메뉴 건너뛰기




Volumn 35, Issue 12, 1992, Pages 2293-2306

Synthesis and Evaluation of Analogues of (Z)-1-(4-Methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene as Potential Cytotoxic and Antimitotic Agents

Author keywords

[No Author keywords available]

Indexed keywords

3,4,4',5 TETRAMETHOXYSTILBENE; ANTIMITOTIC AGENT; BENZOPHENONE DERIVATIVE; BENZYLISOQUINOLINE DERIVATIVE; CINNAMIC ACID DERIVATIVE; COLCHICINE; COMBRETASTATIN A4; CYTOTOXIC AGENT; DOXORUBICIN; PHENANTHRENE DERIVATIVE; PODOPHYLLOTOXIN; PROTOBERBERINE DERIVATIVE; STILBENE DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG;

EID: 0026734208     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00090a021     Document Type: Article
Times cited : (254)

References (42)
  • 1
    • 34547205120 scopus 로고
    • Tropolonic Colchicum Alkaloids
    • Brossi, A., Ed.; Academic Press: New York
    • Capraro, H. G.; Brossi, A. Tropolonic Colchicum Alkaloids. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1984; Vol. 23, pp 1-70
    • (1984) The Alkaloids , vol.23 , pp. 1-70
    • Capraro, H.G.1    Brossi, A.2
  • 2
    • 0022202415 scopus 로고
    • Synthesis and Biological Effects of Novel Thiocolchicines. 3. Evaluation of N-Acyldeacetylthiocolchicines, N-(Alkoxycarbonyl) deacetylthiocolchicines, and O-Ethyldemethylthiocolchicines. New Synthesis of Thiodemecoline and Antileukemic Effects of 2-Demethyl-and 3-Demethylthiocolchicine
    • Kerekes, P.; Sharma, P. N.; Brossi, A.; Chignell, C. F.; Quinn, F. R. Synthesis and Biological Effects of Novel Thiocolchicines. 3. Evaluation of N-Acyldeacetylthiocolchicines, N-(Alkoxycarbonyl) deacetylthiocolchicines, and O-Ethyldemethylthiocolchicines. New Synthesis of Thiodemecoline and Antileukemic Effects of 2-Demethyl-and 3-Demethylthiocolchicine. J. Med. Chem. 1985, 28, 1204-1208
    • (1985) J. Med. Chem. , vol.28 , pp. 1204-1208
    • Kerekes, P.1    Sharma, P.N.2    Brossi, A.3    Chignell, C.F.4    Quinn, F.R.5
  • 3
    • 0023220088 scopus 로고
    • A Novel Synthesis of Colchicide and Analogues from Thiocolchicine and Congeners: Reevaluation of Colchicide as a Potential Antitumor Agent
    • Dumont, R.; Brossi, A.; Chignell, C. F.; Quinn, F. R.; Suffness, M. A Novel Synthesis of Colchicide and Analogues from Thiocolchicine and Congeners: Reevaluation of Colchicide as a Potential Antitumor Agent. J. Med. Chem. 1987, 30, 732-735.
    • (1987) J. Med. Chem. , vol.30 , pp. 732-735
    • Dumont, R.1    Brossi, A.2    Chignell, C.F.3    Quinn, F.R.4    Suffness, M.5
  • 4
    • 0023893833 scopus 로고
    • Comigerine, a Potent Antimitotic Colchicum Alkaloid of Unusual Structure
    • Hamel, E.; Ho, H. H.; Kang, G.-J.; Lin, C. M. Comigerine, a Potent Antimitotic Colchicum Alkaloid of Unusual Structure. Biochem. Pharmacol. 1988, 37, 2445-2449
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 2445-2449
    • Hamel, E.1    Ho, H.H.2    Kang, G.-J.3    Lin, C.M.4
  • 5
    • 0025372840 scopus 로고
    • N-Acetylcolchinol-Methyl Ether and Thiocolchicine, Potent Analogs of Colchicine Modified in the C Ring
    • Kang, G.-J.; Getahun, Z.; Muzaffar, A.; Brossi, A.; Hamel, E. N-Acetylcolchinol-Methyl Ether and Thiocolchicine, Potent Analogs of Colchicine Modified in the C Ring. J. Biol. Chem. 1990, 265, 10255-10259
    • (1990) J. Biol. Chem. , vol.265 , pp. 10255-10259
    • Kang, G.-J.1    Getahun, Z.2    Muzaffar, A.3    Brossi, A.4    Hamel, E.5
  • 6
    • 0025099365 scopus 로고
    • Antitubulin Effects of Derivatives of 3-Demethylthiooolchicine, Methylthio Ethers of Natural Colchicinoids, and Thioketones Derived from Thiocolchicine. Comparison with Colchicinoids
    • Muzaffar, A.; Brossi, A.; Lin, C. M.; Hamel, E. Antitubulin Effects of Derivatives of 3-Demethylthiooolchicine, Methylthio Ethers of Natural Colchicinoids, and Thioketones Derived from Thiocolchicine. Comparison with Colchicinoids. J. Med. Chem. 1990, 33, 567-571
    • (1990) J. Med. Chem. , vol.33 , pp. 567-571
    • Muzaffar, A.1    Brossi, A.2    Lin, C.M.3    Hamel, E.4
  • 7
    • 0001308948 scopus 로고
    • Podophyllotoxins
    • Cassady, J. M., Douros, J., Eds.; Academic Press: New York
    • Jardine, I. Podophyllotoxins. In Anticancer Agents Based on Natural Product Models; Cassady, J. M., Douros, J., Eds.; Academic Press: New York, 1980; pp 319-351
    • (1980) Anticancer Agents Based on Natural Product Models , pp. 319-351
    • Jardine, I.1
  • 8
    • 0018841140 scopus 로고
    • Structure-Antitubulin Activity Relationships of Steganacin and Analogues. Inhibition of Tubulin Polymerization in Vitro by (±)-Isodeoxypodophyllotoxin
    • Zavala, F.; Guenard, D.; Robin, J.-P.; Brown, E. Structure-Antitubulin Activity Relationships of Steganacin and Analogues. Inhibition of Tubulin Polymerization in Vitro by (±)-Isodeoxypodophyllotoxin. J. Med. Chem. 1980, 23, 546-549
    • (1980) J. Med. Chem. , vol.23 , pp. 546-549
    • Zavala, F.1    Guenard, D.2    Robin, J.-P.3    Brown, E.4
  • 11
    • 0017654856 scopus 로고
    • Antimitotic and Antitubulin Activity of the Tumor Inhibitor Steganacin
    • Wang, R. W.-J.; Rebhun, L. I.; Kupchan, S. M. Antimitotic and Antitubulin Activity of the Tumor Inhibitor Steganacin. Cancer Res. 1977, 37, 3071-3079
    • (1977) Cancer Res. , vol.37 , pp. 3071-3079
    • Wang, R.W.-J.1    Rebhun, L.I.2    Kupchan, S.M.3
  • 13
    • 0023718571 scopus 로고
    • Colchicine Models: Synthesis and Binding to Tubulin of Tetramethoxybiphenyls
    • Itoh, Y.; Brossi, A.; Hamel, E.; Lin, C. M. Colchicine Models: Synthesis and Binding to Tubulin of Tetramethoxybiphenyls. Helo. Chim. Acta 1988, 71, 1199-1209
    • (1988) Helo. Chim. Acta , vol.71 , pp. 1199-1209
    • Itoh, Y.1    Brossi, A.2    Hamel, E.3    Lin, C.M.4
  • 14
    • 0021912989 scopus 로고
    • Structure-Function Studies with Derivatives of 6-Benzyl-1,3-benzodioxole, a New Class of Synthetic Compounds Which Inhibit Tubulin Polymerization
    • Batra, J. K.; Jurd, L.; Hamel, E. Structure-Function Studies with Derivatives of 6-Benzyl-1,3-benzodioxole, a New Class of Synthetic Compounds Which Inhibit Tubulin Polymerization. Mol. Pharmacol. 1985, 27, 94-102
    • (1985) Mol. Pharmacol. , vol.27 , pp. 94-102
    • Batra, J.K.1    Jurd, L.2    Hamel, E.3
  • 15
    • 0023918975 scopus 로고
    • Methylenedioxy-Benzopyran Analogs of Podophyllotoxin, a New Synthetic Class of Antimitotic Agents that Inhibit Tubulin Polymerization
    • Batra, J. K.; Kang, G. J.; Jurd, L.; Hamel, E. Methylenedioxy-Benzopyran Analogs of Podophyllotoxin, a New Synthetic Class of Antimitotic Agents that Inhibit Tubulin Polymerization. Biochem. Pharmacol. 1988, 37, 2595-2602
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 2595-2602
    • Batra, J.K.1    Kang, G.J.2    Jurd, L.3    Hamel, E.4
  • 16
  • 17
    • 0023801309 scopus 로고
    • Interactions of Tubulin with Potent Natural and Synthetic Analogs of the Antimitotic Agent Combretastatin: a Structure-Activity Study
    • Lin, C. M.; Singh, S. B.; Chu, P. S.; Dempcy, R. O.; Schmidt, J. M.; Pettit, G. R.; Hamel, E. Interactions of Tubulin with Potent Natural and Synthetic Analogs of the Antimitotic Agent Combretastatin: a Structure-Activity Study. Mol. Pharmacol. 1988, 34, 200-208
    • (1988) Mol. Pharmacol. , vol.34 , pp. 200-208
    • Lin, C.M.1    Singh, S.B.2    Chu, P.S.3    Dempcy, R.O.4    Schmidt, J.M.5    Pettit, G.R.6    Hamel, E.7
  • 18
    • 0025326011 scopus 로고
    • Differential Cytotoxicity of Combretastatins Al and A4 in Two Daunorubicin-Resistant P388 Cell Lines
    • McGown, A. T.; Fox, B. W. Differential Cytotoxicity of Combretastatins Al and A4 in Two Daunorubicin-Resistant P388 Cell Lines. Cancer Chemother. Pharmacol. 1990, 26, 79-81
    • (1990) Cancer Chemother. Pharmacol. , vol.26 , pp. 79-81
    • McGown, A.T.1    Fox, B.W.2
  • 19
    • 0026047751 scopus 로고
    • Synthesis and Evaluation of Stilbene and Dihydrostilbene Derivatives as Potential Anticancer Agents That Inhibit Tubulin Polymerization
    • Cushman, M.; Nagarathnam, D.; Gopal, D.; Chakraborti, A. K.; Lin, C. M.; Hamel, E. Synthesis and Evaluation of Stilbene and Dihydrostilbene Derivatives as Potential Anticancer Agents That Inhibit Tubulin Polymerization. J. Med. Chem. 1991, 34, 2579-2588
    • (1991) J. Med. Chem. , vol.34 , pp. 2579-2588
    • Cushman, M.1    Nagarathnam, D.2    Gopal, D.3    Chakraborti, A.K.4    Lin, C.M.5    Hamel, E.6
  • 20
    • 0013906737 scopus 로고
    • Corpaverine and Related Compounds. II. Synthesis of l-(p-Methoxybenzyl)-2-methyl-6,8-dimethoxy-X,2,3,4-tetrahydroisoquinoline-7-ol. (Studies on the Synthesis of Heterocyclic Compounds. CXL
    • Kametani, T.; Kano, S.; Kikuchi, T. Corpaverine and Related Compounds. II. Synthesis of l-(p-Methoxybenzyl)-2-methyl-6,8-dimethoxy-X,2,3,4-tetrahydroisoquinoline-7-ol. (Studies on the Synthesis of Heterocyclic Compounds. CXL). Yakugaka Zasshi 1966, 86, 423-426
    • (1966) Yakugaka Zasshi , vol.86 , pp. 423-426
    • Kametani, T.1    Kano, S.2    Kikuchi, T.3
  • 21
    • 20444416136 scopus 로고
    • New Substituted Bibenzyls of Frullania brittoniae subsp. truncatifolia
    • Asakawa, Y.; Tanikawa, K.; Aratani, T. New Substituted Bibenzyls of Frullania brittoniae subsp. truncatifolia. Phytochemistry 1976, 15, 1057-1059
    • (1976) Phytochemistry , vol.15 , pp. 1057-1059
    • Asakawa, Y.1    Tanikawa, K.2    Aratani, T.3
  • 22
    • 34249317815 scopus 로고
    • Colchicine and Related Compounds
    • Synthesis of a Simple Analogue of JV-Acetylcolchinol Methyl Ether
    • Cook, J. W.; Engel, L. L. Colchicine and Related Compounds. Part II. Synthesis of a Simple Analogue of JV-Acetylcolchinol Methyl Ether. J. Chem. Soc. 1940, 198-200
    • (1940) J. Chem. Soc. , pp. 198-200
    • Cook, J.W.1    Engel, L.L.2
  • 23
    • 12244276212 scopus 로고
    • Colchicine and Related Compounds
    • Some Observations on the Structure of Colchicine
    • Cohen, A.; Cook, J. W.; Roe, E. M. F. Colchicine and Related Compounds. Part I. Some Observations on the Structure of Colchicine. J. Chem. Soc. 1940,194-197
    • (1940) J. Chem. Soc. , pp. 194-197
    • Cohen, A.1    Cook, J.W.2    Roe, E.M.F.3
  • 24
    • 37049096132 scopus 로고
    • Reactions of Lithium Aluminum Hydride in Hydrocarbon Solvents. Selective Demethylation of Some Substituted Methyl Phenyl Ethers
    • Carroll, J. F.; Kulkowit, S.; McKervy, M. A. Reactions of Lithium Aluminum Hydride in Hydrocarbon Solvents. Selective Demethylation of Some Substituted Methyl Phenyl Ethers. J. Chem. Soc., Chem. Commun. 1980, 507-508
    • (1980) J. Chem. Soc., Chem. Commun , pp. 507-508
    • Carroll, J.F.1    Kulkowit, S.2    McKervy, M.A.3
  • 25
    • 0000748521 scopus 로고
    • The Structure and Total Synthesis of Takatonine
    • Kubota, S.; Masui, T.; Fujita, E.; Kupchan, S. M. The Structure and Total Synthesis of Takatonine. J. Org. Chem. 1966, 31, 516-520
    • (1966) J. Org. Chem. , vol.31 , pp. 516-520
    • Kubota, S.1    Masui, T.2    Fujita, E.3    Kupchan, S.M.4
  • 26
    • 0017354875 scopus 로고
    • Studies on the Synthesis of Heterocyclic Compounds. Part 698. An Alternative Protoberberine Synthesis; Total Synthesis of (±)-Xylopinine, (±)-Schefferine, (±)-Nandanine, (±)-Corydaline, and (±)-Thalictricavine
    • Ninomiya, I.; Naito, T.; Takasugi, H. Studies on the Synthesis of Heterocyclic Compounds. Part 698. An Alternative Protoberberine Synthesis; Total Synthesis of (±)-Xylopinine, (±)-Schefferine, (±)-Nandanine, (±)-Corydaline, and (±)-Thalictricavine. J. Chem. Soc., Perkin Trans. 1 1977, 1151-1155
    • (1977) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1151-1155
    • Ninomiya, I.1    Naito, T.2    Takasugi, H.3
  • 27
    • 0025804962 scopus 로고
    • Quantitative Structure-Activity Relationship Analysis of Combretastatins: A Class of Novel Antimitotic Agents
    • Nandy, P.; Banerjee, S.; Gao, H.; Hui, M. B. V.; Lien, E. J. Quantitative Structure-Activity Relationship Analysis of Combretastatins: A Class of Novel Antimitotic Agents. Pharm. Res. 1991, 8, 776-781
    • (1991) Pharm. Res. , vol.8 , pp. 776-781
    • Nandy, P.1    Banerjee, S.2    Gao, H.3    Hui, M.B.V.4    Lien, E.J.5
  • 28
    • 85022556705 scopus 로고
    • Molecular Structure, Properties and States of Matter
    • 18th ed.; Mack: Easton, PA
    • Lien, E. J. Molecular Structure, Properties and States of Matter. In Remington's Pharmaceutical Sciences, 18th ed.; Mack: Easton, PA, 1990; pp 158-181
    • (1990) Remington's Pharmaceutical Sciences , pp. 158-181
    • Lien, E.J.1
  • 29
    • 0023065565 scopus 로고
    • Isolation, Structure, and Synthesis of Combretastatins A-l and B-l, Potent New Inhibitors of Microtubule Assembly, Derived from Combretum caffrum
    • Pettit, G. R.; Singh, S. B.; Niven, M. L.; Hamel, E.; Schmidt, J. M. Isolation, Structure, and Synthesis of Combretastatins A-l and B-l, Potent New Inhibitors of Microtubule Assembly, Derived from Combretum caffrum. J. Nat. Prod. 1987, 50, 119-131
    • (1987) J. Nat. Prod. , vol.50 , pp. 119-131
    • Pettit, G.R.1    Singh, S.B.2    Niven, M.L.3    Hamel, E.4    Schmidt, J.M.5
  • 30
    • 0003502896 scopus 로고
    • The Crystal and Molecular Structure of 5′-Demethoxy-d-peltatin A Methyl Ether
    • Bates, R. B.; Wood, J. B., III. The Crystal and Molecular Structure of 5′-Demethoxy-d-peltatin A Methyl Ether. J. Org. Chem. 1972, 37, 562-565
    • (1972) J. Org. Chem. , vol.37 , pp. 562-565
    • Bates, R.B.1    Wood, J.B.2
  • 31
    • 0018742295 scopus 로고
    • Conformational Analysis of Podophyllotoxin and Its Congeners. Structure-Activity Relationship in Microtubule Assembly
    • Brewer, C. F.; Loike, J. D.; Horwitz, S. B.; Stemlicht, H.; Gensler, W. J. Conformational Analysis of Podophyllotoxin and Its Congeners. Structure-Activity Relationship in Microtubule Assembly. J. Med. Chem. 1979, 22, 215-221
    • (1979) J. Med. Chem. , vol.22 , pp. 215-221
    • Brewer, C.F.1    Loike, J.D.2    Horwitz, S.B.3    Stemlicht, H.4    Gensler, W.J.5
  • 32
    • 0020602597 scopus 로고
    • Dynamic Nuclear Magnetic Resonance and Empirical Force Field Studies of Podophyllotoxin
    • Rithner, C. D.; Bushweller, C. H.; Gensler, W. J.; Hoogasian, S. Dynamic Nuclear Magnetic Resonance and Empirical Force Field Studies of Podophyllotoxin. J. Org. Chem. 1983, 48, 1491-1495
    • (1983) J. Org. Chem. , vol.48 , pp. 1491-1495
    • Rithner, C.D.1    Bushweller, C.H.2    Gensler, W.J.3    Hoogasian, S.4
  • 33
    • 0016385590 scopus 로고
    • Structure of the Mitotic Spindle Inhibitor Colcemid. JV-Desacetyl-JV-methylcolchicine
    • Margulis, T. N. Structure of the Mitotic Spindle Inhibitor Colcemid. JV-Desacetyl-JV-methylcolchicine. J. Am. Chem. Soc. 1974, 96, 899-902
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 899-902
    • Margulis, T.N.1
  • 34
    • 0004014970 scopus 로고
    • X-ray Analysis of Microtubule Inhibitors
    • Borgers, M., de Brabander, M
    • Margulis, T. N. X-ray Analysis of Microtubule Inhibitors. In Microtubules and Microtubule Inhibitors; Borgers, M., de Brabander, M., Eds.; North-Holland Publishing Co.: Amsterdam, 1975; pp 67-78
    • (1975) Microtubules and Microtubule Inhibitors , pp. 67-78
    • Margulis, T.N.1
  • 35
    • 0017406060 scopus 로고
    • Structure of the Iso Form of Colchicine. Demethylisothiocolchicine
    • Margulis, T. N. Structure of the Iso Form of Colchicine. Demethylisothiocolchicine. Biochem. Biophys. Res. Commun. 1977, 76, 1293-1299
    • (1977) Biochem. Biophys. Res. Commun. , vol.76 , pp. 1293-1299
    • Margulis, T.N.1
  • 36
    • 0024510343 scopus 로고
    • Structural and biochemical comparison of the anti-mitotic agents colchicine, combretastatin A4 and amphethinile
    • McGown, A. T.; Fox, B. W. Structural and biochemical comparison of the anti-mitotic agents colchicine, combretastatin A4 and amphethinile. Anti-Cancer Drug Des. 1989, 3, 249-254
    • (1989) Anti-Cancer Drug Des. , vol.3 , pp. 249-254
    • McGown, A.T.1    Fox, B.W.2
  • 37
    • 33947089482 scopus 로고
    • Formylation of Aromatic Compounds with Hexamethylene Tetramine and Trifluoroacetic Acid
    • Smith, W. E. Formylation of Aromatic Compounds with Hexamethylene Tetramine and Trifluoroacetic Acid. J. Org. Chem. 1972, 37, 3972-3973
    • (1972) J. Org. Chem. , vol.37 , pp. 3972-3973
    • Smith, W.E.1
  • 39
    • 78651141309 scopus 로고
    • Chemical Constituents of Polygonaceous Plants. I. Studies on the Components of Ko-gó-kon. (Polygonum cuspidatum. Sieb et Zucc.)
    • Nonomura, S.; Kanagawa, H.; Makimoto, A. Chemical Constituents of Polygonaceous Plants. I. Studies on the Components of Ko-gó-kon. (Polygonum cuspidatum. Sieb et Zucc.) Yakugaka Zasshi 1963, 83, 988-990
    • (1963) Yakugaka Zasshi , vol.83 , pp. 988-990
    • Nonomura, S.1    Kanagawa, H.2    Makimoto, A.3
  • 41
    • 0021061819 scopus 로고
    • Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays
    • Mossman, T. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays. J. Immunol. Meth. 1983, 65, 55-63
    • (1983) J. Immunol. Meth. , vol.65 , pp. 55-63
    • Mossman, T.1
  • 42
    • 0021163546 scopus 로고
    • Separation of Active Tubulin and Microtubule-Associated Proteins by Ultracentrifugation and Isolation of a Component Causing the Formation of Microtubule Bundles
    • Hamel, E.; Lin, C. M. Separation of Active Tubulin and Microtubule-Associated Proteins by Ultracentrifugation and Isolation of a Component Causing the Formation of Microtubule Bundles. Biochemistry 1984, 23, 4173-4184
    • (1984) Biochemistry , vol.23 , pp. 4173-4184
    • Hamel, E.1    Lin, C.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.