Synthesis of 2-substituted primaquine analogs as potential antimalarials

Rv, Shetty; Cd, Blanton

doi:10.1021/jm00207a030

Cited by 15 publications

(5 citation statements)

References 2 publications

(3 reference statements)

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“…This produced almost 200 PQ derivatives (Tables 2-4) bearing diverse groups in one or more given positions of the ring [6,46,[161][162][163][164][165][166][167][168][169][170][171][172][173][174][175][176][177][178][179]. Globally, the most favourable substituent insertions towards anti-malarial activity where those of methyl groups at positions 4 and 2, tert-butyl at position 2, simultaneous insertion of ethyl substituents at positions 2 and 4 and pentyloxy at position 5, as well as insertion at position 5 of alkoxy, fluoro, and 3-or 4-substituted phenoxy groups [51,163].…”

Section: Modifications At the Quinoline Ringmentioning

confidence: 99%

Primaquine revisited six decades after its discovery

Vale¹,

Moreira²,

Gomes³

2009

European Journal of Medicinal Chemistry

321

308

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Section: Modifications At the Quinoline Ringmentioning

confidence: 99%

Primaquine revisited six decades after its discovery

Vale¹,

Moreira²,

Gomes³

2009

European Journal of Medicinal Chemistry

321

308

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“…Another study on styrylquinolines reported the in vitro activity of the original styrylquinolines on L. panamensis [ 63 ]. In parallel, other series have been prepared with the aim of optimizing 2-substituted quinolines with similar biological properties [ 64 , 65 , 66 , 67 ]. Moreover, quinoline-2-one derivatives exhibited in vitro antileishmanial activity in the range from 1 to 15 µM [ 68 , 69 , 70 , 71 ].…”

Section: The Potential Of 2-substituted Quinolines As Antileishmanial...mentioning

confidence: 99%

The Potential of 2-Substituted Quinolines as Antileishmanial Drug Candidates

et al. 2022

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There is a need for new, cost-effective drugs to treat leishmaniasis. A strategy based on traditional medicine practiced in Bolivia led to the discovery of the 2-substituted quinoline series as a source of molecules with antileishmanial activity and low toxicity. This review documents the development of the series from the first isolated natural compounds through several hundred synthetized molecules to an optimized compound exhibiting an in vitro IC50 value of 0.2 µM against Leishmania donovani, and a selectivity index value of 187, together with in vivo activity on the L. donovani/hamster model. Attempts to establish structure–activity relationships are described, as well as studies that have attempted to determine the mechanism of action. For the latter, it appears that molecules of this series act on multiple targets, possibly including the immune system, which could explain the observed lack of drug resistance after in vitro drug pressure. We also show how nanotechnology strategies could valorize these drugs through adapted formulations and how a mechanistic targeting approach could generate new compounds with increased activity.

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“…Since resistance to the 8-aminoquinolines does not appear to be a problem, numerous efforts to create new PrimQ-analogues with improved potential prophylactic action and/or less toxic [167,168]. Now two promising antimalarial agents, 2-tert-butylprimaquine (64) and tafenoquine (65), are available.…”

Section: Design Of Novel Primq Hybridsmentioning

confidence: 99%