The chemistry of some methoxychlor derivatives

Baarschers, W. H.; Vukmanich, James P.

doi:10.1139/v86-154

Cited by 7 publications

(6 citation statements)

References 4 publications

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“…The synthesis of [2]rotaxane 18 is outlined in Scheme . Ether 19 was first converted into acid 20 according to the condensation method reported by Baarschers …”

Section: Resultsmentioning

confidence: 99%

Recognition through Self-Assembly. A Quadruply-Hydrogen-Bonded, Strapped Porphyrin Cleft That Binds Dipyridyl Molecules and a [2]Rotaxane

et al. 2004

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Quadruply-hydrogen-bonded porphyrin homodimer Zn1.Zn1 has been designed, assembled, and evaluated as a supramolecular cleft-featured receptor for its ability to bind dipyridyl guests in chloroform-d. Monomer Zn1 consists of a 2-ureidopyrimidin-4(1H)-one unit, which was initially reported by Meijer et al., and a zinc porphyrin unit. The zinc porphyrin is strapped with an additional aliphatic chain for controlling the atropisomerization of porphyrin. The 2-ureidopyrimidin-4(1H)-one unit dimerizes exclusively in chloroform even at the dilute concentration of 10(-)(4) M, while the two "strapped" zinc porphyrin units of the homodimer provide additional binding sites for selective guest recognition. (1)H NMR studies indicate that the new homodimer Zn1.Zn1 adopts an S-type conformation due to strong donor-acceptor interaction between the electron-rich porphyrin units and the electron-deficient 2-ureidopyrimidin-4(1H)-one unit. (1)H NMR, UV-vis, and vapor pressure osmometry investigations reveal that Zn1.Zn1 could function as a new generation of assembled supramolecular cleft, to be able to not only efficiently bind linear dipyridyl molecules 14-17, resulting in the formation of stable termolecular complexes, with K(aasoc) values ranging from 3.8 x 10(6) to 8.9 x 10(7) M(-)(1), but also strongly complex a hydrogen-bond-assembled [2]rotaxane, 18, which consists of a rigid fumaramide thread and a pyridine-incorporated tetraamide cyclophane, with K(aasoc) = 1.2 x 10(4) M(-)(1). (1)H NMR competition experiments reveal that complexation to the dipyriyl guests also promotes the stability of the quadruply-hydrogen-bonded dimeric receptor.

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“…The synthesis of [2]rotaxane 18 is outlined in Scheme . Ether 19 was first converted into acid 20 according to the condensation method reported by Baarschers …”

Section: Resultsmentioning

confidence: 99%

Recognition through Self-Assembly. A Quadruply-Hydrogen-Bonded, Strapped Porphyrin Cleft That Binds Dipyridyl Molecules and a [2]Rotaxane

et al. 2004

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“…The reaction pathway used to synthesize the linear compound 5 is shown in Scheme . The halo ester 13 was obtained by esterification of the commercially available 3‐bromopropan‐1‐ol with 2,2‐bis‐(4‐methoxyphenyl)acetic acid19 with the activating agent EDCI in the presence of DMAP. The reaction between 13 and the commercially available amino alcohol 3‐aminopropan‐1‐ol led to 14 , which was alkylated by reductive methylation with HCOOH/HCHO to give the tertiary amine 15 .…”

Section: Methodsmentioning

confidence: 99%

“…The synthesis and configuration of amino alcohols 16 – 19 was reported previously 14. Final compounds 6 – 9 were obtained by esterification of 16 – 19 with 2,2‐bis‐(4‐methoxyphenyl)acetic acid19 after activation with EDCI, as shown in Scheme .…”

Section: Methodsmentioning

confidence: 99%

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Arylamino Esters As P‐Glycoprotein Modulators: SAR Studies to Establish Requirements for Potency and Selectivity

et al. 2015

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A set of basic aryl-group-containing compounds was synthesized with the aim of developing potent and selective P-glycoprotein (P-gp) modulators that are able to reverse multidrug resistance (MDR). The natures of the spacer (dicyclohexylamine or dialkylamine) and the aryl moieties were modified to investigate selectivity and the mechanism of P-gp interaction. The inhibitory activities of the compounds toward P-gp, multidrug resistance-associated protein 1 (MRP1), and breast cancer resistance protein (BCRP), the most relevant ATP binding cassette (ABC) transporters for MDR, were evaluated. The mechanism of P-gp interaction for each compound was investigated with three biological assays: apparent permeability (Papp ) determination (B→A/A→B) in Caco-2 cell monolayers, ATP cell depletion, and inhibition of Calcein-AM transport in MDCK-MDR1 cells. These assays allowed us to estimate the selectivity of the compounds for the three efflux pumps and to identify the structural requirements that define the P-gp-interaction profile. All dicyclohexylamine derivatives were found to be P-gp substrates, whereas one dialkylamine derivative was shown to be a P-gp inhibitor. The good MRP1 activity of one cis/cis isomer highlighted this as a lead candidate for the development of MRP1 ligands.

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“…For example, per(ethynylated) derivatives of the triflate 5 (R = C⋮CR‘) would be remarkably versatile modules for the construction of conjugated oligomers, but the necessary precursors, α,α-diethynyl carboxylic acids or acid chlorides 3 , are to the best of our knowledge an unknown class of molecules. Conversely, alkoxyl-substituted diaryl acetic acid chlorides ( 3 , R = MeOC 6 H 4 ) are available via reported methods , As a result, we have developed, and report herein, a general and versatile method for the formation of highly functionalized vinyl triflate building blocks via the divergent derivatization of ethynyl α,α-dibromomethyl ketones.…”

mentioning

confidence: 99%

Synthesis and Derivatization of Ethynyl α,α-Dibromomethyl Ketones: Formation of Highly Functionalized Vinyl Triflates

Rankin

Tykwinski

2003

Org. Lett.

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[reaction: see text] We describe the synthesis of alpha,alpha-dibromomethyl ynones (8) and their subsequent derivatization to vinyl acetates (10). These vinyl acetates feature a 1,1-dibromo-olefin moiety, which is readily exploited in palladium-catalyzed Sonogashira, Stille, and Suzuki cross-coupling reactions with alkynes, stannanes, and boronic acids, respectively. A novel one-pot process then directly converts the resulting vinyl acetates 11-13 to the vinyl triflate derivatives 14a-j.

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The chemistry of some methoxychlor derivatives

Cited by 7 publications

References 4 publications

Recognition through Self-Assembly. A Quadruply-Hydrogen-Bonded, Strapped Porphyrin Cleft That Binds Dipyridyl Molecules and a [2]Rotaxane

Recognition through Self-Assembly. A Quadruply-Hydrogen-Bonded, Strapped Porphyrin Cleft That Binds Dipyridyl Molecules and a [2]Rotaxane

Arylamino Esters As P‐Glycoprotein Modulators: SAR Studies to Establish Requirements for Potency and Selectivity

Synthesis and Derivatization of Ethynyl α,α-Dibromomethyl Ketones: Formation of Highly Functionalized Vinyl Triflates

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