Tag: 200-300

Radical trifunctionalization of hexenenitrile via remote cyano migration was written by Chang, Chenyang;Zhang, Huihui;Wu, Xinxin;Zhu, Chen. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.Category: bromides-buliding-blocks This article mentions the following:

A novel radical-mediated trifunctionalization of hexenenitriles via the strategy of remote functional group migration is disclosed. A portfolio of functionalized hexenenitriles are employed as substrates. After difunctionalization of the unactivated alkenyl part via remote cyano migration, the in situ formed radical intermediate is captured by an azido radical, thus enabling the trifunctionalization. The reaction features mild conditions and broad functional group compatibility, leading to valuable products bearing multiple useful groups. This protocol further extends the scope of remote functional group migration. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Category: bromides-buliding-blocks).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) 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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

N,C-Disubstituted Biarylpalladacycles as Precatalysts for ppm Pd-Catalyzed Cross Couplings in Water under Mild Conditions was written by Thakore, Ruchita R.;Takale, Balaram S.;Gallou, Fabrice;Reilly, John;Lipshutz, Bruce H.. And the article was included in ACS Catalysis in 2019.Recommanded Product: Methyl 4-bromo-2-fluorobenzoate This article mentions the following:

Various mono- and di-substitution patterns on the parent biarylamine skeleton characteristic of palladacycles, as well as the counterion effect, have been studied looking to increase the effectiveness of the catalyst formed under micellar catalysis conditions in water, with the goal of reducing the amount of Pd needed for coupling reactions. Several substituted palladacycles containing readily accessible ligands were chosen for evaluation. The results indicate that: (1) pre-activation of Pd(II) salts as precursors for Suzuki-Miyaura (SM) couplings via treatment with a reducing agent is not required; (2) reactions could be performed with ca. half the loading of Pd relative to that previously required based on a combination of a Pd(II) salt and ligand; (3) the most effective palladacycle pre-catalyst has been identified as that containing an iso-Pr group on both an aryl ring and on nitrogen, together with the ligand EvanPhos and triflate as the counterion. This pre-catalyst is also effective in other C-C bond forming reactions, such as Heck and Sonogashira couplings. No organic solvents were needed for these processes, while the aqueous reaction medium could be recycled several times. A 1-pot, 4-step sequence involving Suzuki-Miyaura, reduction, alkylation, and acylation reactions highlights the potential for this pre-catalyst to maximize synthetic gain while minimizing costs and waste generation. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Recommanded Product: Methyl 4-bromo-2-fluorobenzoate).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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: Methyl 4-bromo-2-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Systematic Investigation of Halogen Bonding in Protein-Ligand Interactions was written by Hardegger, Leo A.;Kuhn, Bernd;Spinnler, Beat;Anselm, Lilli;Ecabert, Robert;Stihle, Martine;Gsell, Bernard;Thoma, Ralf;Diez, Joachim;Benz, Joerg;Plancher, Jean-Marc;Hartmann, Guido;Banner, David W.;Haap, Wolfgang;Diederich, Francois. And the article was included in Angewandte Chemie, International Edition in 2011.Name: 1-(4-Bromo-2-fluorophenyl)cyclopropanecarboxylic acid This article mentions the following:

Halogen bonding triggers activity. Increasing binding affinity was observed for a series of covalent human Cathepsin L inhibitors by exchanging an aryl ring H atom with Cl, Br, and I, which undergo halogen bonding with the C=O group of Gly61 in the S3 pocket of the enzyme. Fluorine, in contrast, strongly avoids halogen bonding. The strong distance and angle dependence of halogen bonding was confirmed for biol. systems. In the experiment, the researchers used many compounds, for example, 1-(4-Bromo-2-fluorophenyl)cyclopropanecarboxylic acid (cas: 872422-15-6Name: 1-(4-Bromo-2-fluorophenyl)cyclopropanecarboxylic acid).

1-(4-Bromo-2-fluorophenyl)cyclopropanecarboxylic acid (cas: 872422-15-6) 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.Name: 1-(4-Bromo-2-fluorophenyl)cyclopropanecarboxylic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design, synthesis and structure-activity relationship evaluation of novel LpxC inhibitors as Gram-negative antibacterial agents was written by Ding, Shi;Dai, Rui-Yang;Wang, Wen-Ke;Cao, Qiao;Lan, Le-Fu;Zhou, Xian-Li;Yang, Yu-She. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2018.Name: Methyl 4-bromo-2-fluorobenzoate This article mentions the following:

LpxC inhibitors are new-type antibacterial agents developed in the last twenty years, mainly against Gram-neg. bacteria infections. To develop novel LpxC inhibitors with good antibacterial activities and biol. metabolism, the authors summarized the basic skeleton of reported LpxC inhibitors, designed and synthesized several series of compounds and tested their antibacterial activities against Escherichia coli and Pseudomonas aeruginosa in vitro. Structure-activity relations are discussed. The metabolism stability of YDL-2, YDL-5, YDL-8, YDL-14, YDL-20-YDL-23 were evaluated in liver microsomes, which indicated that the 2-amino iso-Pr group may be a preferred structure than the 2-hydroxy Et group in the design of LpxC inhibitors. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Name: Methyl 4-bromo-2-fluorobenzoate).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) 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. 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.Name: Methyl 4-bromo-2-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and biological evaluation of sulforaphane derivatives as potential antitumor agents was written by Hu, Kun;Qi, Yan-jie;Zhao, Juan;Jiang, He-fei;Chen, Xin;Ren, Jie. And the article was included in European Journal of Medicinal Chemistry in 2013.Safety of N-(5-Bromopentyl)phthalimide This article mentions the following:

A series of sulforaphane derivatives, S:C:NCH₂(CH₂)_nCH₂X(O)R [I, R = PhCH₂, Et, 2-furanylmethyl, cyclopentyl, etc., X = S(O), n = 1-4; R = PhCH₂, X = S, n = 2; R = PhCH₂, X = SO₂, n = 2], were synthesized and evaluated in vitro for their cytotoxicity against five cancer cell lines (HepG2, A549, MCF-7, HCT-116 and SH-SY5Y). The pharmacol. results showed that many of the derivatives displayed more potent cytotoxicity than sulforaphane (SFN). Furthermore, SFN and derivative I [R = PhCH₂, X = S(O), n = 2] (II) could induce cell cycle arrest at S or G2/M phase and cell apoptosis. SFN and II exhibited time- and dose-dependent activation on Nrf2 transcription factor, and II acted as a more potent Nrf2 inducer than SFN. 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. 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.Safety of N-(5-Bromopentyl)phthalimide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

An Intermolecular Hydroarylation of Highly Deactivated Styrenes Catalyzed by Re₂O₇/HReO₄ in Hexafluoroisopropanol was written by Hu, Liqun;Liu, Yibing;Fang, Xiong;zheng, Yuzhu;Liao, Rong-zhen;Li, Man;Xie, Youwei. And the article was included in ACS Catalysis in 2022.Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde This article mentions the following:

Here, authors describe an activation mode for unactivated alkenes on the basis of a synergy between Re₂O₇/HReO₄ and hexafluoroisopropanol (HFIP). Highly electron-deficient styrenes have been activated to effect a challenging intermol. hydroarylation with different arenes to give a variety of diarylalkanes in high efficiency. This method is characterized by mild reaction condition, broad substrate scope, high chem. yields, and minimal waste generation. The potential synthetic application of this methodol. was exemplified by the efficient synthesis of a retinoic acid receptor (RAR) agonist. DFT calculations and deuterium-labeling experiments were conducted to elucidate the reaction mechanism, and both confirmed the critical role of HFIP, which significantly reduced the energetical barriers for several key steps of this transformation via a network of hydrogen bonding to perrhenate anion with two equivalent of HFIP. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) 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.Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Chemo-proteomics exploration of HDAC degradability by small molecule degraders was written by Xiong, Yuan;Donovan, Katherine A.;Eleuteri, Nicholas A.;Kirmani, Nadia;Yue, Hong;Razov, Anthony;Krupnick, Noah M.;Nowak, Radoslaw P.;Fischer, Eric S.. And the article was included in Cell Chemical Biology in 2021.Quality Control of N-(5-Bromopentyl)phthalimide This article mentions the following:

Targeted protein degradation refers to the use of small mols. that recruit a ubiquitin ligase to a target protein for ubiquitination and subsequent proteasome-dependent degradation While degraders have been developed for many targets, key questions regarding degrader development and the consequences of acute pharmacol. degradation remain, specifically for targets that exist in obligate multi-protein complexes. Here, we synthesize a pan-histone deacetylase (HDAC) degrader library for the chemo-proteomic exploration of acute degradation of a key class of chromatin-modifying enzymes. Using chemo-proteomics, we not only map the degradability of the zinc-dependent HDAC family identifying leads for targeting HDACs 1-8 and 10 but also explore important aspects of degrading epigenetic enzymes. We discover cell line-driven target specificity and that HDAC degradation often results in collateral loss of HDAC-containing repressive complexes. These findings potentially offer a new mechanism toward controlling chromatin structure, and our resource will facilitate accelerated degrader design and development for HDACs. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Quality Control of N-(5-Bromopentyl)phthalimide).

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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Quality Control of N-(5-Bromopentyl)phthalimide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Optimization of Phenyl-Substituted Benzimidazole Carboxamide Poly(ADP-Ribose) Polymerase Inhibitors: Identification of (S)-2-(2-Fluoro-4-(pyrrolidin-2-yl)phenyl)-1H-benzimidazole-4-carboxamide (A-966492), a Highly Potent and Efficacious Inhibitor was written by Penning, Thomas D.;Zhu, Gui-Dong;Gong, Jianchun;Thomas, Sheela;Gandhi, Viraj B.;Liu, Xuesong;Shi, Yan;Klinghofer, Vered;Johnson, Eric F.;Park, Chang H.;Fry, Elizabeth H.;Donawho, Cherrie K.;Frost, David J.;Buchanan, Fritz G.;Bukofzer, Gail T.;Rodriguez, Luis E.;Bontcheva-Diaz, Velitchka;Bouska, Jennifer J.;Osterling, Donald J.;Olson, Amanda M.;Marsh, Kennan C.;Luo, Yan;Giranda, Vincent L.. And the article was included in Journal of Medicinal Chemistry in 2010.Product Details of 179232-29-2 This article mentions the following:

We have developed a series of phenylpyrrolidine- and phenylpiperidine-substituted benzimidazole carboxamide poly(ADP-ribose) polymerase (PARP) inhibitors with excellent PARP enzyme potency as well as single-digit nanomolar cellular potency. These efforts led to the identification of (S)-2-(2-fluoro-4-(pyrrolidin-2-yl)phenyl)-1H-benzimidazole-4-carboxamide (22b, A-966492) (I). Compound 22b displayed excellent potency against the PARP-1 enzyme with a K_i of 1 nM and an EC₅₀ of 1 nM in a whole cell assay. In addition, 22b is orally bioavailable across multiple species, crosses the blood-brain barrier, and appears to distribute into tumor tissue. It also demonstrated good in vivo efficacy in a B16F10 s.c. murine melanoma model in combination with temozolomide and in an MX-1 breast cancer xenograft model both as a single agent and in combination with carboplatin. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Product Details of 179232-29-2).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Product Details of 179232-29-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design and Synthesis of [(2,3-Dichlorophenyl)piperazin-1-yl]alkylfluorenylcarboxamides as Novel Ligands Selective for the Dopamine D₃ Receptor Subtype was written by Robarge, Michael J.;Husbands, Stephen M.;Kieltyka, Andrzej;Brodbeck, Robbin;Thurkauf, Andrew;Newman, Amy Hauck. And the article was included in Journal of Medicinal Chemistry in 2001.HPLC of Formula: 954-81-4 This article mentions the following:

The dopamine D₃ receptor subtype has been recently targeted as a potential neurochem. modulator of the behavioral actions of psychomotor stimulants, such as cocaine. However, definitive behavioral investigations have been hampered by the lack of highly selective D₃ agonists and antagonists. In an attempt to design a novel class of D₃ ligands with which to study this receptor system, a series of chem. divergent compounds that possessed various structural features that exist within several classes of reputed D₃ agents was screened and compared to the recently reported NGB 2904. On the basis of these results, a novel series of compounds was designed that included functional moieties that were required for high-affinity and selective binding to D₃ receptors. All the compounds in this series included an aryl-substituted piperazine ring, a varying alkyl chain linker (C₃-C₅), and a terminal aryl amide. The compounds were synthesized and evaluated in vitro for binding in CHO cells transfected with human D₂, D₃, or D₄ receptor cDNAs. D₃ binding affinities ranged from K_i = 1.4 to 1460 nM. The most potent analog in this series, I, demonstrated a D₃/D₂ selectivity of 64 and a D₃/D₄ selectivity of 1300. Structure-activity relationships for this class of ligands at D₃ receptors will provide new leads toward the development of highly selective and potent mol. probes that will prove useful in the elucidation of the role D₃ receptors play in the psychomotor stimulant and reinforcing properties of cocaine. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4HPLC of Formula: 954-81-4).

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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.HPLC of Formula: 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of aryl sulfonyl fluorides from aryl sulfonyl chlorides using sulfuryl fluoride (SO₂F₂) as fluoride provider was written by Song, Xuyan;He, Yunlu;Wang, Bo;Peng, Sanwen;Pan, Xi;Wei, Min;Liu, Qiang;Qin, Hua-Li;Tang, Haolin. And the article was included in Tetrahedron in 2022.Product Details of 454-65-9 This article mentions the following:

A highly efficient method for the synthesis of aryl sulfonyl fluorides ArSO₂F [Ar = 4-MeC₆H₄, 4-PhC₆H₄, 4-ClC₆H₄, etc.] was developed from aryl sulfonyl chlorides using SO₂F₂ as fluoride source in up to 98% isolated yield under mild conditions. Gram scale experiments were also conducted, revealing the good practicality of this new protocol. In the experiment, the researchers used many compounds, for example, 3-Bromobenzene-1-sulfonyl fluoride (cas: 454-65-9Product Details of 454-65-9).

3-Bromobenzene-1-sulfonyl fluoride (cas: 454-65-9) 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. 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.Product Details of 454-65-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary