1976
DOI: 10.1021/jm00227a016
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Reactions of 2-acyloxyisobutyryl halides with nucleosides. 6. Synthesis and biological evaluation of some 3'-acyl derivatives of 2,2'-anhydro-1-(.beta.-D-arabinofuranosyl)cytosine hydrochloride

Abstract: The reactions of cytidine with 22 different 2-O-acyloxyisobutyril chlorides lead to the isolation of the corresponding 2,2'-anhydro-1-(3'-O-acyl-beta-d-arabinofuranosyl)cytosine hydrochlorides 9. These compounds, which all show cytotoxicity against HeLa cells in tissue culture, have been examined for antiviral and antileukemic activity. Activity against DNA viruses (vaccinia and Herpes) in tissue culture is maximal in compounds containing acyl groups with 8--12 carbon atoms. Activity against L1210 leukemia in … Show more

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Cited by 34 publications
(13 citation statements)
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“…3'--decanoyl Ara-C was the most active compound among those synthesized in our systematic study (12)(13)(14). The compounds had substantial activity against deoxyribonucleic acid viruses, but were inactive against ribonucleic acid viruses, including measles, Sendai virus, poliovirus, and influenza virus.…”
Section: Resultsmentioning
confidence: 84%
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“…3'--decanoyl Ara-C was the most active compound among those synthesized in our systematic study (12)(13)(14). The compounds had substantial activity against deoxyribonucleic acid viruses, but were inactive against ribonucleic acid viruses, including measles, Sendai virus, poliovirus, and influenza virus.…”
Section: Resultsmentioning
confidence: 84%
“…In fact, the addition of a 3'--acyl group of appropriate chain length (C6 to C02) to cyclo-C was accompanied by enhanced antiviral activity (Table 1). A further increase in chain length, however, led to reduced activity due to the insolubility of such compounds in the culture medium (12)(13)(14)17). The cytotoxicity of these derivatives was examined by two different methods.…”
Section: Discussionmentioning
confidence: 99%
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“…The various 3'--acyl derivatives of cyclo-C and Ara-C were synthesized at Syntex Research, Palo Alto, Calif. (5,6,9). Marboran was kindly provided by N. Ishida, Tohoku University, Sendai, Japan.…”
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confidence: 99%