Category: 215949-57-8

Mel’nikov, N. N.; Turetskaya, R. Kh.; Baskakov, Yu. A.; Boyarkin, A. N.; Kuznetsova, M. S. published the artcile< The structure and the physiological activity of substituted phenylacetic and naphthylacetic acids>, Product Details of C9H9BrO2, the main research area is .

Introduction of halogen into the ring of PhCH2CO2H increases the physiol. activity, which is greatest with Cl; Br is less active; iodine in the p-position does not increase activity. Most active are the 2-halo, least active the 4-halo derivatives, while the 3-halo derivatives are intermediate. This is the reverse order of activity in comparison with phenoxyacetic acids. Introduction of a 2nd halogen does not change the physiol. activity, while a 3rd halogen can either reduce or increase activity. A Me group in the p-position reduces the activity, and 3 Me groups reduce it very much. A smaller decrease in activity is caused by a p-MeO group. Halogenation of m-MeC6H4OCH2CO2H causes increased activity, the greatest activity resulting from 4-substitution, and lesser activity from 2-halogenation. With 2,4-D as the standard which gave 100% increase of wheat coleoptile growth at 1 mg./l. concentration, and heteroauxin as the standard which gave 100% increase of kidneybean root growth, the following physiol. results were obtained in plant tests; (in above order, with 1, 10, and 100 mg./l. concentrations tested for the wheat growth, and 10, 50 and 100 mg./l. concentrations for the kidney bean growth). Substituted phenylacetic acids (substituents given): H, m. 76°, -2%, +45%, -, -, +4%, 0%; ο-Cl, m. 95°, +70%, +84%, – +5%, +150%, -; m-Cl, m. 74°, +9%, +61%, -, -, +62%, +260%; p-Cl, m. 106°, +13%, +71%, -, -, +55%, +91%; ο-Br, m. 104°, +7%, +71%, -, -, +33%, +104%; p-Br, m. 114°, +2%, +80%, -, -, 0%, +8%; p-I, m. 135°, -4%, -6%, -, -, 0%, +21%; 2,4-di-Cl, m. 131°, +10%, +80%, -, -, +58%, +162%; 2,5-di-Cl, m. 105°, +13%, +80%, -, -, +30%, +120%; 2,3,4-tri-Cl, m. 136°, +40%, +71%, -, -, +150%, -60%; 2,4,5-tri-Cl analog, m. 126°, 0%, +56%, -, -, +98%, +100%; p-MeO, m. 83°, -, +20%, +20%, -, 0%, 0%; p-Me, m. 92°, -, +5%, +6%, -, 0%, 0%; 4,3-ClMe, m. 83°, +22%, +73%, -, -, +7%, +69%; 4,3-BrMe, m. 81°, +20%, +71%, -, -, 14%, +90%; 6,3-ClMe, m. 86°, -2%, +40%, -, -, 0%, -25%; 6,3-BrMe, m. 82°, -8%, +59%, -, -, +66%, +66%;, 2,4-ClMe, m. 106°, +13%, +44%, -, -, +12%, +33%; 3,4-Me(MeO), m. 127°, -, +1%, +34%, -, 0%, 0%; 2,4,5-Tri-Me, m. 117°, -, +3%, -6%, -, -21%, -25%; 2,4-Me(MeO), m. 107°, -, -12%, +25%, -, 0%, 0%. In substituted naphthylalkylcarboxylic acids it was shown that removal of CO2H from the ring by more than 1 C atom reduces the physiol. activity and the compounds with an acid group at the 1-position on C10H8 skeleton are the only active ones; substances with 2-substitution are inactive. Substitution of alkyl groups or MeO groups into the C10H8 ring leads to sharp decline in activity. The following results were obtained in biol. tests (same standards as above): Substituted 1-naphthaleneacetic acids (substituents given): H, m. 131°, +77%, + 169%, -, -, +92%, -; 4-MeO, m. 144°, +2%, -12%, -, +10%, +27%, +9%; 4-Me, m. 148°, +1%, +1%, +4%, +36%, +24%, -10%; 4-Et, m. 129°, +9%, -, -, +9%, +6%, +27%; 4-Pr, m. 119°, -5%, -7%, -, +24%, +50%, +32%; 4-Bu, m. 110°, -, -14%, -, +21%, +20%, +33%. 1-C10H7COCH2CH2CO2H, m. 132°, +9%, +60%, -, -, -, -; 1-C10H7(CH2)3CO2H, m. 1602, +9%, +46%, -, -, -, -; 2-C10H7COCH2CH2CO2H, m. 174°, -25%, -9%, -, -, -, -, 2-C10H7(CH2)3CO2H, m. 109°, -3%, -5%, -, -, -, -. Most of the above acids were prepared by the Willgerodt reaction others through the nitriles from the corresponding benzyl halides.

Doklady Akademii Nauk SSSR published new progress about Halogens. 215949-57-8 belongs to class bromides-buliding-blocks, and the molecular formula is C9H9BrO2, Product Details of C9H9BrO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Schuisky, Peter; Federsel, Hans-Jurgen; Tian, Wei published the artcile< Regioisomerism in the Synthesis of a Chiral Aminotetralin Drug Compound: Unraveling Mechanistic Details and Diastereomer-Specific In-Depth NMR Investigations>, Recommanded Product: 2-(4-Bromo-3-methylphenyl)acetic acid, the main research area is regioisomerism synthesis chiral aminotetralin drug ARA2 unraveling mechanism.

During chem. process development of a novel 2-aminotetralin derivative(I) intended for use as an antidepressant, scrutiny of the byproduct present in the drug mol. revealed a set of regioisomers. Detailed studies showed that this impurity issue originated from an early synthetic step in which a brominated tetralone motif was generated in a ring-closing protocol. It was found that this reaction was accompanied by a migration of the aromatic bromo substituent via different bromonium species along two discrete pathways. This example of the halogen dance reaction resulted in the formation of a series of tetralone impurities with a bromine distributed across all available aromatic positions of the tetralin nucleus. Subsequently, when subjected to reductive amination conditions, each of these tetralones gave rise to pairs of aminotetralins in a diastereomeric relationship. NMR investigations revealed that the alicyclic portion of the compounds thus formed displayed very complex signal patterns, which required further in-depth studies using a variety of sophisticated techniques. As a result, a deep insight into the structural features of the current 2-aminotetralin family was obtained, which is emphasized by the definition of a novel “”0.2 ppm rule”” allowing the absolute configuration at tetralin C-2 to be determined

Journal of Organic Chemistry published new progress about Absolute configuration. 215949-57-8 belongs to class bromides-buliding-blocks, and the molecular formula is C9H9BrO2, Recommanded Product: 2-(4-Bromo-3-methylphenyl)acetic acid.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sun, Nannan; Huang, Yafei; Yu, Mingcheng; Zhao, Yunpeng; Chen, Ji-An; Zhu, Chenyu; Song, Meiqi; Guo, Huimin; Xie, Qiong; Wang, Yonghui published the artcile< Discovery of carboxyl-containing biaryl ureas as potent RORγt inverse agonists>, Application In Synthesis of 215949-57-8, the main research area is autoimmune diseases ROR gamma t inverse agonists Th17 cells; Autoimmune diseases; Biaryl ureas; Inverse agonists; RORγt; Th17 cells.

GSK805 (1) is a potent RORγt inverse agonist, but a drawback of 1 is its low solubility, leading to a limited absorption in high doses. We have explored detailed structure-activity relationship on the amide linker, biaryl and arylsulfonyl moieties of 1 trying to improve solubility while maintaining RORγt activity. As a result, a novel series of carboxyl-containing biaryl urea derivatives was discovered as potent RORγt inverse agonists with improved drug-like properties. Compound 3i(I) showed potent RORγt inhibitory activity and subtype selectivity with an IC50 of 63.8 nM in RORγ FRET assay and 85 nM in cell-based RORγ-GAL4 promotor reporter assay. Reasonable inhibitory activity of 3i was also achieved in mouse Th17 cell differentiation assay (76% inhibition at 0.3 μM). Moreover, 3i had greatly improved aqueous solubility at pH 7.4 compared to 1, exhibited decent mouse PK profile and demonstrated some in vivo efficacy in an imiquimod-induced psoriasis mice model.

European Journal of Medicinal Chemistry published new progress about Autoimmune disease. 215949-57-8 belongs to class bromides-buliding-blocks, and the molecular formula is C9H9BrO2, Application In Synthesis of 215949-57-8.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary