메뉴 건너뛰기




Volumn 43, Issue 8, 2000, Pages 1577-1585

Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; CARBOLINE DERIVATIVE; DEMOTHOXYFUMITREMORGIN C; TRYPTOSTATIN B; UNCLASSIFIED DRUG;

EID: 0034692166     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9905662     Document Type: Article
Times cited : (81)

References (36)
  • 3
    • 0031012407 scopus 로고    scopus 로고
    • Screening of Cell Cycle Inhibitors from Microbial Metabolites by a Bioassay Using a Mouse cdc2 Mutant Cell Line, tsFT210
    • Osada, H.; Cui, C.-B.; Onose, R.; Hanaoka, F. Screening of Cell Cycle Inhibitors from Microbial Metabolites by a Bioassay Using a Mouse cdc2 Mutant Cell Line, tsFT210. Bioorg. Med. Chem. 1997, 5, 193-203.
    • (1997) Bioorg. Med. Chem. , vol.5 , pp. 193-203
    • Osada, H.1    Cui, C.-B.2    Onose, R.3    Hanaoka, F.4
  • 4
    • 0031788004 scopus 로고    scopus 로고
    • Bioprobes for Investigating Mammalian Cell Cycle Control
    • Osada, H. Bioprobes for Investigating Mammalian Cell Cycle Control. J. Antibiot. 1998, 57, 973-982.
    • (1998) J. Antibiot. , vol.57 , pp. 973-982
    • Osada, H.1
  • 5
    • 0028834234 scopus 로고
    • Tryprostatins A and B, Novel Mammalian Cell Cycle Inhibitors Produced by Aspergillus fumigatus
    • (a) Cui, C.-B.; Kakeya, H.; Okada, G.; Onose, R.; Ubukata, M.; Takahashi, I.; Isono, K.; Osada, H. Tryprostatins A and B, Novel Mammalian Cell Cycle Inhibitors Produced by Aspergillus Fumigatus. J. Antibiot. 1995, 48, 1382-1384.
    • (1995) J. Antibiot. , vol.48 , pp. 1382-1384
    • Cui, C.-B.1    Kakeya, H.2    Okada, G.3    Onose, R.4    Ubukata, M.5    Takahashi, I.6    Isono, K.7    Osada, H.8
  • 6
    • 0030037137 scopus 로고    scopus 로고
    • Novel mammalian cell cycle inhibitors, tryprostatins A, B and other Diketopiperazines produced by Aspergillus Fumigatus I. Taxonomy, fermentation, isolation and biological properties
    • (b) Cui, C.-B.; Kakeya, H.; Okada, G.; Onose, R.; Osada, H. Novel Mammalian Cell Cycle Inhibitors, Tryprostatins A, B and Other Diketopiperazines Produced by Aspergillus Fumigatus I. Taxonomy, Fermentation, Isolation and Biological Properties. J Antibiot. 1996, 49, 527-533.
    • (1996) J Antibiot. , vol.49 , pp. 527-533
    • Cui, C.-B.1    Kakeya, H.2    Okada, G.3    Onose, R.4    Osada, H.5
  • 7
    • 0029820050 scopus 로고    scopus 로고
    • Spirotryprostatin B, a novel Mammalian cell cycle inhibitor produced by Aspergillus fumigatus
    • (c) Cui, C.-B.; Kakeya, H.; Osada, H. Spirotryprostatin B, a Novel Mammalian Cell Cycle Inhibitor Produced by Aspergillus fumigatus. J. Antibiot. 1996, 49, 832-835.
    • (1996) J. Antibiot. , vol.49 , pp. 832-835
    • Cui, C.-B.1    Kakeya, H.2    Osada, H.3
  • 8
    • 0030599282 scopus 로고    scopus 로고
    • Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit Mammalian cell cycle at G2/M phase
    • (d) Cui, C.-B.; Kakeya, H.; Osada, H. Novel Mammalian Cell Cycle Inhibitors, Spirotryprostatins A and B, Produced by Aspergillus fumigatus, Which Inhibit Mammalian Cell Cycle at G2/M Phase. Tetrahedron 1996, 52, 12651-12666.
    • (1996) Tetrahedron , vol.52 , pp. 12651-12666
    • Cui, C.-B.1    Kakeya, H.2    Osada, H.3
  • 9
    • 0031060189 scopus 로고    scopus 로고
    • Novel Mammalian cell cycle inhibitors, cyclotryprostatins A-D, produced by Aspergillus fumigatus, which inhibit Mammalian cell cycle at G2/M phase
    • (e) Cui, C.-B.; Kakeya, H.; Osada, H. Novel Mammalian Cell Cycle Inhibitors, Cyclotryprostatins A-D, Produced by Aspergillus fumigatus, Which Inhibit Mammalian Cell Cycle at G2/M Phase. Tetrahedron 1997, 53, 59-72.
    • (1997) Tetrahedron , vol.53 , pp. 59-72
    • Cui, C.-B.1    Kakeya, H.2    Osada, H.3
  • 10
    • 0030993237 scopus 로고    scopus 로고
    • Concise synthesis of the cell cycle inhibitor Demethoxyfumitremorgin C
    • Wang, H.; Ganesan, A. Concise Synthesis of the Cell Cycle Inhibitor Demethoxyfumitremorgin C. Tetrahedron Lett. 1997, 38, 4327-4328.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4327-4328
    • Wang, H.1    Ganesan, A.2
  • 11
    • 0001690298 scopus 로고    scopus 로고
    • Total syntheses of Fumitremorgins and Verruculogens
    • For a review of earlier syntheses, see: Hino, T.; Nakagawa, M. Total Syntheses of Fumitremorgins and Verruculogens. Heterocycles 1997, 46, 673-704.
    • (1997) Heterocycles , vol.46 , pp. 673-704
    • Hino, T.1    Nakagawa, M.2
  • 12
    • 0011551580 scopus 로고    scopus 로고
    • The N-Acyliminium pictet-Spengler condensation as a multicomponent combinatorial reaction on solid phase and its application to the synthesis of Demethoxyfumitremorgin C analogues
    • Wang, H.; Ganesan, A. The N-Acyliminium Pictet-Spengler Condensation as a Multicomponent Combinatorial Reaction on Solid Phase and its Application to the Synthesis of Demethoxyfumitremorgin C Analogues. Org. Lett. 1999, 1, 1647-1649.
    • (1999) Org. Lett. , vol.1 , pp. 1647-1649
    • Wang, H.1    Ganesan, A.2
  • 13
    • 0030443081 scopus 로고    scopus 로고
    • Total synthesis of Tryprostatin B: Generation of a nucleophilic prenylating species from a prenylstannane
    • Depew, K. M.; Danishefsky, S. J.; Rosen, N.; Sepp-Lorenzino, L. Total Synthesis of Tryprostatin B: Generation of a Nucleophilic Prenylating Species from a Prenylstannane. J. Am. Chem. Soc. 1996, 118, 12463-12464.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 12463-12464
    • Depew, K.M.1    Danishefsky, S.J.2    Rosen, N.3    Sepp-Lorenzino, L.4
  • 14
    • 0031584890 scopus 로고    scopus 로고
    • Enantioselective total synthesis of Tryprostatin A
    • (a) Gan, T.; Cook, J. M. Enantioselective Total Synthesis of Tryprostatin A. Tetrahedron Lett. 1997, 38, 1301-1304.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1301-1304
    • Gan, T.1    Cook, J.M.2
  • 15
    • 0031436451 scopus 로고    scopus 로고
    • Enantioselective synthesis of optically active 6-methoxytryptophan derivatives and total synthesis of tryprostatin A
    • (b) Gan, T.; Liu, R.; Yu, P.; Zhao, S.; Cook, J. M. Enantioselective Synthesis of Optically Active 6-Methoxytryptophan Derivatives and Total Synthesis of Tryprostatin A. J. Org. Chem. 1997, 62, 9298-9304.
    • (1997) J. Org. Chem. , vol.62 , pp. 9298-9304
    • Gan, T.1    Liu, R.2    Yu, P.3    Zhao, S.4    Cook, J.M.5
  • 16
    • 0032563838 scopus 로고    scopus 로고
    • Total synthesis of tryprostatin A and B as well as their enantiomers
    • (c) Zhao, S.; Gan, T.; Yu, P.; Cook, J. M. Total Synthesis of Tryprostatin A and B as well as Their Enantiomers. Tetrahedron Lett. 1998, 39, 7009-7012.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7009-7012
    • Zhao, S.1    Gan, T.2    Yu, P.3    Cook, J.M.4
  • 17
    • 0028907801 scopus 로고
    • Trimethylorthoformate: A mild and effective dehydrating reagent for solution and solid-phase imine formation
    • Look, G. C.; Murphy, M. M.; Campbell, D. A.; Gallop, M. A. Trimethylorthoformate: A Mild and Effective Dehydrating Reagent for Solution and Solid-Phase Imine Formation. Tetrahedron Lett. 1995, 36, 2937-2940.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2937-2940
    • Look, G.C.1    Murphy, M.M.2    Campbell, D.A.3    Gallop, M.A.4
  • 18
    • 0342993927 scopus 로고    scopus 로고
    • A reductive alkylation procedure applicable to both solution- and solid-phase syntheses of secondary Amines
    • Szardenings, A. K.; Burkoth, T. S.; Look, G. C.; Campbell, D. A. A Reductive Alkylation Procedure Applicable to Both Solution- and Solid-Phase Syntheses of Secondary Amines. J. Org Chem. 1996, 61, 6720-6722.
    • (1996) J. Org Chem. , vol.61 , pp. 6720-6722
    • Szardenings, A.K.1    Burkoth, T.S.2    Look, G.C.3    Campbell, D.A.4
  • 19
    • 33845375891 scopus 로고
    • 9-fluorenylmethyloxy-carbonyl (Fmoc) amino acid chlorides. Synthesis, characterization, and application to the rapid synthesis of short peptide segments
    • Carpino, L. A.; Cohen, B. J.; Stephens, K. E., Jr.; Sadat-Aalaee, S. Y.; Tien, J.-H.; Langridge, D. C. ((9-Fluorenylmethyl)oxy)-carbonyl (Fmoc) Amino Acid Chlorides. Synthesis, Characterization, and Application to the Rapid Synthesis of Short Peptide Segments. J. Org. Chem. 1986, 51, 3732-3734.
    • (1986) J. Org. Chem. , vol.51 , pp. 3732-3734
    • Carpino, L.A.1    Cohen, B.J.2    Stephens K.E., Jr.3    Sadat-Aalaee, S.Y.4    Tien, J.-H.5    Langridge, D.C.6
  • 20
    • 0030932342 scopus 로고    scopus 로고
    • Solid-phase synthesis of 1,4-benzodiazepine-2,5-diones. Library preparation and demonstration of synthesis generality
    • For a discussion of racemization during reductive alkylation, see: Boojamra, C. G.; Burow, K. M.; Thompson, L. A.; Ellman, J. A. Solid-Phase Synthesis of 1,4-Benzodiazepine-2,5-Diones. Library Preparation and Demonstration of Synthesis Generality. J. Org. Chem. 1997, 62, 1240-1256.
    • (1997) J. Org. Chem. , vol.62 , pp. 1240-1256
    • Boojamra, C.G.1    Burow, K.M.2    Thompson, L.A.3    Ellman, J.A.4
  • 21
    • 0012566719 scopus 로고
    • Use of carbonyl derivatives for heterocyclic synthesis
    • Winterfeldt, E., Ed.; Pergamon Press: Oxford
    • For recent reviews, see: (a) Bringmann, G.; Ewers, C. L. J.; Walter, R. Use of Carbonyl Derivatives for Heterocyclic Synthesis. In Comprehensive Organic Synthesis, Vol. 6; Winterfeldt, E., Ed.; Pergamon Press: Oxford, 1991; pp 736-740.
    • (1991) Comprehensive Organic Synthesis, Vol. 6 , vol.6 , pp. 736-740
    • Bringmann, G.1    Ewers, C.L.J.2    Walter, R.3
  • 22
    • 4243241249 scopus 로고
    • The Pictet-spengler condensation: A new direction for an old reaction
    • (b) Cox, E. D.; Cook, J. M. The Pictet-Spengler Condensation: A New Direction for an Old Reaction. Chem. Rev. 1995, 95, 1797-1842.
    • (1995) Chem. Rev. , vol.95 , pp. 1797-1842
    • Cox, E.D.1    Cook, J.M.2
  • 23
    • 37049109471 scopus 로고
    • Synthesis of the two enantiomers of a tetrahydro-β-carboline from L-(-)-tryptophan
    • Massiot, G.; Mulamba, T. Synthesis of The Two Enantiomers of a Tetrahydro-β-carboline from L-(-)-Tryptophan. J. Chem. Soc., Chem. Commun. 1983, 37, 1147-1149.
    • (1983) J. Chem. Soc., Chem. Commun. , vol.37 , pp. 1147-1149
    • Massiot, G.1    Mulamba, T.2
  • 24
    • 85013557062 scopus 로고
    • Synthetic approaches to fumitremorgins. III. Synthesis of optically active pentacyclic ring systems, and their oxidation at ring C
    • Nakagawa, K.; Fukushima, H.; Kawate, T.; Hongu, M.; Une, T.; Kodato, S.-I.; Taniguchi, M.; Hino, T. Synthetic Approaches to Fumitremorgins. III. Synthesis of Optically Active Pentacyclic Ring Systems, and Their Oxidation at Ring C. Chem. Pharm. Bull. 1989, 37, 23-32.
    • (1989) Chem. Pharm. Bull. , vol.37 , pp. 23-32
    • Nakagawa, K.1    Fukushima, H.2    Kawate, T.3    Hongu, M.4    Une, T.5    Kodato, S.-I.6    Taniguchi, M.7    Hino, T.8
  • 27
    • 0001066582 scopus 로고    scopus 로고
    • Stereocontrolled synthesis of 3,6-Dimethyl-2,3,6,7,12,12a-hexahydropyrazino[1,2-b]-β-carboline-1,4-diones
    • Madrigal, A.; Grande, M.; Avendaño, C. Stereocontrolled Synthesis of 3,6-Dimethyl-2,3,6,7,12,12a-hexahydropyrazino[1,2-b]-β-carboline-1,4- diones. J. Org. Chem. 1998, 63, 2724-2727.
    • (1998) J. Org. Chem. , vol.63 , pp. 2724-2727
    • Madrigal, A.1    Grande, M.2    Avendaño, C.3
  • 28
    • 33847086491 scopus 로고
    • General method for the assignment of stereochemistry of 1,3-disubstituted 1,2,3,4-tetrahydro-β-carbolines by carbon-13 spectroscopy
    • Ungemach, F.; Soerens, D.; Weber, R.; DiPierro, M.; Campos, O.; Mokry, P.; Cook, J. M.; Silverton, J. V. General Method for the Assignment of Stereochemistry of 1,3-Disubstituted 1,2,3,4-Tetrahydro-β-carbolines by Carbon-13 Spectroscopy. J. Am. Chem. Soc. 1980, 102, 6976-6984.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 6976-6984
    • Ungemach, F.1    Soerens, D.2    Weber, R.3    DiPierro, M.4    Campos, O.5    Mokry, P.6    Cook, J.M.7    Silverton, J.V.8
  • 29
    • 0342559341 scopus 로고    scopus 로고
    • Information on the NCI's screening program is available on the World Wide Web at
    • Information on the NCI's screening program is available on the World Wide Web at http://dtp.nci.nih.gov.
  • 30
    • 0031810637 scopus 로고    scopus 로고
    • Podophyllotoxins: Current status and recent developments
    • For a review, see: Damayanthi, Y.; Lown, J. W. Podophyllotoxins: Current Status and Recent Developments. Curr. Med. Chem. 1998, 5, 205-252.
    • (1998) Curr. Med. Chem. , vol.5 , pp. 205-252
    • Damayanthi, Y.1    Lown, J.W.2
  • 32
    • 0030880552 scopus 로고    scopus 로고
    • Structure-activity relationship for DNA topoisomerase II-Induced DNA cleavage by Azatoxin analogues
    • Madalengoitia, J. S.; Tepe, J. J.; Werbovetz, K. A.; Lehnert, E. K.; Macdonald, T. L. Structure-Activity Relationship for DNA Topoisomerase II-Induced DNA Cleavage by Azatoxin Analogues. Biochem. Med. Chem. 1997, 5, 1807-1815.
    • (1997) Biochem. Med. Chem. , vol.5 , pp. 1807-1815
    • Madalengoitia, J.S.1    Tepe, J.J.2    Werbovetz, K.A.3    Lehnert, E.K.4    Macdonald, T.L.5
  • 34
    • 0031687689 scopus 로고    scopus 로고
    • Effects of tryprostatin derivatives on microtubule assembly in Vitro and in Situ
    • (b) Kondoh, M.; Usui, T.; Mayumi, T.; Osada, H. Effects of Tryprostatin Derivatives on Microtubule Assembly In Vitro and In Situ. J. Antibiot. 1998. 5, 801-804.
    • (1998) J. Antibiot. , vol.5 , pp. 801-804
    • Kondoh, M.1    Usui, T.2    Mayumi, T.3    Osada, H.4
  • 36
    • 0023902435 scopus 로고
    • A consensus sequence for cleavage by vertebrate DNA topoisomerase II
    • (b) Spitzner, J. R.; Muller, M. T. A Consensus Sequence for Cleavage by Vertebrate DNA Topoisomerase II. Nucleic Acid Res. 1988, 16, 5533-5556.
    • (1988) Nucleic Acid Res. , vol.16 , pp. 5533-5556
    • Spitzner, J.R.1    Muller, M.T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.