1916-04-7Relevant academic research and scientific papers
Rational design of new multitarget histamine H3 receptor ligands as potential candidates for treatment of Alzheimer's disease
?a?ewska, Dorota,Alachkar, Alaa,Bajda, Marek,Doroz-P?onka, Agata,Godyń, Justyna,Handzlik, Jadwiga,Kaleta, Maria,Kie?-Kononowicz, Katarzyna,Kuder, Kamil,Latacz, Gniewomir,Malawska, Barbara,Mogilski, Szczepan,Olejarz-Maciej, Agnieszka,Saad, Ali,Sadek, Bassem,Siwek, Agata,Stary, Dorota,Sudo?, Sylwia,Walczak, Maria,Wi?cek, Ma?gorzata,Zar?ba, Paula
, (2020/09/02)
Design and development of multitarget-directed ligands (MTDLs) has become a very important approach in the search of new therapies for Alzheimer's disease (AD). In our present research, a number of xanthone derivatives were first designed using a pharmaco
Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation
Chang, Xihao,Zhang, Qinglin,Guo, Chang
supporting information, p. 10 - 13 (2019/01/04)
A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochemical radical Smiles rearrangement. Remarkably, an amidyl radical generated from the cleavage of the N-O bond under reductive electrolytic conditions plays a crucial role in this transformation. Various hydroxylamine derivatives bearing different substituents are suitable in this electrochemical transformation, furnishing the corresponding amides in up to 86% yield.
Formal Aniline Synthesis from Phenols through Deoxygenative N-Centered Radical Substitution
Lardy, Samuel W.,Luong, Kristine C.,Schmidt, Valerie A.
supporting information, p. 15267 - 15271 (2019/12/11)
Phenolic, lignin-derived substrates have emerged as desirable biorenewable chemical feedstocks for coupling reactions. A radical-mediated conversion of phenol derivatives to anilines is reported, using unfunctionalized hydroxamic acids as the N-centered radical source. The applicability of this triethyl phosphite mediated O-atom transfer approach, which tolerates a range of steric and electronic demands to naturally occurring phenols and lignin models, has been demonstrated in this work to access the corresponding aniline derivatives.
A photoredox-neutral Smiles rearrangement of 2-aryloxybenzoic acids
Gonzalez-Gomez, Jose C.,Ramirez, Nieves P.,Lana-Villarreal, Teresa,Bonete, Pedro
, p. 9680 - 9684 (2017/11/30)
We report on the use of visible light photoredox catalysis for the radical Smiles rearrangement of 2-aryloxybenzoic acids to obtain aryl salicylates. The method is free of noble metals and operationally simple and the reaction can be run under mild batch or flow conditions. Being a redox neutral process, no stoichiometric oxidants or reductants are needed.
Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis
Wang, Shao-Feng,Cao, Xiao-Ping,Li, Yang
supporting information, p. 13809 - 13813 (2017/10/24)
We have developed a highly efficient aryl migration from an aryl ether to a carboxylic acid group through retro-Smiles rearrangement by visible-light photoredox catalysis at ambient temperature. Transition metals and a stoichiometric oxidant and base are avoided in the transformation. Inspired by the high efficiency of this transformation and the fundamental importance of C?O bond cleavage, we developed a novel approach to the C?O cleavage of a biaryl ether to form two phenolic compounds, as demonstrated by a one-pot, two-step gram-scale reaction under mild conditions. The aryl migration exhibits broad scope and can be applied to the synthesis of pharmaceutical compounds, such as guacetisal. Primary mechanistic studies indicate that the catalytic cycle occurs by a reductive quenching pathway.
Design, synthesis, and anticonvulsant activity of some derivatives of xanthone with aminoalkanol moieties
Waszkielewicz, Anna M.,S?oczyńska, Karolina,P?kala, El?bieta,?mudzki, Pawe?,Siwek, Agata,Grybo?, Anna,Marona, Henryk
, p. 339 - 352 (2017/04/03)
A series of new xanthone derivatives have been synthesized and evaluated for their anticonvulsant properties in the maximal electroshock, subcutaneous metrazole tests and for neurotoxicity in the rotarod in mice, i.p. and rats, p.o. Compound 9: R,S-2-{2-[(1-hydroxybutan-2-yl]amino)ethoxy}-9H-xanthen-9-one and compound 12: R,S-2-{3-[(1-hydroxybutan-2-yl)amino]propoxy}-9H-xanthen-9-one exerted activity in rats, p.o. 2 and 4?h after administration, respectively. Therefore, metabolic stability of the compounds was evaluated with use of rat microsomes, resulting in half-life t1/2 136 and 108?min, respectively, indicating that either the metabolites are very active or the parent compounds exert ADME properties other than metabolism which influence the late onset of activity.
Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement
Hossian, Asik,Jana, Ranjan
, p. 9768 - 9779 (2016/10/31)
We report herein, a silver(i)-catalyzed Smiles rearrangement of 2-aryloxy- or 2-(arylthio)benzoic acids to provide aryl-2-hydroxybenzoate or aryl-2-mercaptobenzoate dimer, respectively, through 1,5-aryl migration from oxygen or sulfur to carboxylate oxygen. Mechanistically, the aryl ether moiety undergoes an intramolecular ipso attack by the carboxyl radical followed by a C-O or C-S bond cleavage. Aryl-2-mercaptobenzoates undergo oxidative dimerization through a thiol moiety in situ.
Synthesis and fluorescence of xanthone amino acids
Hoppmann, Christian,Alexiev, Ulrike,Irran, Elisabeth,Rück-Braun, Karola
supporting information, p. 4585 - 4587 (2013/08/23)
Fmoc- and Boc-protected α-amino acids bearing xanthone as side chain are easily accessible by palladium-catalyzed cross-coupling of a xanthone triflate with appropriate amino acid residues. The xanthone triflate was obtained in three steps taking advantag
Highly efficient and regiospecific photocyclization of 2,2′-diacyl bixanthenylidenes
Mao, Mao,Wu, Qing-Qing,Ren, Ming-Guang,Song, Qin-Hua
supporting information; experimental part, p. 3165 - 3169 (2011/05/12)
In contrast to the reversible photochemistry of the 2,2′-substituted bixanthenylidenes (1a-f), the photocyclization of 2,2′-diacyl bixanthenylidenes (1g-j) reveals an irreversible process where the initial cyclic intermediate C(E) can undergo a rapid [1,1
