Total synthesis and evaluation of vinblastine analogues containing systematic deep-seated modifications in the vindoline subunit ring system: Core redesign

Journal of Medicinal Chemistry

Volumn 56, Issue 2, 2013, Pages 483-495

  Schleicher, Kristin D ^a   Sasaki, Yoshikazu ^a   Tam, Annie ^a   Kato, Daisuke ^a   Duncan, Katharine K ^a   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 DESACETOXY 6,7 DIHYDROVINBLASTINE; 4 DESACETOXYVINBLASTINE; 6,7 DIHYDROANHYDROVINBLASTINE; ANHYDROVINBLASTINE; DELTA 6,7 DIHYDROVINBLASTINE; UNCLASSIFIED DRUG; VINBLASTINE DERIVATIVE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CHEMICAL BOND; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; LEUKEMIA L 1210; MOUSE; NONHUMAN; OXIDATION; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; DRUG EVALUATION, PRECLINICAL; VINBLASTINE;

EID: 84872818405     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3014376     Document Type: Article

References (82)

1. Gorman, M.; Neuss, N.; Biemann, K. Vinca alkaloids. X. The structure of vindoline J. Am. Chem. Soc. 1962, 84, 1058-1059
2. Moncrief, J. W.; Lipscomb, W. N. Structures of leurocristine (vincristine) and vincaleukoblastine. X-ray analysis of leurocristine methiodide J. Am. Chem. Soc. 1965, 87, 4963-4964
3. Noble, R. L.; Beer, C. T.; Cutts, J. H. Role of chance observations in chemotherapy: Vinca rosea Ann. N. Y. Acad. Sci. 1958, 76, 882-894
4. Noble, R. L. Catharanthus roseus (Vinca rosea): The importance and value of a chance observation Lloydia 1964, 27, 280-281
5. Svoboda, G. H.; Neuss, N.; Gorman, M. Alkaloids of Vinca rosea Linn. (Catharanthus roseus G. Don). V. Preparation and characterization of alkaloids J. Am. Pharm. Assoc., Sci. Ed. 1959, 48, 659-666
6. Svoboda, G. H. Alkaloids of Vinca rosea (Catharanthus roseus). 1X: Extraction and characterization of leurosidine and leurocristine Lloydia 1961, 24, 173-178
7. De Bruyn, A.; Sleechecker, J.; De Jonghe, J. P.; Hannart, J. Alkaloids from Catharanthus roseus. Proton NMR study of 20′ S -deoxyvinblastine and its N -2′ borane complex Bull. Soc. Chim. Belg. 1983, 92, 485-494
8. Neuss, N.; Gorman, M.; Cone, N. J.; Huckstep, L. L. Vinca alkaloids. XXX. Chemistry of the deoxyvinblastines (deoxy-vlb), leurosine (vlr), and pleurosine, dimeric alkaloids from Vinca rosea Linn. (Catharanthus roseus G. Don) Tetrahedron Lett. 1968, 9, 783-787
9. Simonds, R.; De Bruyn, A.; De Taeye, L.; Verzele, M.; De Pauw, C. N -Deformyl vincristine, a bisalkaloid from Catharanthus roseus Planta Med. 1984, 50, 274-276
10. Neuss, N.; Barnes, A. J.; Huckstep, L. L. Vinca Alkaloids. XXXV. Desacetoxyvinblastine, a new minor alkaloid from Vinca rosea (Catharanthus roseus) Experientia 1975, 31, 18-20
11. Svoboda, G. H.; Barnes, A. J. Alkaloids of Vinca rosea Linn. (Catharanthus roseus G. Don) XXIV. Vinaspine, vincathicine, rovidine, desacetyl VLB, and vinaphamine J. Pharm. Sci. 1964, 53, 1227-1231
12. Goodbody, A. E.; Watson, C. D.; Chapple, C. C. S.; Vukovic, J.; Misawa, M. Extraction of 3′,4′-anhydrovinblastine from Catharanthus roseus Phytochemistry 1988, 27, 1713-1717
13. Blaskó, G.; Cordell, G. A. Isolation, structure elucidation, and biosynthesis of the bisindole alkaloids of Catharanthus. In The Alkaloids; Brossi, A.; Suffness, M., Eds.; Academic: San Diego, 1990; Vol. 37, pp 1-76.
14. Sottomayor, M.; Barceló, A. R. The Vinca alkaloids: From biosynthesis and accumulation in plant cells, to uptake, activity and metabolism in animal cells. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 2006; Vol. 33, pp 813-857.
15. Pearce, H. L. Medicinal chemistry of bisindole alkaloids from Catharanthus. In The Alkaloids; Brossi, A.; Suffness, M., Eds.; Academic: San Diego, 1990; Vol. 37, pp 145-204.
16. Neuss, N.; Neuss, M. N. Therapeutic use of bisindole alkaloids from Catharanthus. In The Alkaloids; Brossi, A.; Suffness, M., Eds.; Academic: San Diego, 1990; Vol. 37, pp 229-240.
17. Mangeney, P.; Andriamialisoa, R. Z.; Langlois, N.; Langlois, Y.; Potier, P. Preparation of vinblastine, vincristine, and leurosidine, antitumor alkaloids from Catharanthus species (Apocynaceae) J. Am. Chem. Soc. 1979, 101, 2243-2245
18. Kutney, J. P.; Choi, L. S. L.; Nakano, J.; Tsukamoto, H.; McHugh, M.; Boulet, C. A. A highly efficient and commercially important synthesis of the antitumor Catharanthus alkaloids vinblastine and leurosidine from catharanthine and vindoline Heterocycles 1988, 27, 1845-1853
19. Kuehne, M. E.; Matson, P. A.; Bornmann, W. G. Enantioselective syntheses of vinblastine, leurosidine, vincovaline and 20′-epi -vincovaline J. Org. Chem. 1991, 56, 513-528
20. Bornmann, W. G.; Kuehne, M. E. A common intermediate providing syntheses of ψ-tabersonine, coronaridine, iboxyphylline, ibophyllidine, vinamidine, and vinblastine J. Org. Chem. 1992, 57, 1752-1760
21. Kuehne, M. E.; Zebovitz, T. C.; Bornmann, W. G.; Marko, I. Three routes to the critical C16′-C14′ parf relative stereochemistry of vinblastine. Syntheses of 20′-desethyl-20′-deoxyvinblastine and 20′-desethyl-20′-deoxyvincovaline J. Org. Chem. 1987, 52, 4340-4349
22. Magnus, P.; Mendoza, J. S.; Stamford, A.; Ladlow, M.; Willis, P. Nonoxidative coupling methodology for the synthesis of the antitumor bisindole alkaloid vinblastine and a lower-half analog: solvent effect on the stereochemistry of the crucial C-15/C-18′ bond J. Am. Chem. Soc. 1992, 114, 10232-10245
23. Yokoshima, S.; Ueda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.; Tokuyama, H.; Fukuyama, T. Stereocontrolled total synthesis of (+)-vinblastine J. Am. Chem. Soc. 2002, 124, 2137-2139
24. Kuboyama, T.; Yokoshima, S.; Tokuyama, H.; Fukuyama, T. Stereocontrolled total synthesis of (+)-vincristine Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 11966-11970
25. Ishikawa, H.; Colby, D. A.; Boger, D. L. Direct coupling of catharanthine and vindoline to provide vinblastine: total synthesis of (+)-and ent -(-)-vinblastine J. Am. Chem. Soc. 2008, 130, 420-421
26. Ishikawa, H.; Colby, D. A.; Seto, S.; Va, P.; Tam, A.; Kakei, H.; Rayl, T. J.; Hwang, I.; Boger, D. L. Total synthesis of vinblastine, vincristine, related natural products, and key structural analogues J. Am. Chem. Soc. 2009, 131, 4904-4916
27. Jordan, M. A.; Wilson, L. Microtubules as a target for anticancer drugs Nature Rev. Cancer 2004, 4, 253-265
28. Ando, M.; Büchi, G.; Ohnuma, T. Total synthesis of (±)-vindoline J. Am. Chem. Soc. 1975, 97, 6880-6881
29. Kutney, J. P.; Bunzli-Trepp, U.; Chan, K. K.; De Souza, J. P.; Fujise, Y.; Honda, T.; Katsube, J.; Klein, F. K.; Leutweiler, A.; Morehead, S.; Rohr, M.; Worth, B. R. Total synthesis of indole and dihydroindole alkaloids. 14. A total synthesis of vindoline J. Am. Chem. Soc. 1978, 100, 4220-4224
30. Ban, Y.; Sekine, Y.; Oishi, T. A new synthetic route to (±)-vindoline. A synthesis of the Büchi's tetracyclic intermediate Tetrahedron Lett. 1978, 19, 151-154
31. Takano, S.; Shishido, K.; Sato, M.; Yuta, K.; Ogasawara, K. New synthetic routes to synthons for the synthesis of functionalized aspidosperma alkaloids J. Chem. Soc., Chem. Commun. 1978, 943-944
32. Takano, S.; Shishido, K.; Matsuzaka, J.; Sato, M.; Ogasawara, K. A new synthesis of the synthons for the functionalized aspidosperma alkaloids via α-ketocarbonium ion intermediate Heterocycles 1979, 13, 307-320
33. Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. Rapid access to the highly oxygenated aspidosperma alkaloids vindoline, vindorosine, and cathovaline J. Chem. Soc., Chem. Commun. 1984, 909-911
34. Andriamialisoa, R. Z.; Langlois, N.; Langlois, Y. A new efficient total synthesis of vindorosine and vindoline J. Org. Chem. 1985, 50, 961-967
35. Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. Aspidosperma alkaloids. Conversion of tabersonine into vindoline J. Chem. Soc., Perkin Trans. 1 1987, 155-161
36. Zhuo, S.; Bommezijn, S.; Murphy, J. A. Formal total synthesis of (±)-vindoline by tandem radical cyclization Org. Lett. 2002, 4, 443-445
37. Feldman, P. L.; Rapoport, H. Synthesis of (-)-vindoline J. Am. Chem. Soc. 1987, 109, 1603-1604
38. Kuehne, M. E.; Podhorez, D. E.; Mulamba, T.; Bornmann, W. G. Biomimetic alkaloid syntheses. 15. Enantioselective syntheses with epichlorohydrin: total syntheses of (+)-, (-)-, and (±)-vindoline and a synthesis of (-)-vindorosine J. Org. Chem. 1987, 52, 347-353
39. Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. Methods for indole alkaloid synthesis. A study of the compatibility of the indole-2,3- quinodimethane strategy for the synthesis of 16-methoxy-substituted aspidosperma-type alkaloids. Synthesis of (+)-and (-)-16-methoxytabersonine J. Am. Chem. Soc. 1988, 110, 2242-2248
40. Kobayashi, S.; Ueda, T.; Fukuyama, T. An efficient total synthesis of (-)-vindoline Synlett 2000, 883-886
41. Choi, Y.; Ishikawa, H.; Velcicky, J.; Elliott, G. I.; Miller, M. M.; Boger, D. L. Total synthesis of (-)-and ent -(+)-vindoline Org. Lett. 2005, 7, 4539-4542
42. Ishikawa, H.; Elliott, G. I.; Velcicky, J.; Choi, Y.; Boger, D. L. Total synthesis of (-)-and ent -(+)-vindoline and related alkaloids J. Am. Chem. Soc. 2006, 128, 10596-10612
43. Wilkie, G. D.; Elliott, G. I.; Blagg, B. S. J.; Wolkenberg, S. E.; Soenen, D. R.; Miller, M. M.; Pollack, S.; Boger, D. L. Intramolecular Diels-Alder and tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reactions of 1,3,4-oxadiazoles J. Am. Chem. Soc. 2002, 124, 11292-11294
44. Elliott, G. I.; Fuchs, J. R.; Blagg, B. S. J.; Ishikawa, H.; Tao, H.; Yuan, Z.-Q.; Boger, D. L. Intramolecular Diels-Alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles J. Am. Chem. Soc. 2006, 128, 10589-10595
45. Boger, D. L. Diels-Alder reactions of azadienes Tetrahedron 1983, 39, 2869-2939
46. Boger, D. L. Diels-Alder reactions of heterocyclic azadienes. Scope and applications Chem. Rev. 1986, 86, 781-793
47. Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic: San Diego, 1987.
48. Elliott, G. I.; Velcicky, J.; Ishikawa, H.; Li, Y.; Boger, D. L. Total synthesis of (-)-and ent -(+)-vindorosine: tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition of 1,3,4-oxadiazoles Angew. Chem., Int. Ed. 2006, 45, 620-622
49. Yuan, Z. Q.; Ishikawa, H.; Boger, D. L. Total synthesis of natural (-)-and ent -(+)-4-desacetoxy-6,7-dihydrovinblastine and natural and ent -minovine: oxadiazole tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction Org. Lett. 2005, 7, 741-744
50. Ishikawa, H.; Boger, D. L. Total synthesis of (-)-and ent -(+)-4-desacetoxy-5-desethylvindoline Heterocycles 2007, 72, 95-102
51. Campbell, E. L.; Zuhl, A. M.; Liu, C. M.; Boger, D. L. Total synthesis of (+)-fendleridine (aspidoalbidine) and (+)-1-acetylaspidoalbidine J. Am. Chem. Soc. 2010, 132, 3009-3012
52. Lajiness, J. P.; Jiang, W.; Boger, D. L. Divergent total syntheses of (-)-aspidospermine and (+)-spegazzinine Org. Lett. 2012, 14, 2078-2081
53. Wolkenberg, S. E.; Boger, D. L. Total synthesis of anhydrolycorinone using sequential intramolecular Diels-Alder reactions of a 1,3,4-oxadiazole J. Org. Chem. 2002, 67, 7361-7364
54. Kato, D.; Sasaki, Y.; Boger, D. L. Asymmetric total synthesis of vindoline J. Am. Chem. Soc. 2010, 132, 3685-3687
55. Sasaki, Y.; Kato, D.; Boger, D. L. Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues J. Am. Chem. Soc. 2010, 132, 13533-13544
56. Vukovic, J.; Goodbody, A. E.; Kutney, J. P.; Misawa, M. Production of 3′,4′-anhydrovinblastine: a unique chemical synthesis Tetrahedron 1988, 44, 325-331
57. Gotoh, H.; Sears, J. E.; Eschenmoser, A.; Boger, D. L. New insights into the mechanism and an expanded scope of the Fe(III)-mediated vinblastine coupling reaction J. Am. Chem. Soc. 2012, 134, 13240-13243
58. Kuehne, M. E.; Marko, I. Syntheses of vinblastine-type alkaloids. In The Alkaloids; Brossi, A.; Suffness, M., Eds.; Academic: San Diego, 1990; Vol. 37, pp 77-132.
59. Potier, P. Synthesis of the antitumor dimeric indole alkaloids from Catharanthus species (vinblastine group) J. Nat. Prod. 1980, 43, 72-86
60. Kutney, J. P. Biosynthesis and synthesis of indole and bisindole alkaloids in plant cell cultures: a personal overview Nat. Prod. Rep. 1990, 7, 85-103
61. Kutney, J. P. Plant cell cultures and synthetic chemistry-a potentially powerful route to complex natural products Synlett 1991, 11-19
62. Kutney, J. P. Plant cell culture combined with chemistry: a powerful route to complex natural products Acc. Chem. Res. 1993, 26, 559-566
63. Kuehne, M. E.; Bornmann, W. G.; Marko, I.; Qin, Y.; Le Boulluec, K. L.; Frasier, D. A.; Xu, F.; Malamba, T.; Ensinger, C. L.; Borman, L. S.; Huot, A. E.; Exon, C.; Bizzarro, F. T.; Cheung, J. B.; Bane, S. L. Syntheses and biological evaluation of vinblastine congeners Org. Biomol. Chem. 2003, 1, 2120-2136
64. Miyazaki, T.; Yokoshima, S.; Simizu, S.; Osada, H.; Tokuyama, H.; Fukuyama, T. Synthesis of (+)-vinblastine and its analogues Org. Lett. 2007, 9, 4737-4740
65. Tam, A.; Gotoh, H.; Robertson, W. M.; Boger, D. L. Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues Bioorg. Med. Chem. Lett. 2010, 20, 6408-6410
66. Gotoh, H.; Duncan, K. K.; Robertson, W. M.; Boger, D. L. 10′-Fluorovinblastine and 10′-fluorovincristine: synthesis of a key series of modified Vinca alkaloids ACS Med. Chem. Lett. 2011, 2, 948-952
67. 4-mediated additions to unactivated alkenes: Synthesis of novel C20′-vinblastine analogues Org. Lett. 2012, 14, 1428-1431
68. 4-mediated free radical hydrofluorination of unactivated alkenes J. Am. Chem. Soc. 2012, 134, 13588-13591
69. Leggans, E. K.; Duncan, K. K.; Barker, T. J; Schleicher, K. D.; Boger, D. L. A remarkable series of vinblastine analogues displaying enhanced activity and an unprecedented tubulin binding steric tolerance: C20′ urea derivatives. J. Med. Chem. 2013, 56, DOI: 10.1021/jm3015684.
70. Va, P.; Campbell, E. L.; Robertson, W. M.; Boger, D. L. Total synthesis and evaluation of a key series of C5-substituted vinblastine derivatives J. Am. Chem. Soc. 2010, 132, 8489-8495
71. Gigant, B.; Wang, C.; Ravelli, R. B. G.; Roussi, F.; Steinmetz, M. O.; Curmi, P. A.; Sobel, A.; Knossow, M. Structural basis for the regulation of tubulin by vinblastine Nature 2005, 435, 519-522
72. Dumontet, C.; Sikic, B. I. Mechanisms of action of and resistance to antitubulin agents: microtubule dynamics, drug transport, and cell death J. Clin. Oncol. 1999, 17, 1061-1070
73. Kavallaris, M.; Verrills, N. M.; Hill, B. T. Anticancer therapy with novel tubulin-interacting drugs Drug Res. Updates 2001, 4, 392-401
74. Yde, B.; Yousif, N. M.; Pedersen, U.; Thomsen, I.; Lawesson, S. O. Studies on organophosphorus compounds XLVII. Preparation of thiated synthons of amides, lactams, and imides by use of some new P,S-containing reagents Tetrahedron 1984, 40, 2047-2052
75. Raucher, S.; Klein, P. A convenient method for the selective reduction of amides to amines Tetrahedron Lett. 1980, 21, 4061-4064
76. Barnett, C. J.; Cullinan, G. J.; Gerzon, K.; Hoying, R. C.; Jones, W. E.; Nevlon, W. M.; Poore, G. A.; Robinson, R. L.; Sweeney, M. J.; Todd, G. C.; Dyke, R. W.; Nelson, R. L. Structure-activity relationships of dimeric Catharanthus alkaloids. 1. Desacetylvinblastine amide (vindesine) sulfate J. Med. Chem. 1978, 21, 88-96
77. Mitsunobu, O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products Synthesis 1981, 1
78. Iimori, T.; Ohtsuka, Y.; Oishi, T. Regioselective dehydration in cyclic system with triphenylphosphine-azodicarboxylate Tetrahedron Lett. 1991, 32, 1209-1212
79. Kuehne, M. E.; Okuniewicz, F. J.; Kirkemo, C. L.; Bohnert, J. C. Studies in biomimetic alkaloid syntheses. 8. Total syntheses of the C-14 epimeric hydroxyvincadifformines, tabersonine, a (hydroxymethyl)-d -norvincadifformine and the C-20 epimeric pandolines J. Org. Chem. 1982, 47, 1335-1343
80. Nahm, S.; Weinreb, S. M. N -methoxy-N -methylamides as effective acylating agents Tetrahedron Lett. 1981, 22, 3815-3818
81. Tam, T. F.; Fraser-Reid, B. 1,2-O -Isopropylidene furanoses as chiral precursors for α-methylene-γ-butyrolactones J. Chem. Soc., Chem. Commun. 1980, 556-558
82. Owellen, R. J.; Donigian, D. W.; Hartke, C. A.; Hains, F. O. Correlation of biologic data with physicochemical properties among the Vinca alkaloids and their congeners Biochem. Pharmacol. 1977, 26, 1213-1219