Ueber Hydrazinosäuren

Traube, Wilhelm; Longinescu, G. G.

doi:10.1002/cber.189602901123

Cited by 16 publications

(4 citation statements)

References 2 publications

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“…The introduction of metbyl branches (9,10), on the other hand, seems generally to weaken the activity. Incorporation of heteroatoms in the alkyl chain (14,15) seems to result in a distinct loss of activity, whereas substitution with alicycles has no effect on the activity if the whole R-A residue is of an optimal length (16,18).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and hypoglycemic activity of N-alkylated hydrazonopropionic acids

Hp¹,

Hf²

1985

J. Med. Chem.

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A series of N-alkylated 2-hydrazonopropionic acids have been synthesized and evaluated for their hypoglycemic activity. Most of the compounds exhibit a remarkable blood glucose lowering activity in fasted guinea pigs. Some of the structural variables studied were the effects of branching, unsaturation, or substitution on the alkyl side chain and the effect of nuclear substitution on the aralkyl analogues. From these compounds, 2-[[(E)-2-methyl-3-phenyl-2-propenyl]hydrazono]propionic acid (BM 42.304; 42) was selected for further investigation.

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Section: Resultsmentioning

confidence: 99%

Synthesis and hypoglycemic activity of N-alkylated hydrazonopropionic acids

Hp¹,

Hf²

1985

J. Med. Chem.

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“…Most of these acids have previously been reported (1)(2)(3)(4)(5), with the exception of the a-hydrazino derivatives of palmitic and stearic acids, and the m-nitrobenzal hydrazone derivatives (6).…”

Section: Introductionmentioning

confidence: 99%

Reaction of α-hydrazino carboxylic acids with ninhydrin

Ronwin¹,

Roach²,

Tucker³

1968

Can. J. Chem.

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Several a-hydrazino carboxylic acids and their m-nitrobenzal hydrazones have been prepared and characterized. The latter and two of the former have not been previously reported. The a-hydrazino acids were found to react with ninhydrin to yield Ruhemann's purple, but in much lower yield than the corresponding amino acids. However, hydrazine itself yields a different colored product. Various aspects of the reaction between ninhydrin and the a-hydrazino acids were investigated and a mechanism for the formation of Ruhemann's purple is suggested.

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“…Since the first preparation of hydrazino acids in 1896 by Traube, subsequently developed by Darapsky, only a few methods have been established for their selective synthesis and the procedures are sometimes difficult to carry out and/or have a limited scope. A plausible synthetic precursor for a given hydrazino acid is the corresponding amino acid, although the transformation is not always straightforward. ,, l -Azetidinecarboxylic acid is commercially available but prohibitively expensive, and the known synthetic routes to this compound involve several steps .…”

mentioning

confidence: 99%