Recent synthetic efforts in the preparation of 2- (3,4)-alkenyl (aryl) quinoline molecules towards anti-kinetoplastid agents
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2020-05-26
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Abstract
Leishmaniasis, Chagas disease and African sleeping sickness have been considered some of the most
important tropical protozoan afflictions. As the number of drugs currently available to treat these human
illnesses is severely limited and the majority has poor safety profiles and complicated administration
schedules, actually there is an urgent need to develop new effective, safe and cost-effective drugs.
Because quinoline alkaloids with antiprotozoal activity (quinine, chimanine, cryptolepine or huperzine
groups) were historically and are still essential models for drug research to combat these parasitic
infections, synthetic or semi-synthetic quinoline-based molecules are important for anti-kinetoplastid
drug design approaches and synthetic methods of their preparation become a key task that is the central
subject of this review. Its goal is to highlight the advances in the conventional and current syntheses of
new 2-(3,4)-alkenyl (aryl) quinoline derivatives, which kill the most important kinetoplastid protozoa, –
Leishmania and Trypanosoma and could be useful models for antileishmanial and antitrypanosomal
research. An attempt has been made to present and discuss the more recent contributions in this field
over the period 2015–2019, paying special attention to molecular design, synthetic efforts to new green
reaction conditions for classical methods such as Skraup synthesis, Friedlander synthesis, Conrad ¨ –
Limpach, Doebner–Miller, as well as contemporary methods like Gould–Jacobs, Meth–Cohn and
Povarov reactions. This review includes brief general information on these neglected tropical diseases,
their current chemotherapies, and primary natural models (quinoline alkaloids), suitable for development
of anti-kinetoplastid quinoline-based agents. The main part of the review comprises critical discussion
on the synthesis and chemistry of new quinolines diversely substituted by alkyl (alkenyl, aryl) fragments
on the pyridine part of the quinoline skeleton, which could be considered interesting analogues of
chimanine alkaloids. The methods described in this review were developed with the aim of overcoming
the drawbacks of the traditional protocols using revolutionary precursors and strategies.
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Orozco, D., Kouznetsov, V. V., Bermúdez, A., Vargas Méndez, L. Y., Mendoza Salgado, A. R., & Meléndez Gómez, C. M. (2020). Recent synthetic efforts in the preparation of 2-(3,4)-alkenyl (aryl) quinoline molecules towards anti-kinetoplastid agents. RSC Advances, 10(9), 4876-4898. https://doi.org/10.1039/C9RA09905K