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Volumn 54, Issue 43, 1998, Pages 13295-13312

Synthesis of novel 5-fluorouracil derivatives with 1,4-oxaheteroepane moieties

Author keywords

[No Author keywords available]

Indexed keywords

FLUOROURACIL DERIVATIVE; TEGAFUR;

EID: 0032558654     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00815-1     Document Type: Article
Times cited : (14)

References (36)
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    • (1982) Optimization of Drug Delivery , pp. 156-177
    • Bodor, N.1
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    • (Bundgaard, H., ed.) Elsevier, Amsterdam, ch. 1
    • 3. Bundgaard, H. In: Design of Prodrugs (Bundgaard, H., ed.) Elsevier, Amsterdam, 1985, ch. 1, 1-92.
    • (1985) Design of Prodrugs , pp. 1-92
    • Bundgaard, H.1
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    • 4. Hillers, S.; Zhuk, R. A.; Lidaks, M. Dokl. Akad. Nauk USSR, 1967, 176, 332-335; via Chem. Abstr. 1968, 68, 29664j.
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  • 14
    • 0010262764 scopus 로고    scopus 로고
    • note
    • 11. The systematic numbering of the 1,4-oxaheteroepane moiety is as follows: (equation presented)
  • 18
    • 0026620712 scopus 로고
    • 15. This is in contrast with the generally accepted idea that, at least in the field of nucleosides, they are normally formed from a cyclic oxocarbenium ion generated via exocyclic silylation of glycosides. For an exception, see: Jørgensen, T.; Pedersen, E. B.; Nielsen, C. Synthesis, 1992, 1299-1306.
    • (1992) Synthesis , pp. 1299-1306
    • Jørgensen, T.1    Pedersen, E.B.2    Nielsen, C.3
  • 19
    • 0000535305 scopus 로고
    • 16. Gauche rotamers in a chain segment A-B-C-D are preferred electronically to their anti counterparts when A and D either are very electronegative relative to B and C or are unshared electron pairs. For some examples of this, see: (a) Labelle, M.; Morton, H. E.; Guindon, Y.; Springer, J. P. J. Am. Chem. Soc., 1988, 110, 4533-4540;
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 4533-4540
    • Labelle, M.1    Morton, H.E.2    Guindon, Y.3    Springer, J.P.4
  • 22
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    • note
    • 4, the ether oxygen atom and the endocyclic acetal oxygen, probably due to the steric hindrance caused by the isopropoxy group.
  • 23
    • 0010228190 scopus 로고    scopus 로고
    • note
    • 19. When the reaction was carried out on the cis/trans mixture of 5-isopropoxy-3-chloromethyl)-1,4-dioxepane even for 24 h, the starting material was recovered unchanged.
  • 26
    • 0010287025 scopus 로고    scopus 로고
    • note
    • 21. It is not plausible to accept the stabilization of the proximal incipient carbenium ion, which results from the leaving of the methoxy group to form a five-membered ring by the neighbouring-group participation of the chlorine or iodo atoms of 5g and 5h, for the following two reasons: a) trans-5g and trans-5h should be the major compounds but experimentally the cis products predominate, and
  • 27
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    • b) neighbouring-group participation is well documented in carbohydrate chemistry, and is usually Lewis-acid independent; for this, see: Wilson, L. J.; Hager, M. W.; El-Kattan, Y. A.; Liotta, D. C. Synthesis, 1995, 1465-1479. (equation presented)
    • (1995) Synthesis , pp. 1465-1479
    • Wilson, L.J.1    Hager, M.W.2    El-Kattan, Y.A.3    Liotta, D.C.4
  • 28
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    • note
    • 22. We now know the experimental conditions needed to direct the 5-FU nucleophilic-mediated tin (IV) chloride attack to the seven-membered methyl O,O-acetals 5 towards either the cyclic O,N-acetals type 3 or the acyclic ones type 4 (see ref. 12).
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    • note
    • 23. Entrena, A.; Campos, J.; Gómez, J. A.; Gallo, M. A.; Espinosa, A. J. Org. Chem., 1997, 62, 337-349. trans-Configuration of 5-methoxy-3-methyl-1,4-dioxepane 5f was based on the fact that H-3′, which is located cis with respect to the methoxy group, resonated at a markedly lower field than the same proton in its trans isomer.
    • (1997) J. Org. Chem. , vol.62 , pp. 337-349
    • Entrena, A.1    Campos, J.2    Gómez, J.A.3    Gallo, M.A.4    Espinosa, A.5
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    • (1960) Via Chem. Abstr. , vol.54


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.