Synthesis and Reactivity of the 2,5-Bis(Trimethylstannyl) Derivatives of Thiophene and Furan

Seitz, David E.; Lee, Shi-Hung; Hanson, Robert N.; Bottaro, Jeffrey C.

doi:10.1080/00397918308061969

Cited by 79 publications

(62 citation statements)

References 4 publications

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“…For certain substrates, the Ti III -mediated arylation of furans with diazonium salts might have potential as a useful alternative. [14] It has been reported, though, that Meerwein-type arylation reactions cannot be applied to the synthesis of 2,5-diarylfurans such as 6 or 9, [7] which have instead been synthesized from symmetrical 2,5-distannylfurans [15] in double Stille couplings. The disadvantages of this method include potential contamination of the products with organostannane residues, as well as selectivity issues arising when the method is adopted for the synthesis of unsymmetrical 2,5-diarylfurans.…”

Section: Introductionmentioning

confidence: 97%

Ru‐ and Pd‐Catalysed Synthesis of 2‐Arylfurans by One‐Flask Heck Arylation/Oxidation

Schmidt¹,

Geißler²

2011

Eur J Org Chem

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Abstract2,5‐Disubstituted furans were synthesized by one‐flask Heck arylation/oxidation sequences. The starting materials are 2‐substituted 2,3‐dihydrofurans, conveniently available by RCM/isomerization sequences, and arenediazonium salts. These react in ligand‐free Heck reactions to afford 2,5‐disubstituted 2,5‐dihydrofurans, which are oxidized to the corresponding furans without isolation or intermediate workup. The oxidation is conveniently achieved with chloranil or DDQ, depending on the substrate.

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Section: Introductionmentioning

confidence: 97%

Ru‐ and Pd‐Catalysed Synthesis of 2‐Arylfurans by One‐Flask Heck Arylation/Oxidation

Schmidt¹,

Geißler²

2011

Eur J Org Chem

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“…In view of these results, and aiming at the discovery of new trypanocidal compounds we evaluated the effect of the synthetic compounds 5-15 (Fig. 4) on TR and the whole trypomastigote and amastigote forms of the parasite.(trimethylstannyl)furan 16 by reaction of furan with TMEDA and n-butyllithium and subsequent addition of trimethyltin chloride (Seitz et al 1983), and (2) palladium catalyzed coupling reaction between the distannane 16 and various arylhalides (Stille coupling) (Stephens et al 2001).In vitro assay with T. cruzi TR -Recombinant T. cruzi TR was obtained as described by Borges et al (1995). The colorimetric microtitre plate assay was adapted from that described by Hamilton et al (2003).…”

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confidence: 99%

“…(trimethylstannyl)furan 16 by reaction of furan with TMEDA and n-butyllithium and subsequent addition of trimethyltin chloride (Seitz et al 1983), and (2) palladium catalyzed coupling reaction between the distannane 16 and various arylhalides (Stille coupling) (Stephens et al 2001).…”

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confidence: 99%

Arylfurans as potential Trypanosoma cruzi trypanothione reductase inhibitors

Oliveira

Vaz

Alves

et al. 2006

Mem. Inst. Oswaldo Cruz

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The natural lignans veraguensin and grandisin have been reported to be active against Trypanosoma cruzi bloodstream forms. Aiming at the total synthesis of these and related compounds, we prepared three 2-arylfurans and eight 2,5-diarylfurans. They were evaluated for their potential as T. cruzi trypanothione reductase (TR) 60% at 20 µg/ml (59 and 90 µM, respectively). On the other hand, none of the compounds was significantly active against the parasite bloodstream forms even at 250 µg/ml (0.6-1.5 mM).Key words: tropical diseases -Chagas disease -arylfurans -trypanothione reductase Chagas disease, caused by the flagellate protozoan Trypanosoma cruzi, affects 18 million people in Latin America and is responsible for 13,000 deaths every year (WHO 2002). The treatment relies on only two available drugs, nifurtimox and benznidazole, which are relatively efficient in the acute phase of the disease, but almost ineffective in the chronic phase. Nowadays, one of the most important mechanisms of Chagas disease transmission in many countries is by blood transfusion (Schmuñis 1991). In highly endemic areas it is strongly recommended the use of chemoprophylatic measures such as the addition of gentian violet to clear trypomastigotes from blood banked for transfusion (Moraes-Souza et al. 1995). Although effective, this triphenylmethane dye is not well accepted because of undesirable effects such as coloring the skin and possible mutagenicity (Wendel 1993). Thus, new drugs to treat or prevent Chagas disease are still needed.Trypanosoma cruzi enzymes such as the trypanothione reductase (TR) represent a potential drug targets because they play an essential role in the life of this parasite. TR and its substrate trypanothione, the disulfide of a glutathione-spermidine conjugate [N 1 , N 8 -bis(glutathionyl)spermidine, T(SH) 2 ] 1, help to protect the parasite from oxidative stress by maintaining an intracellular reducing environment in a manner analogous to glutathione reductase (GR) and glutathione [L-γ-glutamyl-Lcysteiylglycine, GSH] 2 (Fig. 1a) in mammalian cells (Schmidt & Krauth-Siegel 2002). TR catalyses the NADPHdependent reduction of trypanothione disulfide TS 2 to its dithiol form, T(SH) 2 . Trypanothione may be oxidized back to TS 2 (Fig. 1b) following reaction with potentially damaging radicals and oxidants generated by aerobic metabolism. Another aspect that makes TR an even more attractive target is its structural differences from the human counterpart GR. GR has a narrow positively charged active site, to accommodate the glycine carboxylates of its substrate glutathione, whereas TR has a wider, noncharged, and more hydrophobic active site (Bond et al. 1999). These differences allowed the discovery of several promising selective inhibitors of TR (Schmidt & KrauthSiegel 2002).Lignans is a class of natural products that possess important biological properties (Jensen et al. 1993). Lopes et al. (1998) showed that the tetrahydrofuran lignans veraguensin 3 and grandisin 4 (Fig. 2) were active in vitro at 5 µg/ml aga...

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“…Molecular structures of the chiral monomers were confirmed by nuclear magnetic resonance (NMR) spectroscopy measurements in CDCl 3 solution. 2,5-Di(trimethylstannyl)thiophene (TMSn2Th), [11] 5,5′-bis(trimethylstannyl)-2,2′-bithiophene (TMSn 2 BTh), and 1,3-di(trimethylstannyl)isothianaphthene (TMSn 2 ITN) [12] were prepared by lithiation followed by a reaction with trimethylstannyl chloride.…”

Section: Synthesis and Methodsmentioning

confidence: 99%

Thiophene-based chiral small bandgap π-conjugated polymers: synthesis and optical properties

Wang

Kawabata

Goto

2015

Designed Monomers and Polymers

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A series of thiophene-based chiral small bandgap π-conjugated polymers was successfully synthesized. Optical properties of the polymers were investigated by using UV-vis, photoluminescence (PL), circular dichroism (CD) spectroscopies, and specific rotation measurements. Especially, the isothianaphthene-thiophene based copolymers display 10-20 nm longer absorption maximum than those of thiophene-thiophene copolymers in the UV-vis. PL measurements demonstrate that the polymer exhibit light emission. CD spectroscopy measurements reveal helical π-stacking structure of the polymers.

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Synthesis and Reactivity of the 2,5-Bis(Trimethylstannyl) Derivatives of Thiophene and Furan

Cited by 79 publications

References 4 publications

Ru‐ and Pd‐Catalysed Synthesis of 2‐Arylfurans by One‐Flask Heck Arylation/Oxidation

Ru‐ and Pd‐Catalysed Synthesis of 2‐Arylfurans by One‐Flask Heck Arylation/Oxidation

Arylfurans as potential Trypanosoma cruzi trypanothione reductase inhibitors

Thiophene-based chiral small bandgap π-conjugated polymers: synthesis and optical properties

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