Purine 2′, 3′-acyclonucleosides: Improved synthesis and antiparasitic actimity

Sufrin, Janice R.; Spiess, Arthur J.; Marasco, Canio J.; Croft, Simon L.; Snowdon, Diane; Yardley, Vanessa; Bacchi, Cyrus J.

doi:10.1016/0960-894x(95)00332-n

Cited by 9 publications

(2 citation statements)

References 13 publications

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“…As illustrated in Scheme , the synthesis of the 2‘,3‘-seco-adenosine analogues 14 and 16 was accomplished by an oxidative−reductive cleavage of 5‘-deoxy-5‘-chloroadenosine to give 5‘-deoxy-5‘-chloro-2‘,3‘-seco-adenosine, 11 , which was aminated and N-alkylated as previously described 5 to give 13 . Deprotection of 13 yielded analogue 14 directly.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Evaluation of Analogues of 5‘-([(Z)-4-Amino-2-butenyl]methylamino)-5‘-deoxyadenosine as Inhibitors of Tumor Cell Growth, Trypanosomal Growth, and HIV-1 Infectivity

et al. 2002

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A well-defined series of 5'-([(Z)-4-amino-2-butenyl]methylamino)-5'-deoxyadenosine analogues was designed and synthesized in order to further ascertain the optimal structural requirements for S-adenosylmethionine decarboxylase inhibition and potentially to augment and perhaps separate their antiproliferative and antitrypanosomal activities. Most structural modifications had a deleterious affect on both the antitrypanosomal and antineoplastic activity of 5'-([(Z)-4-amino-2-butenyl]methylamino)-5'-deoxyadenosine. However, di-O-acetylation of the parent compound produced a potential prodrug that caused markedly pronounced inhibition of trypanosomal and neoplastic cell growth and viability. Moreover, the acetylated derivative of 5'-([(Z)-4-amino-2-butenyl]methylamino)-5'-deoxyadenosine did inhibit HIV-1 growth and infectivity, whereas the parent compound did not.

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Section: Chemistrymentioning

confidence: 99%

Synthesis and Evaluation of Analogues of 5‘-([(Z)-4-Amino-2-butenyl]methylamino)-5‘-deoxyadenosine as Inhibitors of Tumor Cell Growth, Trypanosomal Growth, and HIV-1 Infectivity

et al. 2002

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“…The oxidation of ribo-or 2-hexenepyranosyl nucleosides, with cleavage of the 2 0 -3 0 carbon-carbon bond of the sugar moiety, resulting in dialdehyde formation, is known. 8 The platinum-catalyzed oxidation by air, following the procedure of Moss et al, 9 also failed. Finally, the oxidation of the N 1 -protected 2 0 -deoxyinosine, 5, utilizing the in situgeneration of the N-oxoammonium salt derived from TEMPO 10 and following deprotection with methanolic ammonia, gave key acid 6.…”

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confidence: 99%