Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065

Journal of Medicinal Chemistry

Volumn 52, Issue 19, 2009, Pages 5771-5780

  MacMillan, Karen S ^a   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; AMIDE; CONGOCIDINE; DISTAMYCIN A; DUOCARMYCIN DERIVATIVE; DUOCARMYCIN SA; NATURAL PRODUCT; RACHELMYCIN; UNCLASSIFIED DRUG; YATAKEMYCIN;

BIOLOGICAL ACTIVITY; CRYSTAL STRUCTURE; CYTOTOXICITY; DNA ALKYLATION; DNA BINDING; DRUG BINDING; DRUG POTENCY; DRUG STRUCTURE; REVIEW; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

ALKYLATING AGENTS; ANTIBIOTICS, ANTINEOPLASTIC; INDOLES; MOLECULAR STRUCTURE; PYRROLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 70349641991     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9006214     Document Type: Review

References (85)

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52. (a) Lin, C. H.; Beale, J. M.; Hurley, L. H. Structure of the (+)-CC- 1065-DNA Adduct: Critical Role of Ordered Water Molecules and Implications for Involvement of Phosphate Catalysis in the Covalent Reaction. Biochemistry 1991, 30, 3597.
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54. MacMillan, K. S.; Boger, D. L. An Additional Spirocyclization for Duocarmycin SA. J. Am. Chem. Soc. 2008, 130, 16521-16523.
55. 32P-End-Labeled Double- Stranded DNA for Binding Studies: Development of a Protocol for Examination of Functional Features of (+)-CC- 1065 and the Duocarmycins That Contribute to Their Sequence- Selective DNA Alkylation Properties. Tetrahedron 1991, 47, 2661-2682.
56. (a) Boger, D. L.; Garbaccio, R. M.; Jin, Q. Synthesis and Evaluation of CC-1065 and Duocarmycin Analogues Incorporating the iso-CI and iso-CBI Alkylation Subunits: Impact of Relocation of the C-4 Carbonyl. J. Org. Chem. 1997, 62, 8875-8891.
57. (b) Boger, D. L.; Garbaccio, R. M. A Novel Class of CC-1065 and Duocarmycin Analogues Subject to Mitomycin-Related Reductive Activation. J. Org. Chem. 1999, 64, 8350-8362.
58. (a) Boger, D. L.; Boyce, C. W. Selective Metal Cation Activation of a DNA Alkylating Agent: Synthesis and Evaluation of Methyl 1,2,9,9a- Tetrahydrocyclopropa[c]pyrido[3,2-e]indol-4-one-7-carboxylate (CPyI). J. Org. Chem. 2000, 65, 4088-4100.
59. (b) Boger, D. L.; Wolkenberg, S. E.; Boyce, C. W. A New Method of in Situ Activation for a Novel Class of DNA Alkylating Agents: Tunable Metal Cation Complexation and Activation. J. Am. Chem. Soc. 2000, 122, 6325-6326.
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61. (a) Ambroise, Y.; Boger, D. L. The DNA Phosphate Backbone Is Not Involved in Catalysis of the Duocarmycin and CC-1065 DNA Alkylation Reaction. Bioorg. Med. Chem. Lett. 2002, 12, 303-306.
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65. (b) Boger, D. L.; Ishizaki, T.; Kitos, P. A.; Suntornwat, O. Synthesis of N-(tert-Butyloxycarbony1)-CBI, CBI, CBI-CDPI1, and CBI-CDPI2: Enhanced Functional Analogues of CC-1065 Incorporating the 1,2,9,9a- Tetrahydrocyclopropa[c]benz[e]indol-4-one (CBI) Left-Hand Subunit. J. Org. Chem. 1990, 55, 5823-5832.
66. (c) Boger, D. L.; Munk, S. A. DNA Alkylation Properties of Enhanced Functional Analogs of CC-1065 Incorporating the 1,2,9,9a-Tetrahydrocycloprop[1, 2-c]benz- [1,2-e]indol-4-one (CBI) Alkylation Subunit. J. Am. Chem. Soc. 1992, 114, 5487-5496.
67. (d) Boger, D. L.; Yun, W.; Teegarden, B. R. An Improved Synthesis of 1,2,9,9a-Tetrahydrocyclopropa[c]benz[e]indol- 4-one (CBI): A Simplified Analogue of the CC-1065 Alkylation Subunit. J. Org. Chem. 1992, 57, 2873-2876.
68. (e) Boger, D. L.; McKie, J. A. 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 Subunits. J. Org. Chem. 1995, 60, 1271-1275.
69. (f) Boger, D. L.; McKie, J. A.; Boyce, C. W. Asymmetric Synthesis of the CBI Alkylation Subunit of the CC-1065 and Duocarmycin Analogs. Synlett 1997, 515-517. (Pubitemid 127496173)
70. (g) Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Searcey, M. Synthesis of CC-1065 and Duocarmycin Analogs via Intramolecular Aryl Radical Cyclization of a Tethered Vinyl Chloride. Tetrahedron Lett. 1998, 39, 2227-2230. (Pubitemid 28167927)
71. (h) Kastrinsky, D. B.; Boger, D. L. Effective Asymmetric Synthesis of 1,2,9, 9a-Tetrahydrocyclopropa[c]benzo[e]indol-4-one (CBI). J. Org. Chem. 2004, 69, 2284-2289.
72. (i) Boger, D. L.; Yun, W.; Han, N. 1,2,9,9a- Tetrahydrocyclopropa[c] benz[e]indol-4-one (CBI) Analogs of CC- 1065 and the Duocarmycins: Synthesis and Evaluation. Bioorg. Med. Chem. 1995, 3, 1429-1453.
73. Boger, D. L.; Han, N.; Tarby, C. M.; Boyce, C. W.; Cai, H.; Jin, Q.; Kitos, P. A. Synthesis, Chemical Properties, and Preliminary Evaluation of Substituted CBI Analogs of CC-1065 and the Duocarmycins Incorporating the 7-Cyano-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one Alkylation Subunit: Hammett Quantitation of the Magnitude of Electronic Effects on Functional Reactivity. J. Org. Chem. 1996, 61, 4894-4912.
74. (a) Boger, D. L.; McKie, J. A.; Cai, H.; Cacciari, B.; Baraldi, P. G. Synthesis and Properties of Substituted CBI Analogs of CC-1065 and the Duocarmycins Incorporating the 7-Methoxy-1,2,9,9atetrahydrocyclopropa[ c]benz[e]indol-4-one Alkylation Subunit: Magnitude of Electronic Effects on the Functional Reactivity. J. Org. Chem. 1996, 61, 1710-1729.
75. (b) Boger, D. L.; McKie, J. A.; Han, N.; Tarby, C. M.; Riggs, H. W.; Kitos, P. A. A Hammett Correlation for CC-1065 and Duocarmycin Analogs: Magnitude of Substituent Electronic Effects on Functional Reactivity. Bioorg. Med. Chem. Lett. 1996, 6, 659-664.
76. (a) Boger, D. L.; Stauffer, F.; Hedrick, M. P. Substituent Effects within the DNA Binding Subunit of CBI Analogues of the Duocarmycins and CC-1065. Bioorg. Med. Chem. Lett. 2001, 11, 2021-2024.
77. (b) Parrish, J. P.; Kastrinsky, D. B.; Stauffer, F.; Hedrick, M. P.; Hwang, I.; Boger, D. L. Establishment of Substituent Effects in the DNA Binding Subunit of CBI Analogues of the Duocarmycins and CC- 1065. Bioorg. Med. Chem. 2003, 11, 3815-3838.
78. Boger, D. L.; Hughes, T. V.; Hedrick, M. P. Synthesis, Chemical Properties, and Biological Evaluation of CC-1065 and Duocarmycin Analogues Incorporating the 5-Methoxycarbonyl-1,2,9,9a-tetrahydrocyclopropa[ c]benz[e]indol-4-one Alkylation Subunit. J. Org. Chem. 2001, 66, 2207-2216.
79. 2 Substituent: Validation of a Direct Relationship between Solvolysis Chemical Stability and in Vitro Biological Potency. J. Am. Chem. Soc. 1994, 116, 5523-5524.
80. 2: Enhanced Functional Analogs of (+)-CC-1065. A Critical Appraisal of a Proposed Relationship between Electrophile Reactivity, DNA Binding Properties, and Cytotoxic Potency. Tetrahedron Lett. 1990, 31, 793-796.
81. 2: An Enhanced Functional Analog of (+)-CC-1065. Bioorg. Med. Chem. Lett. 1991, 1, 115-120.
82. Boger, D. L.; Munk, S. A.; Ishizaki, T. (+)-CC- 1065 DNA Alkylation: Observation of an Unexpected Relationship between Cyclopropane Electrophile Reactivity and the Intensity of DNA Alkylation. J. Am. Chem. Soc. 1991, 113, 2779-2780.
83. LaBarbera, D. V.; Skibo, E. B. Solution Kinetics of CC-1065 A-Ring Opening: Substituent Effects and General Acid/Base Catalysis. J. Am. Chem. Soc. 2006, 128, 3722-3727.
84. MacMillan, K. S.; Nguyen, T.; Hwang, I.; Boger, D. L. Total Synthesis and Evaluation of iso-Duocarmycin SA and iso-Yatakemycin. J. Am. Chem. Soc. 2009, 131, 1187-1194.
85. Tichenor, M. S.; MacMillan, K. S.; Stover, J. S.; Wolkenberg, S. E.; Pavani, M. G.; Zanella, L.; Zaid, A. N.; Spalluto, G.; Rayl, T. J.; Hwang, I.; Baraldi, P. G.; Boger, D. L. Rational Design, Synthesis, and Evaluation of Key Analogues of CC-1065 and the Duocarmycins. J. Am. Chem. Soc. 2007, 129, 14092-14099.