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A Modular and Catalytic Methodology To Access 2,5-Furan-Based Phenylene/Thiophene Oligomers through a One-Pot Decarboxylative Cross-Coupling from 5-Bromofurfural

Author(s): Cigana B; Lapointe V; Majewski MB; Forgione P;

A library of 2,5-furan-based phenylene/thiophene oligomers were synthesized starting from 5-bromofurfural, a derivative of biomass-derived furfural. Varied electronic groups are coupled onto the furan motif, followed by the installation of a phenylene or thiophene central linker through a one-pot Pd-catalyzed decarboxylative cross-coupling reaction. Resul ...

Article GUID: 38808994


Sterically-Hindered Molecular p-Dopants Promote Integer Charge Transfer in Organic Semiconductors

Author(s): Charoughchi S; Liu JT; Berteau-Rainville M; Hase H; Askari MS; Bhagat S; Forgione P; Salzmann I;

Molecular p-dopants designed to undergo electron transfer with organic semiconductors are typically planar molecules with high electron affinity. However, their planarity can promote the formation of ground-state charge transfer complexes with the semiconductor host and results in fractional inst ...

Article GUID: 37220083


Diverse Applications of Biomass-Derived 5-Hydroxymethylfurfural and Derivatives as Renewable Starting Materials

Author(s): Chacón-Huete F; Messina C; Cigana B; Forgione P;

This Review summarizes recent efforts to capitalize on 5-hydroxymethylfurfural (HMF) and related furans as emerging building blocks for the synthesis of fine chemicals and materials, with a focus on advanced applications within medicinal and polymer chemistry, as well as nanomaterials. As with all chemical industries, these fields have historically relied ...

Article GUID: 35652539


Solvent-free synthesis of 3,5-isoxazoles via 1,3-dipolar cycloaddition of terminal alkynes and hydroxyimidoyl chlorides over Cu/Al2O3 surface under ball-milling conditions

Author(s): Hernandez R RA; Burchell-Reyes K; Braga APCA; Lopez JK; Forgione P;

Scalable, solvent-free synthesis of 3,5-isoxazoles under ball-milling conditions has been developed. The proposed methodology allows the synthesis of 3,5-isoxazoles in moderate to excellent yields from terminal alkynes and hydroxyimidoyl chlorides, using a recyclable Cu/Al2O3 nanocomposite catalyst. Furthermore, the proposed conditions are reproducible to ...

Article GUID: 35424611


Characterization of a recently synthesized microtubule-targeting compound that disrupts mitotic spindle poles in human cells

Author(s): Jaunky DB; Larocque K; Husser MC; Liu JT; Forgione P; Piekny A;

We reveal the effects of a new microtubule-destabilizing compound in human cells. C75 has a core thienoisoquinoline scaffold with several functional groups amenable to modification. Previously we found that sub micromolar concentrations of C75 caused cytotoxicity. We also found that C75 inhibited microtubule polymerization and competed with colchicine for ...

Article GUID: 34880347


Programmed Synthesis of Tetra-Aryl Thiophenes with Stepwise, Ester-Controlled Regioselectivity

Author(s): Messina C; Ottenwaelder X; Forgione P;

Herein, we report a modular synthetic route to access tetra-arylated thiophene compounds with four different substituents with programmed chemical control provided by an ester activating/directing group. This method enables the functionalization of individual positions of thiophene sequentially via regioselective halogenations and cross-coupling reactions ...

Article GUID: 34506149


Design, structure-activity relationship study and biological evaluation of the thieno[3,2-c]isoquinoline scaffold as a potential anti-cancer agent

Author(s): Liu JT; Jaunky DB; Larocque K; Chen F; Mckibbon K; Sirouspour M; Taylor S; Shafeii A; Campbell D; Braga H; Piekny A; Forgione P;

Several derivatives of a series that share a thienoisoquinoline scaffold have demonstrated potent anti-cancer activity against cancer cell lines A549, HeLa, HCT-116 in the submicromolar concentration range. Structure-activity relationship (SAR) studies on a range of derivatives aided in identifyi ...

Article GUID: 34416378


Synthesis of 2,5-Diaryl Nonsymmetric Furans C6-Platform Chemicals via Catalytic Conversion of Biomass and the Formal Synthesis of Dantrolene.

Author(s): Chacón-Huete F, Lasso JD, Szavay P, Covone J, Forgione P

Biomass-derived commodity chemical 5-hydroxymethyl furfural is an underutilized C6-platform chemical derived from cellulose that is ideal to prepare next-generation value-added products. We have developed an efficient synthetic strategy to access 2,5-diaryl nonsymmetric furans from 5-hydroxymethyl furfural utilizing decarboxylative cross-couplings. A key ...

Article GUID: 33253575


Approaching the Integer-Charge Transfer Regime in Molecularly Doped Oligothiophenes by Efficient Decarboxylative Cross-Coupling

Author(s): Liu JT; Hase H; Taylor S; Salzmann I; Forgione P;

A library of symmetrical linear oligothiophene was prepared employing decarboxylative cross-coupling reaction as the key transformation. Thiophene potassium carboxylate salts were used as cross-coupling partners without the need of co-catalyst, base, or additives. This method demonstrates complete chemoselectivity and is a comprehensive greener approach c ...

Article GUID: 31961982


Facile Aqueous-Phase Synthesis of an Ultrasmall Bismuth Nanocatalyst for the Reduction of 4-Nitrophenol.

Author(s): Liang Y, Manioudakis J, Macairan JR, Askari MS, Forgione P, Naccache R

ACS Omega. 2019 Sep 17;4(12):14955-14961 Authors: Liang Y, Manioudakis J, Macairan JR, Askari MS, Forgione P, Naccache R

Article GUID: 31552336


Virtual screening, docking, and dynamics of potential new inhibitors of dihydrofolate reductase from Yersinia pestis.

Author(s): Bastos Lda C, de Souza FR, Guimarães AP, Sirouspour M, Cuya Guizado TR, Forgione P, Ramalho TC, França TC

J Biomol Struct Dyn. 2016 Oct;34(10):2184-98 Authors: Bastos Lda C, de Souza FR, Guimarães AP, Sirouspour M, Cuya Guizado TR, Forgione P, Ramalho TC, França TC

Article GUID: 26494420


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