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Volumn 63, Issue 39, 2007, Pages 9862-9870

Preparation of penta-azole containing cyclopeptides: challenges in macrocyclization

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CYCLOPEPTIDE; IB 01211; METHYL 2' [2 [2' (2 TERT BUTOXY 1 TERT BUTOXYCARBONYLAMINOETHYL)[2,4']BISOXAZOL 4 YL]THIAZOL 4 YL] 5 PHENYL[2,4']BISOXAZOLYL 4 CARBOXYLIC ACID; NATURAL PRODUCT; PENTETRAZOLE; TELOMESTATIN; UNCLASSIFIED DRUG; YM 216391;

EID: 34547764254     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.06.103     Document Type: Article
Times cited : (23)

References (36)
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    • Recent revisions about the chemistry and properties can be found in:
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    • (1999) Chem. Abstr. , vol.131 , pp. 101
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  • 21
    • 19644386054 scopus 로고    scopus 로고
    • Same structure was proposed for Merchercharmycin A isolated from a marine-derived Thermoactinomices sp. by
    • Same structure was proposed for Merchercharmycin A isolated from a marine-derived Thermoactinomices sp. by. Kanoh K., Matsuo Y., Adachi K., Imagawa H., Nishizawa M., and Shizuri Y. J. Antibiot. 58 (2005) 289
    • (2005) J. Antibiot. , vol.58 , pp. 289
    • Kanoh, K.1    Matsuo, Y.2    Adachi, K.3    Imagawa, H.4    Nishizawa, M.5    Shizuri, Y.6
  • 22
    • 34547736365 scopus 로고    scopus 로고
    • Cañedo, M. L.; Martínez, M.; Sánchez, J. M.; Fernández-Puentes J. L.; Malet, L.; Pérez J.; Romero, F.; García, L. F. Fourth Eur. Conference on Marine Natural Products, Paris, 2005; poster 54.
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    • 33750177934 scopus 로고    scopus 로고
    • A penta-azole related to telomestatin has been recently described by
    • A penta-azole related to telomestatin has been recently described by. Marson M.C., and Saadi M. Org. Biomol. Chem. 4 (2006) 3892
    • (2006) Org. Biomol. Chem. , vol.4 , pp. 3892
    • Marson, M.C.1    Saadi, M.2
  • 29
    • 34547765246 scopus 로고    scopus 로고
    • note
    • 7a was obtained as unique stereoisomer as indicated in its H and C NMR maintaining the configuration of starting l-Ser used in the preparation of 5a and 6a.
  • 30
    • 34547766381 scopus 로고    scopus 로고
    • 2O for a concomitant removal of the trityl group and cyclization following the methods developed by Kelly and co-workers:
  • 34
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    • note
    • The peptide 8 was prepared as a stereoisomer mixture from N-Boc-O-t-Bu-l-Ser-OH and d,l-PhSer-OMe as it is described in Ref. 15. The three stereocenters of 8 were lost in the bisoxazole 10.
  • 35
    • 34547804636 scopus 로고    scopus 로고
    • note
    • 2 (30:70) for 1 h at room temperature.
  • 36
    • 34547741449 scopus 로고    scopus 로고
    • note
    • Assays of coelution in the HPLC of the natural product and the obtained macrocyclic peptide demonstrated that both compounds were different. A sample of IB-01211 was kindly supplied by PharmaMar S.L.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.