Design, synthesis and antimalarial evaluation of novel thiazole derivatives

Bueno, José María; Cardá, Miguel; Crespo, Benigno; Cuñat, Ana C.; Cózar, Cristina de; León, María Luisa; Marco, J. Alberto; Roda, Nuria; Sanz‐Cervera, Juan F.

doi:10.1016/j.bmcl.2016.07.010

Cited by 60 publications

(22 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On the basis of the large number of biological agents containing thiazole ring and the increasingly numerous examples of thiazole derivatives that are active as antimalarial agents, [ 11–13 ] it was envisaged that the antiplasmodial activity of these novel thiazole derivatives would be worthwhile. The antiplasmodial activity was tested on asynchronic cultures of Plasmodium falciparum (3D7 strain, sensitive to chloroquine [CQ]) at serial dilution for all compounds, which allowed to determine the EC 50 values of each compound (Table 6).…”

Section: Resultsmentioning

confidence: 99%

“…[ 7 ] However, these emerging resistances could be overcome by the synthesis and modification of new biologically active molecules. Several researchers have demonstrated a broad spectrum of biological activities of the 2‐aminothiazole (2‐AT) derivatives as antibacterial, [ 8 ] antifungal, [ 9 ] antitumoral, [ 10 ] antimalarial, [ 11–13 ] antidiabetic, [ 14 ] anti‐inflammatory, [ 15 ] and antiviral [ 16 ] agents (Figure 1). Many authors have suggested that the 2‐AT moiety may be used for fragment‐based drug discovery strategy, because it plays an important role in the treatment of different diseases.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

Cuartas

Robledo

Vélez

et al. 2020

Archiv der Pharmazie

View full text Add to dashboard Cite

A new series of N-substituted pyrazoline derivatives 6a-g, 7a-g, 8a-g, and 9a-g was synthetized by reaction of hydrazine derivatives and chalcone-thiazole hybrids bearing nitrogen mustard 5a-g. The chalcones 5a-g were obtained by Claisen-Schmidt condensation of thiazole-2-nitrogen mustard 3 and selected acetophenones 4a-g. These new compounds 6/7/8/9a-g were screened for their antifungal activity against Cryptococcus neoformans, with IC 50 values of 3.9-7.8 µg/ml for the N-3, 5-dichlorophenyl pyrazolines 9e-g. Interestingly, those compounds show low cytotoxic effects toward erythrocytes (RBC). In addition, N-acetyl (6a,b) and N-formyl pyrazolines (7a, 7b, 7c, and 7g) showed inhibitory activity against methicillinsusceptible Staphylococcus aureus, methicillin-resistant S. aureus, and vancomycinintermediate S. aureus, with the most important minimum inhibitory concentration values ranging from 31.25 to 125 µg/ml. Regarding the antiprotozoal activity, thiazolyl-pyrazolines 9g, 8f, and 7c display high activity against Plasmodium falciparum, Leishmania (V) panamensis, and Trypanosoma cruzi, with EC 50 values of 11.80, 6.46, and 4.98 μM, respectively, and with 7c being approximately 2.6-fold more potent than benznidazole with a selectivity index of 1.61 on U-937 human cells, showing promising potential as a novel antitrypanosomal agent. K E Y W O R D S antibacterial activity, antifungal activity, antiprotozoal activity, chalcone, pyrazoline

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

Cuartas

Robledo

Vélez

et al. 2020

Archiv der Pharmazie

View full text Add to dashboard Cite

show abstract

“…Although including a thioamide linkage between the phenyl and pyrazole ring distinctly increased ALK5 inhibitory activity, as previously shown [16], the thioamide linkage was rather unstable and was slowly cleaved, to release a pyrazole ring, during long-term storage. of 20 It was reported that compounds containing a thiazole and pyrimidine moiety have useful biological activities, such as antibacterial [17], anticancer [18,19], antiviral [20], anti-inflammatory [21], and antimalarial properties [22].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of 3-Substituted-4-(quinoxalin-6-yl) Pyrazoles as Selective ALK5 Inhibitors

Zhao¹,

Guo²,

Xue³

et al. 2018

Preprint

View full text Add to dashboard Cite

The transforming growth factor-β (TGF-β), in which overexpression have been associated with various diseases, has become an attractive molecular target for the treatment of cancers. Three series of 3-substituted-4-(quinoxalin-6-yl) pyrazoles 14a–h, 15a–h, 16a–h, 22a, 22b, 22d, 23a, 23b, 23d, 24b, and 24d were synthesized and evaluated for their activin receptor-like kinase 5 (ALK5) and p38α mitogen activated protein (MAP) kinase inhibitory activity in an enzymatic assays. Among these compounds, the most active compound 16f inhibited ALK5 phosphorylation with an IC50 value of 0.28 µM, with 98% inhibition at 10 µM. Compound 16f also had good selectivity index of >35 against p38α MAP kinase, with 9.0-fold more selective than clinical candidate, compound 3 (LY-2157299). Molecular docking study was performed to identify the mechanism of action of the synthesized compounds and their good binding interactions were observed. ADMET prediction of good active compounds showed that these ones possess good pharmacokinetics and drug-likeness behavior.

show abstract

“…Moreover, pyrazole, 1,3-thiazole and 1,3,4-oxadiazole moieties have been acknowledged to display various biological activities as antimicrobial [15-18], antitumor [19-22] in addition to antiviral [23-27] activities. Recently many research groups have paid attention for the synthesis of pyrazole, thiazole and oxadiazole due to their interesting pharmaceutical activities [28-31]. …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Oxadiazolyl, Pyrazolyl and Thiazolyl Derivatives of Thiophene-2-Carboxamide as Antimicrobial and Anti-HCV Agents

Rizk

Shaaban

Wahab

2017

TOMCJ

View full text Add to dashboard Cite

Introduction:Three series of pyrazole, thiazole and 1,3,4-oxadiazole, derivatives were synthesized starting from 5-amino-4-(hydrazinocarbonyl)-3-methylthiophene-2-carboxamide (2).Methods:All compounds were investigated for their preliminary antimicrobial activity. They were proved to exhibit remarkable antimicrobial activity against Pseudomonas aeruginosa with insignificant activity towards Gram positive bacterial strains and fungi.Results: In-vitro testing of the new compounds on hepatitis-C virus (HCV) replication in hepatocellular carcinoma cell line HepG2 infected with the virus utilizing the reverse transcription polymerase chain reaction technique (RT-PCR) generally showed inhibition of the replication of HCV RNA (–) strands at low concentration, while, eight compounds; 3a, 6, 7a, 7b, 9a, 9b, 10a and 11b proved to inhibit the replication of HCV RNA (+) and (–) strands at very low concentration range 0.08-0.36 μg/mL.Conclusion:Compounds 7b and 11b displayed the highest anti-HCV and antimicrobial activities in this study.

show abstract

Design, synthesis and antimalarial evaluation of novel thiazole derivatives

Cited by 60 publications

References 32 publications

New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

Synthesis and Biological Evaluation of 3-Substituted-4-(quinoxalin-6-yl) Pyrazoles as Selective ALK5 Inhibitors

Synthesis of Oxadiazolyl, Pyrazolyl and Thiazolyl Derivatives of Thiophene-2-Carboxamide as Antimicrobial and Anti-HCV Agents

Contact Info

Product

Resources

About