Month: February 2023

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

Discovery of Dihydro-1,4-Benzoxazine Carboxamides as Potent and Highly Selective Inhibitors of Sirtuin-1 was written by Spinck, Martin;Bischoff, Matthias;Lampe, Philipp;Meyer-Almes, Franz-Josef;Sievers, Sonja;Neumann, Heinz. And the article was included in Journal of Medicinal Chemistry in 2021.Quality Control of 2-(Bromomethyl)-1,3-dimethylbenzene This article mentions the following:

Sirtuins are signaling hubs orchestrating the cellular response to various stressors with roles in all major civilization diseases. Sirtuins remove acyl groups from lysine residues of proteins, thereby controlling their activity, turnover, and localization. The seven human sirtuins, SirT1-7, are closely related in structure, hindering the development of specific inhibitors. Screening 170,000 compounds, we identify and optimize SirT1-specific benzoxazine inhibitors, Sosbo, which rival the efficiency and surpass the selectivity of selisistat (EX527). The compounds inhibit the deacetylation of p53 in cultured cells, demonstrating their ability to permeate biol. membranes. Kinetic anal. of inhibition and docking studies reveal that the inhibitors bind to a complex of SirT1 and NAD, similar to selisistat. These new SirT1 inhibitors are valuable alternatives to selisistat in biochem. and cell biol. studies. Their greater selectivity may allow the development of better targeted drugs to combat SirT1 activity in diseases such as cancer, Huntington’s chorea, or anorexia. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7Quality Control of 2-(Bromomethyl)-1,3-dimethylbenzene).

2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) 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.Quality Control of 2-(Bromomethyl)-1,3-dimethylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Development of coumarin-based hydroxamates as histone deacetylase inhibitors with antitumor activities was written by Zhao, Na;Yang, Feifei;Han, Lina;Qu, Yuhua;Ge, Di;Zhang, Hua. And the article was included in Molecules in 2020.COA of Formula: C9H11Br This article mentions the following:

Histone deacetylases (HDACs) have been proved to be promising targets for the treatment of cancer, and five histone deacetylase inhibitors (HDACis) have been approved on the market for the treatment of different lymphomas. In our previous work, we designed a series of novel coumarin-containing hydroxamate HDACis, among which compounds 6 and 7 displayed promising activities against tumor growth. Based on a mol. docking study, we further developed 26 addnl. analogs with the aim to improve activity of designed compounds Several of these new derivatives not only showed excellent HDAC1 inhibitory effects, but also displayed significant growth inhibitory activities against four human cancer cell lines. Representative compounds, 13a and 13c, showed potent anti-proliferative activities against solid tumor cell lines with IC₅₀ values of 0.36-2.91 microM and low cytotoxicity against Beas-2B and L-02 normal cells. Immunoblot anal. revealed that 13a and 13c dose-dependently increased the acetylation of histone H3 and H4. Importantly, the two compounds displayed much better anti-metastatic effects than SAHA against the MDA-MB-231 cell line. Moreover, 13a and 13c arrested MDA-MB-231 cells at G2/M phase and induced MDA-MB-231 cell apoptosis. Finally, the mol. docking study rationalized the high potency of compound 13c. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7COA of Formula: C9H11Br).

2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) 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.COA of Formula: C9H11Br

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

High-Temperature and Dynamic RGB (Red-Green-Blue) Long-Persistent Luminescence in an Anti-Kasha Organic Compound was written by Zhang, Qiang-Sheng;Wang, Shi-Cheng;Xiong, Xiao-Hong;Fu, Peng-Yan;Zhang, Xiao-Dong;Fan, Ya-Nan;Pan, Mei. And the article was included in Angewandte Chemie, International Edition in 2022.Application of 128-08-5 This article mentions the following:

Organic LPL (long-persistent luminescence) materials have sparked extensive research interest due to the ultralong-lived triplet states. Although numerous organic LPL materials were reported, most of the triplet emission was static and monotonous. LPL materials with dynamic triplet emission are urgently required. 2,4,6-Tris(diphenylamino)-1,3,5-triazine (1) with dynamic long-persistent luminescence (LPL) was fabricated. The single-crystal structure shows that the abundant intermol. interactions and small free volume restrict the mol. motion and avoid the quenchers. Spectral and theor. calculations upheld the existence of multiple excited states in 1, and the migration of electrons between multiple excited states is sensitive to external stimuli. By modulating the stimulus, the residence of electrons in different triplet states can be manipulated to achieve RGB LPL. Blue LPL was achieved by manipulating the anti-Kasha emission. The red LPL can still be observed at high temperature In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Application of 128-08-5).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) 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.Application of 128-08-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Electrochemically stable carbazole-derived polyaniline for pseudocapacitors was written by Almtiri, Mohammed;Dowell, Timothy J.;Giri, Hari;Wipf, David O.;Scott, Colleen N.. And the article was included in ACS Applied Polymer Materials in 2022.HPLC of Formula: 128-08-5 This article mentions the following:

Supercapacitor energy storage devices are well suited to meet the rigorous demands of future portable consumer electronics (PCEs) due to their high energy and power densities (i.e., longer battery-life and rapid charging, resp.) and superior operational lifetimes (10 times greater than lithium-ion batteries). To date, research efforts have been narrowly focused on improving the specific capacitance of these materials; however, emerging technologies are increasingly demanding competitive performance with regards to other criteria, including scalability of fabrication and electrochem. stability. In this regard, we developed a polyaniline (PANI) derivative that contains a carbazole unit copolymerized with 2,5-dimethyl-p-phenylenediamine (Cbz-PANI-1) and determined its optoelectronic properties, elec. conductivity, processability, and electrochem. stability. Importantly, the polymer exhibits good solubility in various solvents, which enables the use of scalable spray-coating and drop-casting methods to fabricate electrodes. Cbz-PANI-1 was used to fabricate electrodes for supercapacitor devices that exhibits a maximum areal capacitance of 64.8 mF cm^-2 and specific capacitance of 319 F g^-1 at a c.d. of 0.2 mA cm^-2. Moreover, the electrode demonstrates excellent cyclic stability (閳?83% of capacitance retention) over 1000 CV cycles. Addnl., we demonstrate the charge storage performance of Cbz-PANI-1 in a sym. supercapacitor device, which also exhibits excellent cyclic stability (閳?91% of capacitance retention) over 1000 charge-discharge cycles. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5HPLC of Formula: 128-08-5).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) 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. 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.HPLC of Formula: 128-08-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds was written by Pallesen, Jakob S.;Narayanan, Dilip;Tran, Kim T.;Solbak, Sara M. Oe.;Marseglia, Giuseppe;Soerensen, Louis M. E.;Hoej, Lars J.;Munafo, Federico;Carmona, Rosa M. C.;Garcia, Anthony D.;Desu, Haritha L.;Brambilla, Roberta;Johansen, Tommy N.;Popowicz, Grzegorz M.;Sattler, Michael;Gajhede, Michael;Bach, Anders. And the article was included in Journal of Medicinal Chemistry in 2021.Category: bromides-buliding-blocks This article mentions the following:

Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-mol. Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallog. to bind in the Keap1 Kelch binding pocket. Two hits were merged into pyrazole I with a 220-380-fold stronger affinity (K_i = 16娓璏) relative to the parent fragments. Systematic optimization resulted in several novel analogs with K_i values of 0.04-0.5娓璏, binding modes determined by X-ray crystallog., and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI. In the experiment, the researchers used many compounds, for example, 3-Bromo-5-chlorophenylamine (cas: 96558-78-0Category: bromides-buliding-blocks).

3-Bromo-5-chlorophenylamine (cas: 96558-78-0) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary