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Volumn 65, Issue 15, 2000, Pages 4641-4647

Stereoelectronic effect on one-electron reductive release of 5-Fluorouracil from 5-fluoro-1-(2'-oxocycloalkyl)uracils as a new class of radiation-activated antitumor prodrugs

Author keywords

[No Author keywords available]

Indexed keywords

5 FLUORO 1 (2' OXOPROPYL)URACIL; ANTINEOPLASTIC AGENT; FLUOROURACIL; FLUOROURACIL DERIVATIVE; PRODRUG; TRANS 5 FLUORO 1 (5' TERT BUTYL 2' OXOCYCLOHEXYL)URACIL; UNCLASSIFIED DRUG;

EID: 0034725814     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000245u     Document Type: Article
Times cited : (34)

References (35)
  • 7
    • 0004099105 scopus 로고
    • American Chemical Society: Washington, DC
    • (b) Denny, W. A. Cancer Chemotherapeutic Agents; American Chemical Society: Washington, DC, 1995; pp 483-497.
    • (1995) Cancer Chemotherapeutic Agents , pp. 483-497
    • Denny, W.A.1
  • 16
    • 0343995313 scopus 로고    scopus 로고
    • Unpublished data
    • (a) Mori, M.; Teshima, S.; Hatta, H.; Fujita, S.; Taniguchi, R.; Nishimoto, S. Unpublished data. In the pulse radiolysis of 2 in Ar-purged aqueous solution containing 2-methyl-2-propanol using pulsed electron beam with a half-width duration 1 μs, we observed a transient absorption spectrum with a maximum wavelength at 340 nm which was almost identical with that of 5-fluorouracil radical anion (see also ref 11b).
    • Mori, M.1    Teshima, S.2    Hatta, H.3    Fujita, S.4    Taniguchi, R.5    Nishimoto, S.6
  • 18
    • 0342688931 scopus 로고    scopus 로고
    • note
    • The number of molecules produced or changed per 1 J of radiation energy absorbed by the reaction system (see also ref 2).
  • 24
    • 0034677756 scopus 로고    scopus 로고
    • A computational study on the electronic nature of radical anions generated from various N1-substituted 5-fluorouracil derivatives and their preferred fragmentation pathway has been recently reported (Borosky, G. L.; Nishimoto, S.; Pierini, A B. J. Mol. Struct. THEOCHEM 2000, 499, 151-160). This indicated that while the most stable radical anion is of π-type for general N1-substituents, increase in the electron affinity of the N1-substituents can enhance the spin density at the C(1′)-N(1) bond favoring the formation of a C(1′)-N(1) isomer of radical anion intermediates. According to this result, it seems plausible that the electron-adduct of 5-fluorouracil derivatives 3-11 bearing 2′-oxoalkyl substituents at N(1) could have a (π* + σ*) SOMO energy level closer to or even lower than the σ* level.
    • (2000) J. Mol. Struct. THEOCHEM , vol.499 , pp. 151-160
    • Borosky, G.L.1    Nishimoto, S.2    Pierini, A.B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.