Nucleophilic substitutions in the isoindole series as a valuable tool to synthesize derivatives with antitumor activity

Diana, Patrizia; Martorana, Annamaria; Barraja, Paola; Montalbano, Alessandra; Carbone, Anna; Cirrincione, Girolamo

doi:10.1016/j.tet.2011.01.056

Cited by 17 publications

(18 citation statements)

References 14 publications

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“…1 as presented in Scheme 2 was synthesized according to previous literatures with modification [30,31]. A solution of POBr 3 (20 mmol, 5.73 g) in anhydrous dichloromethane (5 mL) was added dropwise to Dimethylformamide (DMF) (20 mmol, 1.46 g) in anhydrous dichloromethane (15 mL) at 0 • C. The mixture was stirred for 30 min at room temperature.…”

Section: Synthetic Of Bobpybxmentioning

confidence: 99%

Thermo-Responsive Fluorescent Polymers with Diverse LCSTs for Ratiometric Temperature Sensing through FRET

Ding¹,

Wang²,

Feng³

et al. 2018

Polymers

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Abstract:Temperature is a significant parameter to regulate biological reactions and functions inside cells. Sensing the intracellular temperature with a competent method is necessary to understand life science. In this work, an energy-transfer polymeric thermometer was designed for temperature sensing. The thermometer was prepared from two thermo-responsive polymers with different lower critical solution temperatures (LCSTs) of 31.1 • C and 48.6 • C, coupling with blue and red fluorescent molecules, respectively, developed for ratiometric temperature sensing based on the Förster resonance energy transfer (FRET) mechanism. The polymers were synthesized from two monomers, N-isopropylacrylamide (NIPA) and N-isopropylmethacrylamide (NIPmA), which provided different temperature responses. The fluorescent intensity of each polymer (peaked at 436 and 628 nm, respectively) decreased upon the heating of the polymer aqueous solution. While these two polymer aqueous solutions were mixed, the fluorescent intensity decrease at 436 nm and substantial fluorescence enhancement at 628 nm was observed with the increasing temperature due to FRET effect. The cell imaging of HeLa cells by these thermo-responsive polymers was explored. The difference of LCSTs resulting in ratiometric fluorescence change would have a potential impact on the various biomedical applications.

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Section: Synthetic Of Bobpybxmentioning

confidence: 99%

Thermo-Responsive Fluorescent Polymers with Diverse LCSTs for Ratiometric Temperature Sensing through FRET

Ding¹,

Wang²,

Feng³

et al. 2018

Polymers

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“…Upon intramolecular hydroamination of the alkyne, an alkylidene isoindoline is formed. After a spontaneous [1,5]-proton shift these isoindolines convert to alkylated isoindoles.…”

Section: Ring Transformationsmentioning

confidence: 99%

“…neutralizing the charges. After [1,5]-H migration, isoindoles were isolated. This ring closure was mediated by microwave irradiation for aminophosphonates 176 82 and by gold catalysis for aminonitriles 178 83 and it was shown by the authors that the reaction mechanism of the alkyl migration clearly differs for both cases.…”

Section: Ring Transformationsmentioning

confidence: 99%

“…They are relatively unstable because of their ortho-quinoid structure and therefore, direct functionalisation of isoindoles has been essentially limited to electrophilic aromatic substitution reactions and very few examples of nucleophilic aromatic substitution reactions. 1 Thus, efficient conversion of a wide variety of stable starting materials to isoindoles is highly desirable. 2 Despite the inherent instability of these aromatic systems, they have found a wide range of applications.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles

2012

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Over the past few years, isoindoles have found wide application in materials science. Isoindole containing BODIPY dyes are highly fluorescent materials and have been extensively used in various fields of science. Phthalocyanines, metal containing cyclic tetramers of isoindole, form coordination complexes with most elements of the periodic table. These complexes are intensely coloured and are used as pigments and dyes. However, isoindoles are relatively unstable 10π-heteroaromatic systems and few synthetic methods provide these compounds in good yields. This tutorial review will give an overview of the reported synthetic methods towards isoindoles and related heteroaromatic systems over a time span of approximately 10 years (2000 to current), including the applications where they have been reported. The importance of the field will be illustrated and factors influencing product stability will be discussed.

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“…The discovery of more potent, clinically safe, and commercially attractive new targeted drugs is the driving force at the base of medicinal chemistry research. Since a long time, our research work focused the attention on the design, synthesis, and biological evaluation of new heterocyclic compounds able to halt tumor cell proliferation (Figure compounds 1 – 4 ) …”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and biological evaluation of a new class of benzo[b]furan derivatives as antiproliferative agents, with in silico predicted antitubulin activity

et al. 2017

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Nucleophilic substitutions in the isoindole series as a valuable tool to synthesize derivatives with antitumor activity

Cited by 17 publications

References 14 publications

Thermo-Responsive Fluorescent Polymers with Diverse LCSTs for Ratiometric Temperature Sensing through FRET

Thermo-Responsive Fluorescent Polymers with Diverse LCSTs for Ratiometric Temperature Sensing through FRET

Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles

Design, synthesis, and biological evaluation of a new class of benzo[b]furan derivatives as antiproliferative agents, with in silico predicted antitubulin activity

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