Tag: 200-300

An improved and practical route for the synthesis of enzalutamide and potential impurities study was written by Zhou, Ai-Nan;Li, Bonan;Ruan, Lejun;Wang, Yeting;Duan, Gengli;Li, Jianqi. And the article was included in Chinese Chemical Letters in 2017.Safety of Methyl 4-bromo-2-fluorobenzoate This article mentions the following:

An improved and practical synthesis of enzalutamide was accomplished in five steps. Starting from 4-bromo-2-fluoro-benzonic acid, a Me esterification, Ullmann ligation, Me esterification, ring closing reaction and final Me amidation provided the target in 35% total yield with 99.8% purity. Five identified impurities were also synthesized. This efficient and economical procedure avoids the use of highly toxic reagents and multiple recrystallization operations, which is suitable for further industrialization. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Safety of Methyl 4-bromo-2-fluorobenzoate).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) 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). Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Safety of Methyl 4-bromo-2-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Novel Deazaflavin Analogues Potently Inhibited Tyrosyl DNA Phosphodiesterase 2 (TDP2) and Strongly Sensitized Cancer Cells toward Treatment with Topoisomerase II (TOP2) Poison Etoposide was written by Kankanala, Jayakanth;Ribeiro, Carlos J. A.;Kiselev, Evgeny;Ravji, Azhar;Williams, Jessica;Xie, Jiashu;Aihara, Hideki;Pommier, Yves;Wang, Zhengqiang. And the article was included in Journal of Medicinal Chemistry in 2019.COA of Formula: C8H7BrO2 This article mentions the following:

Topoisomerase II (TOP2) poisons as anticancer drugs work by trapping TOP2 cleavage complexes (TOP2cc) to generate DNA damage. Repair of such damage by tyrosyl DNA phosphodiesterase 2 (TDP2) could render cancer cells resistant to TOP2 poisons. Inhibiting TDP2, thus, represents an attractive mechanism-based chemosensitization approach. Currently known TDP2 inhibitors lack cellular potency and/or permeability. We report herein two novel subtypes of the deazaflavin TDP2 inhibitor core. By introducing an addnl. Ph ring to the N-10 Ph ring (subtype 11) or to the N-3 site of the deazaflavin scaffold (subtype 12), we have generated novel analogs with considerably improved biochem. potency and/or permeability. Importantly, many analogs of both subtypes, particularly compounds 11a, 11e, 12a, 12b, and 12h, exhibited much stronger cancer cell sensitizing effect than the best previous analog 4a toward the treatment with etoposide, suggesting that these analogs could serve as effective cellular probes. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8COA of Formula: C8H7BrO2).

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) 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.COA of Formula: C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Pyridylbenzimidazole-Based Gold(III) Complexes: Lysozyme Metalation, DNA Binding Studies, and Biological Activity was written by Mansour, Ahmed M.;Shehab, Ola R.. And the article was included in European Journal of Inorganic Chemistry in 2019.Related Products of 954-81-4 This article mentions the following:

The lysozyme binding affinity of new Au(III) complexes, bearing pyridylbenzimidazole ligands, was studied by ESI-MS and UV/visible. Metalation of lysozyme happened mainly by {Au}ⁿ⁺, {AuCl}^0/n+ and {AuCl₂}^n+/-. The appendage sulfonate group of pyridylbenzimidazole ligand system played a role in determining the products of interaction of HEWL with Au(III) complexes. The hydrophilic sulfonate group inhibited the ligand cleavage via the participation in several coulombic and H-bond interactions giving several AuLⁿ⁺ containing adduct peaks (L = 1-[(pyridin-2-yl) benzimidazole]-propyl-sulfonic acid). The stability of the complexes in presence of ascorbic acid was examined by UV/visible and ¹³C NMR. To recognize if His15 side-chain is the metalation site of HEWL, the interactions between the complexes and imidazole, as a simple model of histidine, were studied by ¹H and ¹³C NMR. The DNA binding studies of the complexes are reported. For this class of Au(III) complexes, it is preferred to decorate the pyridylbenzimidazole system with Et group rather than sulfonate and phthalimido group to have a complex with interesting antifungal activity against Candida albicans and Cryptococcus neoformans var. grubii. Au(III) complex, having sulfonate group, is noncytotoxic to non-malignant cells (human embryonic kidney cells (HEK293)), shows negligible Hb release and is safe to the normal cells if applicable. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Related Products of 954-81-4).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Related Products of 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Protein Structure-Based Design, Synthesis, and Biological Evaluation of 5-Thia-2,6-diamino-4(3H)-oxopyrimidines: Potent Inhibitors of Glycinamide Ribonucleotide Transformylase with Potent Cell Growth Inhibition was written by Varney, Michael D.;Palmer, Cindy L.;Romines, William H. III;Boritzki, Theodore;Margosiak, Stephen A.;Almassy, Robert;Janson, Cheryl A.;Bartlett, Charlotte;Howland, Eleanor J.;Ferre, Rosanne. And the article was included in Journal of Medicinal Chemistry in 1997.Product Details of 38239-45-1 This article mentions the following:

The design, synthesis, biochem., and biol. evaluation of a novel series of 5-thia-2,6-diamino-4(3H)-oxopyrimidine inhibitors of glycinamide ribonucleotide transformylase (GART) are described. The compounds were designed using the X-ray crystal structure of human GART. The monocyclic 5-thiapyrimidinones were synthesized by coupling an alkyl thiol with 5-bromo-2,6-diamino-4(3H)-pyrimidinone. The bicyclic compounds were prepared in both racemic and diastereomerically pure forms using two distinct synthetic routes. The compounds were found to have human GART K_is ranging from 30 μM to 2 nM. The compounds inhibited the growth of both L1210 and CCRF-CEM cells in culture with potencies down to the low nanomolar range and were found to be selective for the de novo purine biosynthesis pathway. The most potent inhibitors had 2,5-disubstituted thiophene rings attached to the glutamate moiety. Placement of a Me substituent at the 4-position of the thiophene ring resulted in inhibitors with significantly decreased mFBP (human folate-binding protein) affinity. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-methylthiophene-2-carboxylic acid (cas: 38239-45-1Product Details of 38239-45-1).

5-Bromo-3-methylthiophene-2-carboxylic acid (cas: 38239-45-1) 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. 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 38239-45-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Highly efficient synthesis of alkylboronate esters via Cu(II)-catalyzed borylation of unactivated alkyl bromides and chlorides in air was written by Bose, Shubhankar Kumar;Brand, Simon;Omoregie, Helen Oluwatola;Haehnel, Martin;Maier, Jonathan;Bringmann, Gerhard;Marder, Todd B.. And the article was included in ACS Catalysis in 2016.Synthetic Route of C10H13BrO This article mentions the following:

A copper(II)-catalyzed borylation of alkyl halides with bis(pinacolato)diboron (B₂pin₂) has been developed, which can be carried out in air, providing a wide range of primary, secondary, and some tertiary alkylboronates in high yields. A variety of functional groups are tolerated and the protocol is also applicable to unactivated alkyl chlorides (including 1,1- and 1,2-dichlorides). Preliminary mechanistic investigations show that this borylation reaction involves one-electron processes. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Synthetic Route of C10H13BrO).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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). The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Synthetic Route of C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Aminobenzothiazoles. XI. Synthesis of 5,4′-disubstituted 1-anilinobenzothiazoles from nuclear substituted thiocarbenilides was written by Dyson, George M.;Hunter, Robert F.;Soyka, Charles. And the article was included in Journal of the Chemical Society in 1929.Safety of 3,4-Dibromoaniline This article mentions the following:

(P-BrC₆H₄NH)₂CS and Br in CHCl₃ yield a perbromide, which, on heating, gives a hydropentabromide(I), C₁₃H₈N₂Br₂S.HBr.Br₄, orange-red needles, m. 170° (decomposition) and rapidly loses Br on exposure to moist air suspended in H₂SO₃ and treated with SO₂, there results 5,4′-dibromo-1-anilinobenzothiazole(II), m. 221°; Ac derivative, m. 205-6°; HBr salt, m. 250° (decomposition); Br gives I. 1-Chloro-5-bromobenzothiazole, m. 89°, b₁₃ 157-9°, results by heating p-BrC₆H₄NCS and PCl₅ 30-40 hrs. at 170-80° warming with p-BrC₆H₄NH₂ gives II. p-BrC₆H₄NHCSNHPh and Br in CHCl₃ give the hydrotribromide, m. 148° (decomposition), which is reduced to 4′-bromo-1-anilinobenzothiazole (III), m. 214-5°, also obtained from 1-chlorobenzothiazole and p-BrC₆H₄NH₂. Bromination of III gives II. 1-Anilinobenzothiazole yields a hexabromide, m. 140°, which yields II on being dissolved in boiling absolute EtOH. Hugershoff’s dibromoanilinobenzothiazole (Ber. 36, 3121(1903)) appears to consist mainly of II, although the m. p. could not be raised above 200°. Bromination of II gives an unstable orange hexabromide, m. 254°, which gives with hot absolute EtOH a tetra-Br substitution derivative, m. 196-8°. (p-ClC₆H₄NH)₂CS and Br in CHCl₃ yield a hydrotribromide, orange, m. 165-7° (decompm); reduction gives 5,4′-dichloro-1-aminobenzothiazole, m. 224°; Ac derivative, m. 186-7°; HBr salt. yellow, m. 217°; hexabromide, orange, m. 263° (decomposition). p-ClC₆H₄NHCSNHPh yields a Br addition compound, orange, m. 130° (decomposition); 4′-chloro-1-anilinobenzothiazole, m. 196°; this is also obtained from 1-chlorobenzothiazole and p-ClC₆H₄NH₂. (p-IC₆H₄NH)₂CS and Br in CHCl₃ yield a red bromide, m. 185°, and a yellow, m. 211°; both, on reduction, yield 5,4′-diiodo-1-anilinobenzothiazole, m. 193° (decomposition); this also results by treating 1-anilinobenzothiazole in AcOH with ICl, warming the solution and diluting with H₂O. (p-FC₆H₄NH)₂CS gives a hydrotribromide, orange, m. 150-2° (decomposition); 5,4′-difluoro-1-anilinobenzothiazole, m. 227-8°. 5,4′-Dinitro-1-anilinobenzothiazole, brilliant yellow, in. 280°; this also results on nitration of 1-anilinobenzothiazole. (p-NCC₆H₄NH)₂CS and Br give an addition product, golden, m. 159-60° (decomposition): 5,4′-dicyano-1-anilinobenzothiazole, m. 222°. (p-EtO₂CC₆H₄NH)₂CS yields a hydropentabromide, orange, m. 110° (decompn); reduction gives Et 1-anilinobenzothiazole-5,4′-dicarboxylate, m. 190-2°; hydrolysis gives the free acid, does not m. 290°. (p-MeOC₆H₄NH)₂CS yields a brick-red bromide, m. 137° (decomposition), reduced to a dibromo-5,4′-dimethoxy-1-anilinobenzothiazole, m. 240°. PhNHCSNAcPh yields a hydrotribromide, orange, m. 167° (decomposition); the same compound is obtained from 1-acetanilinobenzothiazole, HBr and Br (Hugershoff, Ber. 36, 3136(1903)); Br in CHCl₃ gives an orange hexa-Br addition compound, m. 163° (decomposition). In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Safety of 3,4-Dibromoaniline).

3,4-Dibromoaniline (cas: 615-55-4) 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.Safety of 3,4-Dibromoaniline

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Structure-Based Design, Synthesis, and Biological Evaluation of Imidazo[4,5-b]Pyridin-2-one-Based p38 MAP Kinase Inhibitors: Part 2 was written by Kaieda, Akira;Takahashi, Masashi;Fukuda, Hiromi;Okamoto, Rei;Morimoto, Shinji;Gotoh, Masayuki;Miyazaki, Takahiro;Hori, Yuri;Unno, Satoko;Kawamoto, Tomohiro;Tanaka, Toshimasa;Itono, Sachiko;Takagi, Terufumi;Sugimoto, Hiroshi;Okada, Kengo;Lane, Weston;Sang, Bi-Ching;Saikatendu, Kumar;Matsunaga, Shinichiro;Miwatashi, Seiji. And the article was included in ChemMedChem in 2019.Product Details of 29421-99-6 This article mentions the following:

We identified novel potent inhibitors of p38 mitogen-activated protein (MAP) kinase using a structure-based design strategy, beginning with lead compound, 3-(butan-2-yl)-6-(2,4-difluoroanilino)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1). To enhance the inhibitory activity of 1 against production of tumor necrosis factor-α (TNF-α) in human whole blood (hWB) cell assays, we designed and synthesized hybrid compounds in which the imidazo[4,5-b]pyridin-2-one core was successfully linked with the p-methylbenzamide fragment. Among the compounds evaluated, 3-(3-tert-butyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)-4-methyl-N-(1-methyl-1H-pyrazol-3-yl)benzamide (25) exhibited potent p38 inhibition, superior suppression of TNF-α production in hWB cells, and also significant in vivo efficacy in a rat model of collagen-induced arthritis (CIA). In this paper, we report the discovery of potent, selective, and orally bioavailable imidazo[4,5-b]pyridin-2-one-based p38 MAP kinase inhibitors. In the experiment, the researchers used many compounds, for example, 4-Bromo-5-methylthiophene-2-carboxylic acid (cas: 29421-99-6Product Details of 29421-99-6).

4-Bromo-5-methylthiophene-2-carboxylic acid (cas: 29421-99-6) 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.Product Details of 29421-99-6

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A simple and mild acylation of alcohols, phenols, amines, and thiols with a reusable heteropoly acid catalyst (H₆P₂W₁₈O₆₂·24 H₂O) was written by Romanelli, Gustavo P.;Bennardi, Daniel O.;Autino, Juan C.;Baronetti, Graciela T.;Thomas, Horacio J.. And the article was included in E-Journal of Chemistry in 2008.Application In Synthesis of 3-Bromophenyl acetate This article mentions the following:

The acylation of alcs., phenols, thiols, and amines with varied substitution using acid anhydrides is efficiently catalyzed by Wells-Dawson heteropoly acid (H₆P₂W₁₈O₆₂·24 H₂O). Reactions proceed with very good to excellent yield in air at room temperature, using toluene as solvent (40 examples). The bulk catalyst was easily reused without appreciable loss of its activity. In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2Application In Synthesis of 3-Bromophenyl acetate).

3-Bromophenyl acetate (cas: 35065-86-2) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.Application In Synthesis of 3-Bromophenyl acetate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palladium-Catalyzed C-H Oxidation of Isoquinoline N-Oxides: Selective Alkylation with Dialkyl Sulfoxides and Halogenation with Dihalo sulfoxides was written by Yao, Bo;Song, Ren-Jie;Liu, Yan;Xie, Ye-Xiang;Li, Jin-Heng;Wang, Meng-Ke;Tang, Ri-Yuan;Zhang, Xing-Guo;Deng, Chen-Liang. And the article was included in Advanced Synthesis & Catalysis in 2012.Name: 2-Bromo-4-(trifluoromethyl)benzaldehyde This article mentions the following:

A novel palladium-catalyzed C-H oxidation of isoquinoline N-oxides has been developed for regioselectively synthesizing substituted isoquinolines, e.g., I (R¹ = F, Cl, MeO, CF₃; R² = Me, n-Bu) and II (R³ = H, CF₃). The method represents the first example of using dialkyl sulfoxides as the alkyl sources for the construction of 1-alkylated isoquinolines. Moreover, the regioselective halogenation of isoquinoline N-oxides is also successful using dihalo sulfoxides as the halide sources. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Name: 2-Bromo-4-(trifluoromethyl)benzaldehyde).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) 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.Name: 2-Bromo-4-(trifluoromethyl)benzaldehyde

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Structure-Based Design of 1,4-Dibenzoylpiperazines as β-Catenin/B-Cell Lymphoma 9 Protein-Protein Interaction Inhibitors was written by Wisniewski, John A.;Yin, Jinya;Teuscher, Kevin B.;Zhang, Min;Ji, Haitao. And the article was included in ACS Medicinal Chemistry Letters in 2016.HPLC of Formula: 334792-52-8 This article mentions the following:

A small-mol. inhibitor with a 1,4-dibenzoylpiperazine scaffold was designed to match the critical binding elements in the β-catenin/B-cell lymphoma 9 (BCL9) protein-protein interaction interface. Inhibitor optimization led to a potent inhibitor that can disrupt the β-catenin/BCL9 interaction and exhibit 98-fold selectivity over the β-catenin/cadherin interaction. The binding mode of new inhibitors was characterized by structure-activity relationships and site-directed mutagenesis studies. Cell-based studies demonstrated that this series of inhibitors can selectively suppress canonical Wnt signaling and inhibit growth of Wnt/β-catenin-dependent cancer cells. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-5-fluorobenzoate (cas: 334792-52-8HPLC of Formula: 334792-52-8).

Methyl 3-bromo-5-fluorobenzoate (cas: 334792-52-8) 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.HPLC of Formula: 334792-52-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary