Category: bromides-buliding-blocks

Synthesis, characterization, and remarkable biological properties of cyclodextrins bearing guanidinoalkylamino and aminoalkylamino groups on their primary side was written by Mourtzis, Nikolaos;Paravatou, Maria;Mavridis, Irene M.;Roberts, Michael L.;Yannakopoulou, Konstantina. And the article was included in Chemistry – A European Journal in 2008.HPLC of Formula: 53784-83-1 This article mentions the following:

The introduction of aminoalkylamino and guanidinoalkylamino substituents on the primary side of β- and γ-cyclodextrin (CDs) resulted in a series of novel compounds that were extensively characterized by NMR spectroscopy and mass spectrometry. Bromination of the primary side of β- and γ-CD, and reaction with neat alkylene diamines at a pressure of 7 atm afforded aminoalkylamino derivatives that were then guanylated at the primary amino group to give the corresponding guanidinoalkylamino-CDs. These compounds are water soluble and display pK_a values that allow them to be mostly protonated at neutral pH; for example, pK_a1 âˆ?.4 and pK_a2 âˆ?.5 for the aminoethylamino-β-CD and pK_a1 âˆ?.8 and pK_a2 âˆ?1.0 for the guanidinoethylamino-β-CD. The title CDs are rigid, cyclic α-D-glucopyranose oligomers (heptamers or octamers) with branches that resemble lysine and arginine side chains that enable multiple interactions with suitable substrates. Thus, they bear similarities to known cell-penetrating peptides. Indeed, the compounds were found to cross the membranes of HeLa cells and penetrate inside the cytoplasm quickly, the guanidinylated ones within 15 min, as shown by fluorescence microscopy using fluorescein-labeled derivatives The toxicity of the compounds, measured by performing MTT tests, ranged from 50 to 300 μM. Furthermore, some of the aminated CDs could facilitate the transfection of DNA expressing the green fluorescent protein (GFP) in HEK 293T cells, with effectiveness comparable to the com. agent Lipofectamine 2000. CD, at. force microscopy and electrophoresis experiments confirmed the strong interaction of the compounds with DNA. Because of their carbohydrate, non-peptide nature the title compounds are not anticipated to be enzymically labile or immunogenic, and thus they fulfill many of the criteria for non-hazardous transport vectors in biol. and pharmaceutical applications. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1HPLC of Formula: 53784-83-1).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) 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.HPLC of Formula: 53784-83-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery of a novel [3.2.1] benzo fused bicyclic sulfonamide-pyrazoles as potent, selective and efficacious γ-secretase inhibitors was written by Ye, Xiaocong M.;Konradi, Andrei W.;Sun, Minghua;Yuan, Shendong;Aubele, Danielle L.;Dappen, Michael;Dressen, Darren;Garofalo, Albert W.;Jagodzinski, Jacek J.;Latimer, Lee;Probst, Gary D.;Sham, Hing L.;Wone, David;Xu, Ying-zi;Ness, Daniel;Brigham, Elizabeth;Kwong, Grace T.;Willtis, Chris;Tonn, George;Goldbach, Erich;Quinn, Kevin P.;Zhang, Hongbin H.;Sauer, John-Michael;Bova, Michael;Basi, Guriqbal S.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.Computed Properties of C8H4BrF3O This article mentions the following:

Structure-activity relation (SAR) of a novel, potent and metabolically stable series of benzo [3.2.1] bicyclic sulfonamide-pyrazoles as γ-secretase inhibitors are described. Compounds that are efficacious in reducing the cortical Aβx-40 levels in FVB mice via oral dose, as well as those with high selectivity over Notch, are highlighted. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Computed Properties of C8H4BrF3O).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) 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). 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.Computed Properties of C8H4BrF3O

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palladium-catalyzed alkoxycarbonylation of unactivated secondary alkyl bromides at low pressure was written by Sargent, Brendon T.;Alexanian, Erik J.. And the article was included in Journal of the American Chemical Society in 2016.Formula: C10H13BrO This article mentions the following:

Catalytic carbonylations of organohalides are important C-C bond formations in chem. synthesis. Carbonylations of unactivated alkyl halides remain a challenge and currently require the use of alkyl iodides under harsh conditions and high pressures of CO. Herein we report a palladium-catalyzed alkoxycarbonylation of secondary alkyl bromides that proceeds at low pressure (2 atm CO) under mild conditions. Preliminary mechanistic studies are consistent with a hybrid organometallic-radical process. These reactions efficiently deliver esters from unactivated alkyl bromides across a diverse range of substrates and represent the first catalytic carbonylations of alkyl bromides with carbon monoxide. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Formula: C10H13BrO).

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). Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Formula: C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

2-Alkyloxyalkylthiohypoxanthines as new potent inhibitors of xanthine oxidase was written by Biagi, Giuliana;Giorgi, Irene;Pacchini, Federica;Livi, Oreste;Scartoni, Valerio. And the article was included in Farmaco in 2001.Reference of 4457-67-4 This article mentions the following:

The title compounds were prepared and tested as xanthine oxidase (XO) inhibitors. Results evidenced that potency was related to the position of the oxygen atom in the 2-linear chain and that it grew with distance from the sulfur atom until it became equipotent to 2-n-hexylthiohypoxanthine. Enzymic oxidation on C(2) occurred in the 8-alkylthiohypoxanthines. On the contrary, oxidation on C(8) did not occur in the 2-alkythioderivatives, demonstrating that the chain forced these mols. to form a complex with molybdenum(VI) involving only the N(3) and N(9) nitrogen atoms. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Reference of 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Reference of 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and anion binding properties of multi-phosphonium triarylboranes: selective sensing of cyanide ions in buffered water at pH 7 was written by Song, Ki Cheol;Lee, Kang Mun;Nghia, Nguyen Van;Sung, Woo Young;Do, Youngkyu;Lee, Min Hyung. And the article was included in Organometallics in 2013.Recommanded Product: 2,5-Dibromo-1,3-dimethylbenzene This article mentions the following:

A series of mono-, di-, and tris-phosphonium-substituted triarylboranes, [Mes₂BAr^P]I ([2]I), [MesBAr^P₂]I₂ ([3]I₂), and [BAr^P₃]I₃ ([4]I₃) (Ar^P = 4-MePh₂P⁺-2,6-Me₂C₆H₂), were prepared from the corresponding neutral boranes 2a–4a. The crystal structure of [4]I₃ determined by x-ray diffraction study reveals peripheral decoration of aryl groups with phosphonium moieties. The anion affinity of the cationic boranes for fluoride and cyanide ions was investigated by UV-vis absorption titrations in aqueous solution The triarylboranes, [2]I-[4]I₃ bind both fluoride and cyanide ions in a DMSO/H₂O (7:3 volume/volume) mixture with high binding constants (K). Comparison of the K values of triarylboranes for fluoride reveals that fluorophilicity increases with the increasing number of phosphonium moieties: [2]⁺ (K = 2.3 × 10¹ M^-1) < [3]²⁺ (3.6 × 10⁵ M^-1) < [4]³⁺ (1.0 × 10⁷ M^-1). A similar trend is also observed in the cyanide binding, with K values that are greater by 2-4 orders of magnitude than those in the fluoride binding. These results indicate an apparent additive effect of multiple phosphonium substitutions on the Lewis acidity enhancement of triarylboranes. The triphosphonium borane [4]Cl₃, a water-soluble form of [4]I₃, was further utilized in evaluating the anion affinity in water. While [4]³⁺ is shown to hardly bind fluoride in buffered aqueous solutions at pH 7, it binds cyanide with a high binding constant (1.7 × 10⁷ M^-1). In the experiment, the researchers used many compounds, for example, 2,5-Dibromo-1,3-dimethylbenzene (cas: 100189-84-2Recommanded Product: 2,5-Dibromo-1,3-dimethylbenzene).

2,5-Dibromo-1,3-dimethylbenzene (cas: 100189-84-2) 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. 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.Recommanded Product: 2,5-Dibromo-1,3-dimethylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A Nickel(II)-Mediated Thiocarbonylation Strategy for Carbon Isotope Labeling of Aliphatic Carboxamides was written by Pedersen, Simon S.;Donslund, Aske S.;Mikkelsen, Jesper H.;Bakholm, Oskar S.;Papp, Florian;Jensen, Kim B.;Gustafsson, Magnus B. F.;Skrydstrup, Troels. And the article was included in Chemistry – A European Journal in 2021.Application In Synthesis of 15-Bromopentadecanoic acid This article mentions the following:

A series of pharmaceutically relevant small mols. and biopharmaceuticals bearing aliphatic carboxamides have been successfully labeled with carbon-13. Key to the success of this novel carbon isotope labeling technique is the observation that ¹³C-labeled Ni(II)-acyl complexes, formed from a ¹³CO insertion step with Ni(II)-alkyl intermediates, rapidly react in less than one minute with 2,2′-dipyridyl disulfide to quant. form the corresponding 2-pyridyl thioesters. Either the use of ¹³C-SilaCOgen or ¹³C-COgen allows for the stoichiometric addition of isotopically labeled carbon monoxide. Subsequent one-pot acylation of a series of structurally diverse amines provides the desired ¹³C-labeled carboxamides in good yields. A single electron transfer pathway is proposed between the Ni(II)-acyl complexes and the disulfide providing a reactive Ni(III)-acyl sulfide intermediate, which rapidly undergoes reductive elimination to the desired thioester. By further optimization of the reaction parameters, reaction times down to only 11 min were identified, opening up the possibility of exploring this chem. for carbon-11 isotope labeling. Finally, this isotope labeling strategy could be adapted to the synthesis of ¹³C-labeled liraglutide and insulin degludec, representing two antidiabetic drugs. In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Application In Synthesis of 15-Bromopentadecanoic acid).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nitric Oxide-Releasing Cyclodextrins was written by Jin, Haibao;Yang, Lei;Ahonen, Mona Jasmine R.;Schoenfisch, Mark H.. And the article was included in Journal of the American Chemical Society in 2018.Synthetic Route of C42H63Br7O28 This article mentions the following:

A series of secondary amine-modified cyclodextrin (CD) derivatives were synthesized with diverse exterior terminal groups (i.e., hydroxyl, Me, methoxyl, and primary amine). Subsequent reaction with nitric oxide (NO) gas under alk. conditions yielded N-diazeniumdiolate-modified CD derivatives Adjustable NO payloads (0.6-2.4 μmol/mg) and release half-lives (0.7-4.2 h) were achieved by regulating both the amount of secondary amine precursors and the functional groups around the NO donor. The bactericidal action of these NO-releasing cyclodextrin derivatives was evaluated against Pseudomonas aeruginosa, a Gram-neg. pathogen with antibacterial activity proving dependent on both the NO payload and exterior modification. Materials containing a high d. of NO donors or primary amines exhibited the greatest ability to eradicate P. aeruginosa. Of the materials prepared, only the primary amine-terminated hepta-substituted CD derivatives exhibited toxicity against mammalian L929 mouse fibroblast cells. The NO donor-modified CD was also capable of delivering promethazine, a hydrophobic drug, thus demonstrating potential as a dual-drug releasing therapeutic. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Synthetic Route of C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Synthetic Route of C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Halogenated Bis(methoxybenzylidene)-4-piperidone Curcuminoids with Improved Anticancer Activity was written by Schmitt, Florian;Subramaniam, Dharmalingam;Anant, Shrikant;Padhye, Subhash;Begemann, Gerrit;Schobert, Rainer;Biersack, Bernhard. And the article was included in ChemMedChem in 2018.Formula: C8H6Br2O2 This article mentions the following:

A series of readily available curcuminoids with a halogenated bis(4-methoxy/4,5-dimethoxybenzylidene)-4-piperidone structure were prepared and analyzed for their cytotoxic impact on eight human cancer cell lines of five different entities. The known 3,4,5-trimethoxybenzylidene curcuminoid 2a and the new bis-(3-bromophenyl) and bis-(3,5-dibromophenyl) derivatives 3c ((E)-1-ethyl-3,5-bis(3-bromo-4,5-dimethoxybenzylidene)-4-piperidone HCl) and 3d ((E)-1-ethyl-3,5-bis(3,5-dibromo-4-methoxybenzylidene)-4-piperidone HCl) proved to be more strongly antiproliferative than the known curcuminoid EF24 against six of these cell lines. Compounds 2a and 3c caused a distinct increase of reactive oxygen species, which eventually elicited apoptosis in 518A2 melanoma cells. Compound 2a arrested 518A2 melanoma cells in G₁ phase of the cell cycle and had no effect on the expression of pro-metastatic matrix metalloproteinases MMP-2 and MMP-9, whereas 3c led to an accumulation of 518A2 cells in the G₂/M phase and to a downregulation of MMP-2 expression. In addition, treatment with 2a and 3c resulted in significant inhibition of colony formation in HCT116 cells. Both 2a and 3c showed antiangiogenic activity, for example, by inhibiting the formation of sub-intestinal veins (SIV) in zebrafish embryos. Compound 3c was also well tolerated by mice and inhibited the growth of HCT116 colon cancer xenografts. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Formula: C8H6Br2O2).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.Formula: C8H6Br2O2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palladium-catalyzed diastereoselective cross-coupling of two aryl halides via C-H activation: synthesis of chiral eight-membered nitrogen heterocycles was written by Cheng, Cang;Zuo, Xiang;Tu, Dongdong;Wan, Bin;Zhang, Yanghui. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.SDS of cas: 173026-23-8 This article mentions the following:

A method for the synthesis of enantiopure eight-membered nitrogen heterocycles, e.g., I was developed through diastereoselective cross-coupling of 2-iodobiphenyls with 2-bromobenzylamines. The products represented a novel type of chiral scaffold, which feature easy modification and high configurative stability and had the potential to be applied in asym. synthesis. Palladacycles that were formed via the C-H activation of 2-iodobiphenyls should act as the intermediates. The reaction provided a new strategy for the synthesis of medium-sized ring compounds In the experiment, the researchers used many compounds, for example, 2-(2-Bromophenyl)propan-2-amine (cas: 173026-23-8SDS of cas: 173026-23-8).

2-(2-Bromophenyl)propan-2-amine (cas: 173026-23-8) 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. 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.SDS of cas: 173026-23-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Non-ionic thiolated cyclodextrins – the next generation was written by Moghadam, Ali;Ijaz, Muhammad;Asim, Mulazim Hussain;Mahmood, Arshad;Jelkmann, Max;Matuszczak, Barbara;Bernkop-Schnuerch, Andreas. And the article was included in International Journal of Nanomedicine in 2018.Synthetic Route of C42H63Br7O28 This article mentions the following:

The current study was aimed at developing a novel mucoadhesive thiolated cyclodextrin (CD) without ionizable groups and an intact ring backbone for drug delivery. Thiolated beta CD (β-CD) was prepared through bromine substitution of its hydroxyl groups followed by replacement to thiol groups using thiourea. The thiolated β-CD was characterized in vitro via dissolution studies, cytotoxicity studies, mucoadhesion studies on freshly excised porcine intestinal mucosa, and inclusion complex formation with miconazole nitrate. Thiolated β-CDs namely β-CD-SH₆₀₀ and β-CD-SH₁₂₀₀ displayed 558.66 ± 78 and 1,163.45 ± 96 μmol thiol groups per g of polymer, resp. Stability constant (Kc) of 190 M^-1 confirmed the inclusion complex formation of miconazole nitrate with β-CD-SH. Inclusion complexes of β-CD-SH₆₀₀ and β-CD-SH₁₂₀₀ resulted in 157- and 257-fold increased solubility of miconazole nitrate, resp. In addition, more than 80% of thiol groups were stable even after 6 h at pH 5. Both β-CD-SH compounds showed at least 1.3-fold improved solubility in water. In contrast to cationic thiolated CDs of the first generation, both thiomers showed no significant cytotoxicity. The mucoadhesive properties of the new thiolated CDs were 39.73- and 46.37-fold improved, resp. These results indicate that β-CD-SH might provide a new favorable tool for delivery of poorly soluble drugs providing a prolonged residence time on mucosal surfaces. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Synthetic Route of C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) 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. 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 C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary