Inhibition of secretory phospholipase A2. 2-Synthesis and structure–activity relationship studies of 4,5-dihydro-3-(4-tetradecyloxybenzyl)-1,2,4-4H-oxadiazol-5-one (PMS1062) derivatives specific for group II enzyme

Dong, Chang‐Zhi; Ahamada-Himidi, Azali; Plocki, Stéphanie; Aoun, Darina; Touaibia, Mohamed; Habich, Nadia Meddad-Bel; Huet, Jack; Redeuilh, Catherine; Ombetta, Jean-Edouard; Godfroid, Jean‐Jacques; Heymans, Françoise

doi:10.1016/j.bmc.2005.01.016

Cited by 26 publications

(24 citation statements)

References 24 publications

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“…The main product of this reaction was ethyl 3,3-difluoropropionate (9, 35%, 19 F NMR). Additionally, ethyl 3-bromo-3-fluoropropionate (10, 2%), ethyl 3,3-dibromo-3-fluoropropionate (11, 17%) and ethyl 2,3,3-tribromo-3-fluoropropionate (12, 2%) were found by 19 F NMR spectroscopy besides other not identified products (Scheme 3). This result shows that the electron withdrawing effect of an ester group in b-position to the reaction centre is not sufficient to prevent the desulfurization step, but decelerated the reaction rate and directed the reaction towards oxidative desulfurization-difluorination and desulfurizationpolybromination.…”

Section: Resultsmentioning

confidence: 95%

“…However, under standard conditions no conversion to the trifluoride was observed by 19 F NMR spectroscopy after 20 h of reaction time at room temperature ( Table 2, entry 1). Also the use of NIS as an electrophile and 20 or 40 equiv.…”

Section: [ ( S C H E M E _ 3 ) T D $ F I G ]mentioning

confidence: 83%

“…Though product 5e was identified in the product mixture by ESI mass spectrometry and 19 F NMR spectroscopy, its separation from also formed bromoaryl compounds was not possible. However, pure compound 5e was synthesized from ethyl 2-bromo-2,2-difluoroacetate by nucleophilic substitution with 4-methoxythiophenol [19].…”

Section: Resultsmentioning

confidence: 99%

“…The reactions with Olah's reagent were performed in Teflon TM flasks. The alkyl aryl thioethers were prepared from the corresponding thiophenols and alkyl halides under basic conditions [19].…”

Section: General Methodsmentioning

confidence: 99%

“…1 H NMR (CDCl 3 , 300 MHz): d 1.27-1.39 (m, 10H, CH 2 ), 1.41-1.65 (m, 2H, CH 2 ), 1.82-2.12 (m, 2H, CH 2 ), 2.30 (t, 2H, CH 2 , 3 J H,H = 7.5 Hz), 3.47 (m, 1H, CH), 3.67 (s, 3H, CH 3 ), 5.77 (tdd, 1H, CH, 2 J H,F = 55.0 Hz, 3 J H,F = 5.8 Hz, 3 J H,H = 4.2 Hz). 13 C NMR (CDCl 3 , 75 MHz): d 24.2 (td, 3 J C,F = 3.0 Hz), 24.9 (t), 28.1 (tdt, 2 J C,F = 20.4 Hz, 3 J C,F = 3.0 Hz),29.0, 29.1, 29.2 (t), 34.0 (t), 51.4 (q), 90.3 (dddd, 1 J C,F = 175.8 Hz, 2 J C,F = 26.9 Hz, 2 J C,F = 25.8 Hz), 113.7 (dtd, 1 J C,F = 244.6 Hz, 2 J C,F = 31.7 Hz), 174.3 (s) 19. F NMR (CDCl 3 ,…”

mentioning

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Facile synthesis of α,α-difluoroalkyl aryl thioethers and their oxidative desulfurization–fluorination to trifluorides

Hugenberg

Haufe

2010

Journal of Fluorine Chemistry

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Section: Resultsmentioning

confidence: 95%

Section: [ ( S C H E M E _ 3 ) T D $ F I G ]mentioning

confidence: 83%

Section: Resultsmentioning

confidence: 99%

Section: General Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

Facile synthesis of α,α-difluoroalkyl aryl thioethers and their oxidative desulfurization–fluorination to trifluorides

Hugenberg

Haufe

2010

Journal of Fluorine Chemistry

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Nitrile Reductase from Geobacillus kaustophilus: A Potential Catalyst for a New Nitrile Biotransformation Reaction

et al. 2012

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Abstract:The cloning, expression and characterization of a nitrile reductase (NRed) from the thermophile Geobacillus kaustophilus is reported. The enzyme shows a 12-fold increase in activity in response to a temperature change from 25 8C to 658C. The substrate scope regarding its biocatalytic applicability was investigated by testing a range of common nitriles. The narrow substrate range observed for the wild-type enzyme prompted the rational design of GkNRed active site mutants based on a previously published homology model from Bacillus subtilis. The activities of the mutants and the wild-type enzyme were investigated in their structure-function relationship regarding the natural substrate 7-cyano-7-deazaguanine (preQ 0 ) as well as a range of synthesized preQ 0 -like substrate structures. A distinct dependence of the wild-type enzyme activity on specific structural modifications of the natural substrate was observed. Two non-natural nitriles derived from preQ 0 could be reduced to their corresponding amino compounds.

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Investigation of Masked N‐Acyl‐N‐isocyanates: Support for Oxadiazolones as Blocked N‐Isocyanate Precursors

Gagné-Monfette

Vincent-Rocan

Lutes

et al. 2021

Chemistry A European J

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In contrast to carbon-substituted isocyanates that are common building blocks, N-substituted isocyanates remain underdeveloped and reports on their N-acyl derivatives (i. e. amido-isocyanates) are exceedingly rare. Herein, amido-isocyanates were investigated in the context of syntheses of aza-tripeptide and hydantoins subunits starting from simple bench-stable precursors. A key finding is that the amido-isocyanate formed in situ cyclized to yield an oxadiazo-lone, and that under suitable reaction conditions this heterocycle is a traceless blocked (masked) N-isocyanate. Using organic bases as catalysts and upon heating, oxadiazolone formation is observed, and various nucleophiles to provide the desired aza-dipeptides or hydantoins in moderate to high yields. Further support for an amido-isocyanate intermediate was obtained using carboxylic acids as nucleophiles, affording N-acylhydrazide products.

show abstract

Inhibition of secretory phospholipase A2. 2-Synthesis and structure–activity relationship studies of 4,5-dihydro-3-(4-tetradecyloxybenzyl)-1,2,4-4H-oxadiazol-5-one (PMS1062) derivatives specific for group II enzyme

Cited by 26 publications

References 24 publications

Facile synthesis of α,α-difluoroalkyl aryl thioethers and their oxidative desulfurization–fluorination to trifluorides

Facile synthesis of α,α-difluoroalkyl aryl thioethers and their oxidative desulfurization–fluorination to trifluorides

Nitrile Reductase from Geobacillus kaustophilus: A Potential Catalyst for a New Nitrile Biotransformation Reaction

Investigation of Masked N‐Acyl‐N‐isocyanates: Support for Oxadiazolones as Blocked N‐Isocyanate Precursors

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