7462-74-0Relevant academic research and scientific papers
Preparation of N-Aryl-2-hydroxypropionamides from hydroxy aromatic compounds using a one-pot smiles rearrangement procedure
Weidner, John J.,Weintraub, Philip M.,Schnettler, Richard A.,Peet, Norton P.
, p. 6303 - 6312 (1997)
Acylation of hydroxy aromatic compounds with 2-bromo-2-methylpropionamide followed by Smiles rearrangement of the resulting 2-aryloxypropionamide in a one-pot procedure produced the corresponding 2-hydroxy-2-methyl-N-arylpropionamides which can be converted to arylamines by hydrolysis. Particularly important applications of this new process were the conversions of estrone (6) and estradiol (14) to the corresponding 3-aminoestrahriene derivatives 8 and 15, respectively. In addition, an improved Semmler-Wolff procedure is described for the conversion of 19-nortestosterone (22) to 3-aminoestra-1,3,5(10)-uien-17β-ol hydrochloride (26).
Discovery of (E)-4-styrylphenoxy-propanamide: A dual PPARα/γ partial agonist that regulates high-density lipoprotein-cholesterol levels, modulates adipogenesis, and improves glucose tolerance in diet-induced obese mice
Dutra, Luiz A.,Lacerda, Mariella G.,Destro Inácio, Maiara,Martins, Johnny W.L.,Lopes Silva, Ana C.,Bento da Silva, Patricia,Chorilli, Marlus,Amato, Angélica A.,Baviera, Amanda M.,Passarelli, Marisa,Guido, Rafael V.C.,Dos Santos, Jean L.
supporting information, (2022/01/26)
Peroxisome proliferator-activated receptors are promising therapeutic targets for metabolic diseases, including obesity, diabetes, and dyslipidemia. This study describes the design, synthesis and pharmacological evaluation of stilbene-based compounds as d
Switchable Smiles Rearrangement for Enantioselective O-Aryl Amination
Chang, Xihao,Zhang, Qinglin,Guo, Chang
supporting information, p. 4915 - 4918 (2019/06/27)
Asymmetric assembly of atropisomeric anilines from abundant and readily available precursors is one of the most challenging but valuable processes in organic synthesis. The use of highly efficient Smiles rearrangement to accomplish switchable enantioselec
Method for synthesizing netarsudil intermediate
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Paragraph 0067-0073; 0088-0093; 0109-0115, (2019/11/20)
The invention relates to a method for synthesizing a netarsudil intermediate that is 6-aminoisoquinoline. The method includes (1) dissolving 2-bromo-2-methylpropionic acid; (2) adding oxalyl chloride,and then reacting the mixture; (3) after the reaction is completed, pouring the reaction solution into aqueous ammonia, stirring the mixture, performing filtration and drying a product. The method utilizes conventional and easily available chemical materials, and has characteristics of mild reactions, a short route and a high yield.
Discovery of Potent and Selective Agonists of δ Opioid Receptor by Revisiting the "message-Address" Concept
Shen, Qing,Qian, Yuanyuan,Huang, Xiaoqin,Xu, Xuejun,Li, Wei,Liu, Jinggen,Fu, Wei
supporting information, p. 391 - 396 (2016/05/19)
The classic "message-address" concept was proposed to address the binding of endogenous peptides to the opioid receptors and was later successfully applied in the discovery of the first nonpeptide δ opioid receptor (DOR) antagonist naltrindole. By revisiting this concept, and based on the structure of tramadol, we designed a series of novel compounds that act as highly potent and selective agonists of DOR among which (-)-6j showed the highest affinity (Ki = 2.7 nM), best agonistic activity (EC50 = 2.6 nM), and DOR selectivity (more than 1000-fold over the other two subtype opioid receptors). Molecular docking studies suggest that the "message" part of (-)-6j interacts with residue Asp1283.32 and a neighboring water molecule, and the "address" part of (-)-6j packs with hydrophobic residues Leu3007.35, Val2816.55, and Trp2846.58, rendering DOR selectivity. The discovery of novel compound (-)-6j, and the obtained insights into DOR-agonist binding will help us design more potent and selective DOR agonists.
A COMPOUND AND A PHARMACEUTICAL COMPOUND FOR TREATMENT OF INFLAMMATORY DISEASES
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Paragraph 0113-0116, (2016/10/09)
The present invention relates to a compound and a pharmaceutical composition for treating inflammatory diseases, and the present invention is characterized by being a compound represented by chemical formula I or a pharmaceutically acceptable salt, hydrat
COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF PARASITIC DISEASES
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Page/Page column 132, (2014/06/11)
The present invention provides compounds of formula I: [INSERT FORMULA HERE] or a pharmaceutically acceptable salt, tautomer, or stereoisomer, thereof, wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds and methods of using such compounds for treating, preventing, inhibiting, ameliorating, or eradicating the pathology and/or symptomology of a disease, such as malaria, caused by a Plasmodium parasite.
Approaches to the synthesis of 2,3-dihaloanilines. Useful precursors of 4-functionalized-1 H-indoles
Guilarte, Veronica,Castroviejo, M. Pilar,Garcia-Garcia, Patricia,Fernandez-Rodriguez, Manuel A.,Sanz, Roberto
body text, p. 3416 - 3437 (2011/06/28)
2,3-Dihaloanilines have been proved as useful starting materials for synthesizing 4-halo-1H-indoles. Subsequent or in situ functionalization of the prepared haloindoles allows the access to a wide variety of 2,4- or 2,3,4-regioselectively functionalized indoles in good overall yields. As no efficient synthetic routes to 2,3-dihaloanilines have been described in the literature, different approaches to the preparation of these 1,2,3-functionalized aromatic precursors are now presented. The most general one involves a Smiles rearrangement from the corresponding 2,3-dihalophenols and allows the preparation of 2,3-dihaloanilides in a straightforward and synthetically useful manner.
Imidazol-4-one and Imidazole-4-thione Compounds
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Page/Page column 15-16, (2010/05/13)
Imidazol-4-one or imidazole-4-thione compounds of formula (I): wherein X, R1, R2, R3, R4, R5, and R6 are defined herein. Also disclosed is a method for treating a cannabinoid receptor-mediated disorder with these compounds.
DIBENZOTHIOPHENE DERIVATIVES AS DNA- PK INHIBITORS
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Page/Page column 71, (2010/12/26)
Compound formula I: wherein: X1 and X2 may be either (a) C and O, (b) N and N, or (c) C and NH, where the dotted bonds represents a double bond in the appropriate location; R1 and R2 are independently selected from hydrogen, an optionally substituted C1-7 alkyl group, an optionally substituted C3-20 heterocyclyl group, or an optionally substituted C5-20 aryl group, or may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; RN1 is selected from hydrogen and an optionally substituted C1-4 alkyl group; RC1 is selected from an optionally substituted C1-7 alkyl group, an optionally substituted C3-20 heterocyclyl group, or an optionally substituted C5-20 aryl group; or RN1 and RC1 may together form an optionally substituted C2-4 alkylene group.
