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Haasbroek, P. P.; Oliver, Douglas W.; Carpy, A.

doi:10.1023/a:1021875603536

Cited by 7 publications

(2 citation statements)

References 3 publications

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“…The same syn arrangement between the ortho-substituent and the benzylidene proton has also been observed in related orthosubstituted unsaturated 4-arylidene-oxazolones [52][53][54][55][56][57][58][59]. The internal bond distances and angles for the 4-arylidene fragment and the oxazolone ring are similar or identical, within experimental error, to those found in related oxazolones reported in the literature [52][53][54][55][56][57][58][59]. The styryl fragment bonded to an oxazolone ring has not been characterized previously by X-ray methods, but it shows internal bond distances and angles similar to those found in related 2-styrylimidazolone species [60].…”

Section: Resultssupporting

confidence: 65%

“…The non-bonding distance Cl1-H7A is 2.565(3) Å, which is much shorter than the sum of the van der Waals radii (2.95 Å) [51]. The same syn arrangement between the ortho-substituent and the benzylidene proton has also been observed in related orthosubstituted unsaturated 4-arylidene-oxazolones [52][53][54][55][56][57][58][59]. The internal bond distances and angles for the 4-arylidene fragment and the oxazolone ring are similar or identical, within experimental error, to those found in related oxazolones reported in the literature [52][53][54][55][56][57][58][59].…”

Section: Resultsmentioning

confidence: 59%

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Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

Urriolabeitia¹,

Sánchez²,

Pop³

et al. 2020

Beilstein J. Org. Chem.

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The stereoselective synthesis of truxillic bis-amino esters from polyfunctional oxazolones is reported. The reaction of 4-((Z)-arylidene)-2-(E)-styryl-5(4H)-oxazolones 2 with Pd(OAc)2 resulted in ortho-palladation and the formation of a dinuclear open-book complexes 3 with carboxylate bridges, where the Pd atom is C^N bonded to the oxazolone. In 3 the two exocyclic C=C bonds of the oxazolone are in a face-to-face arrangement, which is optimal for their [2 + 2] photocycloaddition. Irradiation of dimers 3 in CH2Cl2 solution with blue light (465 nm) promoted the chemo- and stereoselective [2 + 2] photocycloaddition of the exocyclic C=C bonds and the formation of cyclobutane-containing ortho-palladated complexes 4. Treatment of 4 with CO in a MeOH/NCMe mixture promoted the methoxycarbonylation of the palladated carbon and the release of the corresponding ortho-functionalized 1,3-diaminotruxillic bis-amino esters 5 as single isomers.

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Section: Resultssupporting

confidence: 65%

Section: Resultsmentioning

confidence: 59%

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

Urriolabeitia¹,

Sánchez²,

Pop³

et al. 2020

Beilstein J. Org. Chem.

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Design of agents interacting with immunoregulating proteins: Potential inhibitors of the phenylpyruvate tautomerase activity catalysed by macrophage migration inhibitory factor (MIF)

2003

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The macrophage migration inhibitory factor has been implicated in a number of immune and inflammatory processes. M E presents particular opportunities for drug design and development with potential therapeutic applications. Drug design strategies taking into consideration of specific stereochemical and tautomeric requirements in the interaction of MIF with substrates and inhibitors allow several novel structures to be designed. Our investigations successfully explored the tautomeric and stereochemical aspects of new compounds of the 2-phenylpyruvic acid type, both experimentally, through synthesis and structural investigations and computationally, through molecular mechanics and quantum mechanics calculations. Keywords.vale tautomerase activity, azlactone, phenylpyruvic acid derivative macrophage migration inhibitory factor, phenylpym-

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Design and synthesis of 2,4-difluorophenylpyruvic acid and of its azlactone precursor for macrophage migration inhibitory factor (MIF) tautomerase activity

Haasbroek

Oliver

Carpy

2004

Journal of Molecular Structure

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Untitled

Cited by 7 publications

References 3 publications

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

Design of agents interacting with immunoregulating proteins: Potential inhibitors of the phenylpyruvate tautomerase activity catalysed by macrophage migration inhibitory factor (MIF)

Design and synthesis of 2,4-difluorophenylpyruvic acid and of its azlactone precursor for macrophage migration inhibitory factor (MIF) tautomerase activity

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