Synthesis and in vitro leishmanicidal activity of novel [1,2,3]triazolo[1,5-a]pyridine salts

Martín‐Montes, Álvaro; Ballesteros‐Garrido, Rafael; Martín‐Escolano, Rubén; Marı́n, Clotilde; Ramon, Guitierrez-Sanchez; Abarca, Belén; Ballesteros, Rafaél; Sánchez‐Moreno, Manuel

doi:10.1039/c7ra01070b

Cited by 8 publications

(6 citation statements)

References 39 publications

(44 reference statements)

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“…Finally, it is noted that pyridotriazoles have so far received little attention in fields such as medicinal chemistry where nitrogen‐based heterocycles traditionally play dominating roles for example, as privileged scaffolds in drug discovery. A couple of studies suggest that some molecules bearing pyridotriazole structure show antileishmanial activity, and several shown to be efficient DNA photocleavage agents with potential applications in phototherapy [103–106] . There is no doubt that further development in these areas will offer many opportunities.…”

Section: Discussionmentioning

confidence: 99%

“…A couple of studies suggest that some molecules bearing pyridotriazole structure show antileishmanial activity, and several shown to be efficient DNA photocleavage agents with potential applications in phototherapy. [103][104][105][106] There is no doubt that further development in these areas will offer many opportunities. The chemistry of pyridotriazoles is still in its infancy.…”

Section: Discussionmentioning

confidence: 99%

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Progress on Pyridotriazole Chemistry: Synthesis and Transformations

Shen

Yin

et al. 2022

Asian J Org Chem

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Pyridotriazoles are an important subclass of azacyclic compounds. Although known in early 1950s, these compounds aroused little attention in synthetic chemistry for a long time. This situation has changed during the past years as ever-increasing recognitions on their rich properties and reactivities. Particularly, the recent exploration on their potentials as carbene or metal carbene precursors in denitrogenative transformations catalytically or non-catalytically has met considerable success. A lot of new synthetic approaches towards azacyclic compounds such as indolizines, imidazopyridines, pyridoisoquinolinones and pyridoindoles as well as a wide range of functionalized pyridines have been established based on the transformations of pyridotriazoles. Meanwhile, a considerable number of new reactions are developed for the synthesis of pyridotriazoles. In particular, the development of new transition-metal catalyzed tandem reactions has enabled selective generation of diverse pyridotriazoles in efficient manners from simple starting materials. This review surveys main advances in this field over the last two decades and aims to provide an up-to-date overview on the knowledge of pyridotriazole chemistry.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Progress on Pyridotriazole Chemistry: Synthesis and Transformations

Shen

Yin

et al. 2022

Asian J Org Chem

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“…The activities were better than that of the control drug Glucantime, with IC 50 values of 18.0–25.6 μM and 18.4–30.4 μM, respectively. The selectivity index (SI > 56) of compound 40 was higher than the control drug Glucantime (SI < 1) [ 46 ].…”

Section: Antileishmanial Activities Of 123-triazolium Saltsmentioning

confidence: 99%

“…Studies have shown that the triazolium transformated from triazole have good bioactivities [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ]. Molecules containing 1,2,3-triazolium units have been proven to exhibit a variety of biological activities, including antibacterial [ 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ], antifungal [ 5 , 6 , 7 , 8 , 9 , 35 ], anticancer [ 10 , 11 , 36 , 37 , 38 , 39 , 40 , 41 , 42 ], and antileishmanial [ 12 , 43 , 44 , 45 , 46 ] properties.…”

Section: Introductionmentioning

confidence: 99%

Research Advances on the Bioactivity of 1,2,3-Triazolium Salts

Song

Jin

et al. 2023

IJMS

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1,2,3-Triazolium salts have demonstrated significant potential in the fields of medicine and agriculture, exhibiting exceptional antibacterial, antifungal, anticancer, and antileishmanial properties. Moreover, these salts can be utilized as additives or components to produce nano- and fiber-based materials with antibacterial properties. In this review, we summarize several synthetic strategies to obtain 1,2,3-triazolium salts and the structures of 1,2,3-triazolium derivatives with biological activities in the domains of pharmaceuticals, pesticides, and functional materials. Additionally, the structure–activity relationship (SAR) of 1,2,3-triazolium salts with different biological activities has been analyzed. Finally, this review presents the potential applications and prospects of 1,2,3-triazolium salts in the fields of agriculture, medicine, and industrial synthesis.

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“…Although the clinically relevant form of the parasite is the amastigote form, which shows metabolic differences from the extracellular forms, promastigotes can be used for fast screenings of potential compounds (Tempone et al 2005;Martín-Montes et al 2017;Silva et al 2017). Thus, in this study, we evaluated the effect of dihydroquinoline lactone derivatives against promastigote forms of L. (L.) amazonesis in vitro.…”

Section: Antileishmanicidal Activitiesmentioning

confidence: 99%

In vitro leishmanicidal activity of lactone 1,4-dihydroquinoline derivatives against Leishmania (Leishmania) amazonensis

et al. 2018

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A series of lactone 1,4-dihydroquinoline derivatives 4 (4 and 4aa-4cm) was screened for in vitro antileishmanial activity against the promastigote form of Leishmania (Leishmania) amazonensis. Screening results indicate that all of the synthesized compounds significantly reduced the growth of promastigote forms of promastigotes of L. (L.) amazonensis. The cytotoxicity of the most active compounds was also measured on peritoneal macrophage cells. Compounds 4ah and 4bn showed better activities than other derivatives with IC 50 values of 6.22 and 9.05 μM, respectively, with selectivity index 22 and 15 times less toxicity to macrophages cells than to parasites, respectively. The experimental data propose that the compounds may be further investigated against amastigote forms and may contribute to the search of new candidates drugs for treatment of cutaneous leishmaniasis.

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Synthesis and in vitro leishmanicidal activity of novel [1,2,3]triazolo[1,5-a]pyridine salts

Abstract: Leishmaniasis remains a significant worldwide problem; it is of great interest to develop new drugs to fight this disease.

Cited by 8 publications

References 39 publications

Progress on Pyridotriazole Chemistry: Synthesis and Transformations

Progress on Pyridotriazole Chemistry: Synthesis and Transformations

Research Advances on the Bioactivity of 1,2,3-Triazolium Salts

In vitro leishmanicidal activity of lactone 1,4-dihydroquinoline derivatives against Leishmania (Leishmania) amazonensis

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