Synthese des 2‐Oxy‐ und des 2‐Thio‐tryptophans

Wieland, Theodor; Weiberg, Otto; Dilger, Werner

doi:10.1002/jlac.19555920107

Cited by 30 publications

(4 citation statements)

References 13 publications

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“…The starting lH-indole-3-alkanamides (Table 4), required for Schemes 1-3, were prepared by the methods described in Schemes 4-8. The IV-benzylamides 8a, 8j, and 8u derived from the lH-indole-3-alkanoic acids [12][13][14] were prepared in excellent yields by treating the corresponding methyl esters [15][16][17] with neat benzylamine at 140 °C, as described by Katritzky21 (Scheme 4). Other amides of lH-indole-3-propanoic acid (12) were prepared directly in good yield by treatment with the appropriate amine or amine hydrochloride in the presence of DEPC and triethylamine (Scheme 5).…”

Section: Chemistrymentioning

confidence: 99%

Tyrosine kinase inhibitors. 2. Synthesis of 2,2'-dithiobis(1H-indole-3-alkanamides) and investigation of their inhibitory activity against epidermal growth factor receptor and pp60v-src protein tyrosine kinases

Thompson¹,

Fry²,

Kraker³

et al. 1994

J. Med. Chem.

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A series of amide analogues of the 2,2'-dithiobis(1H-indole-3-alkaonic acid) class of tyrosine kinase inhibitors have been prepared, by reaction of 1H-indole-3-alkanamides (8) with S2Cl2, and separation of the desired disulfides from the initial mixtures of mono-, di-, and trisulfides formed. These amides were evaluated in vitro against epidermal growth factor receptor and pp60v-src protein tyrosine kinases. Inhibitory activity against EGF receptor tyrosine kinase was chain-length dependent, with the propanamides being the most effective. Hydrogen bond donor capabilities in the amide function did not appear to be necessary, with an N-benzylamide being the most potent (IC50 = 0.85 microM). Further substitution on the benzyl ring did not increase potency, and substitution in the alpha-position of the propanamide side chain was acceptable. A water-soluble alpha-NH2 derivative showed good inhibitory activity toward the enzyme, was a potent inhibitor of cell growth in fibroblasts, and selectively inhibited intracellular tyrosine phosphorylation patterns. The nonreceptor kinase pp60v-src was in general much more sensitive than EGF receptor kinase to inhibition by these compounds, but with less pronounced structure-activity relationships.

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Section: Chemistrymentioning

confidence: 99%

Tyrosine kinase inhibitors. 2. Synthesis of 2,2'-dithiobis(1H-indole-3-alkanamides) and investigation of their inhibitory activity against epidermal growth factor receptor and pp60v-src protein tyrosine kinases

Thompson¹,

Fry²,

Kraker³

et al. 1994

J. Med. Chem.

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“…The details on analytical conditions are described in the previous paper. 6 ) Isolation of Xl (cl Fig. 1).…”

Section: Amino Acid Analysismentioning

confidence: 99%

Reaction of Cystine with Tryptophan under the Conditions of Acid Hydrolysis of Proteins: Mechanism of Action of Cystine

Ohta

Nakai

1979

Agricultural and Biological Chemistry

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“…The phallotoxins are bicyclic heptapeptides. L-methylthio-indolylacetic acid, 4, from indolylacetic acid and methylsulfenyl chloride (35,36). The latter may be considered a product of an oxidative condensation of L- Tryptathionine is the chromophoric system of the phallotoxins responsible for the u.v.maxima around 290 nm (Fig.…”

Section: Chemistry Of the Phallotoxinsmentioning

confidence: 99%

The toxic peptides from Amanita mushrooms

Wieland

1983

International Journal of Peptide and Protein Research

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143

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The results of 50 years of effort in the chemistry of Amanita toxins are reviewed. The phallotoxins, fast acting components, but not responsible for fatal intoxications after ingestion, are bicyclic heptapeptides. They combine with F-actin, stabilizing this protein against several destabilizing influences. The virotoxins likewise fast acting are monocyclic heptapeptides. The amatoxins which are the real toxins lead to death within several days by inhibiting the enzymatic synthesis of m-RNA. They are bicyclic octapeptides. The' structures of all of these compounds are described, as well as conformations, chemical reactions and modifications, syntheses and correlations between structures and biological activities.

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Synthese des 2‐Oxy‐ und des 2‐Thio‐tryptophans

Abstract: W i e l a n d , W e i b e r g , D i l g e r und F i s c h e r 69 loslich in Chloroform, Aceton, Essigester, leicht loslich in warmem Alkohol, etwas schwerer in Ather, unloslich in Petrolather.

Cited by 30 publications

References 13 publications

Tyrosine kinase inhibitors. 2. Synthesis of 2,2'-dithiobis(1H-indole-3-alkanamides) and investigation of their inhibitory activity against epidermal growth factor receptor and pp60v-src protein tyrosine kinases

Tyrosine kinase inhibitors. 2. Synthesis of 2,2'-dithiobis(1H-indole-3-alkanamides) and investigation of their inhibitory activity against epidermal growth factor receptor and pp60v-src protein tyrosine kinases

Reaction of Cystine with Tryptophan under the Conditions of Acid Hydrolysis of Proteins: Mechanism of Action of Cystine

The toxic peptides from Amanita mushrooms

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