Antileishmanial activity of quinazoline derivatives: Synthesis, docking screens, molecular dynamic simulations and electrochemical studies

Mendoza-Martínez, César; Galindo-Sevilla, Norma; Correa‐Basurto, José; Ugalde‐Saldívar, Víctor M.; Rodríguez-Delgado, Rosa Georgina; Hernández-Pineda, Jessica; Padierna-Mota, Cecilia; Flores-Álamo, Marcos; Hernández‐Luis, Francisco

doi:10.1016/j.ejmech.2014.12.051

Cited by 46 publications

(28 citation statements)

References 32 publications

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“…Leishmaniasis, otherwise known as African trypanosomiasis or Chagas disease are vector-borne infectious diseases whose causative agent are parasites of the kinetoplastida order (WHO, 2016;Mendoza-Martínez et al, 2015). It is quite alarming to note that approximately 1.5 million of new cases of cutaneous leishmaniasis emerge every year while there is an outbreak of about 500 000 of new cases of visceral diseases in similar vein.…”

Section: Antileishmanial Activitymentioning

confidence: 99%

“…A series of quina-zoline-2,4,6-triamine were synthesized and evaluated in vitro against Leishmania mexicana. Among them, N 6 -(ferrocenmethyl)quinazolin-2,4,6-triamine showed activity on promastigotes and intracellular amastigotes as well as low cytotoxicity in mammalian cells (Mendoza-Martínez et al, 2015) as shown in Figure 5. In the recent review by Sangshetti et al (2015) about anti-leishmanial drug discovery, quinazoline core was not left out.…”

Section: Antileishmanial Activitymentioning

confidence: 99%

“…Structure-activity relationship studies have revealed the significant role of 4-anilino substituent in the antitumor diversity of quinazoline motifs. From the screening of a series of structurally related 4-anilinoquinazoline with N-adamantyl formamide in 4-position 10a-f; specifically, compound 10d (R1 = H; R2 = Cl; R3 = 4-morpholinyl-(CH2)3; R4 = CH3), with an IC50 value of 2.06 μM against A431 cells with the wild-type EGFR and of 0.009 μM against the gefitinib-sensitive cells (Mendoza-Martínez et al, 2015) ( Figure 6). It displayed efficacy that was about 5-fold active than the lead compound to inhibit the growth of the cells harboring the EGFR (T790M) mutant (Yu et al, 2016;Mendoza-Martínez et al, 2015).…”

Section: Antitumor Activitymentioning

confidence: 99%

“…From the screening of a series of structurally related 4-anilinoquinazoline with N-adamantyl formamide in 4-position 10a-f; specifically, compound 10d (R1 = H; R2 = Cl; R3 = 4-morpholinyl-(CH2)3; R4 = CH3), with an IC50 value of 2.06 μM against A431 cells with the wild-type EGFR and of 0.009 μM against the gefitinib-sensitive cells (Mendoza-Martínez et al, 2015) ( Figure 6). It displayed efficacy that was about 5-fold active than the lead compound to inhibit the growth of the cells harboring the EGFR (T790M) mutant (Yu et al, 2016;Mendoza-Martínez et al, 2015). The synthesis, structural elucidation as well as in vitro antitumor properties of ruthenium(ii) polypyridyl complexes of 4-anilinoquinazolines was recently reported (Du et al, 2016).…”

Section: Antitumor Activitymentioning

confidence: 99%

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Quinazoline pharmacophore in therapeutic medicine

Ajani

Aderohunmu

Umeokoro

et al. 2016

Bangladesh J Pharmacol

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This present study comprehensively expatiates the functionalized utilization of quinazoline scaffolds in drug development and furnishes latest updates in pharmacological appositeness of its derivatives in order to reveal novel pathways for therapeutic targets. It traverses numerous biological potentials of quinazoline in the contemporary time to allow researchers' unhindered access to the beneficial role of quinazoline in fighting infectious diseases for future drug discovery. This work provides broad overview of medicinal survey of quinazoline chemistry valuable in the discovery of more efficient clinical trials and to summarize the most promising molecular targets for drug design. Article Info

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Section: Antileishmanial Activitymentioning

confidence: 99%

Section: Antileishmanial Activitymentioning

confidence: 99%

Section: Antitumor Activitymentioning

confidence: 99%

Section: Antitumor Activitymentioning

confidence: 99%

See 2 more Smart Citations

Quinazoline pharmacophore in therapeutic medicine

Ajani

Aderohunmu

Umeokoro

et al. 2016

Bangladesh J Pharmacol

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“…[29] Here, we report on the first tricyclic quinazoline alkaloids connected to ferrocene with formation of a more extended π system.…”

Section: Introductionmentioning

confidence: 97%

Tricyclic Quinazoline Alkaloids Conjugated to Ferrocene: Synthesis, Structure, and Redox Behavior of Ferrocenylmethylene‐Substituted 7H‐Deoxyvasicinones

et al. 2015

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Abstract:The first organometallic derivatives of tricyclic quinazoline derivatives are prepared by condensation of the active C-3 methylene group of 7H-deoxyvasicinones with ferrocenecarbaldehyde. By following this route the conjugated parent alkaloid and derivatives with nitro, amino, as well as some alkanoylamino groups at C-7 were attached at the ferrocene moiety, thereby significantly extending the π system. In addition, the parent compound was subjected to the reaction by treatment with ferrocene-1,1′-dicarbaldehyde, giving rise to the

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Synthesis of Quinazolin‐2,4,6‐triamine Derivatives as Non‐purine Xanthine Oxidase Inhibitors and Exploration of Their Toxicological Potential**

Lopez‐Sanchez,

del Carmen Garcia‐Rodriguez,

Aguayo‐Ortiz

et al. 2023

ChemMedChem

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In this work, a new set of quinazolin‐2,4,6‐triamine derivatives were synthesized to explore their potential biological activity as xanthine oxidase (XO) inhibitors, superoxide scavengers and screening of their toxicological profile. Among all the synthesized compounds, B1 exhibited better inhibitory activity against bovine xanthine oxidase (bXO) than allopurinol (IC50=1.56 μM and IC50=6.99 μM, respectively). As superoxide scavengers, B1, B2 and B13 exhibited a better effect than allopurinol (97.3 %, 82.1 %, 87.4 % and 69.4 %, respectively). Regarding the toxicological profile, B1 was less cytotoxic than methotrexate on HCT‐15 cancer cells. Apoptosis results obtained in cells of female and male mice, showed that B1 and B2 presented a similar behaviour to CrO3 (positive control) with respect to the average frequency to induce apoptosis; while B13 apoptosis induced effect was similar to DMSO and control group. Finally, B1, B2, B13 did not induce genotoxicity in a micronuclei murine model compared to CrO3.

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Antileishmanial activity of quinazoline derivatives: Synthesis, docking screens, molecular dynamic simulations and electrochemical studies

Cited by 46 publications

References 32 publications

Quinazoline pharmacophore in therapeutic medicine

Quinazoline pharmacophore in therapeutic medicine

Tricyclic Quinazoline Alkaloids Conjugated to Ferrocene: Synthesis, Structure, and Redox Behavior of Ferrocenylmethylene‐Substituted 7H‐Deoxyvasicinones

Synthesis of Quinazolin‐2,4,6‐triamine Derivatives as Non‐purine Xanthine Oxidase Inhibitors and Exploration of Their Toxicological Potential**

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