42132-07-0Relevant academic research and scientific papers
Catalytic asymmetric cycloetherification via intramolecular oxy-Michael addition of enols
Murata, Ryuichi,Asano, Keisuke,Matsubara, Seijiro
, (2021)
Carbonyl compounds employed as carbon nucleophiles have played a dominant role in synthetic organic chemistry; however, there is very limited use of these compounds as oxygen nucleophiles. In particular, there are only a few reports on the oxy-Michael addition of the enol forms of carbonyl nucleophiles. In this study, we present the asymmetric cycloetherification of enols, which are generated in situ from enone-bearing ketones, using chiral bifunctional organocatalysts bearing amino and squaramide groups. This transformation chemo- and enantioselectively afforded dihydropyran derivatives, which are the core structures of building blocks for synthesizing glycans.
Investigation of Squaramide Catalysts in the Aldol Reaction En Route to Funapide
Sonsona, Isaac G.,Vicenzi, Andrea,Guidotti, Marco,Bisag, Giorgiana Denisa,Fochi, Mariafrancesca,Herrera, Raquel P.,Bernardi, Luca
supporting information, (2021/11/23)
Funapide is a 3,3’-spirocyclic oxindole with promising analgesic activity. A reported pilot-plant scale synthesis of this chiral compound involves an asymmetric aldol reaction, catalyzed by a common bifunctional thiourea structure. In this work, we show that the swapping of the thiourea unit of the catalyst for a tailored squaramide group provides an equally active, but rewardingly more selective, catalyst for this aldol reaction (from 70.5 to 85 % ee). The reaction was studied first on a model oxindole compound. Then, the set of optimal conditions was applied to the target funapide intermediate. The applicability of these conditions seems limited to oxindoles bearing the 3-substituent of funapide. Exemplifying the characteristics of target-focused methodological development, this study highlights how a wide-range screening of catalysts and reaction conditions can provide non-negligible improvements in an industrially viable asymmetric transformation.
3-substituted amino-4-((substituted pyridyl)amino)cyclobutyl-3-ene-1, 2-diketone compound
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Paragraph 0097; 0100-0104, (2021/05/08)
The invention belongs to the technical field of medicines, and discloses a 3-substituted amino-4-((substituted pyridyl) amino) cyclobutyl-3-ene-1, 2-diketone compound, a preparation method thereof, a pharmaceutical composition taking the compound as an active component, and an application of the compound and the pharmaceutical composition in treatment and/or prevention of infectious diseases caused by mycobacterium tuberculosis. Specifically, the invention relates to a compound as shown in a formula (I), pharmaceutically acceptable salts thereof and a pharmaceutical composition containing the compound, and R1 and R2 are described in the specification. The invention aims to prepare a new compound with anti-mycobacterium tuberculosis activity, which can be used as a potential new drug for treatment or prophylactic treatment of infectious diseases caused by bacteria, especially pulmonary tuberculosis (TB) diseases caused by mycobacterium tuberculosis, and also can be used for overcoming problems related to drug resistance of mycobacterium tuberculosis.
Tripodal, squaramide‐based ion pair receptor for effective extraction of sulfate salt
Jagleniec, Damian,Romański, Jan,Wilczek, Marcin
, (2021/05/28)
Combining three features—the high affinity of squaramides toward anions, cooperation in ion pair binding and preorganization of the binding domains in the tripodal platform—led to the effective receptor 2. The lack of at least one of these key elements in
Study on the Catalytic Behavior of Bifunctional Hydrogen-Bonding Catalysts Guided by Free Energy Relationship Analysis of Steric Parameters
Yang, Chen,Wang, Jie,Liu, Yang,Ni, Xiang,Li, Xin,Cheng, Jin-Pei
, p. 5488 - 5497 (2017/04/27)
Free energy relationship (FER) studies to correlate steric parameters with the enantiocatalytic performance of bifunctional tertiary-amine hydrogen-bonding catalysts, including (S,S)-cyclohexane-1,2-diamine-derived thioureas, Cinchona alkaloid derived thioureas, and (S,S)-cyclohexane-1,2-diamine-derived squaramides, in Michael reactions revealed that the reactions are much favored by catalysts with less bulky N-substituents. The observed FERs are independent of the chiral scaffold and hydrogen-bond donor, and deepen the understanding of current bifunctional hydrogen-bonding catalysts. Moreover, DFT calculations were performed to interpret the observed high reactivities of thioureas with less bulky substituents. In particular, the computations demonstrated the advantage of a benzyl thiourea catalyst, in which an extra CH???π interaction between catalyst and substrate is the key factor.
TRIAMINOPYRIMIDINE CYCLOBUTENEDIONE DERIVATIVES USED AS PHOSPHATASE CDC25 INHIBITORS
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Page/Page column 18, (2010/07/10)
The present invention relates to triaminopyrimidine derivatives of formula (I) where Y, R3, W, R4a, R5a, R4b, R5b, n and m are variable. These compounds have CDC25 phosphatase-inhibiting activity and can therefore be used as drugs in diseases in which CDC
