ChemInform Abstract: Synthesis of Amino Acids and Related Compounds. Part 29. Synthesis and Hypolipidemic Activities of 5‐Thienyl‐4‐oxazoleacetic Acid Derivatives.

Moriya, Tamon; Takabe, Seiichi; Maeda, Sadao; MATSUMOTO, K.; TAKASHIMA, K.; MORI, T.; TAKEYAMA, S.

doi:10.1002/chin.198649187

Cited by 3 publications

(3 citation statements)

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“…The title compound has previously been prepared by Buu-Hoi & Jacquignon (1949) and by Kraus & Guo (2009). For the synthesis of the starting material, 4-fluoro-N-(2-oxo-2-phenylethyl)benzamide, see: Moriya et al (1986). There are no structures of closely related compounds in the literature.…”

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confidence: 99%

2-(4-Fluorophenyl)-3-methyl-1H-indole

et al. 2011

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Section: Related Literaturementioning

confidence: 99%

2-(4-Fluorophenyl)-3-methyl-1H-indole

et al. 2011

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“…There is a problem with the mechanism of 4,5-diphenyloxazole formation by this route, whether the formyl group in the -O-CHO moiety (mechanism I) or the formyl group in the -N-CHO moiety (mechanism II) takes part in the In the past three decades, oxazoles have proved quite useful in medicine owing to their curative properties, for example, anti-platelet coagulant, 1,2 anti-articular rheumatism, 3 skeletal muscle relaxant 4 and depressors [5][6][7][8] of aldose reductases, blood sugar and blood lipid, etc. Moreover, since the synthesis of pyridoxine 9 had been accomplished by the Diels-Alder reaction of 5-ethoxy-4methyloxazole with but-2-ene-1,4-diol, oxazoles have been found very useful in organic synthesis.…”

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Convenient Syntheses of 2-Alkyl(Aryl)-4,5-diphenyloxazoles and 2-Alkyl(Aryl)-4-phenyloxazoles

Weiwei¹,

Li²,

Nie³

et al. 1998

Synthesis

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a Route A: PhCOCHClPh; route B: -. b The product obtained in 33% yield was indeed a mixture of the oxazole (4%) and a byproduct, benzil (29%). Abstract:The synthetic methods to prepare 2-alkyl(aryl)-4,5-diphenyloxazoles and 2-alkyl(aryl)-4-phenyloxazoles were improved on the basis of a mechanistic study of oxazole formation from α -hydroxy ketones (carboxylic esters of benzoin and phenacyl alcohols). By these methods, seven trisubstituted oxazoles and twelve disubstituted oxazoles of the title compounds were prepared.

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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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ChemInform Abstract: Synthesis of Amino Acids and Related Compounds. Part 29. Synthesis and Hypolipidemic Activities of 5‐Thienyl‐4‐oxazoleacetic Acid Derivatives.

Abstract: Die aus dem Isocyanester (I) nach literaturbekannten Methoden dargestellten α‐Aminoketone (III) reagieren mit den Säurechloriden (IV) zu den N‐Acyl‐Derivaten (V).

Cited by 3 publications

References 1 publication

2-(4-Fluorophenyl)-3-methyl-1H-indole

2-(4-Fluorophenyl)-3-methyl-1H-indole

Convenient Syntheses of 2-Alkyl(Aryl)-4,5-diphenyloxazoles and 2-Alkyl(Aryl)-4-phenyloxazoles

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

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