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Volumn 24, Issue 3, 2003, Pages 293-301

Synthesis and paralytic activities of squaryl amino acid-containing polyamine toxins

Author keywords

4 Hydroxycyclobuten 1 one, 2,3 dioxocyclobutene; Glutamate receptors; N Acyl squaryl amino acid; Nephilatoxin 8; Paralytic activity; Philanthotoxin; Polyamine toxins; Squaric acid; Squaryl amino acid; Squaryl amino acid containing polyamine toxins

Indexed keywords

AMINO ACID; GLUTAMATE RECEPTOR; NEPHILATOXIN 8; PHILANTHOTOXIN; POLYAMINE; SPIDER VENOM; SQUARIC ACID; UNCLASSIFIED DRUG; WASP VENOM;

EID: 0038408970     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-002-0402-9     Document Type: Article
Times cited : (26)

References (32)
  • 6
    • 0030772608 scopus 로고    scopus 로고
    • Olefination of dialkyl squarates by Wittig and Horner-Emmons reactions. A facile synthesis of 3,4-dioxo-1-cyclobutene-1-acetic acid
    • Hayashi K, Shinada T, Sakaguchi K, Horikawa M, Ohfune Y (1997) Olefination of dialkyl squarates by Wittig and Horner-Emmons reactions. A facile synthesis of 3,4-dioxo-1-cyclobutene-1-acetic acid. Tetrahedron Lett 38: 7091-7094
    • (1997) Tetrahedron Lett , vol.38 , pp. 7091-7094
    • Hayashi, K.1    Shinada, T.2    Sakaguchi, K.3    Horikawa, M.4    Ohfune, Y.5
  • 7
    • 0033794176 scopus 로고    scopus 로고
    • Total synthesis of polyamine toxin HO-416b and Agel-489 using a 2-nitrobenzenesulfonamide strategy
    • Hidai Y, Kan T, Fukuyama T (2000) Total synthesis of polyamine toxin HO-416b and Agel-489 using a 2-nitrobenzenesulfonamide strategy. Chem Pharm Bull 48: 1570-1576
    • (2000) Chem Pharm Bull , vol.48 , pp. 1570-1576
    • Hidai, Y.1    Kan, T.2    Fukuyama, T.3
  • 8
    • 0025121386 scopus 로고
    • Isolation, structure elucidation, and synthesis of novel hydroxylamine-containing polyamines from the venom of the Agelenopsis aperta spider
    • Jasys VJ, Kelbaugh PR, Nason DM, Phillips D, Rosnack KJ, Saccomano NA, Stroh JG, Volkmann RA (1990) Isolation, structure elucidation, and synthesis of novel hydroxylamine-containing polyamines from the venom of the Agelenopsis aperta spider. J Am Chem Soc 112: 6696-6704
    • (1990) J Am Chem Soc , vol.112 , pp. 6696-6704
    • Jasys, V.J.1    Kelbaugh, P.R.2    Nason, D.M.3    Phillips, D.4    Rosnack, K.J.5    Saccomano, N.A.6    Stroh, J.G.7    Volkmann, R.A.8
  • 10
    • 0034768977 scopus 로고    scopus 로고
    • Pharmacology and biochemistry of spider venoms
    • Lachlan DR, Hodgson WC (2002) Pharmacology and biochemistry of spider venoms. Toxicon 40: 225-254
    • (2002) Toxicon , vol.40 , pp. 225-254
    • Lachlan, D.R.1    Hodgson, W.C.2
  • 11
    • 0346814452 scopus 로고
    • Organic photoconductive metals: Recent trends and developments
    • Law KY (1993) Organic photoconductive metals: recent trends and developments. Chem Rev 93: 449-486
    • (1993) Chem Rev , vol.93 , pp. 449-486
    • Law, K.Y.1
  • 12
    • 0000666241 scopus 로고
    • Cyclobutenediones as precursors to quinines and cyclopentenones
    • Liebeskind LS (1989) Cyclobutenediones as precursors to quinines and cyclopentenones. Tetrahedron 45: 3053-3060
    • (1989) Tetrahedron , vol.45 , pp. 3053-3060
    • Liebeskind, L.S.1
  • 13
    • 0027137647 scopus 로고
    • Neurotoxic acylpolyamines from spider venoms
    • McCormick KD, Meinwald JJ (1993) Neurotoxic acylpolyamines from spider venoms. J Chem Ecology 19: 2411-2442
    • (1993) J Chem Ecology , vol.19 , pp. 2411-2442
    • McCormick, K.D.1    Meinwald, J.J.2
  • 14
    • 0024596865 scopus 로고
    • The excitatory amino acid receptors: Their classes, pharmacology and distinct properties in the function of the central nervous system
    • Monaghan DT, Bridges RJ, Cotman CW (1989) The excitatory amino acid receptors: their classes, pharmacology and distinct properties in the function of the central nervous system. Annu Rev Pharmacol Toxicol 29: 365-402
    • (1989) Annu Rev Pharmacol Toxicol , vol.29 , pp. 365-402
    • Monaghan, D.T.1    Bridges, R.J.2    Cotman, C.W.3
  • 15
    • 0002365528 scopus 로고
    • Ring expansion of cyclobutenenones - Synthetic utility
    • Moore HW, Yerxa BR (1992) Ring expansion of cyclobutenenones - synthetic utility. Chemtracts: J Org Chem 5: 273-313
    • (1992) Chemtracts: J Org Chem , vol.5 , pp. 273-313
    • Moore, H.W.1    Yerxa, B.R.2
  • 16
    • 0028340001 scopus 로고
    • Molecular diversity and functions of glutamate receptors
    • Nakanishi S, Masu M (1993) Molecular diversity and functions of glutamate receptors. Annu Rev Biophys Biomol Struct 23: 319-348
    • (1993) Annu Rev Biophys Biomol Struct , vol.23 , pp. 319-348
    • Nakanishi, S.1    Masu, M.2
  • 18
    • 0000937422 scopus 로고    scopus 로고
    • Highly selective synthesis of polyfunctionalized carbo- and heterocycles based on ring expansion of squaric acid derivatives
    • Ohno M, Yamamoto Y, Eguchi S (1998) Highly selective synthesis of polyfunctionalized carbo- and heterocycles based on ring expansion of squaric acid derivatives. Synlett: 1167-1174
    • (1998) Synlett , pp. 1167-1174
    • Ohno, M.1    Yamamoto, Y.2    Eguchi, S.3
  • 19
    • 0001947119 scopus 로고    scopus 로고
    • Cascade rearrangements following twofold addition of alkenyl anions to squarate esters
    • Paquette LA (1998) Cascade rearrangements following twofold addition of alkenyl anions to squarate esters. Eur J Org Chem: 1709-1728
    • (1998) Eur J Org Chem , pp. 1709-1728
    • Paquette, L.A.1
  • 20
    • 0001313579 scopus 로고
    • Oxocarbons and pseudooxocarbons
    • Seitz G, Imming P (1992) Oxocarbons and pseudooxocarbons. Chem Rev 92: 1227-1260
    • (1992) Chem Rev , vol.92 , pp. 1227-1260
    • Seitz, G.1    Imming, P.2
  • 22
    • 84977291942 scopus 로고
    • Reaction of squaric acid and its derivatives
    • Schmidt AH (1980) Reaction of squaric acid and its derivatives. Synthesis: 961-994
    • (1980) Synthesis , pp. 961-994
    • Schmidt, A.H.1
  • 23
    • 0030045674 scopus 로고    scopus 로고
    • Synthesis and conformational analysis of glutamate analogs. 2-(2-Carboxy-3-substituted-cyclopropyl)glycines as useful probes for excitatory amino acid receptors
    • and references cited therein
    • Shimamoto K, Ohfune Y (1996) Synthesis and conformational analysis of glutamate analogs. 2-(2-Carboxy-3-substituted-cyclopropyl)glycines as useful probes for excitatory amino acid receptors. J Med Chem 39: 407-423 and references cited therein
    • (1996) J Med Chem , vol.39 , pp. 407-423
    • Shimamoto, K.1    Ohfune, Y.2
  • 24
  • 25
    • 0033820408 scopus 로고    scopus 로고
    • Squaric acid derivatives prevent the removal of N-Cbz and N-Fmoc groups under catalytic hydrogenation reaction
    • Shinada T, Hayashi K, Yoshida Y, Ohfune Y (2000) Squaric acid derivatives prevent the removal of N-Cbz and N-Fmoc groups under catalytic hydrogenation reaction. Synlett: 1506-1509
    • (2000) Synlett , pp. 1506-1509
    • Shinada, T.1    Hayashi, K.2    Yoshida, Y.3    Ohfune, Y.4
  • 28
    • 0023947370 scopus 로고
    • A new type of spider toxin, nephilatoxin, in the venom of the Joro spider, Nephila clavata
    • Toki T, Yasuhara T, Aramaki Y, Kawai N, Nakajima T (1988) A new type of spider toxin, nephilatoxin, in the venom of the Joro spider, Nephila clavata. Biomedical Res 9: 75-80
    • (1988) Biomedical Res , vol.9 , pp. 75-80
    • Toki, T.1    Yasuhara, T.2    Aramaki, Y.3    Kawai, N.4    Nakajima, T.5
  • 29
    • 0034199961 scopus 로고    scopus 로고
    • Solid phase syntheses of polyamine toxins HO-416b and PhTX-433. Use of an efficient polyamide reduction strategy that facilitates access to branched analogues
    • Wang F, Manku S, Hall DG (2000) Solid phase syntheses of polyamine toxins HO-416b and PhTX-433. Use of an efficient polyamide reduction strategy that facilitates access to branched analogues. Org Lett 2: 1581-1583
    • (2000) Org Lett , vol.2 , pp. 1581-1583
    • Wang, F.1    Manku, S.2    Hall, D.G.3
  • 30
    • 0025191432 scopus 로고
    • Structure-activity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists
    • Watkins JC, Krogsgaard-Larsen P, Honorè T (1990) Structure-activity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists. Trends Pharmacol Sci 11: 25-33
    • (1990) Trends Pharmacol Sci , vol.11 , pp. 25-33
    • Watkins, J.C.1    Krogsgaard-Larsen, P.2    Honorè, T.3
  • 31
    • 0038823416 scopus 로고
    • Snyder JP (ed) Academic Press, New York
    • West R. Niu J (1969) Nonbenzenoid aromatics. In: Snyder JP (ed) Academic Press, New York, pp 311-346
    • (1969) Nonbenzenoid Aromatics , pp. 311-346
    • West, R.1    Niu, J.2
  • 32
    • 0023938882 scopus 로고
    • Color development upon reaction of ferric ion with the toxin JSTX, a glutamate receptor blocker present in the venom gland of the spider Nephila clavata (joro spider)
    • Yoshioka M, Narai N, Pan-Hou H, Shimazaki K, Miwa A, Kawai N (1988) Color development upon reaction of ferric ion with the toxin JSTX, a glutamate receptor blocker present in the venom gland of the spider Nephila clavata (joro spider). Toxicon 26: 414-416
    • (1988) Toxicon , vol.26 , pp. 414-416
    • Yoshioka, M.1    Narai, N.2    Pan-Hou, H.3    Shimazaki, K.4    Miwa, A.5    Kawai, N.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.