Author: Jessica.F

Regioselective halogenation of primary alcohol groups of cyclodextrins with halomethylenemorpholinium halides Vilsmeier-Haack reagents was written by Chmurski, K.;Defaye, J.. And the article was included in Polish Journal of Chemistry in 1999.Recommanded Product: 53784-83-1 This article mentions the following:

Per(6-bromo-6-deoxy)cyclomalto-hexaose, -heptaose, and -octaose and the corresponding per(6-chloro-6-deoxy) derivatives were prepared in high yield by reaction of bromomethylenemorpholinium bromide or chloromethylenemorpholinium chloride, resp., with cyclomaltohexaose, cyclomaltoheptaose and cyclomaltooctaose in DMF. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin (cas: 53784-83-1Recommanded Product: 53784-83-1).

Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin (cas: 53784-83-1) 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鑱砨romine bond is electrophilic in nature. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Recommanded Product: 53784-83-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Arylcyclopropanecarboxyl Guanidines as Novel, Potent, and Selective Inhibitors of the Sodium Hydrogen Exchanger Isoform-1 was written by Ahmad, Saleem;Doweyko, Lidia M.;Dugar, Sundeep;Grazier, Nyeemah;Ngu, Khehyong;Wu, Shung C.;Yost, Kenneth J.;Chen, Bang-Chi;Gougoutas, Jack Z.;DiMarco, John D.;Lan, Shih-Jung;Gavin, Brian J.;Chen, Alice Y.;Dorso, Charles R.;Serafino, Randy;Kirby, Mark;Atwal, Karnail S.. And the article was included in Journal of Medicinal Chemistry in 2001.Recommanded Product: Methyl 3-bromo-4-fluorobenzoate This article mentions the following:

A novel series of arylcyclopropanecarboxyl guanidines was synthesized and evaluated for activity against the sodium hydrogen exchanger isoform-1 (NHE-1). In biol. assays conducted in an AP1 cell line expressing the human NHE-1 isoform, the starting cyclopropane (IC₅₀ = 3.5 娓璏) shows inhibitory activity comparable to cariporide (IC₅₀ = 3.4 娓璏). Structure-activity relationships are used to optimize the affinity of various acyl guanidines for NHE-1 by screening the effect of substituents at both aryl and cyclopropyl rings. It is demonstrated that introduction of appropriate hydrophobic groups at the Ph ring and a gem-di-Me group at the cyclopropane ring enhances the NHE-1 inhibitory activity by up to 3 orders of magnitude (IC₅₀ = 0.003 娓璏). In addition, the gem-di-Me series of analogs seem to display improved oral bioavailability and longer plasma half-life in rats. Furthermore, the lead benzodihydrofuranyl analog (BMS-284640) shows over 380-fold increased NHE-1 inhibitory activity as well as improved selectivity for NHE-1 over NHE-2 compared to cariporide. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-4-fluorobenzoate (cas: 82702-31-6Recommanded Product: Methyl 3-bromo-4-fluorobenzoate).

Methyl 3-bromo-4-fluorobenzoate (cas: 82702-31-6) 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. 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.Recommanded Product: Methyl 3-bromo-4-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

6-Methoxy-1-tetralone Derivatives Bearing an N-Arylpyridinium Moiety as Cholinesterase Inhibitors: Design, Synthesis, Biological Evaluation, and Molecular Docking Study was written by Chehardoli, Gholamabbas;Gholamhoseini, Pooriya;Ebadi, Ahmad;Ziaei, Maral;Akbarzadeh, Tahmineh;Saeedi, Mina;Mahdavi, Mohammad;Khoshneviszadeh, Mehdi;Najafi, Zahra. And the article was included in ChemistrySelect in 2022.Product Details of 954-81-4 This article mentions the following:

A novel series of 6-methoxy-1-tetralone derivatives bearing N-aryl pyridinium moiety I (Ar = C₆H₅, 2-FC₆H₄, 3-ClC₆H₄, etc.; n = 1, 2, 3, 4, 5; X = Cl, Br) were designed, synthesized, and evaluated as acetyl and butyrylcholinesterase inhibitors. The designed derivatives inhibited acetylcholinesterase (AChE) with IC₅₀ values of 0.025-23.743娓璏 and butyrylcholinesterase (BChE) with IC₅₀ values of 0.716-20.588娓璏. The synthesized compounds were divided into two series. Derivatives containing N-benzyl moieties generally were more potent anti-AChE and anti-BChE agents than compounds with N-alkylphthalimide groups. Among them, the compound I (Ar = C₆H₅; n = 1; X = Br) and compound I (Ar = 3-ClC₆H₄; n = 1; X = Br) exhibited significant inhibitory activity against AChE and BChE with IC₅₀ values of 0.025 and 0.716娓璏 in comparison to donepezil as a reference drug (0.029 and 0.948娓璏, resp.). The results of kinetic and mol. modeling studies demonstrated that the synthesized compounds I (Ar = C₆H₅; n = 1; X = Br) and I (Ar = 3-ClC₆H₄; n = 1; X = Br) derivatives can act as mixed and dual binding inhibitors, and bind to both CAS and PAS of AChE and BChE enzymes. Among the assessed compounds, the compound I (Ar = C₆H₅; n = 1; X = Br) indicated significant neuroprotection against H₂O₂-induced cell death in PC12 cells. So, these findings indicate the therapeutic potential of 6-methoxy-1-tetralone derivatives bearing N-aryl pyridinium moiety derivatives as anti-AD agents. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Product Details of 954-81-4).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) 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. 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.Product Details of 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of 9,10-dihydroanthracen-9,10-imines was written by Anderson, Paul S.;Christy, Marcia E.;Colton, C. Dylion;Halczenko, Wasyl;Ponticello, Gerald S.;Shepard, Kenneth L.. And the article was included in Journal of Organic Chemistry in 1979.Reference of 452-62-0 This article mentions the following:

The cycloaddition of benzynes with isoindoles to generate the 9,10-dihydroanthracen-9,10-imine system (I) was examined in detail. A versatile synthesis of these ring-strained heterocycles based on a detailed anal. of the 2,3-dihydro-1H-isoindol-1-one (phthalimidine) approach to the prerequisite isoindoles is presented. A variety of synthetic methods to phthalimidines were evaluated and developed including: reductive amination of o-acylbenzoic acids; amidoalkylation of benzoic acids; halogenation and amination of o-alkylbenzoic acids; and reduction of phthalimides. In addition, generation of benzynes from chlorobenzenes and Li tetramethylpiperidide greatly increase the scope of the Diels-Alder reaction to form the desired products. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-fluorotoluene (cas: 452-62-0Reference of 452-62-0).

3-Bromo-4-fluorotoluene (cas: 452-62-0) 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鑱砨romine bond is electrophilic in nature. 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.Reference of 452-62-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

One-pot cascade synthesis of azabicycles via the nitro-Mannich reaction and N-alkylation was written by Disadee, Wannaporn;Ruchirawat, Somsak. And the article was included in Organic & Biomolecular Chemistry in 2018.Electric Literature of C13H14BrNO2 This article mentions the following:

A one-pot, metal-free process for the synthesis of azabicycles is developed. The key transformations involved a cascade of double intramol. cyclizations via the nitro-Mannich reaction and N-alkylation, providing various ring systems of azabicycles in yields up to 81% and an isomeric ratio of 62 : 1. This approach offers considerable advantages in terms of the handling of small mols., the flexibility to introduce a functionalized side chain, and gives direct access to various azabicycles. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Electric Literature of C13H14BrNO2).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon閳ユ彽romine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Electric Literature of C13H14BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A Bulky Biaryl Phosphine Ligand Allows for Palladium-Catalyzed Amidation of Five-Membered Heterocycles as Electrophiles was written by Su, Mingjuan;Buchwald, Stephen L.. And the article was included in Angewandte Chemie, International Edition in 2012.Computed Properties of C7H8BrNO2 This article mentions the following:

The first palladium-catalyzed amidation of five-membered heterocyclic bromides with multiple heteroatoms was achieved using the Pd/I catalyst system. N-Arylated imidazoles, pyrazoles, thiazoles, pyrroles, and thiophenes were synthesized in moderate to excellent yield. Exptl. results and DFT calculations point to the need for an electron-rich and sterically demanding biaryl phosphine ligand to promote these difficult reactions. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate (cas: 1196-90-3Computed Properties of C7H8BrNO2).

Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate (cas: 1196-90-3) 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. 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.Computed Properties of C7H8BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Methylated 1,2,3-triazoles. II was written by Begtrup, Mikael;Pedersen, Christian. And the article was included in Acta Chemica Scandinavica (1947-1973) in 1966.Reference of 13273-53-5 This article mentions the following:

1-Methyl-5-methoxy-1,2,3-triazole (I) with MeI yielded 1,3-dimethyl-4-methoxy-1,2,3-triazolium iodide (II) which was also prepared from 1,3-dimethyl-1,2,3-triazol-4-one (III) with MeI or from 1,3-dimethyl-4-bromo-1,2,3-triazolium iodide (IV) with NaOMe. II heated or kept in CHCl3 at room temperature lost MeI to give III. The chloride analog (V) of IV with NaOH gave a compound believed to be the 5-Br derivative (VI) of III; it was also obtained by the bromination of III. 1-Methyl-4-bromo-1,2,3-triazole (417 mg.) and 2.5 cc. MeI heated 6 hrs. in a sealed tube, and the product stirred 2 hrs. in EtOH with excess AgCl gave 440 mg. V, m. 193鎺?(EtOH-Et2O). IV (98 mg.), 8.0 mg. Na, and 3.5 cc. MeOH heated 2 hrs. at 75鎺? treated with 70 mg. NaI, stirred 15 min., and filtered gave 3 mg. II; the mother liquors yielded 35 mg. III. V (70 mg.) and 0.17 cc. soln, of 220 mg. Na in 5 cc. EtOH heated 3 hrs. at 70鎺? neutralized with CO2, and worked up gave 63 mg. 1,3-dimethyl-4-ethoxy-1,2,3-triazolium chloride (VII), yellow, hygroscopic oil. III (30 mg.) refluxed 3 hrs. with 2 cc. EtI, and the product (74 mg.) stirred 1 hr. in EtOH with excess AgCl yielded 49 mg. yellowish, oily, hygroscopic VII. III (217 mg.) refluxed 3 hrs. with 2 cc. MeI gave 455 mg. yellow II, m. 111鎺?(MeOH-Et2O). II (19 mg.) in 0.5 cc. CDCl3 in an N.M.R. tube kept at room temperature showed after 4 days the spectrum of III; the solution evaporated gave 9 mg. III, m. 78-85鎺? VII in CHCl3 was unchanged, after 4 days at room temperature, but heated 1 hr. at 80鎺?gave III. I (50 mg.) in 0.5 cc. CDCl3 and 0.10 cc. MeI kept 6 weeks at room temperature in a N.M.R. tube and evaporated left 44 mg. III, m. 78-85鎺? a similar run gave during 48 hrs. 53% II. V (92 mg.) in 4 cc. N NaOH heated 16 hrs. at 100鎺?in a sealed tube and neutralized with N HCl, and the crude product chromatographed on silica gel yielded 22 mg. VI, m. 141鎺? III (112 mg.) in 1 cc. CHCl3 treated with 0.05 cc. Br in 5 cc. cold CHCl3 and filtered after 10 min., and the residue stirred 1 hr. in H2O with excess Amberlite IR-4B gave 84 mg. VI, m. 141鎺? the mother liquor residue treated similarly with Amberlite yielded 48 mg. VI, m. 141鎺? In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methyl-1H-1,2,3-triazole (cas: 13273-53-5Reference of 13273-53-5).

4-Bromo-1-methyl-1H-1,2,3-triazole (cas: 13273-53-5) 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 reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Reference of 13273-53-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Novel polycarboxylated EDTA-type cyclodextrins as ligands for lanthanide binding: study of their luminescence, relaxivity properties of Gd(III) complexes, and PM3 theoretical calculations was written by Maffeo, Davide;Lampropoulou, Maria;Fardis, Michael;Lazarou, Yannis G.;Mavridis, Irene M.;Mavridou, Despoina A. I.;Urso, Elena;Pratsinis, Harris;Kletsas, Dimitris;Yannakopoulou, Konstantina. And the article was included in Organic & Biomolecular Chemistry in 2010.Application In Synthesis of Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin This article mentions the following:

Novel EDTA-type cyclodextrin (CD) derivatives, AEDTA, BEDTA and GEDTA, bearing 6, 7 and 8 bis(carboxymethyl)amino (iminodiacetic acid) groups, resp., were prepared, and their complexation with Eu(III), Tb(III) and Gd(III) ions was studied. Luminescence titrations and mass spectrometry showed formation of multimetal complexes (AEDTA 2 to 3, BEDTA mainly 3 and GEDTA exactly 4 metal ions), whereas luminescence lifetime measurements revealed the presence of exchangeable water mols. Semiempirical quantum mech. calculations, performed by the PM3 method and assessed by DFT calculations on model ligands, indicated efficient multi-metal complexation, in agreement with the experiment The structures showed coordination of the metal ions in the outer primary side of the CDs via 4 carboxylate O atoms, 2 N atoms and a glucopyranose O atom per metal ion. Coordination of water mols. was also predicted, in accordance with exptl. results. Calculated bond lengths and angles were in agreement with literature exptl. values of lanthanide complexes. Calculated energies showed that complex stability decreases in the order GEDTA > BEDTA > AEDTA. ¹H NMR mol. relaxivity measurements for the Gd(iii) complexes of AEDTA, BEDTA or GEDTA in water afforded values 4 to 10 times higher than the relaxivity of a com. contrast agent at 12 MHz, and 6 to 20 times higher at 100 MHz. Solutions of BEDTA and GEDTA Gd(III) complexes in human blood plasma displayed relaxivity values at 100 MHz 7 and 12 times, resp., higher than the com. agent. MTT tests of the Gd(III) complexes using human skin fibroblasts did not show toxicity. Attempts to supramolecularly sensitize the luminescence of the lanthanide complexes using various aromatic CD guests were ineffective, evidently due to large guest-metal distances and inefficient inclusion. The described lanthanide complexes, could be useful as contrast agents in MRI. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin (cas: 53784-83-1Application In Synthesis of Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Influence of Host’s Substitution on the Orientation of the Guest: Pseudo-rotaxanes of Charged Cyclodextrins with Methyl Orange in Solution was written by Mourtzis, Nikolaos;Eliadou, Kyriaki;Yannakopoulou, Konstantina. And the article was included in Supramolecular Chemistry in 2004.Formula: C42H63Br7O28 This article mentions the following:

Methyl orange (MO), an azo-dye mol. with an inherent dipole moment, has been used as a probe to explore the influence of anionic or cationic substituents of cyclodextrins (CDs) on the mode of insertion to form pseudorotaxanes, using NMR spectroscopy. MO is oriented in a single mode inside the 灏綜D cavity, with the dimethylamino group localized at the secondary side. This orientation is completely reversed when MO enters the anionic sodium heptakis[6-deoxy-6-(3-thiopropionate)]-灏綜D (灏緋sp) cavity, whereas inside the cationic heptakis(6-deoxy-6-amino)-灏綜D hydrochloride, MO flips once more, to adopt the same orientation as in 灏綜D. In the latter case the water solubility of MO is significantly lowered. The disposition of the guest in 灏綜D and in each 灏綜D derivative in a single mode was attributed principally to anti-parallel dipole-dipole stabilization. In the wider 绾珻D, the availability of more cavity space leads to 1:2 and 2:2 host/guest stoichiometries and the effect of dipoles is of secondary significance. In the anionic sodium octakis[6-deoxy-6-(3-thiopropionate)]-绾珻D, MO is positioned as in 灏緋sp, but a 1:2 adduct is also detected. Finally, MO does not dissolve in octakis(6-deoxy-6-amino)-绾珻D hydrochloride solution In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin (cas: 53784-83-1Formula: C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-灏?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. 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.Formula: C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery and characterization of AZD9272 and AZD6538-Two novel mGluR5 negative allosteric modulators selected for clinical development was written by Raboisson, Patrick;Breitholtz-Emanuelsson, Anna;Dahlloef, Henrik;Edwards, Louise;Heaton, William L.;Isaac, Methvin;Jarvie, Keith;Kers, Annika;Minidis, Alexander B. E.;Nordmark, Anna;Sheehan, Susan M.;Slassi, Abdelmalik;Stroem, Peter;Terelius, Ylva;Wensbo, David;Wilson, Julie M.;Xin, Tao;McLeod, Donald A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Recommanded Product: Methyl 3-bromo-5-fluorobenzoate This article mentions the following:

AZD9272 and AZD6538 are two novel mGluR5 neg. allosteric modulators selected for further clin. development. An initial high-throughput screening revealed leads with promising profiles, which were further optimized by minor, yet indispensable, structural modifications to bring forth these drug candidates. Advantageously, both compounds may be synthesized in as little as one step. Both are highly potent and selective for the human as well as the rat mGluR5 where they interact at the same binding site than MPEP. They are orally available, allow for long interval administration due to a high metabolic stability and long half-lives in rats and permeate the blood brain barrier to a high extent. AZD9272 has progressed into phase I clin. studies. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-5-fluorobenzoate (cas: 334792-52-8Recommanded Product: Methyl 3-bromo-5-fluorobenzoate).

Methyl 3-bromo-5-fluorobenzoate (cas: 334792-52-8) 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鑱砨romine bond is electrophilic in nature. 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.Recommanded Product: Methyl 3-bromo-5-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary