- L-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction
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l-(+)-Tartaric acid-choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.
- Wang, Ping,Ma, Fei-Ping,Zhang, Zhan-Hui
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- A novel and convenient method for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones; synthesis and mechanistic study
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An efficient, regioselective synthesis has been developed for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones from readily available 1H-pyrroles by sequential dibromination and selective organometallic bromine/lithium exchange followed by reaction with benzophenone. Comparison of various N-substituents was shown to demonstrate the high tolerance of the transformation to functional groups. The structures of the new products were determined by spectroscopic methods and confirmed by single-crystal X-ray diffraction measurement. In addition, theoretical study of the reaction mechanism and selective functionalization of the endocyclic double bond were also presented.
- Faigl, Ferenc,Deák, Szilvia,Mucsi, Zoltán,Hergert, Tamás,Balázs, László,Sándor, Boros,Balázs, Barbara,Holczbauer, Tamás,Nyerges, Miklós,Mátrav?lgyi, Béla
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p. 5444 - 5455
(2016/08/04)
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- Identification of Noncompetitive Inhibitors of Cytosolic 5′-Nucleotidase II Using a Fragment-Based Approach
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We used a combined approach based on fragment-based drug design (FBDD) and in silico methods to design potential inhibitors of the cytosolic 5′-nucleotidase II (cN-II), which has been recognized as an important therapeutic target in hematological cancers. Two subgroups of small compounds (including adenine and biaryl moieties) were identified as cN-II binders and a fragment growing strategy guided by molecular docking was considered. Five compounds induced a strong inhibition of the 5′-nucleotidase activity in vitro, and the most potent ones were characterized as noncompetitive inhibitors. Biological evaluation in cancer cell lines showed synergic effect with selected anticancer drugs. Structural studies using X-ray crystallography lead to the identification of new binding sites for two derivatives and of a new crystal form showing important domain swapping. Altogether, the strategy developed herein allowed identifying new original noncompetitive inhibitors against cN-II that act in a synergistic manner with well-known antitumoral agents.
- Marton, Zsuzsanna,Guillon, Rémi,Krimm, Isabelle,Preeti,Rahimova, Rahila,Egron, David,Jordheim, Lars P.,Aghajari, Nushin,Dumontet, Charles,Périgaud, Christian,Lionne, Corinne,Peyrottes, Suzanne,Chaloin, Laurent
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p. 9680 - 9696
(2016/01/12)
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- Synthesis of heteroaromatic derivatives with nitrogen atoms: Tripyrrolyl pyrimidine and tripyrrolyl[1,3,5]triazine
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As a part of a research program related to the synthetic study of pharmacologically and photoconductively interesting pyrrole derivatives, we have synthesized 1-arylpyrroles (3a-e), 9-arylcarbazoles (4a-e), aminophenylpyrroles (6a,b), dipyrrolylbenzenes (7a-c), 2,4,6-tri-pyrrol-1- yl-pyrimidine (8) and 2,4,6-tri-pyrrol-1-yl[1,3,5]triazine (9). We proposed a plausible mechanism for the formation of 9-arylcarbazole.
- Lee,Lee,Jung,Hahn
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p. 501 - 504
(2013/02/22)
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- A recyclable magnetic nanoparticles supported antimony catalyst for the synthesis of N-substituted pyrroles in water
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A new magnetic nanoparticle-supported antimony catalyst was prepared and evaluated as a recoverable catalyst for Clauson-Kaas reaction. The reaction proceeds efficiently in aqueous medium to give the corresponding N-substituted pyrroles in high yield. The immobilized catalyst could be easily recovered by magnetic separation and recycled for six times without significant loss of its catalytic activity.
- Ma, Fei-Ping,Li, Pei-He,Li, Bao-Le,Mo, Li-Ping,Liu, Ning,Kang, Hui-Jun,Liu, Ya-Nan,Zhang, Zhan-Hui
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- Identification of a novel arylpiperazine scaffold for fatty acid amide hydrolase inhibition with improved drug disposition properties
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We herein describe the systematic approach used to develop new analogues of compound 2, recently identified as a potent and selective fatty acid amide hydrolase (FAAH) inhibitor. Aiming at identifying new scaffolds endowed with improved drug disposition properties with respect to the phenylpyrrole-based lead, we subjected it to two different structural modification strategies. This process allowed the identification of derivatives 4b and 5c as potent, reversible and non-competitive FAAH inhibitors.
- Butini, Stefania,Gemma, Sandra,Brindisi, Margherita,Maramai, Samuele,Minetti, Patrizia,Celona, Diana,Napolitano, Raffaella,Borsini, Franco,Cabri, Walter,Fezza, Filomena,Merlini, Lucio,Dallavalle, Sabrina,Campiani, Giuseppe,MacCarrone, Mauro
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p. 492 - 495
(2013/02/25)
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- Efficient copper-catalyzed N-arylations of nitrogen-containing heterocycles and aliphatic amines in water
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A simple and efficient copper-catalyzed method has been developed for N-arylations of nitrogen-containing heterocycles and aliphatic amines in water. The protocol uses (1E,2E)-oxalaldehyde dioxime (OADO) as the ligand, and water as the solvent, and shows good tolerance towards various functional groups.
- Li, Xufeng,Yang, Daoshan,Jiang, Yuyang,Fu, Hua
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experimental part
p. 1097 - 1105
(2010/08/06)
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- Solvent and ligand effects on selective mono- and dilithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles
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Novel methods for site-selective lithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles are described. Mono- or dilithiations are governed by change of both the temperature and the solvent from tetrahydrofuran to diethyl ether. Regioselectiv
- Fogassy, Katalin,Kovacs, Krisztina,Keseru, Gyoergy M.,Toke, Laszlo,Faigl, Ferenc
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p. 1039 - 1043
(2007/10/03)
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- Synthesis and nuclear magnetic resonance spectroscopic studies of 1- arylpyrroles
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A series of m- and p-substituted 1-phenyl, 1-benzyl, 1-benzoyl, and 1- (2-phenylethyl)pyrroles was prepared and their 1H and 13C nmr spectroscopic characteristics were examined. In general, good correlations were observed between the chemical shift values of the β-H and the β-C of pyrroles [except 1-(2-phenylethyl)pyrroles] and the Hammettt σ. The observation may be explained in terms of the electronic effects of the substituents which are transmitted through bonds and through space by interaction of the p orbitals between β-Cs of the pyrrole ring and m- and p- Cs of the phenyl ring. Substituent constants of 1-pyrrolyl, 1-pyrrolylmethyl, and 1-pyrroloyl groups for the 1H and 13C chemical shifts of phenyl ring are also presented.
- Lee, Chang Kiu,Jun, Jung Ho,Yu, Ji Sook
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- Reductive one batch synthesis of N-substituted pyrrolidines from primary amines and 2,5-dimethoxytetrahydrofuran
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The construction of the pyrrolidine ring about a nitrogen of a primary amine by a reductive condensation reaction using 2,5- dimethoxytetrahydrofuran and sodium borohydride in acidic water medium is described. The reaction is fast, affords good to excellent yields and appears insensitive to electron effects and severe steric hindrance; it is found to be compatible with a large variety of aryl substituents, including nitro and oxo groups. The reaction allows the introduction of two deuterium atoms, with label conservation, in both the α-positions of the pyrrolidine ring by the use of sodium borodeuteride instead of sodium borohydride.
- Verardo, Giancarlo,Dolce, Anna,Toniutti, Nicoletta
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