Month: December 2022

A convenient and efficient H₂SO₄-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide was written by Wu, Yong-Qi;Lu, Hai-Jia;Zhao, Wen-Ting;Zhao, Hong-Yi;Lin, Zi-Yun;Zhang, Dong-Feng;Huang, Hai-Hong. And the article was included in Synthetic Communications in 2020.HPLC of Formula: 4133-72-6 This article mentions the following:

A convenient, rapid H₂SO₄-promoted regioselective monobromination reaction with N-bromosuccinimide was developed. The desired para-monobrominated or ortho-monobrominated products of phenol derivatives e.g., I were obtained in good to excellent yields with high selectivity. Regioselective chlorination and iodination were also achieved in the presence of H₂SO₄ using N-chlorosuccinimide and N-iodosuccinimide, resp. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-4-fluoro-2-hydroxybenzoate (cas: 4133-72-6HPLC of Formula: 4133-72-6).

Methyl 5-bromo-4-fluoro-2-hydroxybenzoate (cas: 4133-72-6) 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. 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.HPLC of Formula: 4133-72-6

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design, synthesis and biological evaluation of multi-substituted N-phenyl-2,2-dichloro acetamide analogues as anti-cancer drugs was written by Li, Tian-wen;Yang, Yong-chong;Cheng, Chang-mei;Wang, Dong-chun;Lu, Ai-jun;Zhao, Yu-fen. And the article was included in Yaoxue Xuebao in 2012.HPLC of Formula: 96558-78-0 This article mentions the following:

Our earlier research has shown that mono-substituted N-phenyl-2,2-dichloro acetamide exhibits much higher anti-cancer activity than the lead compound sodium dichloro acetate (DCA). In this paper, a variety of multi-substituted N-phenyl-2, 2-dichloro acetamide were synthesized and biol. evaluated. The results showed that 3,5-disubstituted N-phenyl-2,2-dichloro acetamide analogs had satisfactory potency. Among them, N-(3,5-diiodophenyl)-2,2-dichloroacetamide had an IC₅₀ of 2.84 μmol·L^-1 against non-small cell lung cancer cell line A549 and could induce cancer cell apoptosis. In the experiment, the researchers used many compounds, for example, 3-Bromo-5-chlorophenylamine (cas: 96558-78-0HPLC of Formula: 96558-78-0).

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. 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.HPLC of Formula: 96558-78-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery of selective glucocorticoid receptor modulator MK-5932 was written by Bungard, Christopher J.;Hartman, George D.;Manikowski, Jesse J.;Perkins, James J.;Bai, Chang;Brandish, Philip E.;Euler, Danielle H.;Hershey, James C.;Schmidt, Azriel;Fang, Yulin;Norcross, Ryan T.;Rushmore, Tom H.;Thompson, Charles D.;Meissner, Robert S.. And the article was included in Bioorganic & Medicinal Chemistry in 2011.Application of 653-92-9 This article mentions the following:

A series of partial agonists of the Glucocorticoid Receptor were prepared targeting reduced transactivation activity, while maintaining significant transrepression activity. Incorporation of an ortho-aryl amide produced compounds with the desired in vitro profile. Bioreactors consisting of Suspension cultures of Sf21 cells co expressing a CYP3A4 and NADPH-cytochrome P 450 oxireductase were used to prepare the major metabolites of these compounds and revealed that oxidative N-dealkylation provided a pathway for formation of metabolites that were more agonistic than the parent partial agonists. Oxidative N-dealkylation was blocked in a new series of compounds, however oxidation alone was capable of producing full agonist metabolites. Incorporation of an ortho-primary amide and utilization of fluorine to modulate agonism afforded partial agonist MK-5932 (I). Synthesis of the major metabolites of MK-5932 using bioreactor technol. revealed that no significant GR-active metabolites were formed. Orally administered MK-5932 displayed anti-inflammatory efficacy in a Rat Oxazolone-induced chronic dermatitis model, while sparing plasma insulin. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Application of 653-92-9).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) 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. 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.Application of 653-92-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synergistic Effect: Hydroalkoxylation of Allenes through Combination of Enantiopure BIPHEP-Gold Complexes and Chiral Anions was written by Aikawa, Kohsuke;Kojima, Masafumi;Mikami, Koichi. And the article was included in Advanced Synthesis & Catalysis in 2010.Category: bromides-buliding-blocks This article mentions the following:

A synergistic effect is observed for the combination of neutral dinuclear gold complex I (R¹ = 3,5-di-MeC₆H₃) with chiral silver phosphate II in the intramol. hydroalkoxylation of allenes to give vinyltetrahydrofuran derivatives in high yields and enantioselectivities. The monocationic dinuclear gold complex affords higher catalytic activity and enantioselectivity than the neutral or dicationic digold complexes. The synergistic effect is thus highly promising to provide a guiding principle in designing an efficient chiral environment for creating an asym. catalyst. In the experiment, the researchers used many compounds, for example, 4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1Category: bromides-buliding-blocks).

4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1) belongs to organobromine compounds. 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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A novel and efficient method for the direct synthesis of pyrrolyl or indolyl substituted 9,10-dihydrophenanthren-9-ol analogues was written by Xia, Qi;Zhao, Xinlei;Zhang, Juan;Wang, Jiayi;Song, Gonghua. And the article was included in Tetrahedron Letters in 2020.SDS of cas: 85118-24-7 This article mentions the following:

A novel domino intramol. [3+2]-cycloaddtion and ring-opening aromatization process has been successfully developed for the efficient direct synthesis of pyrrolyl or indolyl-substituted 9,10-dihydrophenanthren-9-ol analogs. In addition, 1-(phenanthren-9-yl)-1H-pyrroles can be easily obtained via dehydration of 10-(1H-pyrrol-1-yl)-9,10-dihydrophenanthren-9-ols. Furthermore, the MTT assay indicated that four compounds with indolyl substitutions showed obvious inhibitory activities against HepG2 cells, and compound anti-I displayed a lowest IC₅₀ value of 9.99μM. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7SDS of cas: 85118-24-7).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) 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. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. 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.SDS of cas: 85118-24-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Poly-6-cationic amphiphilic cyclodextrins designed for gene delivery was written by Byrne, Colin;Sallas, Florence;Rai, Dilip K.;Ogier, Julien;Darcy, Raphael. And the article was included in Organic & Biomolecular Chemistry in 2009.Related Products of 53784-83-1 This article mentions the following:

A new series of amphiphilic cyclodextrins containing cationic groups at the 6-positions and alkyl or bio-labile ester groups at the 2-positions has been synthesized. Selective 2-O-allylation followed by photochem. addition of lipophilic thiols made it possible to control lipophilicity in these meso-mols. and allow solubility and self-assembly in water. The cationic groups are cysteamine-derived, while the alkyl and ester groups are C₁-C₁₆ and benzyl ester groups. This is a new general synthetic route to a potentially wide range of polycationic cyclodextrins capable of acting as gene delivery vectors by condensing DNA and forming liquid crystalline complexes with oligonucleotides. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Related Products of 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. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. 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.Related Products of 53784-83-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Enhanced reactivity in the ammonolysis of phenyl thiolacetates in aqueous medium was written by Rajarathnam, D.;Babu, J.;Nadar, P. Ananthakrishna. And the article was included in International Journal of Chemical Kinetics in 2002.Reference of 35065-86-2 This article mentions the following:

The ammonolysis of several substituted Ph thiolacetates is kinetically studied in aqueous medium, 18°, ionic strength 0.1 M (KCl). By following the leaving groups spectrophotometrically (λ_max = 260-410 nm), under excess free ammonia, pseudo-first-order rate coefficients (k_obs) are obtained. The plots of (k_obs – k_H) against free ammonia concentration are linear at constant pH. The macroscopic nucleophilic substitution rate coefficients (k_N) are obtained as the slopes of these plots and found to be pH-independent for all the thiolesters. The Bronsted-type plot (log k_N against pK_a of leaving groups) and the Hammett plot (log k_N against σ values of substituents) obtained for the title reactions of thiolesters are linear with slope values of β_lg = -0.34 and ρ = 0.74 resp. From the magnitude of these values, exptl. data, the kinetic law, and the anal. of products, it is deduced that the ammonolysis of thiolesters proceeds through a simple bimol. nucleophilic substitution pathway with a zwitterionic tetrahedral addition intermediate whereby its formation is rate-determining (k₁ step). Comparison of this reaction of thiolesters with a similar reaction of analog oxyesters shows a mechanistic difference. Further, for thiolesters there is a rate enhancement with larger k_N values. The change in mechanism and enhanced reactivity observed by substitution of the oxygen atom by sulfur atom on the Ph moiety are discussed in detail. In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2Reference of 35065-86-2).

3-Bromophenyl acetate (cas: 35065-86-2) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Reference of 35065-86-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery of 1-(phenylsulfonyl)-1H-indole-based multifunctional ligands targeting cholinesterases and 5-HT₆ receptor with anti-aggregation properties against amyloid-beta and tau was written by Wichur, Tomasz;Pasieka, Anna;Godyn, Justyna;Panek, Dawid;Goral, Izabella;Latacz, Gniewomir;Honkisz-Orzechowska, Ewelina;Bucki, Adam;Siwek, Agata;Gluch-Lutwin, Monika;Knez, Damijan;Brazzolotto, Xavier;Gobec, Stanislav;Kolaczkowski, Marcin;Sabate, Raimon;Malawska, Barbara;Wieckowska, Anna. And the article was included in European Journal of Medicinal Chemistry in 2021.Safety of N-(5-Bromopentyl)phthalimide This article mentions the following:

Multifunctional ligands as an essential variant of polypharmacol. are promising candidates for the treatment of multi-factorial diseases like Alzheimer’s disease. Based on clin. evidence and following the paradigm of multifunctional ligands we have rationally designed and synthesized a series of compounds targeting processes involved in the development of the disease. The biol. evaluation led to the discovery of two compounds with favorable pharmacol. characteristics and ADMET profile. Compounds I [n = 1] and II [R = [ethyl(methyl)carbamoyl]oxidanyl, n =1] are 5-HT₆R antagonists (K_i = 13 nM and K_i = 15 nM resp.) and cholinesterase inhibitors with distinct mechanisms of enzyme inhibition. Compound I [n = 1], a tacrine derivative is a reversible inhibitor of acetyl- and butyrylcholinesterase (IC₅₀ = 8 nM and IC₅₀ = 24 nM resp.), while compound II [R = [ethyl(methyl)carbamoyl]oxidanyl, n =1] with rivastigmine-derived Ph N-ethyl-N-methylcarbamate fragment is a selective, pseudo-irreversible inhibitor of butyrylcholinesterase (IC₅₀ = 455 nM). Both compounds inhibit aggregation of amyloid β in vitro (75% for compound I [n = 1] and 68% for II [R = [ethyl(methyl)carbamoyl]oxidanyl, n =1] at 10μM) moreover, compound II [R = [ethyl(methyl)carbamoyl]oxidanyl, n =1] is a potent tau aggregation inhibitor in cellulo (79%). In ADMET in vitro studies both compounds showed acceptable metabolic stability on mouse liver microsomes (28% and 60% for compound I [n = 1] and II [R = [ethyl(methyl)carbamoyl]oxidanyl, n =1] resp.), no or little effect on CYP3A4 and 2D6 up to a concentration of 10μM and lack of toxicity on HepG2 cell line (IC₅₀ values of 80 and 21μM, for I [n = 1] and II [R = [ethyl(methyl)carbamoyl]oxidanyl, n =1] resp.). Based on the pharmacol. characteristics and favorable pharmacokinetic properties, we propose compounds I [n = 1] and II [R = [ethyl(methyl)carbamoyl]oxidanyl, n =1] as an excellent starting point for further optimization and in-depth biol. studies. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Safety of N-(5-Bromopentyl)phthalimide).

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–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. 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.Safety of N-(5-Bromopentyl)phthalimide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Titanium isopropoxide-mediated cis-selective synthesis of 3,4-substituted butyrolactones from CO₂ was written by Sahari, Aleksi;Do, Cuong Dat;Mannisto, Jere K.;Antico, Emanuele;Amaratunga, Angelo;Hopmann, Kathrin H.;Repo, Timo. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.Name: 1-Bromo-4-methoxybutane This article mentions the following:

A Ti(OiPr)₄-mediated multicomponent reaction, which produced 3,4-substituted cis-δ-lactones from alkyl magnesium chloride, benzaldehyde and CO₂ was reported. The key intermediate, titanacyclopropane, was formed in-situ from Ti(OiPr)₄ and a Grignard reagent, which enabled 1,2-dinucleophilic reactivity that is used to insert carbon dioxide and an aldehyde. An alternative reaction route was also described where a primary alkene was used to create the titanacyclopropane. A computational anal. of the elementary steps showed that the carbon dioxide and the aldehyde insertion proceeded through an inner-sphere mechanism. A variety of cis-butyrolactones were synthesized with up to 7 : 1 diastereoselectivity and 77% yield. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Name: 1-Bromo-4-methoxybutane).

1-Bromo-4-methoxybutane (cas: 4457-67-4) 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–bromine 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.Name: 1-Bromo-4-methoxybutane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Organocatalytic Asymmetric Dearomatizing Hetero-Diels-Alder Reaction of Nonactivated Arenes was written by Li, Kai;Huang, Shengli;Liu, Tianyu;Jia, Shiqi;Yan, Hailong. And the article was included in Journal of the American Chemical Society in 2022.Quality Control of 1-Bromopyrrolidine-2,5-dione This article mentions the following:

Nonactivated arenes, such as benzene derivatives, are chem. inert due to their intrinsic aromaticity and low polarity. The catalytic asym. dearomatization (CADA, coined by You and co-workers) of the nonactivated arenes represents a formidable challenge. Herein, the authors demonstrate an organocatalytic asym. dearomatizing hetero-Diels-Alder reaction of benzene derivatives The tunable regioselectivity of this strategy allowed delivery of a diversity of stereochem. complex polycyclic compounds, e.g., I, and oxahelicenes, e.g., II, with excellent stereoselectivity. The high complexity and three-dimensionality of the products were crucial for their potential applications in materials science and drug discovery. Mechanistic studies suggested that this reaction proceeded through a chiral tetra-substituted vinylidene ortho-quinone methide (VQM) intermediate, which was extremely active to overcome the loss of aromaticity of benzene derivatives with concomitant chirality transfer. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Quality Control of 1-Bromopyrrolidine-2,5-dione).

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–bromine bond is electrophilic in nature. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Quality Control of 1-Bromopyrrolidine-2,5-dione

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary