66056-40-4Relevant articles and documents
The total large-scale synthesis of argiopine
Formanovsky,Popova,Mikhura
experimental part, p. 752 - 758 (2010/07/15)
The total large-scale synthesis of a natural toxin argiopine, a polymethylenepolyamine derivative, was developed. It consisted of 26 stages and included three key block schemes. Most of the stages proceeded quantitatively, which excluded the necessity of using the chromatographic separation of intermediates.
Total syntheses of spidamine and joramine, polyamine toxins from the joro spider, Nephila clavata
Chiba, Tadashige,Akizawa, Toshifumi,Matsukawa, Motomi,Nishi, Masatoshi,Kawai, Nobufumi,Yoshioka, Masanori
, p. 972 - 979 (2007/10/03)
In order to confirm the structures of spidamine and joramine, identified from the venom of a spider (nephila clavata), we convergently synthesized both compounds, which have a common side chain of N-(L-asparaginyl)-N'-(3- aminopropyl-β-alanyl)-1,5-pentanediamine. A synthon of the common side chain was synthesized by starting with n-propanolamine which was converted to 7- azido-N-benzyloxycarbonyl-4-azaheptanoic acid N-hydroxysuccinimidyl ester. The ester was coupled with tert-butyloxycarbonyl-L-asparaginyl-1,5- pentanediamine to give the synthon of the common side chain. In the final synthesis of spidamine, the synthon of the common side chain was reacted with 2,4-dibenzyloxyphenylacetic acid N-hydroxysuccinimidyl ester, obtained by Willgerodt-kindler reaction of 2,4-dihydroxyacetophenone. The protected spidamine was catalytically hydrogenated to remove protective groups, affording spidamine itself in 13% yield from n-propanolamine. In the final synthesis of joramine, the synthon of the common side chain was reacted with 4-benzyloxyphenyl acetic acid N-hydroxysuccinimidyl ester. The protected joramine was also catalytically hydrogenated to produce joramine itself in 11% yield. The conformations of both synthesized compounds were analyzed by 1H-NMR and 13C-NMR. Their blocking activities on glutamate receptors were examined using lobster neuromuscular synapses.
Synthesis and assay of hybrid analogs of argiotoxin-636 and philanthoxin-433: Glutamate receptor antagonists
Choi,Nakanishi,Usherwood
, p. 5777 - 5790 (2007/10/02)
The synthesis of the non-competitive glutamate receptor antagonist, argiotoxin-636 is described. Furthermore, synthetic routes are presented for the preparation of structural analogs including argiotoxin-philanthotoxin hybrids. Biological activities on gl