Chemical reactivities and oncogenicities of a series of N-hydroxyheterocycles

Lee, Tzoong-Chyh; Teller, Morris N.; Budinger, John M.; Klötzer, W.; Brown, George Bosworth

doi:10.1016/0009-2797(79)90059-0

Cited by 4 publications

(1 citation statement)

References 15 publications

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“…Some studies demonstrated the weak oncogenic activity of 3-hydroxyxanthine 97 (Fig. 24), that may be due to its metabolization by xanthine oxidase that lead to the formation of oncogenic metabolites [154,155]. …”

Section: N-hydroxy-substituted Fused Six-membered Ring Systemsmentioning

confidence: 99%

Bioactive heterocycles containing endocyclic N-hydroxy groups

Rani

Granchi

2015

European Journal of Medicinal Chemistry

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Drug-likeness rules consider N-O single bonds as “structural alerts” which should not be present in a perspective drug candidate. In most cases this concern is correct, since it is known that N-hydroxy metabolites of branded drugs produce reactive species that cause serious side effects. However, this dangerous reactivity of the N-OH species generally takes place when the nitrogen atom is not comprised in a cyclic moiety. In fact, the same type of metabolic behavior should not be expected when the nitrogen atom is included in the ring of an aromatic heterocyclic scaffold. Nevertheless, heterocycles bearing endocyclic N-hydroxy portions have so far been poorly studied as chemical classes that may provide new therapeutic agents. This review provides an overview of N-OH-containing heterocycles with reported bioactivities that may be considered as therapeutically relevant and, therefore, may extend the chemical space available for the future development of novel pharmaceuticals. A systematic treatment of the various chemical classes belonging to this particular family of molecules is described along with a discussion of the biological activities associated to the most important examples.

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Section: N-hydroxy-substituted Fused Six-membered Ring Systemsmentioning

confidence: 99%