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Volumn 12, Issue 7, 1997, Pages 555-576

Synthesis, cytotoxicity, antitumor activity and sequence selective binding of two pyrazole analogs structurally related to the antitumor agents U-71, 184 and adozelesin

Author keywords

Adozelesin; Antitumor agents; CC 1065; Cytotoxicity; Polymerase chain reaction; Synthesis

Indexed keywords

ADOZELESIN; ANTINEOPLASTIC AGENT; ANTINEOPLASTIC ANTIBIOTIC; DNA; PYRAZOLE DERIVATIVE; RACHELMYCIN; U 71184;

EID: 9844257035     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (25)

References (55)
  • 1
    • 0002223415 scopus 로고
    • CC-1065 analogs: Sequence specific DNA-alkylating antitumor agents
    • ARISTOFF, P.A. (1993). CC-1065 analogs: sequence specific DNA-alkylating antitumor agents. Advances in Medicinal Chemistry, 2, 67.
    • (1993) Advances in Medicinal Chemistry , vol.2 , pp. 67
    • Aristoff, P.A.1
  • 2
    • 0026677093 scopus 로고
    • Synthesis of CBI-PDE-I-dimer, the benzannelated analogue of CC-1065
    • ARISTOFF, P.A. & JOHNSON, P.D. (1992). Synthesis of CBI-PDE-I-dimer, the benzannelated analogue of CC-1065. Journal of Organic Chemistry, 57, 6234.
    • (1992) Journal of Organic Chemistry , vol.57 , pp. 6234
    • Aristoff, P.A.1    Johnson, P.D.2
  • 3
    • 0027237623 scopus 로고
    • Synthesis and biochemical evaluation of the CBI-PDE-I-dimer, a benzannelated analog of (+)-CC-1065 that also produces delayed toxicity in mice
    • ARISTOFE, P.A., JOHNSON, P.D., SUN, D & HURLEY, L.H. (1993). Synthesis and biochemical evaluation of the CBI-PDE-I-dimer, a benzannelated analog of (+)-CC-1065 that also produces delayed toxicity in mice. Journal of Medicinal Chemistry, 36, 1956.
    • (1993) Journal of Medicinal Chemistry , vol.36 , pp. 1956
    • Aristofe, P.A.1    Johnson, P.D.2    Sun, D.3    Hurley, L.H.4
  • 4
    • 0031028037 scopus 로고    scopus 로고
    • Synthesis, chemical solvolytic stability and preliminary biological evaluation of (±)-N-Boc-CPzI: A pyrazole analog of the left-hand segment of the antitumor agent CC-1065
    • BARALDI, P.G., CACCIARI, B , PINEDA DE LAS INFANTAS, M.J., ROMAGNOLI, R., SPALLUTO, G , COZZI, P. & MONGELLI, N (1997a). Synthesis, chemical solvolytic stability and preliminary biological evaluation of (±)-N-Boc-CPzI: a pyrazole analog of the left-hand segment of the antitumor agent CC-1065. Anti-Cancer Drug Design, 12, 67.
    • (1997) Anti-Cancer Drug Design , vol.12 , pp. 67
    • Baraldi, P.G.1    Cacciari, B.2    Pineda De Las Infantas, M.J.3    Romagnoli, R.4    Spalluto, G.5    Cozzi, P.6    Mongelli, N.7
  • 6
    • 0002145941 scopus 로고
    • Removal of O-benzyl protective groups by catalytic transfer hydrogenation
    • BEIG, T. & SZEJA, W. (1985). Removal of O-benzyl protective groups by catalytic transfer hydrogenation. Synthesis, 76.
    • (1985) Synthesis , vol.76
    • Beig, T.1    Szeja, W.2
  • 7
    • 0019966533 scopus 로고
    • CC-1065 (NCS-298223), a most potent antitumor agent: Kinetics of inhibition of growth, DNA synthesis and cell survival
    • BHUYAN, B.K , NEWELL, K.A., CRAMPTON, S.L. & VON HOFF, D.D (1982). CC-1065 (NCS-298223), a most potent antitumor agent: kinetics of inhibition of growth, DNA synthesis and cell survival. Cancer Research, 42, 3532.
    • (1982) Cancer Research , vol.42 , pp. 3532
    • Bhuyan, B.K.1    Newell, K.A.2    Crampton, S.L.3    Von Hoff, D.D.4
  • 8
    • 0030598375 scopus 로고    scopus 로고
    • Targeting of Sp1 binding sites of HIV-1 long terminal repeat with Chromomycin. Disruption of nuclear factor-DNA complexes and inhibition of in vivo transcription. Biochemical
    • BIANCHI, N., PASSADORE, M., RUTIGLIANO, C., FERIOTTO, G., MISCHIATI, C. & GAMBARI, R (1996). Targeting of Sp1 binding sites of HIV-1 long terminal repeat with Chromomycin. Disruption of nuclear factor-DNA complexes and inhibition of in vivo transcription. Biochemical Pharmacology, 52, 1489.
    • (1996) Pharmacology , vol.52 , pp. 1489
    • Bianchi, N.1    Passadore, M.2    Rutigliano, C.3    Feriotto, G.4    Mischiati, C.5    Gambari, R.6
  • 9
    • 0029782488 scopus 로고    scopus 로고
    • CC-1065 and the duocarmycins: Understanding their biological function through mechanistic studies
    • BOGER, D.L. & JOHNSON, D.S. (1996). CC-1065 and the duocarmycins: understanding their biological function through mechanistic studies. Angewante Chemie International Edition English, 35, 1438.
    • (1996) Angewante Chemie International Edition English , vol.35 , pp. 1438
    • Boger, D.L.1    Johnson, D.S.2
  • 10
    • 0028920020 scopus 로고
    • An efficient synthesis of 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]-indol-4-one (CBI): An enhanced and simplified analog of the CC-1065 and duocarmycin alkylation subunit
    • BOGER, D L & MCKIE, J (1995). An efficient synthesis of 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]-indol-4-one (CBI): an enhanced and simplified analog of the CC-1065 and duocarmycin alkylation subunit. Journal of Organic Chemistry, 60, 1271.
    • (1995) Journal of Organic Chemistry , vol.60 , pp. 1271
    • Boger, D.L.1    McKie, J.2
  • 13
    • 0025119357 scopus 로고
    • 2: Enhanced functional analogues of CC-1065 incorporating the 1,2,9,9a-tetrahydrocyclopropa [c]benz[e]indol-4-one (CBI) left hand subunit
    • 2: enhanced functional analogues of CC-1065 incorporating the 1,2,9,9a-tetrahydrocyclopropa [c]benz[e]indol-4-one (CBI) left hand subunit. Journal of Organic Chemistry, 55, 5823.
    • (1990) Journal of Organic Chemistry , vol.55 , pp. 5823
    • Boger, D.L.1    Ishizaki, T.2    Kitos, P.A.3    Suntornwat, O.4
  • 14
    • 0025143478 scopus 로고
    • Synthesis and preliminary evaluation of agents incorporating the pharmacophore of the duocarmycin/pyrindamycin alkylation subunit: Identification of the CC-1065/duocarmycin common pharmacophore
    • BOGER, D.L., ISHIZAKI, T., ZARRINMAYEH, H., KITOS, P.A & SUNTORWAT, O (1990c). Synthesis and preliminary evaluation of agents incorporating the pharmacophore of the duocarmycin/pyrindamycin alkylation subunit: identification of the CC-1065/duocarmycin common pharmacophore. Journal of Organic Chemistry, 55, 4499.
    • (1990) Journal of Organic Chemistry , vol.55 , pp. 4499
    • Boger, D.L.1    Ishizaki, T.2    Zarrinmayeh, H.3    Kitos, P.A.4    Suntorwat, O.5
  • 15
    • 0025900895 scopus 로고
    • (+)-CC-1065 DNA Alkylation: Key studies demonstrating a non-covalent binding selectivity contribution to the alkylation selectivity
    • BOGER, D.L , MUNK, S.A & ZARRINMAYEH, H.J. (1991a). (+)-CC-1065 DNA Alkylation: key studies demonstrating a non-covalent binding selectivity contribution to the alkylation selectivity. Journal of American Chemical Society, 113, 3980.
    • (1991) Journal of American Chemical Society , vol.113 , pp. 3980
    • Boger, D.L.1    Munk, S.A.2    Zarrinmayeh, H.J.3
  • 16
    • 0026092765 scopus 로고
    • Demonstration of a pronounced effect of non-covalent binding selectivity on the (+)-CC-1065 DNA alkylation and identification of the pharmacophore of the alkylation subunit
    • BOGER, D.L., ZARRINMAYEH, H., MUNK, S.A , KITOS, P.A. & SUNTORNWAT, O. (1991b). Demonstration of a pronounced effect of non-covalent binding selectivity on the (+)-CC-1065 DNA alkylation and identification of the pharmacophore of the alkylation subunit. Proceedings of the National Academy of Sciences, USA, 88, 1431.
    • (1991) Proceedings of the National Academy of Sciences, USA , vol.88 , pp. 1431
    • Boger, D.L.1    Zarrinmayeh, H.2    Munk, S.A.3    Kitos, P.A.4    Suntornwat, O.5
  • 17
    • 0026638104 scopus 로고
    • An improved synthesis of 1,2,9,9a-[c]benz[e]indol-4-one (CBI): A simplified analogue of the CC-1065 alkylation subunit
    • BOGER, D.L., YUN, W. & TEEGARDEN, B R. (1992). An improved synthesis of 1,2,9,9a-[c]benz[e]indol-4-one (CBI): a simplified analogue of the CC-1065 alkylation subunit. Journal of Organic Chemistry, 57, 2873.
    • (1992) Journal of Organic Chemistry , vol.57 , pp. 2873
    • Boger, D.L.1    Yun, W.2    Teegarden, B.R.3
  • 18
    • 0029980340 scopus 로고    scopus 로고
    • Synthesis and properties of substituted CBI analogs of CC-1065 and the duocarmycins incorporating the 7-methoxy-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (MCBI) alkylation subunit: Magnitude of electronic effects on the functional reactivity
    • BOGER, D.L., MCKIE, J.A, CAI, H., CACCIARI, B., BARALDI, P G (1996). Synthesis and properties of substituted CBI analogs of CC-1065 and the duocarmycins incorporating the 7-methoxy-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (MCBI) alkylation subunit: magnitude of electronic effects on the functional reactivity. Journal of Organic Chemistry, 61, 1710.
    • (1996) Journal of Organic Chemistry , vol.61 , pp. 1710
    • Boger, D.L.1    Mckie, J.A.2    Cai, H.3    Cacciari, B.4    Baraldi, P.G.5
  • 19
    • 3743064992 scopus 로고
    • γ, γ-Disubstituted itaconic acids. Part 1. the Stobbe condensation of 1-arylnaphthyl ketones with diethyl succinate
    • BOGHOS, V.B., NARS, F.H & GINDY, M. (1979). γ, γ-Disubstituted itaconic acids. Part 1. The Stobbe condensation of 1-arylnaphthyl ketones with diethyl succinate. Helvetica Chimica Acta, 62, 90.
    • (1979) Helvetica Chimica Acta , vol.62 , pp. 90
    • Boghos, V.B.1    Nars, F.H.2    Gindy, M.3
  • 21
    • 0000829322 scopus 로고
    • Organosilanes as radical-based reducing agents in synthesis
    • CHATGILIALOGLU, C (1992). Organosilanes as radical-based reducing agents in synthesis. Account of Chemical Research, 25, 188.
    • (1992) Account of Chemical Research , vol.25 , pp. 188
    • Chatgilialoglu, C.1
  • 22
    • 0018570084 scopus 로고
    • Total synthesis of (±)-5,6-oxido-7,9-trans 11,14-ciseicosapentaenoic acid, a possible precursor of SRSA
    • COREY, E.J , ARAI, Y. & MIOSKOWSKI, C (1979). Total synthesis of (±)-5,6-oxido-7,9-trans 11,14-ciseicosapentaenoic acid, a possible precursor of SRSA. Journal of American Chemical Society, 101, 6748.
    • (1979) Journal of American Chemical Society , vol.101 , pp. 6748
    • Corey, E.J.1    Arai, Y.2    Mioskowski, C.3
  • 23
    • 9844232236 scopus 로고    scopus 로고
    • Indazole [3,2-e]-pyrrole and 1,2,3-benzotriazole [3,2-e]-pyrrole derivatives. UK Patent, Appl. GB 2300857 A
    • COZZI, P., BERIA, I , CAPOLONGO, L., BARALDI, P.G. & SPALLUTO, G. (1996). Indazole [3,2-e]-pyrrole and 1,2,3-benzotriazole [3,2-e]-pyrrole derivatives. UK Patent, Appl. GB 2300857 A.
    • (1996)
    • Cozzi, P.1    Beria, I.2    Capolongo, L.3    Baraldi, P.G.4    Spalluto, G.5
  • 24
    • 0001773083 scopus 로고
    • The Stobbe condensation
    • DAUB, G H. (1951). The Stobbe condensation. Organic Reaction, 6, 1.
    • (1951) Organic Reaction , vol.6 , pp. 1
    • Daub, G.H.1
  • 25
    • 0026906898 scopus 로고
    • Dinucleotide repeat polymorphism in the human estrogen receptor (ER) gene
    • DEL SENNO, L., AGUIARI, G.L. & PIVA, R. (1992). Dinucleotide repeat polymorphism in the human estrogen receptor (ER) gene. Human Molecular Genetics, 1, 354.
    • (1992) Human Molecular Genetics , vol.1 , pp. 354
    • Del Senno, L.1    Aguiari, G.L.2    Piva, R.3
  • 27
    • 0022653964 scopus 로고
    • Human estrogen receptor cDNA: Sequence, expression and homology to v-erb-A
    • GREEN, S., WALTER, P., KUMAR, V , KRUST, A , BORNERT, J.M , ARGOS P. & CHAMBON, P. (1986). Human estrogen receptor cDNA: sequence, expression and homology to v-erb-A. Nature, 320, 134.
    • (1986) Nature , vol.320 , pp. 134
    • Green, S.1    Walter, P.2    Kumar, V.3    Krust, A.4    Bornert, J.M.5    Argos, P.6    Chambon, P.7
  • 28
    • 0018239716 scopus 로고
    • CC-1065 (NSC-298223) a new antitumor antibiotic. Production, in vitro biological activity, microbiological assays and taxonomy of the producing microorganism
    • HANKA, L.J , DIETZ, A., GERPHEIDE, S A , KUENTZEL, S L , & MARTIN, D.G. (1978). CC-1065 (NSC-298223) a new antitumor antibiotic. Production, in vitro biological activity, microbiological assays and taxonomy of the producing microorganism. Journal of Antibiotics, 31, 1211.
    • (1978) Journal of Antibiotics , vol.31 , pp. 1211
    • Hanka, L.J.1    Dietz, A.2    Gerpheide, S.A.3    Kuentzel, S.L.4    Martin, D.G.5
  • 29
    • 0003054921 scopus 로고
    • A rapid mild procedure for the preparation of alkyl chlorides and bromides
    • HOOZ, J. & GILAN, S.S.H. (1968). A rapid mild procedure for the preparation of alkyl chlorides and bromides. Canadian Journal Chemistry, 46, 86.
    • (1968) Canadian Journal Chemistry , vol.46 , pp. 86
    • Hooz, J.1    Gilan, S.S.H.2
  • 30
    • 0021715394 scopus 로고
    • Reaction of the antitumor antibiotic CC-1065 with DNA: Structure of a DNA adduct with DNA sequence specificity
    • HURLEY, L.H., REYNOLDS, V L., SWENSON, D.H., PETZOLD, G.L & SCAHILL, T.A. (1984). Reaction of the antitumor antibiotic CC-1065 with DNA: structure of a DNA adduct with DNA sequence specificity. Science, 226, 843.
    • (1984) Science , vol.226 , pp. 843
    • Hurley, L.H.1    Reynolds, V.L.2    Swenson, D.H.3    Petzold, G.L.4    Scahill, T.A.5
  • 33
    • 84987311765 scopus 로고
    • The Vilsmeier-Haack reaction. IV. Reaction of phosphorus oxychloride-dimethylformamide with semicarbazones
    • KIRA, M.A., ABOUL-ENEIN, N. & KARKOR, M.I. (1970). The Vilsmeier-Haack reaction. IV. Reaction of phosphorus oxychloride-dimethylformamide with semicarbazones. Journal of Heterocyclic Chemistry, 7, 25.
    • (1970) Journal of Heterocyclic Chemistry , vol.7 , pp. 25
    • Kira, M.A.1    Aboul-Enein, N.2    Karkor, M.I.3
  • 35
    • 0026069617 scopus 로고
    • (+)-CC-1065 produces bending of DNA that appears to resemble adenine/thymine tracts
    • LIN, C.H., SUN, D. & HURLEY, L.H. (1991). (+)-CC-1065 produces bending of DNA that appears to resemble adenine/thymine tracts. Chemical Research Toxicology, 4, 21.
    • (1991) Chemical Research Toxicology , vol.4 , pp. 21
    • Lin, C.H.1    Sun, D.2    Hurley, L.H.3
  • 38
    • 35848945419 scopus 로고
    • Diphenyl phosphorazide (DPPA), a new convenient reagent for a modified Curtius reaction
    • NINOMIYA, K , SHIOIRI, T. & YAMADA, S (1974). Diphenyl phosphorazide (DPPA), a new convenient reagent for a modified Curtius reaction. Tetrahedron, 30, 2151.
    • (1974) Tetrahedron , vol.30 , pp. 2151
    • Ninomiya, K.1    Shioiri, T.2    Yamada, S.3
  • 40
    • 0029024894 scopus 로고
    • Differential effects of distamycin analogues on amplification of human gene sequences by polymerase-chain reaction
    • PASSADORE, M., BIANCHI, N., FERIOTTO, G , MISCHIATI, C , GIACOMINI, P., PIVA, R. & GAMBARI, R. (1995) Differential effects of distamycin analogues on amplification of human gene sequences by polymerase-chain reaction. Biochemical Journal, 308, 513.
    • (1995) Biochemical Journal , vol.308 , pp. 513
    • Passadore, M.1    Bianchi, N.2    Feriotto, G.3    Mischiati, C.4    Giacomini, P.5    Piva, R.6    Gambari, R.7
  • 42
    • 0027316969 scopus 로고
    • Analysis of a DNA sequence upstream of the human estrogen receptor gene
    • PIVA, R. & DEL SENNO, L. (1993). Analysis of a DNA sequence upstream of the human estrogen receptor gene. Annals of New York Academy of Sciences, USA, 68, 235.
    • (1993) Annals of New York Academy of Sciences, USA , vol.68 , pp. 235
    • Piva, R.1    Del Senno, L.2
  • 45
    • 0022358966 scopus 로고
    • Reaction of the a ntitumor antibiotic CC-1065 with DNA. Location of the site of thermally induced strand breakage and analysis of DNA sequence specificity
    • REYNOLDS, V.L., MOLINEUX, I.J., KAPLAN, D.J., SWENSON, D.H & HURLEY, L.H. (1985). Reaction of the a ntitumor antibiotic CC-1065 with DNA. Location of the site of thermally induced strand breakage and analysis of DNA sequence specificity. Biochemistry, 24, 6228.
    • (1985) Biochemistry , vol.24 , pp. 6228
    • Reynolds, V.L.1    Molineux, I.J.2    Kaplan, D.J.3    Swenson, D.H.4    Hurley, L.H.5
  • 46
    • 0022586257 scopus 로고
    • The chemistry, mechanism of actions and biological properties of CC-1065, a potent antitumor antibiotic
    • REYNOLDS, V.L., MCGOVERN, J.P & HURLEY, L.H. (1986). The chemistry, mechanism of actions and biological properties of CC-1065, a potent antitumor antibiotic. Journal of Antibiotics, 39, 319.
    • (1986) Journal of Antibiotics , vol.39 , pp. 319
    • Reynolds, V.L.1    Mcgovern, J.P.2    Hurley, L.H.3
  • 47
    • 49549141296 scopus 로고
    • A new phosphonium salts for the Wittig synthesis of aldehydes from ketones
    • SCHLUDE, H. (1975). A new phosphonium salts for the Wittig synthesis of aldehydes from ketones. Tetrahedron, 31, 89.
    • (1975) Tetrahedron , vol.31 , pp. 89
    • Schlude, H.1
  • 48
    • 0015520853 scopus 로고
    • Diphenyl phosphorazide (DPPA), a new convenient reagent for a modified Curtius reaction and for the peptide synthesis
    • SHIOIRI, T , NINOMIYA, K. & YAMADA, S. (1972). Diphenyl phosphorazide (DPPA), a new convenient reagent for a modified Curtius reaction and for the peptide synthesis. Journal of American Chemical Society, 94, 6203.
    • (1972) Journal of American Chemical Society , vol.94 , pp. 6203
    • Shioiri, T.1    Ninomiya, K.2    Yamada, S.3
  • 49
    • 0028968427 scopus 로고
    • Synergistic and additive combinations of several antitumor drugs and other agents with the potent alkylating agent adozelesin
    • SMITH, K.S., FOLZ, B A., ADAMS, E.G. & BHUYAN, B.K. (1995). Synergistic and additive combinations of several antitumor drugs and other agents with the potent alkylating agent adozelesin. Cancer Chemotherapy Pharmacology, 35, 471.
    • (1995) Cancer Chemotherapy Pharmacology , vol.35 , pp. 471
    • Smith, K.S.1    Folz, B.A.2    Adams, E.G.3    Bhuyan, B.K.4
  • 50
    • 0021203313 scopus 로고
    • Malignant transformation of early passage rodent cells by a single mutated human oncogene
    • SPANDIDOS, D.A &. WILKIE, N.M. (1984). Malignant transformation of early passage rodent cells by a single mutated human oncogene. Nature, 310, 469.
    • (1984) Nature , vol.310 , pp. 469
    • Spandidos, D.A.1    Wilkie, N.M.2
  • 51
    • 84980108391 scopus 로고
    • Eine neue synthese der tetraconsäure
    • STOBBE, H W. (1893). Eine neue synthese der tetraconsäure. Chemische Bericte, 26, 2312.
    • (1893) Chemische Bericte , vol.26 , pp. 2312
    • Stobbe, H.W.1
  • 52
    • 0027049574 scopus 로고
    • A new approach to the synthesis of CC-1065/duocarmycin pharmacophore
    • TIDWELL, J H & BUCHWALD, S.L. (1992). A new approach to the synthesis of CC-1065/duocarmycin pharmacophore. Journal of Organic Chemistry, 57, 6380.
    • (1992) Journal of Organic Chemistry , vol.57 , pp. 6380
    • Tidwell, J.H.1    Buchwald, S.L.2
  • 53
    • 0027748198 scopus 로고
    • CC-1065 functional analogues possessing different electron-withdrawing and leaving groups: Synthesis, kinetics and sequence specificity of reaction with DNA and biological evaluation
    • WANG, Y , GUPTA, R., HUANG, L. & LOWN, J.W. (1993). CC-1065 functional analogues possessing different electron-withdrawing and leaving groups: synthesis, kinetics and sequence specificity of reaction with DNA and biological evaluation. Journal of Medicinal Chemistry, 36, 4172.
    • (1993) Journal of Medicinal Chemistry , vol.36 , pp. 4172
    • Wang, Y.1    Gupta, R.2    Huang, L.3    Lown, J.W.4
  • 54
    • 0029915634 scopus 로고    scopus 로고
    • Design, synthesis, cytotoxic properties and preliminary DNA sequencing evaluation of CPI-N-methylpyrrole hybrids. Enhancing effects of a trans double bond linker and role of the terminal amide functionality on cytotoxic potency
    • WANG, Y , GUPTA, R., HUANG, L., LUO, W. & LOWN, J.W. (1996). Design, synthesis, cytotoxic properties and preliminary DNA sequencing evaluation of CPI-N-methylpyrrole hybrids. Enhancing effects of a trans double bond linker and role of the terminal amide functionality on cytotoxic potency. Anti-Cancer Drug Design, 11, 15-34.
    • (1996) Anti-Cancer Drug Design , vol.11 , pp. 15-34
    • Wang, Y.1    Gupta, R.2    Huang, L.3    Luo, W.4    Lown, J.W.5


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