Month: October 2022

In 2016,Mistry, Shailesh N.; Jorg, Manuela; Lim, Herman; Vinh, Natalie B.; Sexton, Patrick M.; Capuano, Ben; Christopoulos, Arthur; Lane, J. Robert; Scammells, Peter J. published 《4-Phenylpyridin-2-one Derivatives: A Novel Class of Positive Allosteric Modulator of the M1 Muscarinic Acetylcholine Receptor》.Journal of Medicinal Chemistry published the findings.Reference of Methyl 3-(bromomethyl)benzoate The information in the text is summarized as follows:

Pos. allosteric modulators (PAMs) of the M1 muscarinic acetylcholine receptor (M1 mAChR) are a promising strategy for the treatment of the cognitive deficits associated with diseases including Alzheimer’s and schizophrenia. Herein, we report the design, synthesis, and characterization of a novel family of M1 mAChR PAMs. The most active compounds of the 4-phenylpyridin-2-one series exhibited comparable binding affinity to the reference compound, 1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (BQCA), but markedly improved pos. cooperativity with acetylcholine, and retained exquisite selectivity for the M1 mAChR. Furthermore, the pharmacol. characterization revealed ligands with a diverse range of activities, including modulators that displayed both high intrinsic efficacy and PAM activity, those that showed no detectable agonism but robust PAM activity and ligands that displayed robust allosteric agonism but little modulatory activity. Compound I was found to have the best pharmacol. profile. Thus, the 4-phenylpyridin-2-one scaffold offers an attractive starting point for further lead optimization. In the experiment, the researchers used Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8Reference of Methyl 3-(bromomethyl)benzoate)

Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8) belongs to organobromine compounds.Depending on the type of carbon to which the bromine is bonded, organic bromide could be alkyl, alkenyl, alkynyl, or aryl. Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides. Reference of Methyl 3-(bromomethyl)benzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2017,Zou, Ya-Ling; Wang, Zhen-Yu; Feng, Yin-Mao; Li, You-Gui; Kantchev, Eric Assen B. published 《Solvent and Base in One: Tetra-n-butylammonium Acetate as a Multi-Purpose Ionic Liquid Medium for Ru-Catalyzed Directed Mono- and Di-o-C-H Arylation Reactions》.European Journal of Organic Chemistry published the findings.Safety of 1-Bromo-2-isopropylbenzene The information in the text is summarized as follows:

Ru-catalyzed directed o-C-H arylation reactions of 2-phenylpyridine, N-phenylpyrazole, acetophenone N-(p-methoxyphenyl)imine, and 2-phenyloxazoline proceed in good to excellent yields with a number of functionalized aryl and heteroaryl bromides in neat Bu4NOAc at 120°. The acetate ion acts as the base and the relatively low m.p. Bu4N salts (a mixture of acetate and bromide) behave as an ionic liquid Arylation reactions of 2-phenyloxazoline proceed with concomitant oxazolidine cleavage to give 2-(N-acetylamino)ethyl benzoates promoted by side product CH3COOH. The dual-purpose ionic liquid medium is compatible with both ligandless Ru for di-arylation (optimal pre-catalyst: RuCl3·xH2O) and Ru-phosphine (optimal pre-catalyst: [RuCl2(p-cymene)]2/P(p-Tol)3 1:4) catalysts (1-5 mol-%) for selective mono-arylation. The experimental part of the paper was very detailed, including the reaction process of 1-Bromo-2-isopropylbenzene(cas: 7073-94-1Safety of 1-Bromo-2-isopropylbenzene)

1-Bromo-2-isopropylbenzene(cas: 7073-94-1) belongs to organobromine compounds.Depending on the type of carbon to which the bromine is bonded, organic bromide could be alkyl, alkenyl, alkynyl, or aryl. Alkyl bromides are mainly used as alkylating agents and also find application as a solvent to extract oil from seeds and wool. Safety of 1-Bromo-2-isopropylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2018,Dong, Zhe; Lu, Gang; Wang, Jianchun; Liu, Peng; Dong, Guangbin published 《Modular ipso/ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis》.Journal of the American Chemical Society published the findings.Application of 7073-94-1 The information in the text is summarized as follows:

Palladium/norbornene (Pd/NBE) cooperative catalysis has emerged as a useful tool for preparing poly substituted arenes; however, its substrate scope was largely restricted to aryl iodides. While aryl bromides are considered as standard substrates for Pd-catalyzed cross coupling reactions, their use in Pd/NBE catalysis remains elusive. Here we describe the development of general approaches for aryl bromide-mediated Pd/NBE cooperative catalysis. Through careful tuning the phosphine ligands and quenching nucleophiles, ortho amination, acylation and alkylation of aryl bromides were realized in good efficiency. Importantly, various heteroarene substrates also work well and a wide range of functional groups are tolerated. In addition, the utility of these methods was demonstrated in sequential cross coupling/ortho functionalization reactions, consecutive Pd/NBE-catalyzed difunctionalization to construct penta-substituted aromatics and two-step meta functionalization reactions. Moreover, the origin of the ligand effect in ortho amination reactions was explored through DFT studies. This effort would significantly expand the reaction scope and enhance the synthetic potential for Pd/NBE catalysis in preparing complex aromatic compounds In the experimental materials used by the author, we found 1-Bromo-2-isopropylbenzene(cas: 7073-94-1Application of 7073-94-1)

1-Bromo-2-isopropylbenzene(cas: 7073-94-1) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. Application of 7073-94-1 Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2019,Medicinal Chemistry Research included an article by Lopez-Munoz, Marisol; Gomez-Pena, Jessica Johanna; Rios-Vasquez, Luz Amalia; Ocampo-Cardona, Rogelio; Jones, Marjorie A.; Haynes, Craig S.; Wallace, Craig; Robledo, Sara M.. SDS of cas: 14660-52-7. The article was titled 《Novel fluorinated quaternary ammonium salts and their in vitro activity as trypanocidal agents》. The information in the text is summarized as follows:

As the impact of aromatic rings and fluorine substituents in com. drugs is attributed to their electronic distribution and structure rigidity that determine metabolic stability and toxicity, 30 quaternary ammonium salts (QAS) of the form [X-CH2N(CH3)2(CH2)nCH = C(Ar2)]+I- (where X=H, Cl or I, n = 2 or 3, and Ar = m-C6H4CF3, p-C6H4CF3, m-C6H4F, p-C6H4F or C6H5) were tested as potential trypanocidal agents and assessed their cytotoxicity on U-937 cells. CF3-substituted QASs exhibited LC50 values in the range of 0.5 to 6.4 μg/mL and trypanocidal EC50 values between 0.6 and 7.0 μg/mL, while the LC50 values for F-substituted analogs are between 7.0 and 207 μg/mL and EC50 values range from 3.8 to 40.9 μg/mL. As a general trend, the more effective are those bearing an N-iodomethyl moiety or having a longer tether, and para-substituted ones. Few drugs therapies are in use for Chagas disease, so this study becomes a promising contribution. The experimental part of the paper was very detailed, including the reaction process of Ethyl 5-bromovalerate(cas: 14660-52-7SDS of cas: 14660-52-7)

Ethyl 5-bromovalerate(cas: 14660-52-7) belongs to bromides. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.SDS of cas: 14660-52-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2019,Angewandte Chemie, International Edition included an article by Wang, Bing; Chou, Kuang-Hua; Queenan, Bridget N.; Pennathur, Sumita; Bazan, Guillermo C.. HPLC of Formula: 623-24-5. The article was titled 《Molecular Design of a New Diboronic Acid for the Electrohydrodynamic Monitoring of Glucose》. The information in the text is summarized as follows:

A new dicationic diboronic acid structure, DBA2+, was designed to exhibit good affinity (Kd ≈ 1 mM) and selectivity toward glucose. Binding of DBA2+ to glucose changes the pKa of DBA2+ from 9.4 to 6.3, enabling opportunities for detection of glucose at physiol. pH. Proton release from DBA2+ is firmly related to glucose concentrations within the physiol. relevant range (0-30 mM), as verified by conductometric monitoring. Negligible interference from other sugars (for example, maltose, fructose, sucrose, lactose, and galactose) was observed These results demonstrate the potential of DBA2+ for selective, quant. glucose sensing. The nonenzymic strategy based on electrohydrodynamic effects may enable the development of stable, accurate, and continuous glucose monitoring platforms.1,4-Bis(bromomethyl)benzene(cas: 623-24-5HPLC of Formula: 623-24-5) was used in this study.

1,4-Bis(bromomethyl)benzene(cas: 623-24-5) 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. HPLC of Formula: 623-24-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Design, synthesis and preliminary bioactivity evaluations of 8-hydroxyquinoline derivatives as matrix metalloproteinase (MMP) inhibitors》 were Chen, Chen; Yang, Xinying; Fang, Hao; Hou, Xuben. And the article was published in European Journal of Medicinal Chemistry in 2019. Synthetic Route of C4H7BrO2 The author mentioned the following in the article:

8-Hydroxyquinoline-substituted amides such as I were prepared as matrix metalloproteinase-2 and -9 (MMP-2/MMP-9) inhibitors for potential use in treating cancer. I and a related indolylethylamide inhibited MMP-2 and MMP-9 with IC50 values of 0.66-1.3 μM, inhibited the proliferation of human cancer cells with IC50 values of 0.69-22 μM, and inhibited angiogenesis while inhibiting human non-tumor cell growth with IC50 values > 50 μM. I and a related indolylethylamide down-regulated the expression of MMP-2 and MMP-9 in A549 cells; I promoted the apoptosis of A549 cells in vitro. Mol. docking calculations of I in the active sites of MMP-2 and MMP-9 were performed. In the experiment, the researchers used many compounds, for example, 4-Bromobutanoic acid(cas: 2623-87-2Synthetic Route of C4H7BrO2)

4-Bromobutanoic acid(cas: 2623-87-2) belongs to carboxylic acids. The chief chemical characteristic of the carboxylic acids is their acidity. They are generally more acidic than other organic compounds containing hydroxyl groups but are generally weaker than the familiar mineral acids (e.g., hydrochloric acid, HCl, sulfuric acid, H2SO4, etc.).Synthetic Route of C4H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Novel Features of 9-Methylene-9H-thioxanthene (MTAE) in Living Anionic Polymerization》 were Chang, Shuang; Han, Li; Ma, Hongwei; Bai, Hongyuan; Li, Cun; Liu, Pibo; Yang, Lincan; Shen, Heyu; Li, Chao; Zhang, Songbo. And the article was published in Macromolecular Chemistry and Physics in 2019. COA of Formula: C19H18BrP The author mentioned the following in the article:

For this study, a new epithio-1,1-diphenylethylene (DPE) derivative, namely, 9-Methylene-9H-thioxanthene (MTAE), is synthesized, and its copolymerization reactions are investigated, showing distinctive features in living anionic copolymerization At room temperature and hydrocarbon solvents, MTAE cannot be copolymerized with styrene (St) but can be copolymerized with 1,4-divinylbenzene (DVB), forming a linear alternating copolymer. Based on this finding, ter-polymerization of MTAE, DVB and St is conducted to generate a special alternating structure. Addnl., MTAE is found to exhibit fairly high reactivity in copolymerization with Isoprene (Ip) under the same conditions. An alternating sequence of alt-MTAE/Ip containing high trans-geometric Ip content (76% of trans-1,4) and a di-block sequence of alt-MTAE/Ip-b-Ip are easily obtained. Its exptl. reactivity ratio with Ip is investigated via the in situ 1H NMR method (rIp = 0.28), and the corresponding kinetic behaviors and sequence structure are elucidated. Finally, the origin of the effect of MTAE on the isomerism of Ip during chain propagation is investigated by d. functional theory (DFT) calculations, and it is found that the bridge sulfur atom in MTAE interacts strongly with living species. This special finding provides a novel approach for the sequence regulation, precise functionalization, and stereo-structure control in living anionic polymerization originating from monomer structure design. The experimental process involved the reaction of Methyltriphenylphosphonium bromide(cas: 1779-49-3COA of Formula: C19H18BrP)

Methyltriphenylphosphonium bromide(cas: 1779-49-3) is a lipophilic molecule with a cation allowing for it to be used to deliver molecules to specific cell components. Also considered an antineoplastic agent.COA of Formula: C19H18BrP

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《A new family of oxime palladacycles mixed with unsymmetrical phosphorus ylides; synthesis, structural, cytotoxicity and catalytic activity studies》 were Samiee, Sepideh; Shiralinia, Ahmadreza; Hoveizi, Elham; Gable, Robert W.. And the article was published in Journal of Organometallic Chemistry in 2019. Product Details of 586-76-5 The author mentioned the following in the article:

In the present investigation, the reactivity of an oxime-derived palladacycle [Pd{C,N-C6H4{C(Me) = NOH}-2}(μ-Cl)]2 toward various unsym. phosphorus ylides has been studied. When the ylide was added to a solution of oxime complex in dichloromethane (2:1 ratio), the new oxime palladacycles of the types [Pd{C,N-C6H4{C(Me) = NOH}-2}(Ph2PCH2PPh2C(H)C(O)C6H4X)]ClO4 (X = Cl (1), Br (2), NO2(3) or OCH3 (4)) were formed by means of bridge-splitting reaction. These are the first description of oxime-based palladacycles mixed with phosphorus ylides. All of complexes were fully characterized by elemental anal., IR and NMR spectroscopies. The crystal structure of 3 were determined by single-crystal x-ray diffraction anal. that confirmed breaking of Pd-Cl bonds in the initial precursor and allowing phosphorus ylide act as P,C-chelating ligand. In addition, the catalytic activity of 3 was evaluated in the Suzuki cross-coupling reactions of a variety of arylbromides with phenylboronic acid. This complex was also used for the assessment of their anticancer activities against three human carcinoma cell lines: A549 (human lung carcinoma), HT29 (human colon carcinoma), and HeLa (human cervical carcinoma). The results show that the new family of oxime-derived palladacycles could be introduced as promising innovative anticancer complexes and considered as an efficient catalyst in the cross coupling reactions. In the experiment, the researchers used 4-Bromobenzoic acid(cas: 586-76-5Product Details of 586-76-5)

4-Bromobenzoic acid(cas: 586-76-5) has been used to study the metabolic fate of 2-,3-and 4-bromo benzoic acids in rat hepatocytes incubation using high temperature liquid chromatography. It was used in bromine-specific detection of the metabolites of 2-,3-and 4-bromobenzoic acid in the urine and bile of rats by inductively coupled plasma mass spectrometry.Product Details of 586-76-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《New Synthesis of 2-Oxoalkanamide Oximes》 were Mantrov, S. N.; Lapina, Yu. M.; Shukhtina, E. A.. And the article was published in Russian Journal of Organic Chemistry in 2019. Name: 3,5-Dibromoaniline The author mentioned the following in the article:

Reactions of α-halocarboxylic acid amides R1NHC(O)CH(X)R (R = H, Me, Bu; R1 = C6H5, 4-BrC6H4, 1,3-thiazol-2-yl, etc.; X = Cl, Br) with 3 equiv of hydroxylamine hydrochloride in the presence of bases involves formation of products of nucleophilic substitution of the halogen atom and their subsequent oxidation to the corresponding oximes R1NHC(O)C(=NOH)R. This one-pot transformation can be accomplished in various aprotic solvents or ethanol at 80°C. DMSO as solvent ensures the highest selectivity for the oxidation products. The yields of N-substituted 2-(hydroxyimino)carboxylic acid amides range from 22 to 92%. The results came from multiple reactions, including the reaction of 3,5-Dibromoaniline(cas: 626-40-4Name: 3,5-Dibromoaniline)

3,5-Dibromoaniline(cas: 626-40-4) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Name: 3,5-Dibromoaniline

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《P-Chiral Phosphines Enabled by Palladium/Xiao-Phos-Catalyzed Asymmetric P-C Cross-Coupling of Secondary Phosphine Oxides and Aryl Bromides》 were Dai, Qiang; Li, Wenbo; Li, Zhiming; Zhang, Junliang. And the article was published in Journal of the American Chemical Society in 2019. Reference of 1-Bromo-4-(trifluoromethyl)benzene The author mentioned the following in the article:

The development of transition-metal-catalyzed methods for the synthesis of P-chiral phosphine derivatives poses a considerable challenge. Herein, the authors present a direct Pd/Xiao-Phos-catalyzed cross-coupling reaction of easily accessible secondary phosphine oxides and aryl bromides, which provides rapid access to P-chiral phosphine oxides. The reaction proceeds efficiently with a wide array of reaction partners to deliver various tertiary phosphine oxides in up to 96% yield and 97% ee. Also, the synthesis of DiPAMP ligand and its analogs was also realized, which demonstrates a suitable pathway to switching the branched chain of DiPAMP. The experimental process involved the reaction of 1-Bromo-4-(trifluoromethyl)benzene(cas: 402-43-7Reference of 1-Bromo-4-(trifluoromethyl)benzene)

1-Bromo-4-(trifluoromethyl)benzene(cas: 402-43-7) belongs to organobromine compounds.Depending on the type of carbon to which the bromine is bonded, organic bromide could be alkyl, alkenyl, alkynyl, or aryl. Reference of 1-Bromo-4-(trifluoromethyl)benzene Alkyl bromides are mainly used as alkylating agents and also find application as a solvent to extract oil from seeds and wool.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary