic anal., as well as from a single crystal x-ray anal. Subsequent treatment of this complex with KOtBu (potassium tertiary butoxide) causes a double P-C coupling reaction, with defluorination of two aryl groups, and gives a nine-membered triphosphine macrocyclic complex. Methylation (KOtBu/MeI) of the two remaining secondary phosphine function yields the complex [Mn(CO)3(1)][OTf], which was characterized similarly by multinuclear NMR and IR spectroscopy, and by electrospray mass spectrometry. A single crystal x-ray structure determination confirms the distorted octahedral coordination at Mn(I), with the triphosphine macrocycle occupying three mutually facial coordination sites. As expected, this complex is extremely thermodynamically stable and kinetically inert, being unaffected by prolonged refluxing with either Me3NO or thiophenolate in MeCN. After reading the article, we found that the author used Bromopentacarbonylmanganese(I)(cas: 14516-54-2Safety of Bromopentacarbonylmanganese(I))

Bromopentacarbonylmanganese(I)(cas: 14516-54-2) has many other uses. It is used in the formation of (eta6-arene)tricarbonylmanganese(I) by reacting with arene (arene= hexamethyl benzene, 1,2,4,5-tetramethyl benzene, mesitylene, p-xylene and toluene) in the presence silver salt.Safety of Bromopentacarbonylmanganese(I)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

HPLC of Formula: 523-27-3In 2022 ,《Four- and two-armed hetero porphyrin dimers: their specific recognition and self-sorting behaviours》 appeared in Organic & Biomolecular Chemistry. The author of the article were Ueda, Masahiro; Kimura, Masaki; Miyagawa, Shinobu; Naito, Masaya; Takaya, Hikaru; Tokunaga, Yuji. The article conveys some information:

In this study we self-assembled the four-armed porphyrin hetero dimer capsule Cap4, stabilized through amidinium-carboxylate salt bridges, in CH2Cl2 and CHCl3. The dimer capsule Cap4 was kinetically and thermodynamically more stable than the corresponding two-armed dimer Cap2. The number of arms strongly influenced their recognition behavior; guests possessing small aromatic faces (e.g., 1,3,5-trinitrobenzene) preferred residing in the cavity of the two-armed capsule Cap2, rather than in Cap4, both thermodynamically and kinetically; in contrast, large aromatic guests (e.g., 9,10-dibromoanthracene) were encapsulated predominantly by Cap4 because of favorable entropic effects. The number of arms enabled self-sorting behavior of the dimer formation; complexation studies using an equimolar mixture of the four porphyrin constituents of the two capsules revealed the quant. formation of the corresponding dimers Cap2 and Cap4. Furthermore, we examined the specific mol. recognition of Cap2 and Cap4; NMR experiments of mixtures of Cap2 and Cap4 in the presence of favorable guests for Cap2 and Cap4 revealed that these guest mols. were encapsulated selectively by their preferred hosts. In the experimental materials used by the author, we found 9,10-Dibromoanthracene(cas: 523-27-3HPLC of Formula: 523-27-3)

9,10-Dibromoanthracene(cas: 523-27-3) is a dibrominated polycyclic aromatic hydrocarbon (PAH). 9,10-Dibromoanthracene is often used as an energy acceptor and activator in reactions that produce chemiluminescence.HPLC of Formula: 523-27-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Quality Control of Tris(4-bromophenyl)amineIn 2021 ,《Porosity Design on Conjugated Microporous Poly(Aniline)S for Exceptional Mercury(II) Removal》 appeared in ACS Applied Materials & Interfaces. The author of the article were Lou, Xiaoyu; Chen, Jie; Xiong, Zhuo; Tang, Duanlian; Chen, Xiaoyan; Chen, Song; Dong, Rong; Ye, Changshen; Qiu, Ting. The article conveys some information:

The use of conjugated microporous polymers (CMPs) in practical wastewater treatment demands further design on the pore structure, otherwise their adsorption capacities toward heavy-metal ions were moderate. Here, we report a rational design approach, which produces hybrid mol. pores in conjugated microporous poly(aniline)s (CMPAs) for mercury removal. It is achieved through a delicate interval introduction of linkers with differential mol. lengths during polymerization, acquiring both diffusion channels and storage pores for radical enhancement of mass transfer and adsorption storage. The resulting CMPA-M featured a large adsorption capacity of 975 mg g-1 and rapid kinetics that could remove 94.8% of 50 mg g-1 of mercury(II) within a very short contact time of 48 s, with a promising initial adsorption rate h as high as 113 mg g-1 min-1, which was 2.54-fold larger in the adsorption capacity and 45.2-fold faster in the adsorption efficiency compared with the undeveloped CMPAs. More importantly, our CMPA-M-2, with robust stability and easy reusability, was able to scavenge over 99.9% of mercury(II) from the actual wastewater in a harsh condition with a very low pH of 0.77, extremely high salinity of 53,157 mg L-1, and complex impurities, featuring exceptional selectivity that allows us to extract and recycle a high purity of 99.1% of mercury from the wastewater. These outcomes demonstrate the unprecedented potential of CMPs for environmental remediation and real-world mercury extraction and present benchmarks for CMP-based mercury adsorbents. In the experiment, the researchers used many compounds, for example, Tris(4-bromophenyl)amine(cas: 4316-58-9Quality Control of Tris(4-bromophenyl)amine)

In general, Tris(4-bromophenyl)amine(cas: 4316-58-9) is often used in the synthesis of porous luminescent covalent–organic polymers (COPs)Quality Control of Tris(4-bromophenyl)amine

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Motornov, Vladimir A.; Tabolin, Andrey A.; Ioffe, Sema L. published an article in New Journal of Chemistry. The title of the article was 《Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(II): efficient synthesis of [5,5]-annulated N-fused heterocycles》.Computed Properties of C9H9BrO2 The author mentioned the following in the article:

A facile synthesis of [5,5]-annulated N-fused heterocycles – pyrrolo[2,1-b]thiazoles and pyrrolo[1,2-b]indazoles via oxidative [3+2]-annulation between nitroalkenes and azolium ylides in the presence of copper(II) was developed. The reaction proceeds in mild conditions with the copper(II) trifluoroacetate/2,6-lutidine system. The method is applicable to a broad range of nitroalkenes and azolium salts, providing the target N-fused heterocycles in moderate to good yields. In the case of α-fluoronitroalkenes, unique fluorinated derivatives were accessed via this methodol. The experimental process involved the reaction of Benzyl 2-bromoacetate(cas: 5437-45-6Computed Properties of C9H9BrO2)

Benzyl 2-bromoacetate(cas: 5437-45-6) has been used in the alkylation of (-)-2,3-O-isopropylidene-D-threitol that afforded lipopeptide, 2-[(4R,5R)-5-({[(9H-fluoren-9-yl)methoxy]carbonylaminomethyl}-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]acetic acid.Computed Properties of C9H9BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Panagiotakis, Stylianos; Mavroidi, Barbara; Athanasopoulos, Alexandros; Charalambidis, Georgios; Coutsolelos, Athanassios G.; Paravatou-Petsotas, Maria; Pelecanou, Maria; Mavridis, Irene M.; Yannakopoulou, Konstantina published an article in Carbohydrate Polymers. The title of the article was 《Unsymmetrical, monocarboxyalkyl meso-arylporphyrins in the photokilling of breast cancer cells using permethyl-β-cyclodextrin as sequestrant and cell uptake modulator》.Computed Properties of C7H13BrO2 The author mentioned the following in the article:

In the search for photosensitizers with chem. handles to facilitate their integration into complex drug delivery nanosystems, new, unsym. substituted, water insoluble meso-tetraphenylporphyrin and meso-tetra(m-hydroxyphenyl)porphyrin derivatives bearing one carboxyalkyl side chain were synthesized. Permethyl-β-cyclodextrin (pMβCD) was their ideal monomerizing host and highly efficient shuttle to transfer them into water. New assembly modes of the extremely stable (Kbinding > 1012 M-2) 2:1 complexes were identified. The complexes are photostable and do not disassemble in FBS-containing cell culture media for 24 h. Incubation of breast cancer MCF-7 cells with the complexes results in intense intracellular fluorescence, strongly enhanced in the endoplasmic reticulum (ER), high photokilling efficiency (∼90%) and low dark toxicity. pMβCD stands out as a very capable mol. isolator of mono-carboxyalkyl-arylporphyrins that increases uptake and modulates their localization in the cells. The most efficient porphyrins are envisaged as suitable photosensitizers that can be linked to biocompatible drug carriers for photo- and chemo-therapy applications. In the experimental materials used by the author, we found Ethyl 5-bromovalerate(cas: 14660-52-7Computed Properties of C7H13BrO2)

Ethyl 5-bromovalerate(cas: 14660-52-7) belongs to bromides. 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.Computed Properties of C7H13BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Kaya, Kemal; Khalil, Mohammed; Fetrow, Benjamin; Fritz, Hugh; Jagadesan, Pradeepkumar; Bondu, Virginie; Ista, Linnea; Chi, Eva Y.; Schanze, Kirk S.; Whitten, David G.; Kell, Alison published an article in ACS Applied Materials & Interfaces. The title of the article was 《Rapid and Effective Inactivation of SARS-CoV-2 with a Cationic Conjugated Oligomer with Visible Light: Studies of Antiviral Activity in Solutions and on Supports》.Reference of 2,5-Dibromothiophene The author mentioned the following in the article:

This paper presents results of a study of a new cationic oligomer that contains end groups and a chromophore affording inactivation of SARS-CoV-2 by visible light irradiation in solution or as a solid coating on paper wipes and glass fiber filtration substrates. A key finding of this study is that the cationic oligomer with a central thiophene ring and imidazolium charged groups gives outstanding performance in both the killing of E. coli bacterial cells and inactivation of the virus at very short times. Our introduction of cationic N-Me imidazolium groups enhances the light activation process for both E. coli and SARS-CoV-2 but dampens the killing of the bacteria and eliminates the inactivation of the virus in the dark. For the studies with this oligomer in solution at a concentration of 1μg/mL and E. coli, we obtain 3 log killing of the bacteria with 10 min of irradiation with LuzChem cool white lights (mimicking indoor illumination). With the oligomer in solution at a concentration of 10μg/mL, we observe 4 log inactivation (99.99%) in 5 min of irradiation and total inactivation after 10 min. The oligomer is quite active against E. coli on oligomer-coated paper wipes and glass fiber filter supports. The SARS-CoV-2 is also inactivated by oligomer-coated glass fiber filter papers. This study indicates that these oligomer-coated materials may be very useful as wipes and filtration materials. In the part of experimental materials, we found many familiar compounds, such as 2,5-Dibromothiophene(cas: 3141-27-3Reference of 2,5-Dibromothiophene)

2,5-Dibromothiophene(cas: 3141-27-3) , is mainly used as pharmaceutical intermediate and synthesis intermediate. 2,5-Dibromothiophene may be used as starting reagent for the synthesis of α,α′-didecylquater-, -quinque- and -sexi-thiophenes.Reference of 2,5-Dibromothiophene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Guan, Xianghong; Cheryala, Narsihmulu; Karim, Rezaul Md.; Chan, Alice; Berndt, Norbert; Qi, Jun; Georg, Gunda I.; Schonbrunn, Ernst published an article in Journal of Medicinal Chemistry. The title of the article was 《Bivalent BET Bromodomain Inhibitors Confer Increased Potency and Selectivity for BRDT via Protein Conformational Plasticity》.Application In Synthesis of Ethyl 4-bromobutyrate The author mentioned the following in the article:

Bromodomain and extraterminal domain (BET) proteins are important regulators of gene transcription and chromatin remodeling. BET family members BRD4 and BRDT are validated targets for cancer and male contraceptive drug development, resp. Due to the high structural similarity of the acetyl-lysine binding sites, most reported inhibitors lack intra-BET selectivity. We surmised that protein-protein interactions induced by bivalent inhibitors may differ between BRD4 and BRDT, conferring an altered selectivity profile. Starting from nonselective monovalent inhibitors, we developed cell-active bivalent BET inhibitors with increased activity and selectivity for BRDT. X-ray crystallog. and solution studies revealed unique structural states of BRDT and BRD4 upon interaction with bivalent inhibitors. Varying spacer lengths and sym. vs unsym. connections resulted in the same dimeric states, whereas different chemotypes induced different dimers. The findings indicate that the increased intra-BET selectivity of bivalent inhibitors is due to the differential plasticity of BET bromodomains upon inhibitor-induced dimerization. The results came from multiple reactions, including the reaction of Ethyl 4-bromobutyrate(cas: 2969-81-5Application In Synthesis of Ethyl 4-bromobutyrate)

Ethyl 4-bromobutyrate(cas: 2969-81-5) belongs to bromides. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.Application In Synthesis of Ethyl 4-bromobutyrate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Geniller, Lilian; Taillefer, Marc; Jaroschik, Florian; Prieto, Alexis published an article in 2022. The article was titled 《Photo-Induced Halogen-Atom Transfer: Generation of Halide Radicals for Selective Hydrohalogenation Reactions》, and you may find the article in Chemistry – A European Journal.Formula: C5H9BrO2 The information in the text is summarized as follows:

The first photo-mediated process enabling the generation of halide radicals by Halogen-Atom Transfer (XAT) is described. Contrary to radical transformations involving XAT reactivity, which exploit stable carbon radicals, this unique approach uses 1,2-dihaloethanes for the generation of unstable carbon radicals by XAT. These transient radicals then underwent β-scission with release of ethylene and formation of more stable halide radicals which have been used in selective hydrohalogenations of a large number of unsaturated hydrocarbons, including Michael acceptors, unactivated alkenes and alkynes. This hydrohalogenation is tolerant of a broad range of functionalities and is believed to proceed through a radical-chain manifold that propagates by the use of silane derivatives In addition to this study using Ethyl 3-bromopropanoate, there are many other studies that have used Ethyl 3-bromopropanoate(cas: 539-74-2Formula: C5H9BrO2) was used in this study.

Ethyl 3-bromopropanoate(cas: 539-74-2) 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. Formula: C5H9BrO2 In contrast, terrestrial plants account only for a few bromine-containing compounds.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary