Abstract::
Heterocyclic compounds containing the quinoline ring play a significant role in organic synthesis and therapeutic
chemistry. Polyfunctionalized quinolines have attracted the attention of many research groups, especially those who work on
the drug discovery and development. These derivatives have been widely explored by the research biochemists and are
reported to possess wide biological activities. This review focuses on the recent progress in the synthesis of heterocyclic
compounds based-quinoline and their… Show more
“…With the optimized reaction conditions in hand, we investigated the scope of the transformation of the imidazothiazolotriazine derivative 1 (Scheme 2), since quinoline is a well-known pharmacophore fragment. 8 It was found that substituents, especially on the oxindole moiety of substrate 1 , dramatically affected the formation of the quinoline derivatives 3 . Target compounds 3a–c with 3-pentyl substituents at the nitrogen atom of the quinoline moiety were formed selectively in good to high yields.…”
A simple method for the synthesis of water soluble potassium 3-[(imidazotriazin-3-yl)thio]-2-oxoquinoline-4-carboxylates was developed based on a new reversible transformation of oxindolylidene derivatives of imidazothiazolotriazine upon treatment with potassium hydroxide. The...
“…With the optimized reaction conditions in hand, we investigated the scope of the transformation of the imidazothiazolotriazine derivative 1 (Scheme 2), since quinoline is a well-known pharmacophore fragment. 8 It was found that substituents, especially on the oxindole moiety of substrate 1 , dramatically affected the formation of the quinoline derivatives 3 . Target compounds 3a–c with 3-pentyl substituents at the nitrogen atom of the quinoline moiety were formed selectively in good to high yields.…”
A simple method for the synthesis of water soluble potassium 3-[(imidazotriazin-3-yl)thio]-2-oxoquinoline-4-carboxylates was developed based on a new reversible transformation of oxindolylidene derivatives of imidazothiazolotriazine upon treatment with potassium hydroxide. The...
“…Among these, quinolones attracted our attention, because of their low cytotoxicity on Vero cells (CC50 > 200 µ M) compared to the other compounds isolated [4] and because of their easy access by synthesis [5,6], facilitating the preparation of various analogs. Furthermore, quinoline derivatives are compounds of choice because they are known to possess a wide range of biological properties including anti-leishmanial activities [7][8][9][10][11][12]. They are considered as privileged structures in drug development [13,14].…”
Section: Resultsmentioning
confidence: 99%
“…13 C NMR (125 MHz, CDCl 3 , 25 [M+H] + 310.1802, found 310.1799. 1,1,3a,9-Tetramethyl-1,1a,1a1,2,3,3a,9,10b-octahydro-10H-4-oxa-9-azacyclobuta [7,1]indeno [5,6-a]naphthalen-10-one (12). To a solution of zanthosimuline 7 (50 mg, 0.16 mmol, 1 eq.)…”
Section: Procedures and Analytical Description Of Compoundsmentioning
Quinoline derivatives and especially quinolones are considered as privileged structures in medicinal chemistry and are often associated with various biological properties. We recently isolated a series of original monoterpenyl quinolones from the bark of Codiaeum peltatum. As this extract was found to have a significant inhibitory activity against a Leishmania species, we decided to study the anti-leishmanial potential of this type of compound. Leishmaniasis is a serious health problem affecting more than 12 million people in the world. Available drugs cause harmful side effects and resistance for some of them. With the aim of finding anti-leishmanial compounds, we developed a synthetic strategy to access natural quinolones and analogues derived from zanthosimuline. We showed the versatility of this natural compound toward cyclization conditions, leading to various polycyclic quinolone-derived structures. The natural and synthetic compounds were evaluated against amastigote forms of Leishmania infantum. The results obtained confirmed the interest of this family of natural compounds but also revealed promising activities for some intermediates deriving from zanthosimuline. Following the same synthetic strategy, we then prepared 14 new analogues. In this work, we identified two promising molecules with good activities against intramacrophage L. infantum amastigotes without any cytotoxicity. We also showed that slight changes in amide functional groups affect drastically their anti-parasitic activity.
“…3 Shiro and coworkers addressed the chemistry and biological activity of quinoline up to 2015, 1 while Dib and coworkers reviewed the recent works on the synthesis and biological potential of quinoline-based compound up to 2021. 23 Hence, there is a need to bridge the gap regarding these potent pharmacological compounds since then to date. Our present review also presents diverse methods for the synthesis of quinoline, which can pave the way for synthetic chemists to achieve various synthetic modifications to access a new series of quinoline motifs for novel drug design.…”
Quinoline, which consists of benzene fused with N-heterocyclic pyridine, has received considerable attention as a core template in drug design because of its broad spectrum of bioactivity.
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