Technology of Preparing 8-Hydroxy-5-nitroquinoline

Исаев, А. А.; Lomovskii, I. I.; Korolev, K. G.; Karimov, R. K.

doi:10.1007/s10593-005-0273-6

Cited by 11 publications

(2 citation statements)

References 7 publications

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“…29 Aminoquinolines 34 and 45 were prepared by subjecting nitroquinolines 5 and 44 , respectively, to catalytic hydrogenation. 30 …”

Section: Resultsmentioning

confidence: 99%

“…Nitrosoquinolinol 33 was prepared according to the reported procedure by treating 8-hydroxyquinoline 1 with nitrous acid. 29 Aminoquinolines 34 and 45 were prepared by subjecting nitroquinolines 5 and 44, respectively, to catalytic hydrogenation. 30 Initially we attempted monoalkylation of aminoquinoline 34 using 1.2 equivalents of an aldehyde as shown in Chart 1, eqn 5; but we obtained a mixture of mono and dialkylated products.…”

Section: Synthesis Of Oxine Derivativesmentioning

confidence: 99%

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Substituted oxines inhibit endothelial cell proliferation and angiogenesis

et al. 2012

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Two substituted oxines, nitroxoline (5) and 5-chloroquinolin-8-yl phenylcarbamate (22), were identified as hits in a high-throughput screen aimed at finding new anti-angiogenic agents. In a previous study, we have elucidated the molecular mechanism of antiproliferative activity of nitroxoline in endothelial cells, which comprises of a dual inhibition of type 2 human methionine aminopeptidase (MetAP2) and sirtuin 1 (SIRT1). Structure–activity relationship study (SAR) of nitroxoline offered many surprises where minor modifications yielded oxine derivatives with increased potency against human umbilical vein endothelial cells (HUVEC), but with entirely different as yet unknown mechanisms. For example, 5-nitrosoquinolin-8-ol (33) inhibited HUVEC growth with sub-micromolar IC50, but did not affect MetAP2 or MetAP1, and it only showed weak inhibition against SIRT1. Other sub-micromolar inhibitors were derivatives of 5-aminoquinolin-8-ol (34) and 8-sulfonamidoquinoline (32). A sulfamate derivative of nitroxoline (48) was found to be more potent than nitroxoline with the retention of activities against MetAP2 and SIRT1. The bioactivity of the second hit, micromolar HUVEC and MetAP2 inhibitor carbamate 22 was improved further with an SAR study culminating in carbamate 24 which is a nanomolar inhibitor of HUVEC and MetAP2.

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“…29 Aminoquinolines 34 and 45 were prepared by subjecting nitroquinolines 5 and 44 , respectively, to catalytic hydrogenation. 30 …”

Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Oxine Derivativesmentioning

confidence: 99%

Substituted oxines inhibit endothelial cell proliferation and angiogenesis

et al. 2012

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Technology of Preparing 8‐Hydroxy‐5‐nitroquinoline.

Исаев¹,

Lomovskii²,

Korolev³

et al. 2006

ChemInform

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Anion-π interactions in layered structures of salts of 5-(hydroxyimino) quinolin-8-one and related salts

Khakhlary

Baruah

2015

J Chem Sci

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Relevance of anion-π interactions in chloride, bromide, nitrate and perchlorate salts of 5-(hydroxyimino)quinolin-8-one are discussed. Structures of nitrate salt of 5-aminoquinoline as well as nitrate salt of 4-hydroxyquinazoline are compared with the structure of nitrate salt of 5-(hydroxyimino)quinolin-8-one. From such a comparison, two different arrangements of nitrate ions with respect to the respective cations are discerned. Nitrate ions are sandwiched between aromatic planes of cations in nitrate salts of 5-(hydroxyimino)quinolin-8-one or 4-hydroxyquinazoline; whereas, nitrate ions are in oblique positions with respect to aromatic planes of counter cations in nitrate salt of 5-aminoquinoline. Binding constants of different nitrate salts in solution are determined by UV-visible spectroscopic titrations. Solution study shows formation of ion-pairs of these salts in solution.

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Technology of Preparing 8-Hydroxy-5-nitroquinoline

Cited by 11 publications

References 7 publications

Substituted oxines inhibit endothelial cell proliferation and angiogenesis

Substituted oxines inhibit endothelial cell proliferation and angiogenesis

Technology of Preparing 8‐Hydroxy‐5‐nitroquinoline.

Anion-π interactions in layered structures of salts of 5-(hydroxyimino) quinolin-8-one and related salts

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