Anti-leishmanial effect of spiro dihydroquinoline-oxindoles on volume regulation decrease and sterol biosynthesis of Leishmania braziliensis

Leañez, Jacques; Núñez, Jorge; García-Marchán, Yael; Sojo, Felipe; Arvelo, Francisco; Rodríguez, Daniel Salazar; Buscema, Ignacio; Álvarez-Aular, Álvaro; Forero, Josué S. Bello; Kouznetsov, Vladímir V.; Serrano-Martín, Xenón

doi:10.1016/j.exppara.2019.01.011

Cited by 23 publications

(23 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Another group of spirooxindole derivatives 170 – 172 , containing a dihydroquinoline group, was prepared by an imino Diels–Alder reaction between ketimine-isatins and trans-isoeugenol, using boron trifluoride etherate as acid catalyst [ 116 ]. Alternatively, two other spiro compounds were synthetized by a three-component reaction of isatin, aniline and thioglycolic acid and by a two-component reaction of isatin and thioglycolic acid ( Scheme 16 ).…”

Section: Recent Development Of Indole-based Small Molecules Targeting Malaria Trypanosomiasis and Leishmaniasismentioning

confidence: 99%

Recent Progress in the Development of Indole-Based Compounds Active against Malaria, Trypanosomiasis and Leishmaniasis

Pacheco

Santos

2022

Molecules

View full text Add to dashboard Cite

Human protozoan diseases represent a serious health problem worldwide, affecting mainly people in social and economic vulnerability. These diseases have attracted little investment in drug discovery, which is reflected in the limited available therapeutic arsenal. Authorized drugs present problems such as low efficacy in some stages of the disease or toxicity, which result in undesirable side effects and treatment abandonment. Moreover, the emergence of drug-resistant parasite strains makes necessary an even greater effort to develop safe and effective antiparasitic agents. Among the chemotypes investigated for parasitic diseases, the indole nucleus has emerged as a privileged molecular scaffold for the generation of new drug candidates. In this review, the authors provide an overview of the indole-based compounds developed against important parasitic diseases, namely malaria, trypanosomiasis and leishmaniasis, by focusing on the design, optimization and synthesis of the most relevant synthetic indole scaffolds recently reported.

show abstract

Section: Recent Development Of Indole-based Small Molecules Targeting Malaria Trypanosomiasis and Leishmaniasismentioning

confidence: 99%

Recent Progress in the Development of Indole-Based Compounds Active against Malaria, Trypanosomiasis and Leishmaniasis

Pacheco

Santos

2022

Molecules

View full text Add to dashboard Cite

show abstract

“…The indolone‐connected substituted dihydroquinoline derivatives appended with an aromatic ring at 4‐position have exerted appreciable antileishmanial potencies towards L. braziliensis strain at cytotoxic level (CC 50 >300 μM) [46] . The pharmacological evaluation has revealed moderate antileishmanial activity with IC 50 values of less than 50 μM.…”

Section: Antileishmanial Activitymentioning

confidence: 99%

“…Depiction of the structures of potent inhibitors of L. donovani. [45][46][47] larial drugs and antileishmanial drugs are emphasized and importance for structural features are explained. The review indicates that quinoline can be used to engineer pharmacological agents with enhanced activity.…”

Section: Future Perspectivesmentioning

confidence: 99%

Quinoline: A Promising Scaffold in Recent Antiprotozoal Drug Discovery

Dorababu¹

2021

ChemistrySelect

View full text Add to dashboard Cite

Protozoal infections malaria and leishmania have become most prevalent in recent times. A high death rate is reported world‐wide because of these diseases. Although there are only a few antiprotozoal drugs but could not be used anymore to cure protozoal diseases because of their toxic effects. Despite the non‐ceasing attempts to discover the drugs to cure malaria and leishmania, efficient drug‐design with low toxicity could not be achieved. A wide range of heterocyclic pharmacophores have been utilized to design efficient drugs. Amongst these heterocycles, quinoline bicycle is given a high priority, since a vast literature of quinoline derivatives relevant to potent pharmacological properties is available. The efficacy of the drugs lies upon the good bioavailability, favorable pharmacokinetics, and pharmacodynamics of the molecule. In view of these, the continual efforts are being put to bring about potent anti‐protozoal agents to clinical stage. In this review, the potential research done recently towards the anti‐protozoal drug‐design and discovery is compiled comprehensively. The importance of structural features attributed to remarkable activity is described taking consideration of structure‐activity relationship. Safety Index (SI), crucial for clinical efficiency of a drug is compared amongst a set of derivatives which involve inhibitory properties, in addition to the cytotoxic effects.

show abstract

“…Isatin (1H-indole-2,3-dione) is a versatile heterocyclic compound which has been attracting the attention of medicinal chemists worldwide as a synthetic building block due to the various biological activities of its derivatives. Among the latter, compounds bearing an oxindole scaffold constitute a group of promising compounds endowed with significant biological activities, such as anticonvulsant, antimicrobial, antitubercular [10], antileishmanial [11], anti-HIV [12], antioxidative [13], antiproliferative [14], and anticancer [15,16] activities.…”

Section: Introductionmentioning

confidence: 99%

Novel N-Substituted Amino Acid Hydrazone-Isatin Derivatives: Synthesis, Antioxidant Activity, and Anticancer Activity in 2D and 3D Models In Vitro

Tumosienė

Jonuškienė

Kantminienė

et al. 2021

IJMS

View full text Add to dashboard Cite

A series of novel mono and bishydrazones each bearing a 2-oxindole moiety along with substituted phenylaminopropanamide, pyrrolidin-2-one, benzimidazole, diphenylmethane, or diphenylamine fragments were synthesized, and their anticancer activities were tested by MTT assay against human melanoma A375 and colon adenocarcinoma HT-29 cell lines. In general, the synthesized compounds were more cytotoxic against HT-29 than A375. 3-((4-Methoxyphenyl)(3-oxo-3-(2-(2-oxoindolin-3-ylidene)hydrazinyl)propyl)amino)-N’-(2-oxoindolin-3-ylidene)propanehydrazide and (N’,N’’’)-1,1’-(methylenebis(4,1-phenylene))bis(5-oxo-N’-(2-oxoindolin-3-ylidene)pyrrolidine-3-carbohydrazide) were identified as the most active compounds against HT-29 in 2D and 3D cell cultures. The same compounds showed the highest antioxidant activity among the synthesized compounds screened by ferric reducing antioxidant power assay (FRAP). Their antioxidant activity is on par with that of a well-known antioxidant ascorbic acid.

show abstract

Anti-leishmanial effect of spiro dihydroquinoline-oxindoles on volume regulation decrease and sterol biosynthesis of Leishmania braziliensis

Cited by 23 publications

References 44 publications

Recent Progress in the Development of Indole-Based Compounds Active against Malaria, Trypanosomiasis and Leishmaniasis

Recent Progress in the Development of Indole-Based Compounds Active against Malaria, Trypanosomiasis and Leishmaniasis

Quinoline: A Promising Scaffold in Recent Antiprotozoal Drug Discovery

Novel N-Substituted Amino Acid Hydrazone-Isatin Derivatives: Synthesis, Antioxidant Activity, and Anticancer Activity in 2D and 3D Models In Vitro

Contact Info

Product

Resources

About