Biological activities of 3-isoadenosine

Gerzon, Koert; Johnson, Irving S.; Boder, George B.; Cline, J. C.; Simpson, Patrick J.; Speth, Carla; Leonard, Nelson J.; Laursen, Richard A.

doi:10.1016/0005-2787(66)90120-1

Cited by 16 publications

(4 citation statements)

References 36 publications

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“…The chloromercury salt was condensed with 1 in refluxing toluene to give a low yield of 3 isomer and a much higher yield of the 9 isomer. The 3 isomer (4) was debenzoylated and gave a 95% yield of 6-amino-8-bromo-3-/3-D-ribofuranosylpurine (6). Hydrogenolysis of 4 (to give 5) followed by debenzoylation afforded known4 3-0-D-ribofuranosyladenine (7) in 61% yield from 3.…”

mentioning

confidence: 99%

Directed glycosidation of 8-bromoadenine. Synthesis and reactions of 8-substituted 3-glycosyladenine derivatives

Tindall¹,

Robins²,

Tolman³

et al. 1972

J. Org. Chem.

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confidence: 99%

Directed glycosidation of 8-bromoadenine. Synthesis and reactions of 8-substituted 3-glycosyladenine derivatives

Tindall¹,

Robins²,

Tolman³

et al. 1972

J. Org. Chem.

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“…33). (Leonard and Laursen, 1963, 1965; Kumar et al, 1988; Leonard et al, 1986) This modification was associated with various biological activities, most notably against lymphoblastic leukemia cells in vitro (Gerzon et al, 1966). Unfortunately, Iso-A is not particularly stable since it is hyperconjugated and has a tendency to rearrange in an effort to restore the aromaticity, thus resulting in re-forming adenosine (Seley et al, 2003).…”

Section: Other Structural Modificationsmentioning

confidence: 99%

The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold

2018

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This is the first of two invited articles reviewing the development of nucleoside-analogue antiviral drugs, written for a target audience of virologists and other non-chemists, as well as chemists who may not be familiar with the field. Rather than providing a simple chronological account, we have examined and attempted to explain the thought processes, advances in synthetic chemistry and lessons learned from antiviral testing that led to a few molecules being moved forward to eventual approval for human therapies, while others were discarded. The present paper focuses on early, relatively simplistic changes made to the nucleoside scaffold, beginning with modifications of the nucleoside sugars of Ara-C and other arabinose-derived nucleoside analogues in the 1960's. A future paper will review more recent developments, focusing especially on more complex modifications, particularly those involving multiple changes to the nucleoside scaffold. We hope that these articles will help virologists and others outside the field of medicinal chemistry to understand why certain drugs were successfully developed, while the majority of candidate compounds encountered barriers due to low-yielding synthetic routes, toxicity or other problems that led to their abandonment.

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“…This reverses the conformation of the split purine base, which can also be viewed as a C5-substituted pyrimidine. This type of connectivity is also found in Isoadenosine (IsoA) [16,17] and while IsoA exhibited interesting biological properties, it was not extensively pursued because of instability to both acidic and basic conditions, resulting in a 1,3-migration to afford adenosine. [17] …”

Section: Introductionmentioning

confidence: 99%

“Reverse” Carbocyclic Fleximers: Synthesis of a New Class of Adenosine Deaminase Inhibitors

Zimmermann¹,

Sadler²,

O’Daniel³

et al. 2013

Nucleosides, Nucleotides and Nucleic Acids

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A series of flexible carbocyclic pyrimidine nucleosides has been designed and synthesized. In contrast to previously reported “fleximers” from our laboratory, these analogues have the connectivity of the heterocyclic base system “reversed”, where the pyrimidine ring is attached to the sugar moiety, rather than the five membered imidazole ring. As was previously seen with the ribose fleximers, their inherent flexibility should allow them to adjust to enzyme binding site mutations, as well as increase the affinity for atypical enzymes. Preliminary biological screening has revealed surprising inhibition of adenosine deaminase, despite their lack of resemblance to adenosine.

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Biological activities of 3-isoadenosine

Cited by 16 publications

References 36 publications

Directed glycosidation of 8-bromoadenine. Synthesis and reactions of 8-substituted 3-glycosyladenine derivatives

Directed glycosidation of 8-bromoadenine. Synthesis and reactions of 8-substituted 3-glycosyladenine derivatives

The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold

“Reverse” Carbocyclic Fleximers: Synthesis of a New Class of Adenosine Deaminase Inhibitors

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