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Actin-binding marine macrolides: Total synthesis and biological importance
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Yeung, K.; Paterson, I. Actin-binding marine macrolides: total synthesis and biological importance. Angew. Chem., Int. Ed. 2002, 41, 4632-4653.
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0033118907
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Recent revisions about the chemistry and properties can be found in the following: (a) Roy, R. S.; Gehring, A. M.; Milne, J. C.; Belshaw, P. J.; Walsh, C. T. Thiazole and oxazole peptides: biosynthesis and molecular machinery. Nat. Prod. Rep. 1999, 16, 249-263.
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Recent revisions about the chemistry and properties can be found in the following: (a) Roy, R. S.; Gehring, A. M.; Milne, J. C.; Belshaw, P. J.; Walsh, C. T. Thiazole and oxazole peptides: biosynthesis and molecular machinery. Nat. Prod. Rep. 1999, 16, 249-263.
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3
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9644264170
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Recent advances in the total syntheses of oxazole-containing natural products
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(b) Yeh, V. S. C. Recent advances in the total syntheses of oxazole-containing natural products. Tetrahedron 2004, 60, 11995-12042.
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Tetrahedron
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Yeh, V.S.C.1
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23744461968
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Directly linked polyazoles: Important moieties in natural products
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(c) Riego, E.; Hernández, D.; Albericio, F.; Álvarez, M. Directly linked polyazoles: important moieties in natural products. Synthesis 2005, 1907-1922.
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Synthesis
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Riego, E.1
Hernández, D.2
Albericio, F.3
Álvarez, M.4
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33744958901
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Imidazole, oxazole and thiazole alkaloids
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(d) Jin, Z. Imidazole, oxazole and thiazole alkaloids. Nat. Prod. Rep. 2006, 23, 464-496.
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Jin, Z.1
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0029016680
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Nagatsu, A.; Kajitani, H.; Sakakibara, J. Muscoride A: a new oxazole peptide alkaloid from freshwater cyanobacterium Nostoc muscorum. Tetrahedron Lett. 1995, 36, 4097-4100.
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Nagatsu, A.; Kajitani, H.; Sakakibara, J. Muscoride A: a new oxazole peptide alkaloid from freshwater cyanobacterium Nostoc muscorum. Tetrahedron Lett. 1995, 36, 4097-4100.
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7
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0037067342
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Kehraus, S.; König, G. M.; Wright, A. D. Leucamide A: a new cytotoxic heptapeptide from the australian sponge Leucetta microraphis. J. Org. Chem. 2002, 67, 4989-4992.
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Kehraus, S.; König, G. M.; Wright, A. D. Leucamide A: a new cytotoxic heptapeptide from the australian sponge Leucetta microraphis. J. Org. Chem. 2002, 67, 4989-4992.
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8
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0035857396
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Shin-ya, K.; Wierzba, K.; Matsuo, K.; Ohtani, T.; Yamada, Y.; Furihata, K.; Hayakawa, Y.; Seto, H. Telomestatin, a novel telomerase inhibitor from Streptomyces anulatus. J. Am. Chem. Soc. 2001, 123, 1262-1263.
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(a) Shin-ya, K.; Wierzba, K.; Matsuo, K.; Ohtani, T.; Yamada, Y.; Furihata, K.; Hayakawa, Y.; Seto, H. Telomestatin, a novel telomerase inhibitor from Streptomyces anulatus. J. Am. Chem. Soc. 2001, 123, 1262-1263.
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9
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33748948394
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Total synthesis of (R)-telomestatin
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Doi, T.1
Yoshida, M.2
Shin-ya, K.3
Takahashi, T.4
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10
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0025904512
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Isolation and structure determination of diazonamides A and B, unusual cytotoxic metabolites from the marine ascidian Diazona chinensis
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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.
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Fenical, W.2
Van Duyne, G.D.3
Clardy, J.4
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11
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52449089249
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IB-01211 was isolated from the marine microorganism strain ES7-008: Romero, F, Malet, L, Cañedo, L, M, Cuevas, C, Reyes, J. New Cytotoxic Depsipeptides. WO 2005/000880 A2, 2005
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(a) IB-01211 was isolated from the marine microorganism strain ES7-008: Romero, F.; Malet, L.; Cañedo, L, M.; Cuevas, C.; Reyes, J. New Cytotoxic Depsipeptides. WO 2005/000880 A2, 2005.
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12
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19644386054
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The same structure was proposed for mechercharmycin A, isolated from a marine-derived Thermoactinomices sp: Kanoh, K.; Matsuo.Y.; Adachi, K.; Imagawa, H.; Nishizawa, M.; Shizuri, Y. Mechercharmycins A and B, cytotoxic substances from marine-derived Thermoactinomyces sp. YM3-251. J. Antibiot. 2005, 58, 289-292.
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(b) The same structure was proposed for mechercharmycin A, isolated from a marine-derived Thermoactinomices sp: Kanoh, K.; Matsuo.Y.; Adachi, K.; Imagawa, H.; Nishizawa, M.; Shizuri, Y. Mechercharmycins A and B, cytotoxic substances from marine-derived Thermoactinomyces sp. YM3-251. J. Antibiot. 2005, 58, 289-292.
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13
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33947132690
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Synthesis of IB-01211, a cyclic peptide containing 2,4-concatenated thia- and oxazoles, via Hantzsch macrocyclization
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(a) Hernández, D.; Vilar, G.; Riego, E.; Cañedo, L. M.; Cuevas, C.; Albericio, F.; Álvarez, M. Synthesis of IB-01211, a cyclic peptide containing 2,4-concatenated thia- and oxazoles, via Hantzsch macrocyclization. Org. Lett. 2007, 9, 809-811.
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Hernández, D.1
Vilar, G.2
Riego, E.3
Cañedo, L.M.4
Cuevas, C.5
Albericio, F.6
Álvarez, M.7
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14
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34547764254
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Preparation of penta-azole containing cyclopeptides: Challenges in macrocyclization
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(b) Hernández, D.; Riego, E.; Francesch, A.; Cuevas, C.; Albericio, F.; Álvarez, M. Preparation of penta-azole containing cyclopeptides: challenges in macrocyclization. Tetrahedron 2007, 63, 9862-9870.
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Hernández, D.1
Riego, E.2
Francesch, A.3
Cuevas, C.4
Albericio, F.5
Álvarez, M.6
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15
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14544307527
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YM-216391, a novel cytotoxic cyclic peptide from Streptomyces nobilis
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Sohda, K-y.; Nagai, K.; Yamori, T.; Suzuki, K-i.; Tanaka, A. YM-216391, a novel cytotoxic cyclic peptide from Streptomyces nobilis. J. Antibiot. 2005, 58, 27-31.
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Sohda, K.-Y.1
Nagai, K.2
Yamori, T.3
Suzuki, K.-I.4
Tanaka, A.5
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16
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52449130477
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Hydrolysis of the methyl ester was performed using LiOH in aqueous THF and MeOH as detailed in the Experimental Section
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Hydrolysis of the methyl ester was performed using LiOH in aqueous THF and MeOH as detailed in the Experimental Section.
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17
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52449133023
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These conditions for the thiazole Hantzsch synthesis afforded an easier purification of crude material than conditions obtained before; see ref 8
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These conditions for the thiazole Hantzsch synthesis afforded an easier purification of crude material than conditions obtained before; see ref 8.
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18
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52449117273
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Using the standard conditions of Pd(PPh3)4, PhSiH3, in CH2Cl2
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2.
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19
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52449108772
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50 for YM-216391 in HeLa S3 is 14 nM: Sanada, K.; Takeba-yashi, Y.; Nagai, K.; Hiramoto, M. New antitumor compound. Jpn. Kokai Tokkyo Koho 1999, JP11180997-A; Chem. Abstr. 1999, 131, 101307j.
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50 for YM-216391 in HeLa S3 is 14 nM: Sanada, K.; Takeba-yashi, Y.; Nagai, K.; Hiramoto, M. New antitumor compound. Jpn. Kokai Tokkyo Koho 1999, JP11180997-A; Chem. Abstr. 1999, 131, 101307j.
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52449085116
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Synthesis of natural product derivatives containing 2,4-concatenated oxazoles
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Hernández, D.; Riego, E.; Albericio, F.; Álvarez, M. Synthesis of natural product derivatives containing 2,4-concatenated oxazoles. Eur. J. Org. Chem. 2008, 3389-3396.
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Albericio, F.3
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0032785553
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Caspase inhibitors synthesis of natural product derivatives containing 2,4-concatenated oxazoles
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Ekert, P. G.; Silke, J.; Vaux, D. L. Caspase inhibitors synthesis of natural product derivatives containing 2,4-concatenated oxazoles. Cell Death Differ. 1999, 6, 1081-1086.
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0025341331
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New colorimetric cytotoxicity assay for anticancer drug screening
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Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen
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The three-dimensional structure of apopain/CPP32, a key mediator of apoptosis
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Rotonda, J.; Nicholson, D. W.; Fazil, K. M.; Gallart, Y. G.; Labelle, M.; Peterson, E. P.; Rasper, D. M.; Ruel, R.; Vaillancourt, J. P.; Thornberry, N. A.; Becker, J. W. The three-dimensional structure of apopain/CPP32, a key mediator of apoptosis. Nat. Struct. Biol. 1996, 3, 619-625.
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