90765-38-1Relevant academic research and scientific papers
Manganese-Pincer-Catalyzed Nitrile Hydration, α-Deuteration, and α-Deuterated Amide Formation via Metal Ligand Cooperation
Ben-David, Yehoshoa,Diskin-Posner, Yael,Kar, Sayan,Milstein, David,Zhou, Quan-Quan,Zou, You-Quan
, p. 10239 - 10245 (2021/08/24)
A simple and efficient system for the hydration and α-deuteration of nitriles to form amides, α-deuterated nitriles, and α-deuterated amides catalyzed by a single pincer complex of the earth-abundant manganese capable of metal-ligand cooperation is reported. The reaction is selective and tolerates a wide range of functional groups, giving the corresponding amides in moderate to good yields. Changing the solvent from tert-butanol to toluene and using D2O results in formation of α-deuterated nitriles in high selectivity. Moreover, α-deuterated amides can be obtained in one step directly from nitriles and D2O in THF. Preliminary mechanistic studies suggest the transformations contributing toward activation of the nitriles via a metal-ligand cooperative pathway, generating the manganese ketimido and enamido pincer complexes as the key intermediates for further transformations.
A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids
Han, Buxing,Ke, Zhengang,Li, Ruipeng,Liu, Zhimin,Tang, Minhao,Wang, Yuepeng,Zeng, Wei,Zhang, Fengtao,Zhao, Yanfei
supporting information, p. 9870 - 9875 (2021/12/27)
Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.
Fragment based drug design and diversity-oriented synthesis of carboxylic acid isosteres
Alunno, Manuel,Camaioni, Emidio,Carotti, Andrea,Ferri, Martina,Greco, Francesco Antonio,Liscio, Paride,Macchiarulo, Antonio,Mammoli, Andrea,Saluti, Giorgio,Sardella, Roccaldo
, (2020/09/15)
The medicinal chemist toolbox is plenty of (bio)isosteres when looking for a carboxylic acid replacement. However, systematic assessment of acid surrogates is often time consuming and expensive, while prediction of both physicochemical properties (logP and logD) as well as acidity would be desirable at early discovery stages for a better analog design. Herein in this work, to enable decision making on a project, we have synthesized by employing a Diversity-Oriented Synthetic (DOS) methodology, a small library of molecular fragments endowed with acidic properties. By combining in-silico and experimental methodologies these compounds were chemically characterized and, particularly, with the aim to know their physicochemical properties, the aqueous ionization constants (pKa), partition coefficients logD and logP of each fragment was firstly estimated by using molecular modeling studies and then validated by experimental determinations. A face to face comparison between data and the corresponding carboxylic acid might help medicinal chemists in finding the best replacement to be used. Finally, in the framework of Fragment Based Drug Design (FBDD) the small library of fragments obtained with our approach showed good versatility both in synthetic and physico-chemical properties.
Pd(OAc)2-catalyzed lactonization of arylacetamides involving oxidation of C-H bonds
Uemura, Takeshi,Igarashi, Takuya,Noguchi, Moe,Shibata, Kaname,Chatani, Naoto
, p. 621 - 623 (2015/05/20)
The reaction of arylacetamides that contain a quinolin-8-ylmethylamine as the directing group with PhI(OAc)2, in the presence of Pd(OAc)2 as the catalyst, results in lactonization to give γ-lactones, the formation of which involves activation of the ortho C-H bonds, with concomitant cleavage of the directing group.
Aryl-indolyl maleimides as inhibitors of CaMKIIδ. Part 1: SAR of the aryl region
Levy, Daniel E.,Wang, Dan-Xiong,Lu, Qing,Chen, Zheng,Perumattam, John,Xu, Yong-jin,Liclican, Albert,Higaki, Jeffrey,Dong, Hanmin,Laney, Maureen,Mavunkel, Babu,Dugar, Sundeep
, p. 2390 - 2394 (2008/09/21)
A family of aryl-substituted maleimides was prepared and studied for their activity against calmodulin dependant kinase. Inhibitory activities against the enzyme ranged from 34 nM to >20 μM and were dependant upon both the nature of the aryl group and the hydrogen bond donating potential of the maleimide ring. Key interactions with the kinase ATP site and hinge region were found to be consistent with homology modeling predictions.
PHENYLTHIOACETIC ACID DERIVATIVES AND USE THEREOF
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Page/Page column 63, (2010/02/14)
The invention relates to novel phenylthioacetic acid derivatives of formula (I), to a method for the production thereof, to the use thereof for the treatment and/or prophylaxis of diseases, in addition to the use thereof in the production of medicaments for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prevention of cardiovascular diseases, in particular dyslipidaemia and arteriosclerosis. The compounds act as modulators for the PRAR-alpha receptor.
