18159-24-5Relevant academic research and scientific papers
Magnetic sulfonated polysaccharides as efficient catalysts for synthesis of isoxazole-5-one derivatives possessing a substituted pyrrole ring, as anti-cancer agents
Amale, Afsaneh Hamidian,Azizi, Sajjad,Ghasemi, Zarrin,Soleymani, Jafar,Valizadeh, Sepideh
, p. 36958 - 36964 (2021/12/02)
Four polysaccharides (chitosan, cellulose, starch, and pectin) were magnetized with magnetic iron oxide (Fe3O4) and then sulfonated (except pectin) with chlorosulfonic acid. The obtained solid acids were used as a catalyst in three-component reactions bet
Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- And pyrrolo-fused polycyclic indoles from 2-formylpyrrole
Camacho-Dávila, Alejandro A.,Delgado, Francisco,Escalante, Carlos H.,Espinoza-Hicks, Carlos,Martínez-Mora, Eder I.,Ramos-Morales, Fernando R.,Tamariz, Joaquín
supporting information, p. 1320 - 1334 (2020/07/10)
A highly regio-, chemo- and stereoselective divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles is herein described, starting from 2-formylpyrrole and employing Diels–Alder and Heck arylation reactions. 3-(N-Benzyl-2-pyrrolyl)acrylates and 4-(pyrrol-2-yl)butenones underwent a highly endo-Diels–Alder cycloaddition with maleimides to furnish octahydropyrrolo[3,4e]indoles, which served as precursors in the regioselective synthesis of aza-polycyclic skeletons via an intramolecular Heck arylation reaction. Through the latter reaction, the 3-(N-benzyl-2-pyrrolyl)acrylates give rise to 3-(pyrrolo[2,1-a]isoindol-3-yl)acrylates. A further oxidative aromatization of the polycyclic intermediates provides the corresponding polycyclic pyrrolo-isoindoles and isoindolo-pyrrolo-indoles. A theoretical study on the stereoselective Diels–Alder reactions, carried out by calculating the endo/exo transition states, revealed the assistance of non-covalent interactions in governing the endo stereocontrol.
N-Heterocyclic Carbene Catalyzed Deuteration of Aldehydes in D 2 O
Miki, Yuya,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 699 - 702 (2020/04/07)
An N-heterocyclic carbene (NHC)-catalyzed direct deuteration of aldehydes in a mixed solvent of deuterium oxide (D 2 O) and cyclopentyl methyl ether was established. The present deuteration is possibly initiated by the formation of a Breslow intermediate from the aldehyde and the NHC, with subsequent trapping by D 2 O providing the monodeuterated aldehyde.
Ru-Catalyzed Carbonylative Murai Reaction: Directed C3-Acylation of Biomass-Derived 2-Formyl Heteroaromatics
Sala, Roberto,Roudesly, Fares,Veiros, Luis F.,Broggini, Gianluigi,Oble, Julie,Poli, Giovanni
supporting information, p. 2486 - 2493 (2020/05/06)
The Murai reaction is a ruthenium-catalyzed transformation leading to alkylated arenes through the C?C bond formation between an alkene and an arene bearing a directing group. Discovered in the nineties, this useful C?H activation based coupling has been the object of intense study since its discovery. After having studied the Murai reaction on 2-formylfurans of biomass derivation, we describe here the carbonylative version applied to 2-formylfurans, 2-formylpyrrols and 2-formylthiophenes. This acylation reaction takes place regioselectively at C3 position of the heterocyclopentadienes thanks to the installation of removable imine directing groups. The transformation can be achieved by treating the two reaction partners with a catalytic amount of Ru3(CO)12, in toluene at 120–150 °C, after CO bubbling, at atmospheric pressure. DFT computations of the full catalytic cycle help in deciphering the mechanism of this transformation, and to rationalize the different behaviors depending on the nature of imine directing groups. (Figure presented.).
Serendipitous base catalysed condensation-heteroannulation of iminoesters: a regioselective route to the synthesis of 4,6-disubstituted 5-azaindoles
Chelvam, Venkatesh,Dudhe, Premansh,Pathak, Biswarup,Venkatasubbaiah, Krishnan
supporting information, p. 1582 - 1587 (2020/03/06)
A serendipitous discovery of a novel one-pot synthesis of 4,6-disubstituted 5-azaindoles is reported herein. In the presence of Hunig's base, various N-substituted pyrrole-2-carboxaldehydes have been efficiently transformed into their corresponding 4,6-disubstituted 5-azaindoles through an imine mediated cascade condensation-heteroannulation. The synthetic value of the methodology is established by preparing a novel chemical analogue of a cannabinoid receptor type 2 (CB2) agonist.
Reduction of N,N-Dimethylcarboxamides to Aldehydes by Sodium Hydride–Iodide Composite
Chan, Guo Hao,Ong, Derek Yiren,Yen, Zhihao,Chiba, Shunsuke
, (2018/05/14)
A new and concise protocol for selective reduction of N,N-dimethylamides into aldehydes was established using sodium hydride (NaH) in the presence of sodium iodide (NaI) under mild reaction conditions. The present protocol with the NaH-NaI composite allows for reduction of not only aromatic and heteroaromatic but also aliphatic N,N-dimethylamides with wide substituent compatibility. Retention of α-chirality in the reduction of α-enantioriched amides was accomplished. Use of sodium deuteride (NaD) offers a new step-economical alternative to prepare deuterated aldehydes with high deuterium incorporation rate. The NaH-NaI composite exhibits unique chemoselectivity for reduction of N,N-dimethylamides over ketones.
Rational modification of semaxanib and sunitinib for developing a tumor growth inhibitor targeting ATP binding site of tyrosine kinase
Kaur, Jagroop,Kaur, Baljit,Singh, Palwinder
supporting information, p. 129 - 133 (2017/12/08)
Analysis of the crystal structure of tyrosine kinase in complexation with an ATP analogue, supplemented with the molecular docking studies of semaxanib and sunitinib in the ATP binding site of the enzyme enabled us to make design of a series of tyrosine k
Design, synthesis and biological evaluation of matrine derivatives as potential anticancer agents
Li, Zheng,Luo, Mengyang,Cai, Bin,Wu, Lichuan,Huang, Mengtian,Haroon-Ur-Rashid,Jiang, Jun,Wang, Lisheng
supporting information, p. 677 - 683 (2018/02/06)
Using matrine (1) as the lead compound, a series of new 14-(N-substituted-2-pyrrolemethylene) matrine and 14-(N-substituted-indolemethylene) matrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H NMR, 13C NMR and ESI-MS spectral analyses. The target compounds were evaluated for their in vitro cytotoxicity against three human cancer cell lines (SMMC-7721, A549 and CNE2). The results revealed that compound A6 and B21 displayed the most significant anticancer activity against three cancer cell lines with IC50 values in range of 3.42–8.05 μM, which showed better activity than the parent compound (Matrine) and positive control Cisplatin. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound A6 and B21 could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. The cell cycle analysis also revealed that compound A6 could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase.
A Novel and Chemoselective Process of N -Alkylation of Aromatic Nitrogen Compounds Using Quaternary Ammonium Salts as Starting Material
González-González, Carlos A.,Vega, Juan Javier Mejía,Monroy, Ricardo García,González-Calderón, Davir,Corona-Becerril, David,Fuentes-Benítes, Aydeé,Mascarúa, Joaquín Tamariz,González-Romero, Carlos
, (2018/02/28)
The process of N-alkylation of several pyrroles, indoles, and derivative heterocycles is herein described, using quaternary ammonium salts as the source of an alkylating agent. These reactions were carried out on several heterocyclic rings with triethylbenzylammonium chloride or tetradecyltrimethylammonium bromide and an NaOH solution at 50%, leading to a chemoselective N-alkylated product and an average yield of 73%. This is an alternative process to the traditional benzylation and methylation of N-heterocycles with direct handling of alkyl halides.
Synthesizing process of nitrogen-heterocyclic high-selectivity aldehyde
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Paragraph 0014; 0022; 0023; 0035; 0036; 0048; 0049, (2017/09/05)
The invention relates to a synthesizing process of nitrogen-heterocyclic high-selectivity aldehyde. The synthesizing process is characterized in that when nitrogen-heterocyclic nitrogen atoms have hydrogen atoms, pyrrole, piperidine and pyrazole are used as the initial raw materials, and the pyrrole, the piperidine and the pyrazole are allowed to have reaction with piperidine-1-formaldehyde under nitrogen atom protection to obtain required nitrogen-atom ortho-position aldehyde; when nitrogen-heterocyclic nitrogen atoms have no hydrogen atoms, pyridine and pyrimidine are used to have reaction with the piperidine-1-formaldehyde to obtain the required nitrogen-atom ortho-position aldehyde. The synthesizing process is simple to operate, few in steps and high in selectivity and is a universal method using nitrogen heterocycle to synthesize the nitrogen ortho-position aldehyde.
