Category: bromides-buliding-blocks

In 2019,Bioorganic & Medicinal Chemistry included an article by Nowikow, Christina; Fuerst, Rita; Kauderer, Maria; Dank, Christian; Schmid, Walther; Hajduch, Marian; Rehulka, Jiri; Gurska, Sona; Mokshyna, Olena; Polishchuk, Pavel; Zupko, Istvan; Dzubak, Petr; Rinner, Uwe. Quality Control of 1-Bromo-3,4,5-trimethoxybenzene. The article was titled 《Synthesis and biological evaluation of cis-restrained carbocyclic combretastatin A-4 analogs: Influence of the ring size and saturation on cytotoxic properties》. The information in the text is summarized as follows:

Combretastatin A-4 (CA-4) is a highly cytotoxic natural product and several derivatives have been prepared which underwent clin. trial. These investigations revealed that the cis-stilbene moiety of the natural product is prone to undergo cis/trans isomerization under physiol. conditions, reducing the overall activity of the drug candidates. Herein, we report the preparation of cis-restrained carbocyclic analogs of CA-4. The compounds, which differ by the size and hybridization of the carbocyclic ring have been evaluated for their cytotoxic properties and their ability to inhibit tubulin polymerization Biol. data, supported by mol. docking studies, identified cyclobutenyl and cyclobutyl derivatives of the natural product as highly promising drug candidates. In addition to this study using 1-Bromo-3,4,5-trimethoxybenzene, there are many other studies that have used 1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8Quality Control of 1-Bromo-3,4,5-trimethoxybenzene) was used in this study.

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.Quality Control of 1-Bromo-3,4,5-trimethoxybenzene1-Bromo-3,4,5-trimethoxybenzene can be used to synthesize N,N′-diarylated indolo[3,2-b]carbazole derivatives, which can find applications in electrophotography.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2019,Reaction Chemistry & Engineering included an article by Aand, Dnyaneshwar; Mahajan, Bhushan; Pabbaraja, Srihari; Singh, Ajay K.. Electric Literature of C8H7BrO2. The article was titled 《Integrated continuous flow/batch protocol for the photoreduction of ortho-methyl phenyl ketones using water as the hydrogen source》. The information in the text is summarized as follows:

Direct utilization of the abundant hydrogen in water for the transfer hydrogenation reaction (THR) is a very attractive and challenging research area. Herein, the first integrated photo-transfer hydrogenation reaction (PTHR) platform for the synthesis of benzhydrol derivatives R1CH(OH)R2 (R1 = Ph, 2-MeC6H4, 4-FC6H4, etc.; R2 = Ph, 2,5-(Me)2C6H3, 3,4-(Me)2C6H3) (26 examples, 33-89% yields) with water as a green reducing agent is reported. This transformation is time and labor-efficient, catalyst-free, and economical and utilizes readily available hydrocarbon(s) (o-Me Ph ketones) as starting materials.3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Electric Literature of C8H7BrO2) was used in this study.

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) 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. Electric Literature of C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2019,Angewandte Chemie, International Edition included an article by Wang, Wang; Ding, Chao; Li, Yangyang; Li, Zheqi; Li, Yuqiang; Peng, Long; Yin, Guoyin. Safety of 1-Bromo-3,4,5-trimethoxybenzene. The article was titled 《Migratory Arylboration of Unactivated Alkenes Enabled by Nickel Catalysis》. The information in the text is summarized as follows:

An unprecedented arylboration of unactivated terminal alkenes, featuring 1,n-regioselectivity, has been achieved by nickel catalysis. The nitrogen-based ligand plays an essential role in the success of this three-component reaction. This transformation displays good regioselectivity and excellent functional-group tolerance. In addition, the incorporation of a boron group into the products provides substantial opportunities for further transformations. Also demonstrated is that the products can be readily transformed into pharmaceutically relevant mols. Unexpectedly, preliminary mechanistic studies indicate that although the metal migration favors the α-position of boron, selective and decisive bond formation is favored at the benzylic position. In the experiment, the researchers used 1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8Safety of 1-Bromo-3,4,5-trimethoxybenzene)

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.Safety of 1-Bromo-3,4,5-trimethoxybenzene1-Bromo-3,4,5-trimethoxybenzene can be used to synthesize symmetric 3,3′,4,4′,5,5′-hexamethoxydiphenylacetylene via Stille-type coupling with bis-(tributylstannyl)acetylene.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2018,Alonso-Maranon, Lorena; Sarandeses, Luis A.; Martinez, M. Montserrat; Perez Sestelo, Jose published 《Synthesis of fused chromenes by the indium(III)-catalyzed cascade hydroarylation/cycloisomerization reactions of polyyne-type aryl propargyl ethers》.Organic Chemistry Frontiers published the findings.Product Details of 13465-09-3 The information in the text is summarized as follows:

Fused 2H-chromenes were prepared by the cascade hydroarylation/cycloisomerization reactions of polyyne-type aryl propargyl ethers using indium(III) catalysis. The transformation proceeded with 6-endo-dig regioselectivity using InBr3 (5 mol%). The method was extended to triynes allowing the formation of three bonds in one pot. Indium(III) also catalyzed the hydroamination/hydroarylation cascade reaction of o-aryldiynyl anilines to form fused carbazoles. In the experimental materials used by the author, we found Indium(III) bromide(cas: 13465-09-3Product Details of 13465-09-3)

Indium(III) bromide(cas: 13465-09-3) is used as a catalyst to produce dithioacetals when unactivated alkynes react with thiols and fields such as optics and microelectronics that utilize semiconductor technology have wide uses for indium in high-performing solar cells.Product Details of 13465-09-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2018,Shibuya, Kimiyuki; Kawamine, Katsumi; Miura, Toru; Ozaki, Chiyoka; Edano, Toshiyuki; Mizuno, Ken; Yoshinaka, Yasunobu; Tsunenari, Yoshihiko published 《Design, synthesis and pharmacology of aortic-selective acyl-CoA: Cholesterol O-acyltransferase (ACAT/SOAT) inhibitors》.Bioorganic & Medicinal Chemistry published the findings.COA of Formula: C8H15BrO2 The information in the text is summarized as follows:

We describe our mol. design of aortic-selective acyl-CoA:cholesterol O-acyltransferase (ACAT, also abbreviated as SOAT) inhibitors, their structure-activity relationships (SARs) and their pharmacokinetic (PK) and pharmacol. profiles. The connection of two weak ligands-N-(2,6-diisopropylphenyl)acetamide (50% inhibitory concentration [IC50] = 8.6 μM) and 2-(methylthio)benzo[d]oxazole (IC50 = 31 μM)-via a linker comprising a 6 methylene group chains yielded a highly potent mol., 9-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)nonanamide (3h) that exhibited high potency (IC50 = 0.004 μM) toward aortic ACAT. This head-to-tail design made it possible to markedly enhance the activity to 2150- to 7750-fold and to discriminate the isoform-selectivity based on the double-induced fit mechanism. At doses of 1 and 3 mg/kg, 3h significantly decreased the lipid-accumulation areas in the aortic arch to 74 and 69%, resp. without reducing the plasma total cholesterol level in high fat- and cholesterol-fed F1B hamsters. Here, we demonstrate the antiatherosclerotic effect of 3h in vivo via its direct action on aortic ACAT and its powerful modulator of cholesterol level. This mol. is a potential therapeutic agent for the treatment of diseases involving ACAT-1 overexpression. In the experiment, the researchers used 8-Bromooctanoic acid(cas: 17696-11-6COA of Formula: C8H15BrO2)

8-Bromooctanoic acid(cas: 17696-11-6) acid is used in the synthesis of 8-(N-Methyl-4,4′-bipyridinyl)- octanoic acid. 8-Mercaptooctanoic acid was prepared from 8-bromooctanoic acid. And 8-Bromooctanoic Acid is a useful compound for sonodynamic therapy.COA of Formula: C8H15BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2017,Zhu, Ru-Yi; Saint-Denis, Tyler G.; Shao, Ying; He, Jian; Sieber, Joshua D.; Senanayake, Chris H.; Yu, Jin-Quan published 《Ligand-Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp3)-H Bonds》.Journal of the American Chemical Society published the findings.Application In Synthesis of Methyl 3-bromopropanoate The information in the text is summarized as follows:

We herein report the palladium(II)-catalyzed bromination and iodination of a variety of α-hydrogen-containing carboxylic acid and amino acid-derived amides. These reactions are exclusively enabled by quinoline-type ligands. The halogenated products obtained in this reaction are highly versatile and rapidly undergo further diversification. Further, we report the first example of a free carboxylic acid-directed Pd(II)-catalyzed C(sp3)-H bromination, enabled by quinoline ligands. The experimental process involved the reaction of Methyl 3-bromopropanoate(cas: 3395-91-3Application In Synthesis of Methyl 3-bromopropanoate)

Methyl 3-bromopropanoate(cas: 3395-91-3) 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.Application In Synthesis of Methyl 3-bromopropanoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Tang, Qun; Xie, Yu; Liu, Yongpeng; Zheng, Lifang published an article in Bioorganic & Medicinal Chemistry Letters. The title of the article was 《Synthesis of mitochondria-targeted menadione cation derivatives: Inhibiting mitochondrial thioredoxin reductase (TrxR2) and inducing apoptosis in MGC-803 cells》.Application In Synthesis of 8-Bromooctanoic acid The author mentioned the following in the article:

Menadione (VK3) is used as a powerful inducer of cellular reactive oxygen species (ROS) for many years and displays high anti-cancer activities in vivo. Recently, the development of mitochondria-targeted drugs has been more and more appreciated. Here, thirteen derivatives of VK3, I [R1 = H, Me, MeO, R2 = pyridinium, quinolinium, triphenylphosphonium, n = 9, 6, 4], were synthesized, which could localize in mitochondria by the triphenylphosphonium (TPP) cation or the nitrogen-based cation. The results of cytotoxicity from six human cancer cell lines showed that the targeted compounds I displayed higher activity than VK3 with the average IC50 value around 1μM. The results of cytotoxicity indicated that the substituents on C-2, the linear alkyl chains on C-3 and the cation moiety all could affect the cytotoxicity. The mechanistic studies showed that five representative compounds, I [R1 = Me, R2 = triphenylphosphonium, n = 9; R1 = MeO, R2 = triphenylphosphonium, n = 9; R1 = Me, R2 = pyridinium, n = 9; R1 = Me, R2 = quinolinium, n = 9; R1 = Me, R2 = triphenylphosphonium, n = 4], could localize in cellular mitochondria, elicit ROS burst and collapse mitochondrial membrane potential (ΔΨm), leading to cytochrome C release and apoptosis in MGC-803 cells. Particularly, they could obviously inhibit mitochondrial thioredoxin reductase TrxR2 expression, thus leading to aggravate cellular oxidative stress. In the experiment, the researchers used 8-Bromooctanoic acid(cas: 17696-11-6Application In Synthesis of 8-Bromooctanoic acid)

8-Bromooctanoic acid(cas: 17696-11-6) acid is used in the synthesis of 8-(N-Methyl-4,4′-bipyridinyl)- octanoic acid. 8-Mercaptooctanoic acid was prepared from 8-bromooctanoic acid. And 8-Bromooctanoic Acid is a useful compound for sonodynamic therapy.Application In Synthesis of 8-Bromooctanoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Powell, Chelsea E.; Hatcher, John M.; Jiang, Jie; Vatsan, Prasanna S.; Che, Jianwei; Gray, Nathanael S. published an article in ACS Medicinal Chemistry Letters. The title of the article was 《Selective Macrocyclic Inhibitors of DYRK1A/B》.Related Products of 14660-52-7 The author mentioned the following in the article:

Dual-specificity tyrosine-(Y)-phosphorylation regulated kinase 1A (DYRK1A) is a therapeutic target of interest due to the roles it plays in both neurol. diseases and cancer. We present the development of the first macrocyclic inhibitors of DYRK1A. Initial lead inhibitor JH-XIV-68-3 (3) displayed selectivity for DYRK1A and close family member DYRK1B in biochem. and cellular assays, and demonstrated antitumor efficacy in head and neck squamous cell carcinoma (HNSCC) cell lines. However, we noted that it suffered from rapid aldehyde oxidase (AO)-mediated metabolism To overcome this liability, we generated a derivative (JH-XVII-10 (10)), where fluorine was introduced to block the 2-position of the azaindole and render the mol. resistant to AO activity. We showed that 10 maintains remarkable potency and selectivity in biochem. and cellular assays as well as antitumor efficacy in HNSCC cell lines and improved metabolic stability. Therefore, 10 represents a promising new scaffold for developing DYRK1A-targeting chem. probes and therapeutics.Ethyl 5-bromovalerate(cas: 14660-52-7Related Products of 14660-52-7) was used in this study.

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.Related Products of 14660-52-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Ahmed, Mostafa; Kotp, Mohammed G.; Mansoure, Tharwat Hassan; Lee, Rong-Ho; Kuo, Shiao-Wei; El-Mahdy, Ahmed F. M. published an article in Microporous and Mesoporous Materials. The title of the article was 《Ultrastable carbazole-tethered conjugated microporous polymers for high-performance energy storage》.Application of 6825-20-3 The author mentioned the following in the article:

Conjugated microporous polymers (CMPs) have considered as organic porous polymers featuring combination of p-conjugated skeletons with permanent micro-porosity. In the present study, we report the synthesis of carbazole-tethered conjugated microporous polymers, BC-Py-CMP and BC-BF-CMP, resp., through the Suzuki-Miyaura coupling polymerization of the novel 3,3′,6,6′-tetraboronic-pinacolate-9,9′-bicarbazole (BC-4Bpin) with 1,3,6,8-tetrabromopyrene (Py-4Br) and 3,3′,6,6′-tetrabromo-9,9′-bifluorenylidene (BF-4Br). These CMPs exhibited extraordinary thermal stabilities (up to ca. 694 and 569 °C) and high surface areas (up to ca. 1030 m2 g-1). Moreover, the as-prepared BC-BF-CMP exhibited a high specific capacitance of 260 F g-1 at 0.5 A g-1 and showed outstanding cycling stability, having 89.60% capacitance retention of its authentic capacitance over 6000 cycles. The excellent electrochem. capacitances of the BC-BF-CMP were presumably due to the 9,9′-BF could easily accept one electron, causing the reduced form acquiring greater aromaticity by meeting Huckel′s requirements, as a result improving the electron transporting properties. Such CMPs tend to have tremendous potential to be used as a high-performance supercapacitors in energy storage systems. In addition to this study using 3,6-Dibromo-9H-carbazole, there are many other studies that have used 3,6-Dibromo-9H-carbazole(cas: 6825-20-3Application of 6825-20-3) was used in this study.

3,6-Dibromo-9H-carbazole(cas: 6825-20-3) is used as a pharmaceutical intermediate, and also an important intermediate of synthesizing optoelectronic materials. It has been used as a reagent in the synthesis of P7C3-A20 which is a potent neuroprotective agent.Application of 6825-20-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Liao, Gang; Zhang, Tao; Jin, Liang; Wang, Bing-Jie; Xu, Cheng-Kai; Lan, Yu; Zhao, Yu; Shi, Bing-Feng published an article in Angewandte Chemie, International Edition. The title of the article was 《Experimental and Computational Studies on the Directing Ability of Chalcogenoethers in Palladium-Catalyzed Atroposelective C-H Olefination and Allylation》.Synthetic Route of C9H11Br The author mentioned the following in the article:

The exptl. and DFT computational studies on the directing ability of chalcogenoether motifs in Pd-catalyzed atroposelective C-H functionalization was presented. The thioether motif was found to be a superior directing group compared to the corresponding ether and selenoether in terms of reactivity and enantiocontrol. Remarkably, DFT calculation provided a predictive model for the optimization of reaction conditions and the interpretation of the origin of enantioselectivity. Both Pd-catalyzed enantioselective C-H olefination and allylation reactions were successfully developed using chiral phosphoric acids as efficient ligands, providing a broad range of axially chiral biaryls in good yields with excellent enantioselectivities. The highly enantio- and diastereoselective construction of polyaryls bearing multiple stereogenic axes, gram-scale reaction and various chem. transformations make this protocol more attractive and significant. In the part of experimental materials, we found many familiar compounds, such as 1-Bromo-2-isopropylbenzene(cas: 7073-94-1Synthetic Route of C9H11Br)

1-Bromo-2-isopropylbenzene(cas: 7073-94-1) 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. Synthetic Route of C9H11Br Moreover, several studies demonstrate that the average proportion of bromine in drugs is significantly higher than that in natural products.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary