66056-40-4Relevant academic research and scientific papers
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.
Selective endothelin A receptor ligands. 1. Discovery and structure-activity of 2,4-disubstituted benzoic acid derivatives
Astles,Brown,Handscombe,Harper,Harris,Lewis,Lockey,McCarthy,McLay,Porter,Roach,Smith,Walsh
, p. 409 - 423 (2007/10/03)
This paper describes the discovery of a new non-peptide endothelin A (ET(A)) selective ligand, 2,4-dibenzyloxybenzoic acid 3, which inhibits the binding of [125I]ET-1 to ET(A) receptors with an IC50 of 9 μM (ET-1 = endothelin-1). Optimisation of 3 resulted in compound 52 which had an IC50 of 1 μM. One of the analogues of 3, compound 15, was examined in a functional assay and shown to antagonise ET-1-induced contraction of rat aorta. The identification of 3 was made through the application of ChemDBS-3D searching of our corporate database. The 3D query, using an aromatic ring to a carboxylic acid group separated by 10.2 ± 1.1 A, was derived from an examination of common pharmacophoric distances found in the low energy conformations of two known ET(A) antagonists, the cyclic pentapeptide BQ 123 1 and myriceron caffeoyl ester 2.
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.
An efficient synthesis of JSTX-3, a potent neurotoxin of Joro spider (Nephila clavata)
Matsushita, Masayuki,Kanemura, Takanori,Hatakeyama, Susumi,Irie, Hiroshi,Toki, Takashi,Miyashita, Masaaki
, p. 10687 - 10698 (2007/10/02)
JSTX-3 (Joro spider toxin-3) (1), a potent neurotoxin isolated from Joro spider (Nephila clavata), has been efficiently synthesized starting from 5-azido-1-N-Boc-pentylamine (11) via the convergent synthetic strategy in which the characteristic polyamine
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
Amide compounds, their production and use
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, (2008/06/13)
A compound is provided which has the formula STR1 wherein m is an integer of 1 to 3; n is an integer of 1 or 2; p is an integer of 1 or 2; q is an integer of 1 to 6; x is an integer of 2 to 6; Ph is phenylene or a pharmceutically acceptable salt thereof. Also provided is a method for glutamate receptor inhibition which comprises administering to a mammal in need thereof an effective amount of said compound or a pharmaceutically acceptable salt thereof. Compositions for glutamate receptor inhibition are provided which contain an effective amount of said compound to provide a glutamate receptor inhibition effect, together with at least one pharmaceutically acceptable carrier, dilient or excipient therefor.
N-heterocyclic amides
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, (2008/06/13)
A compound of the formula: STR1 wherein STR2 represents a cyclic amino group, A represents a methylene group or a carbonyl group, m represents an integer of 1 to 3, n represents an integer of 0 to 4 and p represents an integer of 1 to 2, or a salt thereof, which has glutamate receptor inhibiting activity is provided.
Glutamate receptor inhibitor and insecticidal composition
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, (2008/06/13)
A compound of the formula STR1 wherein R' is hydrogen atom or an alkyl group, m is an integer of 1 to 3, p is 1 or 2, x is an integer of 2 to 6, and y is an integer of 1 to 3, or a salt thereof, which has glutamate receptor inhibitor activity, a process for preparing the same and an insecticidal composition containing the same are provided.
SYNTHESIS OF SPIDER TOXIN (JSTX-3) AND ITS ANALOGS
Hashimoto, Yuichi,Endo, Yasuyuki,Shudo, Koichi,Aramaki, Yoshio,Kawai, Nobufumi,Nakajima, Terumi
, p. 3511 - 3514 (2007/10/02)
One of the active principles isolated from spider venom, JSTX-3, and its analogs of the polyamine part were synthesized.
