Joys of molecules. 2. Endeavors in chemical biology and medicinal chemistry

Journal of Medicinal Chemistry

Volumn 48, Issue 18, 2005, Pages 5613-5638

  Nicolaou, K C ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,6 METHANOLEUKOTRIENE A4; 11,12 DIDEHYDRO 8,15 DIHYDROEICOSATETRAENOIC ACID; 12 HYDROXYICOSATETRAENOIC ACID; 15 HYDROXYICOSATETRAENOIC ACID; 5 HYDROXYICOSATETRAENOIC ACID; 8,9,11,12 TETRAHYDRO 1,15 DIHYDROEICOSATETRAENOIC ACID; ANTINEOPLASTIC ANTIBIOTIC; ARACHIDONIC ACID; ARACHIDONIC ACID DERIVATIVE; BENZENE; CALICHEAMICIN GAMMA1; CARBOCYCLIC THROMBOXANE A2; DYNEMICIN A; ETHANOARACHIDONIC ACID; GLYCOSPHINGOLIPID; ICOSATETRAENOIC ACID; LEUKOTRIENE A4 DERIVATIVE; LEUKOTRIENE B4 DERIVATIVE; LIPOXIN A; LIPOXIN B; LIPOXYGENASE INHIBITOR; NATURAL PRODUCT; PINANE THROMBOXANE A2; PROSTACYCLIN; PROSTACYCLIN DERIVATIVE; PROSTAGLANDIN H2; SOMATOSTATIN DERIVATIVE; THROMBOXANE A2; UNCLASSIFIED DRUG; UNINDEXED DRUG; ZINOSTATIN;

AGAR GEL ELECTROPHORESIS; ANTINEOPLASTIC ACTIVITY; AROMATIZATION; BIOLOGY; CANCER; CHEMICAL BIOLOGY; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG POTENCY; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; IC 50; ISOMER; MEDICINAL CHEMISTRY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR MODEL; NONHUMAN; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; THROMBOCYTE AGGREGATION; VASOCONSTRICTION;

ANIMALS; BIOLOGICAL FACTORS; DRUG DESIGN; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 24744457957     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050524f     Document Type: Review

References (216)

1. Corey, E. J.; Nicolaou, K. C.; Machida, Y.; Malmsten, C. L.; Samuelsson, B. Synthesis and Biological Properties of a 9,11-Azo-Prostanoid. A Highly Active Biochemical Mimic of Prostaglandin Endoperoxides. Proc. Natl. Acad. Sci. U.S.A. 1975, 72, 3355-3358.
2. Nicolaou, K. C. Joys of Molecules. 1. Campaigns in Total Synthesis. J. Org. Chem. 2005, 48, 7007-7027.
3. Johnson, R. A.; Morton, D. R.; Kinner, J. H.; German, R. R.; McGuire, J. C.; Sun, F. F.; Whittaker, N.; Bunting, S.; Salmon, J.; Moncada, S.; Vane, J. R. The Chemical Structure of Prostaglandin X (Prostacyclin). Prostaglandins 1976, 12, 915-928.
4. Nicolaou, K. C.; Magolda, R. L.; Sipio, W. J.; Barnette, W. E.; Lysenko, Z.; Joullie, M. M. A Highly Efficient Cyclization Process for the Synthesis of O- and S-Heterocycles. J. Am. Chem. Soc. 1980, 102, 3784-3793.
5. Nicolaou, K. C.; Barnette, W. E.; Magolda, R. L. Organoselenium-Based Synthesis of Oxygen-Containing Prostacyclins. J. Am. Chem. Soc. 1981, 103, 3480-3485.
6. Nicolaou, K. C.; Barnette, W. E.; Magolda, R. L. Synthesis of 5Z- and 5E-6,9-Thiaprostacyclins. J. Am. Chem. Soc. 1981, 103, 3472-3480.
7. 2). J. Chem. Soc., Chem. Commun. 1978, 1067-1068.
8. 2). J. Chem. Soc., Chem. Commun. 1977, 630-631.
9. Hamberg, M.; Svensson, J.; Samuelsson, B. Thromboxanes. New Group of Biologically Active Compounds Derived from Prostaglandin Endoperoxides. Proc. Natl. Acad. Sci. U.S.A. 1975, 75, 2994-2998.
10. 2). J. Am. Chem. Soc. 1980, 102, 1404-1409.
11. 2). A Selective Inhibitor of Coronary Artery Constriction, Platelet Aggregation and Thromboxane Formation. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 2566-2570.
12. 2 Antagonist with Antithrombotic Properties. Adv. Prostaglandin Thromboxane Res. 1980, 6, 489-492.
13. Nicolaou, K. C.; Smith, J. B.; Lefer, A. M. Chemistry and Pharmacology of a Series of New Thromboxane Analogs. Drugs Future 1982, 7, 331-340.
14. Samuelsson, B. The Leukotrienes: A New Group of Biologically Active Compounds. Pure Appl. Chem. 1981, 53, 1203-1213.
15. Nicolaou, K. C.; Ramphal, J. Y.; Petasis, N. A.; Serhan, C. N. Lipoxins and Related Eicosanoids: Biosynthesis, Chemical Synthesis and Biological Properties. Angew. Chem., Int. Ed. Engl. 1991, 30, 1100-1116.
16. Nicolaou, K. C.; Hernandez, P. E.; Ladduwahetty, T.; Randall, J. L.; Webber, S. E.; Li, W. S.; Petasis, N. A. Ethanoarachidonic Acids. A New Class of Arachidonic Acid Cascade Modulators. 2. Polyethanocompounds. J. Org. Chem. 1983, 48, 5403-5404.
17. (a) Smith, J. B.; Roth, D. M.; Lefer, A. M.; Petasis, N. A.; Nicolaou, K. C. Modulation of Leukotriene Synthesis and Actions by Synthetic Derivatives of Arachidonic Acid. Prostaglandins 1985, 29, 765-771.
18. (b) Yanagisawa, A.; Brezinski, M.; Lefer, A. M.; Webber, S. E.; Nicolaou, K. C. Coronary Vasoactivity of Four 7,13-Bridged Analogs of Arachidonic Acid. Prostaglandins, Leukotrienes Med. 1986, 23, 15-19.
19. Nicolaou, K. C.; Ladduwahetty, T.; Taffer, I. M.; Zipkin, R. E. A General Strategy for the Synthesis of Monohydroxy-eicosatetraenoic Acids: Total Synthesis of 5(S)-Hydroxy-6(E),8,11,14(Z)-eicosatetraenoic Acid (5-HETE) and 12(S)-Hydroxy-5,8,14(Z)-10(E)-eicosatetraenoic Acid (12-HETE). Synthesis 1986, 344-347.
20. Nicolaou, K. C.; Ramphal, J. Y.; Abe, Y. Stereocontrolled Total Synthesis of 12(R)-Hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic Acid [12(R)-HETE]. Synthesis 1989, 898-901.
21. Nicolaou, K. C.; Ladduwahetty, T.; Elisseou, E. M. Stereo-controlled Total Synthesis of (5Z, 8Z, 11Z, 13E) (15S)-15-Hydroxyeicosa-5,8,11,13- tetraenoic Acid (15S-HETE) and Analogues. J. Chem. Soc., Chem. Commun. 1985, 1580-1581.
22. Borgeat, P.; Samuelsson, B. Transformation of Arachidonic Acid by Rabbit Polymorphonuclear Leukocytes. Formation of a Novel Dihydroxyeicosatetraenoic Acid. J. Biol. Chem. 1979, 254, 2643-2646.
23. 4 and Analogs. J. Am. Chem. Soc. 1984, 106, 3548-3551.
24. 4 on Human Neutrophil Functions. Prostaglandins 1989, 37, 287-302.
25. 4. Tetrahedron Lett. 1986, 27, 1881-1882.
26. 4. J. Chem. Soc., Chem. Commun. 1981, 1195-1196.
27. 4: A Potent Specific Inhibitor for 5-Lipoxygenase. Adv. Prostaglandin, Thromboxane, Leukotriene Res. 1983, 11, 163-167.
28. (a) Nicolaou, K. C.; Webber, S. E. Total Synthesis of 5(S),15(S)-Dihydroxy-6,13-trans-8,11-cis-eicosatetraenoic Acid (5,15-DiHETE), and 8(S),15(S)-Dihydroxy-5,11-cis-9,13-trans-eicosatetraenoic Acid (8,15-DiHETE): Two Novel Metabolites of Arachidonic Acid. J. Am. Chem. Soc. 1984, 106, 5734-5736.
29. (b) Nicolaou, K. C.; Ladduwahetty, T.; Elisseou, E. M. Stereo-controlled Total Synthesis of (5Z, 8Z, UZ, 13E) (15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoic Acid (15S-HETE) and Analogues. J. Chem. Soc., Chem. Commun. 1985, 1580-1581.
30. (a) Serhan, C. N.; Hamberg, M.; Samuelsson, B. Trihydroxytetraenes: A Novel Series of Compounds Formed from Arachidonic Acid in Human Leukocytes. Biochem. Biophys. Res. Commun. 1984, 118, 943-949.
31. (b) Serhan, C. N.; Hamberg, M.; Samuelsson, B. Lipoxins: Novel Series of Biologically Active Compounds Formed from Arachidonic Acid in Human Leukocytes. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 5335-5339.
32. (a) Nicolaou, K. C.; Veale, C. A.; Webber, S. E.; Katerinopoulos, H. Stereocontrolled Total Synthesis of Lipoxins A. J. Am. Chem. Soc. 1985, 107, 7515-7518.
33. (b) Nicolaou, K. C.; Webber, S. E. Stereoselective Total Synthesis of the Presumed Biosynthetic Precursor to Lipoxins A and B: Methyl (7E, 9E, 11Z, 13E, 5S, 6S, 15S)-5,6-Epoxy-15-hydroxyicosa-7,9,11,13-tetraenoate and Its 5,6-Methano Analogue. J. Chem. Soc., Chem. Commun. 1986, 1816-1817.
34. 4 Methyl Ester and 19,19,20,20,20-Pentadeuterated Arachidonic Acid and Demonstration of Their Use in the Quantitative Detection of Naturally Occurring Eicosanoids. J. Org. Chem. 1989, 54, 5522-5527.
35. 4. J. Org. Chem. 1989, 54, 5527-5535.
36. 5. Angew. Chem., Int. Ed. Engl. 1987, 26, 1019-1021.
37. (f) Nicolaou, K. C.; Webber, S. E. A General Strategy for the Total Synthesis of the Presumed Lipoxin Structures. J. Chem. Soc., Chem. Commun. 1985, 297-298.
38. (g) Nicolaou, K. C.; Webber, S. E. Stereocontrolled Total Synthesis of Lipoxins B. Synthesis 1986, 453-461.
39. 5: New Biologically Active Eicosanoids. Eur. J. Pharmacol. 1989, 163, 55-60.
40. (b) For the biology of 35 and 36, see the following: Palmblad, J.; Gyllenhammar, H.; Ringertz, B.; Serhan, C. N.; Samuelsson, B.; Nicolaou, K. C. The Effects of Lipoxin A and Lipoxin B on Functional Responses of Human Granulocytes. Biochem. Biophys. Res. Commun. 1987, 145, 168-175.
41. (c) For the biology of 35, see the following: Badr, K. F.; Serhan, C. N.; Nicolaou, K. C.; Samuelsson, B. The Action of Lipoxin-A on Glomerular Microcirculatory Dynamics in the Rat. Biochem. Biophys. Res. Commun. 1987, 145, 408-414.
42. 4-Induced Inflammation in the Hamster Cheek Pouch. Acta Physiol. Scand. 1989, 137, 571-572.
43. (e) For the biology of 35, 36, and 48, see the following: Brezinski, M. E.; Gimbrone, M. A., Jr.; Nicolaou, K. C.; Serhan, C. N. Lipoxin Stimulate Prostacyclic Generation by Human Endothelial Cells. FEBS Lett. 1989, 245, 167-172.
44. 4. Biochim. Biophys. Acta 1989, 1003, 44-53.
45. (g) For the biology of 35-37, 39, 44, and 45, see the following: Serhan, C. N.; Nicolaou, K. C.; Webber, S. E.; Veale, C. A.; Dahlén, S.-E.; Puustinen, T. J.; Samuelsson, B. Lipoxin A: Stereochemistry and Biosynthesis. J. Biol. Chem. 1986, 261, 16340-16345.
46. 4: Comparison of Eicosanoids Having Bronchoconstrictor and Vasodilator Actions but Lacking Platelet Aggregatory Activity. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8340-8344.
47. Puustinen, T.; Webber, S. E.; Nicolaou, K. C.; Haeggstrom, J.; Serhan, C. N.; Samuelsson, B. Evidence for a 5(6)-Epoxytetraene Intermediate in the Biosynthesis of Lipoxins in Human Leukocytes: Conversion into Lipoxin by Cytosolic Epoxide Hydrolase. FEBS Lett. 1986, 207, 127-132.
48. Nicolaou, K C.; Mitchell, H. J. Adventures in Carbohydrate Chemistry: New Synthetic Technologies, Chemical Synthesis, Molecular Design and Chemical Biology. Angew. Chem., Int. Ed. 2001, 40, 1576-1624.
49. Strobel, G. A. Phytotoxins. Annu. Rev. Biochem. 1982, 51, 309-333.
50. Nicolaou, K. C.; Randall, J. L.; Furst, G. Stereospecific Synthesis of Rhynchosporosides: A Family of Fungal Metabolites Causing Scald Disease in Barley and Other Grasses. J. Am. Chem. Soc. 1985, 107, 5556-5558.
51. 3). J. Am. Chem. Soc. 1988, 110, 7910-7912.
52. 3). Carbohydr. Res. 1990, 202, 177-191.
53. Nicolaou, K. C. Chemical Synthesis of Glycosphingolipids. ChemTracts 1991, 4, 181-198.
54. Fiore, S.; Nicolaou, K. C.; Caulfield, T.; Kataoka, H.; Serhan, C. N. Evaluation of Synthetic Sphingosine, Lysosphingolipids and Glycosphingolipids as Inhibitors of Functional Responses of Human Neutrophils. Biochem. J. 1990, 266, 25-31.
55. x Family of Glycosphingolipids. J. Am. Chem. Soc. 1990, 112, 3693-3697.
56. x, the Oligosaccharide Binding Ligand to ELAM-1. J. Chem. Soc., Chem. Commun. 1991, 870-872.
57. x. J. Am. Chem. Soc. 1992, 114, 3126-3128.
58. Ling, Y.-C.; Hummel, C. W.; Huang, D.-H.; Ichikawa, Y.; Nicolaou, K. C.; Wong, C.-H. Conformational Studies of Sialyl Lewis x in Aqueous Solution. J. Am. Chem. Soc. 1992, 114, 5452-5454.
59. +2 Dependent Carbohydrate Association through Ion Spray Mass Spectrometry. J. Am. Chem. Soc. 1993, 115, 2877-2881.
60. Siuzdak, G.; Zheng, Z.-L.; Ramphal, J. R.; Ichikawa, Y.; Nicolaou, K. C.; Gaeta, F. C. A.; Chatman, K. S.; Wong, C.-H. Examination of the Sialyl Lewis X-Calcium Complex by Electrospray Mass Spectrometry. Bioorg. Med. Chem. Lett. 1994, 4, 2863-2866.
61. Demont-Caulet, N.; Maillet, F.; Tailler, D.; Jacquinet, J.-C.; Prome, J. C.; Nicolaou, K. C.; Truchet, G.; Beau, J.-M.; Denarie, J. Nodule-Inducing Activity of Synthetic Sinorhizobium meliloti Nodulation Factors and Related Lipo-chitooligoasaccharides on Alfalfa. Importance of the Acyl Chain Structure. Plant Physiol. 1999, 120, 83-92.
62. Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R.; Hummel, C. W.; Even, L. F. Total Synthesis of the NodRm-IV Factors, the Rhizobium Nodulation Signals. J. Am. Chem. Soc. 1992, 114, 8701-8702.
63. Bono, J.-J.; Riond, J.; Nicolaou, K. C.; Bockovich, N. J.; Estevez, V. A.; Cullimore, J. V.; Ranjeva, R. Characterization of a Binding Site for Chemically Synthesized Lipo-oligosaccharidic NodRm Factors in Particulate Fractions Prepared from Roots. Plant J. 1995, 7, 253-260.
64. a-Type Oligosaccharide Selectin Ligands. J. Am. Chem. Soc. 1993, 115, 8843-8844.
65. Yuen, C.-T.; Bezouska, K.; Brien, J. O.; Stoll, M.; Lemoine, R.; Lubineau, A.; Kiso, M.; Hasegawa, A.; Bockovich, N. J.; Nicolaou, K. C.; Feizi, T. Sulfated Blood Group Lewis a. A Superior Oligosaccharide Ligand for Human E-Selectin. J. Biol. Chem. 1994, 269, 1595-1598.
66. Green, P. J.; Yuen, C.-T.; Childs, R. A.; Chai, W.; Miyasaka, M.; Lemoine, R.; Lubineau, A.; Smith, B.; Ueno, H.; Nicolaou, K. C.; Feizi, T. Further Studies of the Binding Specificity of the Leucocyte Adhesion Molecule, L-Selectin, towards Sulphated Oligosaccharides. Suggestion of a Link between the Selectin- and the Integrin-Mediated Lymphocyte Adhesion Systems. Glycobiology 1995, 5, 29-38.
67. (a) Sharp, J. K.; Valent, B.; Albersheim, P. Purification and Partial Characterization of a β-Glucan Fragment That Elicits Phytoalexin Accumulation in Soybean. J. Biol. Chem. 1984, 259, 11312-11320.
68. (b) Sharp, J. K.; Valent, B.; Albersheim, P. Host-Pathogen Interactions. XXVII. The Primary Structures of One Elicitor-Active and Seven Elicitor-Inactive Hexa(β-D-glucopyranosyl)-D-glucitols Isolated from the Mycelial Walls of Phytophthora megasperma f. sp. glycinea. J. Biol. Chem. 1984, 259, 11321-11336.
69. Nicolaou, K. C.; Wissinger, N.; Pastor, J.; Deroose, F. A General and Highly Efficient Solid Phase Synthesis of Oligosaccharides. Total Synthesis of Heptasaccharide Phytoalexin Elicitor (HPE). J. Am. Chem. Soc. 1997, 119, 449-450.
70. Costantino, V.; Fattorusso, E.; Mangoni, A.; Di Rosa, M.; Ianaro, A. Glycolipids from Sponges. 6. Plakoside A and B, Two Unique Prenylated Glycophingolipids with Immunosuppressive Activity from the Marine Sponge Plakortis simplex. J. Am. Chem. Soc. 1997, 119, 12465-12470.
71. Nicolaou, K. C.; Li, J.; Zenke, G. Total Synthesis and Biological Evaluation of Glycolipids Plakosides A, B and Their Analogs. Helv. Chim. Acta 2000, 83, 1977-2006.
72. Brazeau, P.; Vale, W.; Burgus, R.; Guillemin, R. Isolation of Somatostatin (A Somatotropin Release Inhibiting Factor) of Ovine Hypothalamic Origin. Can. J. Biochem. 1974, 52, 1067-1072.
73. Nicolaou, K. C.; Salvino, J. M.; Raynor, K.; Pietranico, S.; Reisine, T.; Freidinger, R. M.; Hirschmann, R. Peptides: Chemistry, Structure and Biology. In Peptides: Chemistry, Structure and Biology; Rivier, J. E., Marshall, G. R., Eds.; Escom: Leiden, The Netherlands, 1990; pp 881-883.
74. Hirschmann, R.; Nicolaou, K. C.; Pietranico, S.; Salvino, J.; Leahy, E. M.; Sprengler, P. A.; Furst, G.; Smith, A. B., III; Strader, C. D.; Cascier, M. A.; Candelore, M. R.; Donaldson, C.; Vale, W.; Maechler, L. Nonpeptidal Peptidomimetic with a β-D-Glucose Scaffolding. A Partial Somatostatin Agonist Bearing a Close Structural Relationship to a Potent, Selective Substance P Antagonist. J. Am. Chem. Soc. 1992, 114, 9217-9218.
75. Hirschmann, R.; Nicolaou, K. C.; Pietranico, S.; Leahy, E. M.; Salvino, J.; Arison, B.; Cichy, M. A.; Grant Spoors, P.; Shakespeare, W. C.; Sprengeler, P. A.; Hamley, P.; Smith, A. B., III; Reisine, T.; Raynor, K.; Maechler, L.; Donaldson, C.; Vale, W.; Freidinger, R. M.; Cascieri, M. R.; Strader, C. D. De Novo Design and Synthesis of Somatostatin Non-Peptide Peptidomimetics Utilizing β-D-Glucose as a Novel Scaffolding. J. Am. Chem. Soc. 1993, 115, 12550-12568.
76. Nicolaou, K. C.; Watanabe, N.; Li, J.; Pastor, J.; Winssinger, N. Solid Phase Synthesis of Oligosaccharides. Construction of a Dodecasaccharide. Angew. Chem., Int. Ed. 1998, 37, 1559-1561.
77. Nicolaou, K. C.; Dai, W.-M. Chemistry and Biology of the Enediyne Anticancer Antibiotics. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416.
78. Nicolaou, K. C.; Ogawa, Y.; Zuccarello, G.; Kataoka, H. DNA Cleavage by a Synthetic Mimic of the Calicheamicin-Esperamicin Class of Antibiotics. J. Am. Chem. Soc. 1988, 110, 7247-7248.
79. Nicolaou, K. C.; Zuccarello, G.; Reimer, C.; Estevez, V. A.; Dai, W.-M. Design, Synthesis and Study of Simple Monocyclic Conjugated Enediynes. The 10-Membered Ring Enediyne Moiety of the Enediyne Anticancer Antibiotics. J. Am. Chem. Soc. 1992, 114, 7360-7371.
80. Nicolaou, K. C.; Liu, A.; Zeng, Z.; McComb, S. Redox-Controlled Bergman Cycloaromatizations. Designed Enediynes with DNA Cleaving Properties and Antitumor Activity. J. Am. Chem. Soc. 1992, 114, 9279-9282.
81. Nicolaou, K. C.; Sorensen, E.; Discordia, R.; Hwang, C.-K.; Minto, R. E.; Bharucha, K. N.; Bergman, R. G. 10-Membered Ring Enediynes with Remarkable Chemical and Biological Profiles. Angew. Chem., Int. Ed. Engl. 1992, 31, 1044-1046.
82. Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. Cyclic Conjugated Enediynes Related to Calicheamicins and Esperamicins: Calculations, Synthesis and Properties. J. Am. Chem. Soc. 1988, 110, 4866-4868.
83. Nicolaou, K. C.; Pitsinos, E. N.; Theodorakis, E. A.; Saimoto, H.; Wrasidlo, W. Synthetic Calicheamicin Mimics with Novel Initiation Mechanisms: DNA Cleavage, Cytotoxicity, and Apoptosis. Chem. Biol. 1994, 1, 57-66.
84. Nicolaou, K. C. The Battle of Calicheamicin. Angew. Chem., Int. Ed. Engl. 1993, 32, 1377-1385.
85. I: A Rationally Designed Molecule with Extremely Potent and Selective DNA Cleaving Properties and Apoptosis Inducing Activity. Angew. Chem., Int. Ed. Engl. 1994, 33, 183-186.
86. I Oligosaccharide with Duplex DNA J. Am. Chem. Soc. 1992, 114, 7555-7557.
87. (a) Konishi, M.; Ohkuma, H.; Matsumoto, K.; Tsuno, T.; Kamei, H.; Miyaki, T.; Oki, T.; Kawaguchi, H.; VanDuyne, G. D.; Clardy, J. Dynemicin A, a Novel Antibiotic with the Anthraquinone and 1,5-Diyn-3-ene Subunit. J. Antibiot. 1989, 42, 1449-1452.
88. (b) Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.; VanDuyne, G. D.; Clardy, J. Crystal and Molecular Structure of Dynemicin A: A Novel 1,5-Diyn-3-ene Antitumor Antibiotic. J. Am. Chem. Soc. 1990, 112, 3715-3716.
89. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C.; Estevez, V. A.; Wrasidlo, W. Designed Enediynes. A New Class of DNA-Cleaving Molecules with Potent and Selective Anticancer Activity. Science 1992, 256, 1172-1178.
90. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. Molecular Design and Chemical Synthesis of Potent Enediynes 1. Dynemicin Model Systems Equipped with N-Tethered Triggering Devices. J. Am. Chem. Soc. 1992, 114, 8890-8907.
91. Nicolaou, K. C.; Dai, W.-M. Molecular Design and Chemical Synthesis of Potent Enediynes. 2. Dynemicin Model Systems Equipped with C-3 Triggering Devices and Evidence for Quinone Methide Formation in the Mechanism of Action of Dynemicin A. J. Am. Chem. Soc. 1992, 114, 8908-8921.
92. Nicolaou, K. C.; Dai, J. W.-M.; Hong, Y. P.; Tsay, S.-C.; Baldridge, K. K.; Siegel, J. S. Molecular Design, Chemical Synthesis, Kinetic Studies, Calculations, and Biological Studies of Novel Enediynes Equipped with Triggering, Detection and Deactivating Devices. Model Dynemicin A Epoxide and cis-Diol Systems. J. Am. Chem. Soc. 1993, 115, 7944-7953.
93. Nicolaou, K. C.; Wendeborn, S.; Maligres, P.; Isshiki, K.; Zein, N.; Ellestad, G. Selectivity and Mechanism of Action of Novel DNA Cleaving Agents. Angew. Chem., Int. Ed. Engl. 1991, 30, 418-420.
94. Nicolaou, K. C.; Maligres, P.; Shin, J.; de Leon, E.; Rideout, D. DNA-Cleavage and Antitumor Activity of Designed Molecules with Conjugated Phosphine-allene-ene-yne Functionalities. J. Am. Chem. Soc. 1990, 112, 7825-7826.
95. Nicolaou, K. C.; Skokotas, G.; Furuya, S.; Suemune, H.; Nicolaou, D. C. Golfomycin A: A Novel Designer Molecule with DNA-Cleaving Properties and Antitumor Activity. Angew. Chem., Int. Ed. Engl. 1990, 29, 1064-1067.
96. I to Duplex DNA. J. Am. Chem. Soc. 1994, 116, 3709-3715.
97. (a) Liu, C.; Smith, B. M.; Ajito, K.; Komatsu, H.; Gomez-Paloma, L.; Li, T.; Theodorakis, E. A.; Nicolaou, K. C.; Vogt, P. K. Sequence Selective Carbohydrate-DNA Interactions: Dimeric and Monomeric Forms of the Calicheamicin Oligosaccharide Interfere with Transciption Factor Function. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 940-944.
98. (b) Nicolaou, K. C.; Smith, B. M.; Ajito, K.; Komatsu, H.; Gomez-Paloma, L.; Tor, Y. DNA-Carbohydrate Interactions. Specific Binding of Head-to-Head and Head-to-Tail Dimers of the Calicheamicin Oligosaccharide to Duplex DNA. J. Am. Chem. Soc. 1996, 118, 2303-2304.
99. (c) Nicolaou, K. C.; Ajito, K.; Komatsu, H.; Smith, B. M.; Bertinato, P.; Gomez-Paloma, L. DNA-Carbohydrate Interactions. Design and Synthesis of Head-to-Tail Dimer of the Calicheamicin Oligosaccharide. Chem. Commun. 1996, 1495-1496.
100. (d) Nicolaou, K. C.; Smith, B. M.; Pastor, J.; Watanabe, Y.; Weinstein, D. S. Synthesis of DNA-Binding Oligosaccharides. Synlett 1997, 401-410.
101. I Oligosaccharide and a DNA Duplex Containing d(ACCT) and d(TCCT) High Affinity Binding Systems. J. Am. Chem. Soc. 1998, 120, 7183-7191.
102. 2. J. Am. Chem. Soc. 1996, 118, 8817-8824.
103. Nicolaou, K. C.; Schreiner, E. P.; Iwabuchi, Y.; Suzuki, T. Total Synthesis of Calicheamicin-Dynemicin Hybrid Molecules. Angew. Chem., Int. Ed. Engl. 1992, 31, 340-342.
104. Nicolaou, K. C.; Claiborne, C. F.; Nantermet, P. G.; Couladouros, E. A.; Sorensen, E. J. Synthesis of Novel Taxoids. J. Am. Chem. Soc. 1994, 116, 1591-1592.
105. Nicolaou, K. C.; Claiborne, C. F.; Paulvannan, K.; Postema, M. H. D.; Guy, R. K. The Chemical Synthesis of C-Ring Aryl Taxoids. Chem.-Eur. J. 1997, 3, 399-409.
106. Nicolaou, K. C.; Couladouros, E. A.; Nantermet, P. G.; Renaud, J.; Guy, R. K.; Wrasidlo, W. Synthesis of C-2 Taxol Analogues. Angew. Chem., Int. Ed. Engl. 1994, 33, 1581-1583.
107. Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. Chemical Synthesis and Biological Evaluation of C-2 Taxoids. J. Am. Chem. Soc. 1995, 117, 2409-2420.
108. Nicolaou, K. C.; Riemer, C.; Kerr, M. A.; Rideout, D.; Wrasidlo W. Design, Synthesis and Biological Activity of Protaxols. Nature 1993, 364, 464-466.
109. Nicolaou, K. C.; Guy, R. K.; Pitsinos, E. C.; Wrasidlo, W. A Water-Soluble Prodrug of Taxol with Self-Assembling Properties. Angew. Chem., Int. Ed. Engl. 1994, 33, 1583-1587.
110. Paloma, L. G.; Guy, R. K.; Wrasidlo, W.; Nicolaou, K. C. Conformation of Water-Soluble Derivative of Taxol in Water by 2D-NMR Spectroscopy. Chem. Biol. 1994, 1, 107-112.
111. Guy, R. K.; Scott, Z. A.; Sloboda, R. S.; Nicolaou, K. C. Flourescent Taxoids. Chem. Biol. 1996, 3, 1021-1031.
112. Höfle, G.; Bedorf, K.; Gerth, H.; Reichenbach, H. Epothilone Derivatives. GBF, DE-B 4138042, 1993; Chem. Abstr. 1993, 120, 52841.
113. Bollag, D. M.; McQueney, P. A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M.; Lazarides, E.; Woods, C. M. Epothilones, a New Class of Microtubule-Stabilizing Agents with a Taxol-like Mechanism of Action. Cancer Res. 1995, 55, 2325-2333.
114. Bollag, D. M. Epothilones: Novel Microtubule-Stabilizing Agents. Expert Opin. Invest. Drugs 1997, 6, 867-873.
115. (a) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Total Synthesis of Epothilone A: The Olefin Metathesis Approach. Angew. Chem., Int. Ed. Engl. 1997, 36, 166-168.
116. (b) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. An Approach to Epothilones Based on Olefin Metathesis. Angew. Chem., Int. Ed. Engl. 1996, 35, 2399-2401.
117. (c) Nicolaou, K. C.; Sarabia, F.; Ninkovic, S.; Yang, Z. Total Synthesis of Epothilone A: The Macrolactonization Approach. Angew. Chem., Int. Ed. Engl. 1997, 36, 525-527.
118. (d) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Roschangar, F.; Sarabia, F.; Ninkovic, S.; Yang, Z.; Trujillo, J. I. The Olefin Metathesis Approach to Epothilone A and Its Analogs. J. Am. Chem. Soc. 1997, 119, 7960-7973.
119. (e) Nicolaou, K. C.; Ninkovic, S.; Sarabia, F.; Vourloumis, D.; He, Y.; Vallberg, H.; Finlay, M. R. V.; Yang, Z. Total Syntheses of Epothilones A and B via a Macrolactonization Based Strategy. J. Am. Chem. Soc. 1997, 119, 7974-7991.
120. (f) Nicolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Winssinger, N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschangar, F.; King, N. Award Address P.; Finlay, M. R. V.; Giannakakou, P.; Verdier-Pinard, P.; Hamel, E. Designed Epothilones: Combinatorial Synthesis, Tubulin Assembly Properties and Cytotoxic Action against Taxol-Resistant Tumor Cells. Angew. Chem., Int. Ed. Engl. 1997, 36, 2097-2103.
121. (g) Nicolaou, K. C.; Ninkovic, S.; Finlay, M. R. V.; Sarabia, F. Total Synthesis of 26-Hydroxyepothilone B and Related Analogs. Chem. Commun. 1997, 2343-2344.
122. (h) Nicolaou, K. C.; Vallberg, H.; King, N. P.; Roschangar, F.; He, Y.; Vourloumis, D.; Nicolaou C. G. Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone A Analogues by the Olefin Metathesis Approach. Chem.-Eur. J. 1997, 3, 1957-1970.
123. (i) Nicolaou, K. C.; Sarabia, F.; Finlay, M. R. V.; Ninkovic, S.; King, N. P.; Vourloumis, D.; He, Y. Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone B Analogues by the Macrolactonization Approach. Chem.-Eur. J. 1997, 3, 1971-1986.
124. (j) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E. Synthesis of Epothilones A and B in Solid and Solution Phase. Nature 1997, 387, 268-272.
125. (k) Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Chemical Biology of Epothilones. Angew. Chem., Int. Ed. 1998, 37, 2014-2045.
126. (l) Nicolaou, K. C.; Sarabia, F.; Ninkovic, S.; Finlay, M. R. V.; Boddy, C. N. C. Probing the Ring Size of Epothilones. Total Synthesis of [14]-, [15]-, [17]-, and [18]-Epothilones A. Angew. Chem., Int. Ed. 1998, 37, 81-84.
127. (m) Nicolaou, K. C.; He, Y.; Roschangar, F.; King, N. P.; Vourloumis, D.; Li, T. Total Synthesis of Epothilone E and Side-Chain Epothilone Analogs via the Stille Coupling Reaction. Angew. Chem., Int. Ed. 1998, 37, 84-87.
128. (n) Nicolaou, K. C.; Finlay, M. R. V.; Ninkovic, S.; King, N. P.; He, Y.; Li, T.; Sarabia, F.; Vourloumis, D. Synthesis and Biological Properties of C12,13-Cyclopropyl-epothilone A and Related Epothilones. Chem. Biol. 1998, 5, 365-372.
129. (o) Nicolaou, K. C.; Finlay, M. R. V.; Ninkovic, S.; Sarabia, F. Total Synthesis of 26-Hydroxy-epothilone B and Related Analogs via a Macrolactonization Based Strategy. Tetrahedron 1998, 54, 7127-7166.
130. (p) Nicolaou, K. C.; Hepworth, D.; Finlay, M. R. V.; King, N. P.; Werschkun, B.; Bigot, A. Synthesis of 16-Desmethylepothilone B: Improved Metholodgy for the Rapid, Highly Selective and Convergent Construction of Epothilone B and Related Analogues. Chem. Commun. 1999, 519-520.
131. (q) Nicolaou, K. C.; King, N. P.; Finlay, M. R. V.; He, Y.; Roschangar, F.; Vourloumis, D.; Vallberg, H.; Sarabia, F.; Ninkovic, S.; Hepworth, D. Total Synthesis of Epothilone E and Related Side Chain Modified Analogs via a Stille Coupling Based Strategy. Bioorg. Med. Chem. 1999, 7, 665-697.
132. (r) Nicolaou, K. C.; Hepworth, D.; King, N. P.; Finlay, M. R. V. Chemistry, Biology and Medicine of Selected Tubulin Polymerizing Agents. Pure Appl. Chem. 1999, 71, 989-997.
133. (s) Giannakakou, P.; Gussio, R.; Nogales, E.; Downing, K. H.; Zaharevitz, D.; Bollbuck, B.; Poy, G.; Sackett, D.; Nicolaou, K. C.; Fojo, T. A Common Pharmacophore for Epothilones and Taxol: Molecular Basis for Drug Resistance-Conferred by Tubulin Mutations in Human Cancer Cells. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 2904-2909.
134. (t) Nicolaou, K. C.; Scarpelli, R.; Bollbuck, B.; Werschkun, B.; Pereira, M. M. A.; Wartmann, M.; Altmann, K. H.; Zaharevitz, D.; Gussio, R.; Giannakakou, P. Chemical Synthesis and Biological Properties of Pyridine Epothilones. Chem. Biol. 2000, 7, 593-599.
135. 10, Epothilone F, and Related Side Chain Modified Epothilone B Analogues. Chem.-Eur. J. 2000, 6, 2783-2800.
136. (v) Nicolaou, K. C.; Namoto, K.; Li, J.; Ritzen, A.; Ulven, T.; Shoji, M.; Zaharevitz, D.; Gussio, R.; Sackett, D. L.; Ward, R. D.; Hensler, A.; Fojo, T.; Giannakakou, P. Synthesis and Biological Evaluation of 12,13-Cyclopropyl and 12,13-Cyclobutyl Epothilones. ChemBioChem 2001, 2, 69-75.
137. (w) Nicolaou, K. C.; Ritzen, A.; Namoto, K. Recent Developments in the Chemistry, Biology and Medicine of the Epothilones. Chem. Commun. 2001, 1523-1535.
138. (x) Newman, R. A.; Yang, J.; Finlay, M. R. V.; Cabral, F.; Vourloumis, D.; Stevens, C.; Troncoso, P.; Wu, X.; Logothetis, C. J.; Nicolaou, K. C.; Navone, N. M. Cancer Chemother. Pharmacol. 2001, 48, 319-326.
139. (y) Nicolaou, K. C.; Namoto, K.; Ritzen, A.; Ulven, T.; Shoji, M.; Li, J.; D'Amico, G.; Liotta, D.; French, C. T.; Wartmann, M.; Altmann, K.-H.; Giannakakou, P. Chemical Synthesis and Biological Evaluation of cis- and trans-12,13-Cyclopropyl and 12,13-Cyclobutyl Epothilones and Related Pyridine Side Chain Analogues. J. Am. Chem. Soc. 2001, 123, 9313-9323.
140. (z) Nicolaou, K. C.; Ritzen, A.; Namoto, K.; Buet, R. M.; Diaz, J. F.; Andreu, J. M.; Wartmann, M.; Altmann, K.-H.; O'Brate, A.; Giannakakou, P. Chemical Synthesis and Biological Evaluation of Novel Epothilone B and trans-12,13-Cyclopropyl Epothilone B Analogues. Tetrahedron 2002, 58, 6413-6432.
141. (aa) Nicolaou, K. C.; Sasmal, P. K.; Rassias, G.; Reddy, M. V.; Altmann, K.-H.; Wartmann, M.; O'Brate, A.; Giannakakou, P. Design, Synthesis and Biological Properties of Highly Potent Epothilone B Analogs. Angew. Chem., Int. Ed. 2003, 42, 3515-3520.
142. (ab) Buey, R. M.; Diaz, J. F.; Andreu, J. M.; O'Brate, A.; Giannakakou, P.; Nicolaou, K. C.; Sasmal, P. K.; Ritzen, A.; Namoto, K. Interaction of Epothilone Analogs with the Paclitaxel Binding Site: Relationship between Binding Affinity, Microtubule Stabilization, and Cytotoxicity. Chem. Biol. 2004, 11, 225-236.
143. (ac) Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Chemical Biology of Epothilones. Angew. Chem., Int. Ed. 1998, 37, 2014-2045.
144. Heinz, D. W.; Schubert, W.-D.; Höfle, G. Much Anticipated - The Bioactive Conformation of Epothilone and Its Binding to Tubulin. Angew. Chem., Int. Ed. 2005, 44, 1298-1301.
145. (a) Fenical, W. H.; Jensen, P. R.; Lindel, T. Eleutherobin and Its Analogs. U.S. Patent 5,473,057, December 5, 1995.
146. (b) Lindel, T.; Jensen, P. R.; Fenical, W.; Long, B. H.; Casazza, A. M.; Carboni, J.; Fairchild, C. R. Eleutherobin, a New Cytotoxin That Mimics Paclitaxel (Taxol) by Stabilizing Microtubules. J. Am. Chem. Soc. 1997, 119, 8744-8745.
147. Ketzinel, S.; Rudi, A.; Schleyer, M.; Benayahu, Y.; Kashman, Y. Sarcodictyin A and Two Novel Diterpenoid Glycosides, Eleuthosides A and B, from the Soft Coral Eleutherobia aurea. J. Nat. Prod. 1996, 59, 873-875.
148. Ciomei, M.; Albanese, C.; Pastori, W.; Grandi, M.; Pietra, F.; D'Ambrosio, M.; Guerriero, A.; Battistini, C. Sarcodictyins: A New Class of Marine Derivatives with Mode of Action Similar to Taxol. Proc. Am. Assoc. Cancer Res. 1997, 38, 55 (Abstract 30).
149. (a) D'Ambrosio, M.; Guerriero, A.; Pietra, F. Sarcodictyin A and Sarcodictyin B, Novel Diterpenoidic Alcohols Esterified by (E)-N(1)- Methylurocanic Acid. Isolation from the Mediterranean Stolonifer Sarcodictyon roseum. Helv. Chim. Acta 1987, 70, 2019-2027.
150. (b) D'Ambrosio, M.; Guerriero, A.; Pietra, F. Isolation from the Mediterranean Stoloniferan Coral Sarcodictyon roseum of Sarcodictyin C, D, E, and F, Novel Diterpenoidic Alcohols Esterified by (E)- or (Z)-MD-Methylurocamc Acid. Failure of the Carbon-Skeleton Type as a Classification Criterion. Helv. Chim. Acta 1988, 71, 964-976.
151. Nicolaou, K. C.; Pfefferkorn, J.; Xu, J.; Winssinger, N.; Ohshima, T.; Kim, S.; Hosokawa, S.; Vourloumis, D.; van Delft, F.; Li, T. Total Synthesis and Chemical Biology of the Sarcodictyins. Chem. Pharm. Bull. 1999, 47, 1199-1213 and references therein.
152. Nicolaou, K. C.; van Delft, F.; Ohshima, T.; Vourloumis, D.; Xu, J.; Hosokawa, S.; Pfefferkorn, J.; Kim, S.; Li, T. Total Synthesis of Eluetherobin. Angew. Chem., Int. Ed. Engl. 1997, 36, 2520-2524.
153. Nicolaou, K. C.; Ohshima, T.; Hosokawa, S.; van Delft, F. L.; Vourloumis, D.; Xu, J. Y.; Pfefferkorn, J.; Kim, S. Total Synthesis of Eleutherobin and Eleuthosides A and B. J. Am. Chem. Soc. 1998, 120, 8674-8680.
154. (a) Nicolaou, K. C.; Xu, J.-Y.; Kim, S.; Ohshima, T.; Hosokawa, S.; Pfefferkorn, J. Synthesis of the Tricyclic Core of Eleutherobin and Sarcodictyins and Total Synthesis of Sarcodictyin A. J. Am. Chem. Soc. 1997, 119, 11353-11354.
155. (b) Nicolaou, K. C.; Kim, S.; Pfefferkorn, J.; Xu, J.; Ohshima, T.; Hosokawa, S.; Vourloumis, D.; Li, T. Synthesis and Biological Activity of Sarcodictyins. Angew. Chem., Int. Ed. 1998, 37, 1418-1421.
156. (c) Nicolaou, K. C.; Xu, J. Y.; Kim, S.; Pfefferkorn, J.; Ohshima, T.; Vourloumis, D.; Hosokawa, S. Total Synthesis of Sarcodictyins A and B. J. Am. Chem. Soc. 1998, 120, 8661-8673.
157. Nicolaou, K. C.; Winssinger, N.; Vourloumis, D.; Ohshima, T.; Kim, S.; Pfefferkorn, J.; Xu, J.-Y.; Li, T. Solid and Solution Phase Synthesis and Biological Evaluation of Combinatorial Sarcodictyin Libraries. J. Am. Chem. Soc. 1998, 120, 10814-10826.
158. Hamel, E.; Sackett, D. L.; Vourloumis, D.; Nicolaou, K. C. The Coral-Derived Natural Products Eleutherobin and Sarcodictyins A and B: Effects on the Assembly of Purified Tubulin with and without Microtubule-Associated Proteins and Binding at the Polymer Taxoid Site. Biochemistry 1999, 38, 5490-5498.
159. (a) Williams, D. H.; Bardsley, B. The Vancomycin Group of Antibiotics and the Fight against Resistant Bacteria. Angew. Chem., Int. Ed. 1999, 38, 1172-1193.
160. (b) Nicolaou, K. C.; Boddy, C. N. C.; Brasse, S.; Winssinger, N. Chemistry, Biology, and Medicine of the Glycopeptide Antibiotics. Angew. Chem., Int. Ed. 1999, 38, 2096-2152.
161. (a) Nicolaou, K. C.; Cho, S. Y.; Hughes, R.; Winssinger, N.; Smethurst, C.; Labischinski, H.; Endermann, R. Solid- and Solution-Phase Synthesis of Vancomycin and Vancomycin Analogues with Activity against Vancomycin-Resistant Bacteria. Chem.-Eur. J. 2001, 7, 3798-3823.
162. (b) Nicolaou, K. C.; Hughes, R.; Cho, S. Y.; Winssinger, N.; Labischinski, H.; Endermann, R. Synthesis and Biological Evaluation of Vancomycin Dimers with Potent Activity against Vancomycin-Resistant Bacteria. Target-Accelerated Combinatorial Synthesis. Chem.-Eur. J. 2001, 7, 3824-3843.
163. Nicolaou, K. C.; Hughes, R.; Cho, S. Y.; Winssinger, N.; Smethurst, C.; Labischinski, H.; Endermann, R. Target-Accelerated Combinatorial Synthesis and Discovery of Highly Potent Antibiotics Effective against Vancomycin-Resistant Bacteria. Angew. Chem., Int. Ed. 2000, 39, 3823-3828.
164. Stromblad, S.; Cheresh, D. A. Integrins, Angiogenesis, and Vascular Cell Survival. Chem. Biol. 1996, 3, 881-885.
165. Nicolaou, K. C.; Trujillo, J. I.; Chibale, K. Design, Synthesis and Biological Evaluation of Carbohydrate-Based Mimetics of cRGDFV. Tetrahedron 1997, 53, 8751-8778.
166. Nicolaou, K. C.; Trujillo, J. I.; Jandeleit, B.; Chibale, K.; Rosenfeld, M.; Diefenbach, B.; Cheresh, D. A.; Goodman, S. L. Design, Synthesis and Biological Evualation of Nonpeptide Integrin Antagonists. Bioorg. Med. Chem. 1998, 6, 1185-1208.
167. (a) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Selenium-Based Solid-Phase Synthesis of Benzopyrans I: Applications to Combinatorial Synthesis of Natural Products. Angew. Chem., Int. Ed. 2000, 39, 734-739.
168. (b) Nicolaou, K. C.; Cao, G.-Q.; Pfefferkorn, J. A. Selenium-Based Solid-Phase Synthesis of Benzopyrans II: Applications to Combinatorial Synthesis of Medicinally Relevant Small Organic Molecules. Angew. Chem., Int. Ed. 2000, 39, 739-743.
169. (c) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans. J. Am. Chem. Soc. 2000, 122, 9939-9953.
170. (d) Nicolaou, K. C.; Pfefferkorn, J. A.; Mitchell, H. J.; Roecker, A. J.; Barluenga, S.; Cao, G.-Q.; Affleck, R. L.; Lillig, J. E. Natural Product-like Combinatorial Libraries Based on Privileged Structures. 2. Construction of a 10,000-Membered Benzopyran Library by Directed Split-and-Pool Chemistry Using NanoKans and Optical Encoding. J. Am. Chem. Soc. 2000, 122, 9954-9967.
171. (e) Nicolaou, K. C.; Pfefferkorn, J. A.; Barluenga, S.; Mitchell, H. J.; Roecker, A. J.; Cao, G.-Q. Natural Product-like Combinatorial Libraries Based on Privileged Structures. 3. The "Libraries from Libraries" Principle for Diversity Enhancement of Benzopyran Libraries. J. Am. Chem. Soc. 2000, 122, 9968-9976.
172. Nicolaou, K. C.; Roecker, A. J.; Barluenga, S.; Pfefferkorn, J. A.; Cao, G.-Q. Discovery of Novel Antibacterial Agents Active against Methicillin-Resistant Staphylococcus aureus (MRSA) from Combinatorial Benzopyran Libraries. ChemBioChem 2000, 2, 460-465.
173. Nicolaou, K. C.; Pfefferkorn, J. A.; Schuler, F.; Roecker, A. J.; Cao, G.-Q.; Casida, J. E. Combinatorial Synthesis of Novel and Potent Inhibitors of NADH: Ubiquinone Oxidoreductase. Chem. Biol. 2000, 7, 979-992.
174. Nicolaou, K. C.; Evans, R. M.; Roecker, A. J.; Hughes, R.; Downes, M.; Pfefferkorn, J. A. Discovery and Optimization of Non-Steroidal FXR Agonists from Natural Product-like Libraries. Org. Biomol. Chem. 2003, 1, 908-920.
175. Nicolaou, K. C.; Noronha, R. G.; Evans, R. M.; Downes, M. Unpublished results.
176. Tan, C.; de Noronha, R. G.; Roecker, A. J.; Pyrzynska, B.; Khwaja, F.; Zhang, Z.; Zhang, H.; Teng, Q.; Nicholson, A. C.; Giannakakou, P.; Zhou, W.; Olson, J. J.; Pereira, M. M.; Nicolaou, K. C.; Van Meir, E. G. Identification of a Novel Small Molecule Inhibitor of the Hypoxia-Inducible Factor 1α (HIF-1α) Pathway. Cancer Res. 2005, 65, 605-612.
177. The term bisorbicillinoids to describe all dimeric sorbicillin-derived natural products was introduced in the following: Nicolaou, K. C.; Jautelat, R.; Vassilikogiannakis, G.; Baran, P. S.; Simonsen, K. B. Studies Towards Trichodimerol: Novel Cascade Reactions and Polycyclic Frameworks. Chem.-Eur. J. 1999, 5, 3651-3665.
178. (a) Andrade, R.; Ayer, W. A.; Mebe, P. P. The Metabolites of Trichoderma longibrachiatum. Part 1. Isolation of the Metabolites and the Structure of Trichodimerol. Can. J. Chem. 1992, 70, 2526-2535.
179. (b) Warr, G. A.; Veitch, J. A.; Walsh, A. W.; Hesler, G. A.; Pirnik, D. M.; Leet, J. E.; Lin, P.-F. M.; Medina, I. A.; McBrien, K. D.; Forenza, S.; Clark, J. M.; Lam, K. S. BMS-182123, a Fungal Metabolite That Inhibits the Production of TNF-α by Macrophages and Monocytes. J. Antibiot. 1996, 49, 234-240.
180. (c) Abe, N.; Murata, T.; Hirota, A. Novel DPPH Radical Scavengers, Bisorbicillinol and Demethyltrichodimerol, from a Fungus. Biosci., Biotechnol., Biochem. 1998, 62, 661-666.
181. Abe, N.; Murata, T.; Hirota, A. Novel Oxidized Sorbicillin Dimers with 1,1-Diphenyl-2-picrylhydrazyl Radical Scavenging Activity from a Fungus. Biosci., Biotechnol., Biochem. 1998, 62, 2120-2126.
182. Nicolaou, K. C.; Vassilikogiannakis, G.; Simonsen, K. B.; Baran, P. S.; Zhong, Y.-L.; Vidali, V. P.; Pitsinos, E. N.; Couladouros, E. A. Biomimetic Total Synthesis of Bisorbicillinol, Bisorbitutenolide, Trichodimerol, and Designed Analogues of the Bisorbicillinoids. J. Am. Chem. Soc. 2000, 122, 3071-3079.
183. Wellington, K. D.; Cambie, R. C.; Rutledge, P. S.; Bergquist, P. R. Chemistry of Sponges. 19. Novel Bioactive Metabolites from Hamigera tarangaensis. J. Nat. Prod. 2000, 63, 79-85.
184. Nicolaou, K. C.; Gray, D. L. F.; Tae, J. Total Synthesis of Hamigerans and Analogues Thereof. Photochemical Generation and Diels-Alder Trapping of Hydroxy-o-quinodimethanes. J. Am. Chem. Soc. 2004, 126, 613-627.
185. Kim, J. W.; Adachi, H.; Shin-Ya, K.; Hayakawa, Y.; Seto, H. Apoptolidin, a New Apoptosis Inducer in Transformed Cells from Nocardiopsis sp. J. Antibiot. 1997, 50, 628-630.
186. (a) Nicolaou, K. C.; Fylaktakidou, K. C.; Monenschein, H.; Li, Y.; Weyershausen, B.; Mitchell, H. J.; Wei, H. W.; Guntupalli, P.; Hepworth, D.; Sugita, K. Total Synthesis of Apoptolidin: Construction of Enantiomerically Pure Fragments. J. Am. Chem. Soc. 2003, 125, 15433-15442.
187. (b) Nicolaou, K. C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupalli, P.; Mitchell, H. J.; Fylaktakidou, K. C.; Vourloumis, D.; Giannakakou, P.; O'Brate, A. Total Synthesis of Apoptolidin: Completion of the Synthesis and Analogue Synthesis and Evaluation. J. Am. Chem. Soc. 2003, 125, 15443-15454.
188. (a) Arabshahi, L.; Schmitz, F. J. Brominated Tyrosine Metabolites from an Unidentified Sponge. J. Org. Chem. 1987, 52, 3584-3586.
189. (b) Quinoa, E.; Crews, P. Phenolic Constituents of Psammaplysilla. Tetrahedron Lett. 1987, 28, 3229-3232.
190. Kim, D.; Lee, I. S.; Jung, J. H.; Yang, S.-I. Psammaplin A, a Natural Bromotyrosine Derivative from a Sponge, Possesses the Antibacterial Activity against Methicillin-Resistant Staphylococcus auresu and the DNA Gyrase-Inhibitory Activity. Arch. Pharmacal Res. 1999, 22, 25-29.
191. (a) Nicolaou, K. C.; Hughes, R.; Pfefferkorn, J. A.; Barluenga, S.; Roecker, A. J. Combinatorial Synthesis through Disulfide Exchange: Discovery of Potent Psammaplin A Type Antibacterial Agents Active against Methicillin-Resistant Staphylococcus aureus (MRSA). Chem.-Eur. J. 2001, 7, 4280-4295.
192. (b) Nicolaou, K. C.; Hughes, R.; Pfefferkorn J. A.; Barluenga, S. Optimization and Mechanistic Studies of Psammaplin A Type Antibacterial Agents Active against Methicillin-Resistant Staphylococcus aureus (MRSA). Chem.-Eur. J. 2001, 7, 4296-4310.
193. Nicholas, G. M.; Eckmen, L. L.; Ray, S.; Hughes, R. O.; Pfefferkorn, J. A.; Barluenga, S.; Nicolaou, K. C.; Bewley, C. A. Bromotyrosine-Derived Natural and Synthetic Products as Inhibitors of Mycothiol-S-Conjugate Amidase. Bioorg. Med. Chem. Lett. 2002, 12, 2487-2490.
194. (a) Nicolaou, K. C.; Chen, D. Y.-K.; Huang, X.; Ling, T.; Bella, M.; Snyder, S. A. Chemistry and Biology of Diazonamide A: First Total Synthesis and Confirmation of the True Structure. J. Am. Chem. Soc. 2004, 126, 12888-12896.
195. (b) Nicolaou, K. C.; Hao, J.; Reddy, M. V.; Bheema Rao, P.; Rassias, G.; Snyder, S. A.; Huang, X.; Chen, D. Y.-K.; Brenzovich, W. E.; Giuseppone, N.; Giannakakou, P.; O'Brate, A. Chemistry and Biology of Diazonamide A: Second Total Synthesis of Diazonamide A and Biological Investigations. J. Am. Chem. Soc. 2004, 126, 12897-12906.
196. Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. Isolation and Structure Determination of Diazonamides A and B, Unusual Cytotoxic Metabolites from the Marine Ascidian Diazona chinensis. J. Am. Chem. Soc. 1991, 113, 2303-2304.
197. Kunze, B.; Jansen, R.; Sasse, F.; Höfle, G.; Reichenbach, H. Apicularens A and B, New Cytostatic Macrolides from Chondromyces Species (Myxobacteria): Production, Physicochemical and Biological Properties. J. Antibiot. 1998, 51, 1075-1080.
198. 17,18 Z Isomer. Angew. Chem., Int. Ed. 2002, 41, 3701-3704.
199. Nicolaou, K. C.; Kim, D. W.; Baati, R.; O'Brate, A.; Giannakakou, P. Total Synthesis and Biological Evaluation of (-)-Apicularen A and Analogs Thereof. Chem.-Eur. J. 2003, 9, 6177-6191.
200. Kosela, S.; Cao, S.-G.; Wu, X.-H.; Vittal, J. J.; Sukri, T.; Masdianto; Goh, S.-H.; Sim, K.-Y. Lateriflorone, a Cytotoxic Spiroxalactone with a Novel Skeleton, from Garcinia lateriflora B1. Tetrahedron Lett. 1999, 40, 157-160.
201. Asano, J.; Chiba, K.; Tada, M.; Yoshii, T. Cytotoxic Xanthones from Garcinia hanburyi. Phytochemistry 1996, 41, 815-820.
202. Nicolaou, K. C.; Li, J. "Biomimetic" Cascade Reactions in Organic Synthesis: Construction of 4-Oxatricyclo[4.3.1.0]decan-2-one Systems and Total Synthesis of 1-O-Methylforbesione via Tandem Claisen Rearrangement/Diels- Alder Reactions. Angew. Chem., Int. Ed. 2001, 40, 4264-4268.
203. Nicolaou, K. C.; Sasmal, P. K.; Xu, H.; Namoto, K.; Ritzen, A. Total Synthesis of 1-O-Methyllateriflorone. Angew. Chem., Int. Ed. 2003, 42, 4225-4229.
204. Nicolaou, K. C.; Xu, H.; Wartmann, M. Biomimetic Total Synthesis of Gambogin and Rate Acceleration of Pericyclic Reactions in Aqueous Media. Angew. Chem., Int. Ed. 2005, 44, 756-761.
205. Snyder, S. H.; Sabatini, D. M. Immunophilins and the Nervous System. Nat. Med. 1995, 1, 32-37.
206. Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. Total Synthesis of Rapamycin. J. Am. Chem. Soc. 1993, 115, 4419-4420.
207. Chakraborty, T. K.; Weber, H. P.; Nicolaou, K. C. Design and Synthesis of a Rapamycin-Based High Affinity Binding FKBP12 Ligand. Chem. Biol. 1995, 2, 157-161.
208. Nicolaou, K. C.; Koide, K.; Bunnage, M. E. Total Synthesis of Balanol and Designed Analogues. Chem.-Eur. J. 1995, 1, 454-466.
209. Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Molecular Design and Biological Activity of Potent and Selective Protein Kinase Inhibitors Related to Balanol. Chem. Biol. 1995, 2, 601-608.
210. Nicolaou, K. C. Total Synthesis of Brevetoxin B. A Twelve-Year Synthetic Odyssey in Organic Synthesis. Angew. Chem., Int. Ed. Engl. 1996, 35, 589-607.
211. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Koide, K.; Sato, M.; Untersteller, E. Total Synthesis of Truncated Brevetoxin B [AFGHIJK]. J. Am. Chem. Soc. 1994, 116, 9371-9372.
212. Gawley, R. E.; Rein, K. S.; Jeglitsch, G.; Adams, D. J.; Theodorakis, E. A.; Tiebes, J.; Nicolaou, K. C.; Baden, D. G. The Relationship of Brevetoxin "Length" and A-Ring Functionality to Binding and Activity in Neuronal Sodium Channels. Chem. Biol. 1995, 2, 533-541.
213. (a) Nicolaou, K. C.; Vyskocil, S.; Koftis, T. V.; Yamada, Y. M. A.; Ling, T.; Chen, D. Y.-K.; Tang, W.; Petrovic, G.; Frederick, M. O.; Li, Y.; Satake, M. Structural Revision and Total Synthesis of Azaspiracid-1. Part 1: Intelligence Gathering and Tentative Proposal. Angew. Chem., Int. Ed. 2004, 43, 4312-4318.
214. (b) Nicolaou, K. C.; Koftis, T. V.; Vyskocil, S.; Petrovic, G.; Ling, T.; Yamada, Y. M. A.; Tang, W.; Frederick, M. O. Structural Revision and Total Synthesis of Azaspiracid-1. Part 2: Definition of the ABCD Domain and Total Synthesis. Angew. Chem., Int. Ed. 2004, 43, 4318-4324.
215. Satake, M.; Ofuji, K.; Naoki, H.; James, K. J.; Fruey, A.; McMahon, T.; Silke, J.; Yasumoto, T. Azaspiracid, a New Marine Toxin Having Unique Spiro Ring Assemblies, Isolated from Irish Mussels, Mytilus edulis. J. Am. Chem. Soc. 1998, 120, 9967-9968.
216. Ito, E.; Frederick, M. O.; Koftis, T. V.; Tang, W.; Petrovic, G.; Ling, T.; Nicolaou, K. C. Unpublished results.