Hypolipidemic analogs of ethyl 4-benzyloxybenzoate

Baggaley, Keith H.; Fears, Robin; Hindley, Richard M.; Morgan, B. L.; Murrell, Elspeth A.; Thorne, D. E.

doi:10.1021/jm00221a007

Cited by 25 publications

(12 citation statements)

References 6 publications

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“…The crude product was recrystallized in a mixture of hexane and ethyl acetate (250 mL, 1:6) to afford a white solid (68.0 g, 79%), mp 43.3-44.3 °C (lit. 23 45.5 °C). 1 H NMR: 1.37 (t, J ) 7.0, 3H), 4.33 (q, J ) 7.0, 2H), 5.12 (s, 2H), 6.99 (d, J ) 8.4, 2H), 7.34-7.44 (m, 5H), 7.98 (d, J ) 8.4, 2H).…”

Section: Methodsmentioning

confidence: 97%

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Synthesis and Characterization of a Polyester/Crown Ether Rotaxane Derived from a Difunctional Blocking Group

Gong

Gibson

1996

Macromolecules

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A diol with a sterically large core, namely bis(p-tert-butylphenyl)bis[p-(2-(2-hydroxyethoxy)ethoxy)phenyl]methane (diol BG 7), was synthesized by a multiple step method and successfully used for the preparation of a sebacate-based polyester 30-crown-10 (30C10) rotaxane with blocking groups or stoppers along the backbone. It was found that the resulting polyrotaxane had a threading efficiency (m/n value, the average number of cyclic molecules threaded per repeat unit) 5 times as high as that without BG under the same conditions, which proved that the BG can effectively prevent threaded 30C10 from slipping off the polymeric backbone during the preparation of the polyrotaxane. Additionally, new evidence for the formation of the polyrotaxane was demonstrated, including a chemical shift of threaded 30C10 protons different from that of the unthreaded species, a through-space interaction between 30C10 and the backbone proved by 2D NOESY measurements, and hydrolytic recovery of 30C10.

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Section: Methodsmentioning

confidence: 97%

“…A yellow solid was obtained after the solvent in the organic phase had been removed. The crude product was recrystallized in a mixture of hexane and ethyl acetate (250 mL, 1:6) to afford a white solid (68.0 g, 79%), mp 43.3−44.3 °C (lit …”

Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of a Polyester/Crown Ether Rotaxane Derived from a Difunctional Blocking Group

Gong

Gibson

1996

Macromolecules

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“…The precipitate is filtered and washed with cyclohexane to afford a white solid. Selective protection of dihydroxybenzoic and gallic acids is performed according to Baggaley et al 52 esterification : A required diol (100–200 mg), DMAP (2.1 equiv) and the phenol-protected benzylic acid derivative (2.5 equiv) are dissolved in toluene (10 mL per 100 mg diol). Then, DCC (2.3 equiv) are added.…”

Section: Methodsmentioning

confidence: 99%

Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli

Lamoral-Theys

Pottier

Kerff

et al. 2010

Bioorganic & Medicinal Chemistry

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A series of 33 novel divanillates and trivanillates were synthesized and found to possess promising cyto-static rather than cytotoxic properties. Several compounds under study decreased by >50% the activity of Aurora A, B, and C, and WEE1 kinase activity at concentrations <10% of their IC50 growth inhibitory ones, accounting, at least partly, for their cytostatic effects in cancer cells and to a lesser extent in normal cells. Compounds 6b and 13c represent interesting starting points for the development of cytostatic agents to combat cancers, which are naturally resistant to pro-apoptotic stimuli, including metastatic malignancies.

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“…These known compounds were prepared following a procedure slightly different from that described in the literature. 39 To a stirred and cooled suspension of sodium hydride (2.4 g, 100 mmol) in dry DMF (20 mL) was added dropwise a solution of ethyl 4-hydroxybenzoate (8) (16.6 g, 100 mmol) in dry DMF (40 mL). The stirred mixture was allowed to stand for 30 min at room temperature.…”

Section: Methodsmentioning

confidence: 99%

5-[4-(Benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives and related analogs: new reversible, highly potent, and selective monoamine oxidase type B inhibitors

Mazouz¹,

Gueddari²,

Burstein³

et al. 1993

J. Med. Chem.

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Thirty-three new 5-[4-(benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives including related analogues, designed as inhibitors of monoamine oxidase type B (MAO B), were synthesized and investigated both in vitro and ex vivo for their abilities to inhibit selectively rat brain MAO B over MAO A. Three inhibitors were found to act as reversible, highly potent, and selective MAO B inhibitors, namely the nitrile derivative 5-[4-(benzyloxy)phenyl]-3-(2-cyanoethyl)-1,3,4-oxadiazol-2(3H)-one (12a) and two closely related homologues, the corresponding oxadiazolethione 13a and the alcohol 14b. Their IC50 (MAO B) values are in the low nanomolar range of 1.4-4.6 nM and their selectivities, estimated by the ratio of IC50 values (A/B), are from 3200 to> 71,400. Compound 12a exhibited the highest activity against MAO B. Its IC50 was evaluated to be 1.4 nM with a quasitotal selectivity (> 71,400) toward this enzyme. In ex vivo studies, 12a showed a reversible and short duration of action. MAO B was markedly inhibited with the oral dose of 1 mg/kg without any alteration of MAO A, and the inhibition almost did not exceed 24 h. Its ED50 (1 h after oral administration) was evaluated to be 0.56 mg (1.7 mumol)/kg. Remarkably, MAO A was not affected at doses as high as 1500 mg/kg, po. In addition, no apparent toxicity or behavioral anomaly was observed during the treatment even at the maximum administrated dose. SAR studies emphasize the existence of three binding sites to the enzyme with a special importance of the terminal phenyl. Analysis of the inhibition kinetics indicated that 12a acts in a two-step mechanism as a competitive, slow, and tight-binding inhibitor of MAO B with a Ki value of 0.22 microM and an overall Ki* value at equilibrium of 0.7 nM.

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Hypolipidemic analogs of ethyl 4-benzyloxybenzoate

Cited by 25 publications

References 6 publications

Synthesis and Characterization of a Polyester/Crown Ether Rotaxane Derived from a Difunctional Blocking Group

Synthesis and Characterization of a Polyester/Crown Ether Rotaxane Derived from a Difunctional Blocking Group

Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli

5-[4-(Benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives and related analogs: new reversible, highly potent, and selective monoamine oxidase type B inhibitors

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