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Volumn 43, Issue 2, 2000, Pages 224-235

Synthesis and evaluation of hydroxylated polyamine analogues as antiproliferatives

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; N1,N11 DIETHYL 2,10 DIHYDROXYHOMOSPERMINE; N1,N11 DIETHYL 2,10 DIHYDROXYNORSPERMINE; N1,N14 DIETHYL 3,12 DIHYDROXYHOMOSPERMINE; N1,N14 DIETHYL 3,12 DIHYDROXYNORSPERMINE; POLYAMINE DERIVATIVE; SPERMINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0343775818     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990375z     Document Type: Article
Times cited : (35)

References (44)
  • 2
    • 0026647229 scopus 로고
    • Antitumor activity of N,N'-Bis(ethyl)spermine homologues against human MALME-3 melanoma xenografts
    • Bernacki, R. J.; Bergeron, R. J.; Porter, C. W. Antitumor Activity of N,N'-Bis(ethyl)spermine Homologues against Human MALME-3 Melanoma Xenografts. Cancer Res. 1992, 52, 2424-2430.
    • (1992) Cancer Res. , vol.52 , pp. 2424-2430
    • Bernacki, R.J.1    Bergeron, R.J.2    Porter, C.W.3
  • 3
    • 0020335341 scopus 로고
    • 4-Spermidine derivatives and their potential in anticancer chemotherapy
    • 4-Spermidine Derivatives and Their Potential in Anticancer Chemotherapy. Cancer Res. 1982, 42, 4072-4078.
    • (1982) Cancer Res. , vol.42 , pp. 4072-4078
    • Porter, C.W.1    Bergeron, R.J.2    Stolowich, N.J.3
  • 4
    • 0021325432 scopus 로고
    • Aliphatic chain length specificity of the polyamine transport system in ascites L1210 leukemia cells
    • Porter, C. W.; Miller, J.; Bergeron, R. J. Aliphatic Chain Length Specificity of the Polyamine Transport System in Ascites L1210 Leukemia Cells. Cancer Res. 1984, 44, 126-128.
    • (1984) Cancer Res. , vol.44 , pp. 126-128
    • Porter, C.W.1    Miller, J.2    Bergeron, R.J.3
  • 5
    • 0024319054 scopus 로고
    • Role of the methylene backbone in the antiproliferative activity of polyamine analogues on L1210 cells
    • Bergeron, R. J.; Hawthorne, T. R.; Vinson, J. R. T.; Beck, D. E., Jr.; Ingeno, M. J. Role of the Methylene Backbone in the Antiproliferative Activity of Polyamine Analogues on L1210 Cells. Cancer Res. 1989, 49, 2959-2964.
    • (1989) Cancer Res. , vol.49 , pp. 2959-2964
    • Bergeron, R.J.1    Hawthorne, T.R.2    Vinson, J.R.T.3    Beck, D.E.J.4    Ingeno, M.J.5
  • 6
    • 0023707798 scopus 로고
    • Control of ornithine decarboxylase activity in α-difluoromethylornithine-resistant L1210 cells by polyamines and synthetic analogues
    • Pegg, A. E.; Madhubala, R.; Kameji, T.; Bergeron, R. J. Control of Ornithine Decarboxylase Activity in α-Difluoromethylornithine-resistant L1210 Cells by Polyamines and Synthetic Analogues. J. Biol. Chem. 1988, 263, 11008-11014.
    • (1988) J. Biol. Chem. , vol.263 , pp. 11008-11014
    • Pegg, A.E.1    Madhubala, R.2    Kameji, T.3    Bergeron, R.J.4
  • 8
    • 0023223138 scopus 로고
    • Relative abilities of bis(ethyl) derivatives of putrescine, spermidine, and spermine to regulate polyamine biosynthesis and inhibit L1210 leukemia cell growth
    • Porter, C. W.; McManis, J.; Casero, R. A.; Bergeron, R. J. Relative Abilities of Bis(ethyl) Derivatives of Putrescine, Spermidine, and Spermine to Regulate Polyamine Biosynthesis and Inhibit L1210 Leukemia Cell Growth. Cancer Res. 1987, 47, 2821-2825.
    • (1987) Cancer Res. , vol.47 , pp. 2821-2825
    • Porter, C.W.1    McManis, J.2    Casero, R.A.3    Bergeron, R.J.4
  • 9
    • 0024474487 scopus 로고
    • 12-Bis(ethyl)spermine and related compounds on growth and polyamine acetylation, content, and excretion in human colon tumor cell
    • 12-Bis(ethyl)Spermine and Related Compounds on Growth and Polyamine Acetylation, Content, and Excretion in Human Colon Tumor Cell. J. Biol. Chem. 1989, 264, 11744-11749.
    • (1989) J. Biol. Chem. , vol.264 , pp. 11744-11749
    • Pegg, A.E.1    Wechter, R.2    Pakala, R.3    Bergeron, R.J.4
  • 10
    • 0024395636 scopus 로고
    • 1-Acetyltransferase activity by spermine analogues and their relationship to polyamine depletion and growth inhibition in L1210 cells
    • 1-Acetyltransferase Activity by Spermine Analogues and Their Relationship to Polyamine Depletion and Growth Inhibition in L1210 Cells. Cancer Res. 1989, 49, 6226-6231.
    • (1989) Cancer Res. , vol.49 , pp. 6226-6231
    • Libby, P.R.1    Henderson, M.2    Bergeron, R.J.3    Porter, C.W.4
  • 11
    • 0024588671 scopus 로고
    • Structure - Function correlations of polyamine analog-induced increases in Spermidine/Spermine acetyltransferase activity
    • Libby, P. R.; Bergeron, R. J.; Porter, C. W. Structure - Function Correlations of Polyamine Analog-Induced Increases in Spermidine/Spermine Acetyltransferase Activity. Biochem. Pharmacol. 1989, 38, 1435-1442.
    • (1989) Biochem. Pharmacol. , vol.38 , pp. 1435-1442
    • Libby, P.R.1    Bergeron, R.J.2    Porter, C.W.3
  • 13
    • 0025833516 scopus 로고
    • 1-Acetyltransferase activity, polyamine pool depletion, and growth inhibition in human melanoma cell lines
    • 1-Acetyltransferase Activity, Polyamine Pool Depletion, and Growth Inhibition in Human Melanoma Cell Lines. Cancer Res. 1991, 51, 3715-3720.
    • (1991) Cancer Res. , vol.51 , pp. 3715-3720
    • Porter, C.W.1    Ganis, B.2    Libby, P.R.3    Bergeron, R.J.4
  • 14
  • 16
    • 0027450179 scopus 로고
    • 1-Acetyltransferase by intracellular polyamine pools - Evidence for a functional role in polyamine homeostasis
    • 1-Acetyltransferase by Intracellular Polyamine Pools - Evidence for a Functional Role in Polyamine Homeostasis. FEBS Lett. 1993, 321, 179-183.
    • (1993) FEBS Lett. , vol.321 , pp. 179-183
    • Shappell, N.W.1    Fogel-Petrovic, M.F.2    Porter, C.W.3
  • 18
    • 0028875187 scopus 로고
    • The impact of polyamine analogues on the blood pressure of normotensive and hypertensive rats
    • Bergeron, R. J.; Wiegand, J.; Sninsky, C. A.; Katovich, M. J. The Impact of Polyamine Analogues on the Blood Pressure of Normotensive and Hypertensive Rats. Clin. Exp. Hypertension 1995, 17, 1197-1217.
    • (1995) Clin. Exp. Hypertension , vol.17 , pp. 1197-1217
    • Bergeron, R.J.1    Wiegand, J.2    Sninsky, C.A.3    Katovich, M.J.4
  • 21
    • 85004366699 scopus 로고
    • Syntheses of a series of linear polyamines with three and four methylene chain intervals
    • Niitsu, M.; Samejima, K. Syntheses of a Series of Linear Polyamines with Three and Four Methylene Chain Intervals. Chem. Pharm. Bull. 1986, 34, 1032-1038.
    • (1986) Chem. Pharm. Bull. , vol.34 , pp. 1032-1038
    • Niitsu, M.1    Samejima, K.2
  • 24
    • 0001019782 scopus 로고
    • Mitsunobu reactions of N-Alkyl and N-Acyl sulfonamides - An efficient route to protected amines
    • Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, G. D., Jr. Mitsunobu Reactions of N-Alkyl and N-Acyl Sulfonamides - An Efficient Route to Protected Amines. Tetrahedron Lett. 1989, 30, 5709-5712.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 5709-5712
    • Henry, J.R.1    Marcin, L.R.2    McIntosh, M.C.3    Scola, P.M.4    Harris G.D., Jr.5
  • 25
    • 0028298605 scopus 로고
    • Use of the mitsunobu reaction in the synthesis of polyamines
    • Edwards, M. L.; Stemerick, D. M.; McCarthy, J. R. Use of the Mitsunobu Reaction in the Synthesis of Polyamines. Tetrahedron 1994, 50, 5579-5590.
    • (1994) Tetrahedron , vol.50 , pp. 5579-5590
    • Edwards, M.L.1    Stemerick, D.M.2    McCarthy, J.R.3
  • 26
    • 0030221296 scopus 로고    scopus 로고
    • An efficient synthesis of (3R)-4-Amino-3-hydroxy butyric acid (GABOB) via cyclic sulfite methodology
    • Lohray, B. B.; Reddy, A. S.; Bhushan, V. An Efficient Synthesis of (3R)-4-Amino-3-hydroxy Butyric Acid (GABOB) via Cyclic Sulfite Methodology. Tetrahedron: Asymmetry 1996, 7, 2411-2416.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 2411-2416
    • Lohray, B.B.1    Reddy, A.S.2    Bhushan, V.3
  • 27
    • 0342302906 scopus 로고    scopus 로고
    • note
    • The less acidic ethyltosylamide 1 reacted with (R)-(-)-2,2-dimethyl-1,3-dioxolane-4-methanol in a less satisfactory yield of 43%.
  • 28
    • 0001953104 scopus 로고
    • Triflamides for protection and monoalkylation of amines and a new Gabriel synthesis
    • Hendrickson, J. B.; Bergeron, R. J. Triflamides for Protection and Monoalkylation of Amines and a New Gabriel Synthesis. Tetrahedron Lett. 1973, 39, 3839-3842.
    • (1973) Tetrahedron Lett. , vol.39 , pp. 3839-3842
    • Hendrickson, J.B.1    Bergeron, R.J.2
  • 29
    • 33947085552 scopus 로고
    • Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-Methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters
    • Dale, J. A.; Mosher, H. S. Nuclear Magnetic Resonance Enantiomer Reagents. Configurational Correlations via Nuclear Magnetic Resonance Chemical Shifts of Diastereomeric Mandelate, O-Methylmandelate, and α-Methoxy-α-trifluoromethylphenylacetate (MTPA) Esters. J. Am. Chem. Soc. 1973, 95, 512-519.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 512-519
    • Dale, J.A.1    Mosher, H.S.2
  • 30
    • 0343607959 scopus 로고    scopus 로고
    • note
    • 3OD, at 45 °C) of 18a.
  • 31
    • 0343607958 scopus 로고    scopus 로고
    • note
    • Partial racemization in the epoxide synthons (5, 13, or 23) or the alternate synthon (34) would lead to meso-tetraamines as the main contaminants. Since the stereocenters in the hydroxylated polyamines are far apart, the Mosher's esters of the respective CBZ-protected enantiomers were employed as model compounds.
  • 32
    • 0032563895 scopus 로고    scopus 로고
    • Synthesis of reagents for the construction of hypusine and deoxyhypusine peptides and their application as peptidic antigens
    • Bergeron, R. J.; Weimar, W. R.; Müller, R.; Zimmerman, C. O.; McCosar, B. H.; Yao, H.; Smith, R. E. Synthesis of Reagents for the Construction of Hypusine and Deoxyhypusine Peptides and their Application as Peptidic Antigens. J. Med. Chem. 1998, 41, 3888-3900.
    • (1998) J. Med. Chem. , vol.41 , pp. 3888-3900
    • Bergeron, R.J.1    Weimar, W.R.2    Müller, R.3    Zimmerman, C.O.4    McCosar, B.H.5    Yao, H.6    Smith, R.E.7
  • 33
    • 0029076657 scopus 로고
    • Efficient pathways to (R)- and (S)-5-Hydroxymethyl-2-oxazolidinone and some derivatives
    • Danielmeier, K.; Steckhan, E. Efficient Pathways to (R)- and (S)-5-Hydroxymethyl-2-oxazolidinone and Some Derivatives. Tetrahedron: Asymmetry 1995, 6, 1181-1190.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 1181-1190
    • Danielmeier, K.1    Steckhan, E.2
  • 34
    • 0027199501 scopus 로고
    • A novel synthesis of optically active 4-Benzyloxy- and 4-Alkyloxycarbonyl-2-Oxetanones
    • Cammas, S.; Renard, I.; Boutault, K.; Guérin, P. A Novel Synthesis of Optically Active 4-Benzyloxy- and 4-Alkyloxycarbonyl-2-Oxetanones. Tetrahedron: Asymmetry 1993, 4, 1925-1930.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1925-1930
    • Cammas, S.1    Renard, I.2    Boutault, K.3    Guérin, P.4
  • 35
    • 0001561441 scopus 로고
    • Enantioselective syntheses of 3-Substituted 4-(Alkoxycarbonyl)-2-azetidinones from malic acid
    • Miller, M. J.; Bajwa, J. S.; Mattingly, P.; Peterson, K. Enantioselective Syntheses of 3-Substituted 4-(Alkoxycarbonyl)-2-azetidinones from Malic Acid. J. Org. Chem. 1982, 47, 4928-4933.
    • (1982) J. Org. Chem. , vol.47 , pp. 4928-4933
    • Miller, M.J.1    Bajwa, J.S.2    Mattingly, P.3    Peterson, K.4
  • 36
    • 85082728756 scopus 로고
    • A convenient benzylation procedure for β-Hydroxy ethers
    • Widmer, U. A Convenient Benzylation Procedure for β-Hydroxy Ethers. Synthesis 1987, 568-570.
    • (1987) Synthesis , pp. 568-570
    • Widmer, U.1
  • 37
    • 0029012271 scopus 로고
    • Regioselective transformation of malic acid: A practical method for the construction of enantiomerically pure indolizidines
    • Gmeiner, P.; Junge, D. Regioselective Transformation of Malic Acid: A Practical Method for the Construction of Enantiomerically Pure Indolizidines. J. Org. Chem. 1995, 60, 3910-3915.
    • (1995) J. Org. Chem. , vol.60 , pp. 3910-3915
    • Gmeiner, P.1    Junge, D.2
  • 38
    • 0000496212 scopus 로고
    • Catalysis by metal complexes. XXXIX. Synthesis of some phosphines containing chiral substituents
    • Benes, J.; Hetflejs, J. Catalysis by Metal Complexes. XXXIX. Synthesis of Some Phosphines Containing Chiral Substituents. Collect. Czech. Chem. Commun. 1976, 41, 2256-2263.
    • (1976) Collect. Czech. Chem. Commun. , vol.41 , pp. 2256-2263
    • Benes, J.1    Hetflejs, J.2
  • 41
    • 0001021477 scopus 로고
    • Rapid removal of protecting groups from peptides by catalytic transfer hydrogenation with 1,4-Cyclohexadiene
    • Felix, A. M.; Heimer, E. P.; Lambros, T. J.; Tzougraki, C.; Meienhofer, J Rapid Removal of Protecting Groups from Peptides by Catalytic Transfer Hydrogenation with 1,4-Cyclohexadiene. J. Org. Chem. 1978, 43, 4194-4196.
    • (1978) J. Org. Chem. , vol.43 , pp. 4194-4196
    • Felix, A.M.1    Heimer, E.P.2    Lambros, T.J.3    Tzougraki, C.4    Meienhofer, J.5
  • 43
    • 0020643516 scopus 로고
    • Ornithine decarboxylase (Mouse Kidney)
    • Seely, J. E.; Pegg, A. E. Ornithine Decarboxylase (Mouse Kidney). Methods Enzymol. 1983, 94, 158-161.
    • (1983) Methods Enzymol. , vol.94 , pp. 158-161
    • Seely, J.E.1    Pegg, A.E.2
  • 44
    • 0020643519 scopus 로고
    • S-Adenosylmethionine decarboxylase (Rat Liver)
    • Pegg, A. E.; Pösö, H. S-Adenosylmethionine Decarboxylase (Rat Liver). Methods Enzymol. 1983, 94, 234-239.
    • (1983) Methods Enzymol. , vol.94 , pp. 234-239
    • Pegg, A.E.1    Pösö, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.