Useful syntheses of .BETA.-amino-.GAMMA.-ketobutyric acid derivatives from aspartic acid.

Shimada, Masahiko; Kubota, Hitoshi; Moriya, Tamon; Yamagishi, Masafumi; Nishimoto, Shigeru; Matsumoto, Kazuo

doi:10.1248/cpb.34.4516

Cited by 7 publications

(4 citation statements)

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“…The biphasic mixture was stirred for an additional 10 min followed by separation and direct use of the organic phase. Starting amides 11a − h were prepared by literature methods as described in Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Application of the Dakin−West Reaction for the Synthesis of Oxazole-Containing Dual PPARα/γ Agonists

et al. 2003

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Section: Methodsmentioning

confidence: 99%

Application of the Dakin−West Reaction for the Synthesis of Oxazole-Containing Dual PPARα/γ Agonists

et al. 2003

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“…While there have been many synthetic efforts directed toward the preparation of β-amino acids, 8 there are almost no reports of the synthesis of β-amino-γ-keto acids. 9 Herein we describe an efficient preparation of several β-amino-γ-keto acids from commercially available L-homoserine and the synthesis of a trimer derived from one of these compounds.…”

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confidence: 99%

“…We are interested in preparing a wide variety of β-amino-γ-keto acids to explore the oligomeric properties of such compounds, as well as for their use as chiral building blocks in combinatorial library synthesis and as modules in protease inhibitors. While there have been many synthetic efforts directed toward the preparation of β-amino acids, there are almost no reports of the synthesis of β-amino-γ-keto acids . Herein we describe an efficient preparation of several β-amino-γ-keto acids from commercially available l -homoserine and the synthesis of a trimer derived from one of these compounds.…”

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Efficient Synthesis of Enantiopure β-Amino-γ-Keto Acids froml-Homoserine

Sharma

Hergenrother

2003

Org. Lett.

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“…Chemistry Ethyl 4-oxazoleacetates(17-25)and the acids(26-31)were synthesized(as outlined in Chart 1)according to our previously reported method. 2,3)The key intermediates,ethyl 3-(Nacylamino)-4-oxobutyrates (8)(9)(10)(11)(12)(13)(14)(15)(16),were prepared in two ways: by introduction of an acetic (6H,d,J=6Hz). MS m/z:340(M+).…”

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Synthesis of 5-alkyl-4-oxazoleacetic acid derivatives with hypolipidemic activities.

Shimada

Moriya

Matsumoto

et al. 1988

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of 2-aryl and 2-alkyl derivatives of 5-alkyl-4-oxazoleacetic acids was synthesized and tested for hypolipidemic activity.Among them,5-isopropyl-2-(4-fluorophenyl)-4-oxazoleacetates exhibited potent activities,being more active than clofibrate [ethyl 2-(4-chlorophenoxy)isobutvratel. Keywords-hypolipidemic agent; 5-alkyl-4-oxazoleacetic acid; hypocholesterolemic activity; hypotriglyceridemic activity; platelet aggregation inhibition; aspartic acid azlactone; Dakin-West reactionIn the course of our studies on the development of hypolipidemic agents,a series of 2,5-disubstituted 4-oxazoleacetic acid derivatives was previously prepared and screened for hypolipidemic activity.Among them,some derivatives carrying thienyl 2)and furyl 3)groups at C-5 on the oxazole ring showed moderate to high activities.Above all,ethyl 2-(4-chlorophenyl)-5-(2-furyl)-4-oxazoleacetate has been found to be the most promising candidate for development with reduction of serum cholesterol and triglyceride in normal rats and especially in THLR/1 rats,a model of hereditary hyperlipidemia developed in our laboratory.4) Meanwhile,several research groups have also prepared 4-oxazoleacetic acid derivatives with various pharmaceutical activities.Brown reported that 2,5-diaryl and 2-cycloalkyl-4-oxazoleacetic acids were effective antiinflammatory agents.5) Yamanaka et al.showed ethyl 2-(4-chlorophenyl)-5-ethoxy-4-oxazoleacetate to be hypolipidemic.6)Recently,Meguro et al. reported 5-alkyl-2-cycloalkyl-4-oxazoleacetic acid derivatives as hypoglycemic agents.7)Thus, the substituents on the oxazole ring of 4-oxazoleacetic acid derivatives were considered to play an important role in the various physiological activities.Consequently,the relationships between structure and physiological properties are of much interest.The present study was undertaken to obtain a further insight into the hypolipidemic activity-structure relationships of 4-oxazoleacetic acid derivatives carrying 5-alkyl substituents. ChemistryEthyl 4-oxazoleacetates(17-25)and the acids(26-31)were synthesized(as outlined in Chart 1)according to our previously reported method.2,3)The key intermediates,ethyl 3-(Nacylamino)-4-oxobutyrates(8-16),were prepared in two ways: by introduction of an acetic

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Useful syntheses of .BETA.-amino-.GAMMA.-ketobutyric acid derivatives from aspartic acid.

Cited by 7 publications

References 0 publications

Application of the Dakin−West Reaction for the Synthesis of Oxazole-Containing Dual PPARα/γ Agonists

Application of the Dakin−West Reaction for the Synthesis of Oxazole-Containing Dual PPARα/γ Agonists

Efficient Synthesis of Enantiopure β-Amino-γ-Keto Acids froml-Homoserine

Synthesis of 5-alkyl-4-oxazoleacetic acid derivatives with hypolipidemic activities.

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