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Volumn 62, Issue 10, 1997, Pages 3140-3152

A Novel Synthesis of 2′-Modified 2′-Deoxy-4′-thiocytidines from D-Glucose

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXY 2' FLUORO 4' THIOARABINOSYLCYTOSINE; 2' DEOXY 4' THIOCYTIDINE DERIVATIVE; 4' THIOGEMCITABINE; ANTINEOPLASTIC AGENT; CYTARABINE; CYTIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030917732     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9700540     Document Type: Article
Times cited : (124)

References (76)
  • 6
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    • (b) Richman, D. D. Science, 1996, 272, 1886-1888.
    • (1996) Science , vol.272 , pp. 1886-1888
    • Richman, D.D.1
  • 26
    • 0011125471 scopus 로고
    • Townsend, L, Tipson, R. S., Eds.; John Wiley & Sons: New York
    • Fu, Y.-L.; Bobek, M. In Nucleic Acid Chemistry; Townsend, L, Tipson, R. S., Eds.; John Wiley & Sons: New York, 1978; pp 317-323.
    • (1978) Nucleic Acid Chemistry , pp. 317-323
    • Fu, Y.-L.1    Bobek, M.2
  • 51
    • 1542564980 scopus 로고    scopus 로고
    • note
    • The stereochemistry at the anomeric carbon was determined by an NOE analysis of the free nucleoside 10 (minor isomer). It showed 7.1% NOE at the H-3′ proton when irradiated H-6.
  • 58
    • 1542460568 scopus 로고    scopus 로고
    • note
    • Difluoro substituent at the 2′-position potentiates the stability of the glycosidic bond, due to its potent -I effect with destabilizing β-cation.
  • 59
    • 1542669986 scopus 로고    scopus 로고
    • note
    • The stereochemistry at the 1′-position was determined, after deprotection, by comparison of coupling constants of H-1′ with that of gemcitabine described in ref 3a.
  • 71
    • 1542775377 scopus 로고    scopus 로고
    • The stereochemistry of 54 was determined by an NOE analysis: a 1.5% NOE at H-5a was observed when H-2 was irradiated
    • The stereochemistry of 54 was determined by an NOE analysis: a 1.5% NOE at H-5a was observed when H-2 was irradiated.
  • 74
    • 1542775375 scopus 로고    scopus 로고
    • note
    • 4′-ThioFAC administered i.p. daily for 8 consecutive days increased the life span of mice bearing P388 leukemia, showing T/C values of 163% and 205% at doses of 3 and 10 mg/kg/day, respectively. In the same assay, araC showed T/C values of 184% and 200% at doses of 3 and 10 mg/kg/day, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.