Preliminary antifungal and cytotoxic evaluation of synthetic cycloalkyl[b]thiophene derivatives with PLS-DA analysis

Souza, Beatriz Constante; Oliveira, Tiago De; Aquino, Thiago Mendonça de; Lima, Maria de Fátima Rocha de; Pitta, Ivan da Rocha; Galdino, Suely Lins; Lima, Edeltrudes de Oliveira; Gonçalves-Silva, Teresinha; Militão, Gardênia Carmen Gadelha; Scotti, Luciana; Scotti, Marcus Tullius; Mendonça, Francisco Jaime Bezerra

doi:10.2478/v10007-012-0017-y

Cited by 35 publications

(12 citation statements)

References 17 publications

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“…For performing chemometric analysis (Principal Component Analysis (PCA)), and Partial Least Square Regression (PLS) the MIC values for Aspergillus fumigatus ATCC-16913 were used [21,39,40]. Inhibitory activity data of the investigated compounds determined as micrograms per milliliter were converted to the negative logarithms of molar MICs (log1/ c MIC ) (Table 2) which was used as a dependent variables set in this study.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structure-Activity Relationships (SAR) and in Silico Studies of Coumarin Derivatives with Antifungal Activity

Araújo

Guerra

Lima

et al. 2013

IJMS

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The increased incidence of opportunistic fungal infections, associated with greater resistance to the antifungal drugs currently in use has highlighted the need for new solutions. In this study twenty four coumarin derivatives were screened in vitro for antifungal activity against strains of Aspergillus. Some of the compounds exhibited significant antifungal activity with MICs values ranging between 16 and 32 μg/mL. The structure-activity relationships (SAR) study demonstrated that O-substitutions are essential for antifungal activity. It also showed that the presence of a short aliphatic chain and/or electron withdrawing groups (NO2 and/or acetate) favor activity. These findings were confirmed using density functional theory (DFT), when calculating the LUMO density. In Principal Component Analysis (PCA), two significant principal components (PCs) explained more than 60% of the total variance. The best Partial Least Squares Regression (PLS) model showed an r2 of 0.86 and q2cv of 0.64 corroborating the SAR observations as well as demonstrating a greater probe N1 interaction for active compounds. Descriptors generated by TIP correlogram demonstrated the importance of the molecular shape for antifungal activity.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Structure-Activity Relationships (SAR) and in Silico Studies of Coumarin Derivatives with Antifungal Activity

Araújo

Guerra

Lima

et al. 2013

IJMS

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“…1 This class of heterocycles has attracted great interest from researchers due to their great versatility as precursors of molecules with pharmacological properties. 2 6CN10 is a 2-aminothiophene derivative synthesized via two-step reaction, starting with the obtainment of 2-amino-4,5,6,7-tetrahydro-4H-benzo [b]thiophene-3-carbonitrile through the Gewald reaction, followed by condensation with 4-nitro-benzaldehyde to produce the 2-[(4-nitrobenzylidene)amino]-4,5,6,7-tetrahydro-4H-benzo [b]thiophene-3-carbonitrile, called 6CN10 (Table 1). 3 This lipophilic drug showed good antifungal activity, with fungicidal profile, especially against Cryptococcus and can be considered a good prototype for the development of a new antimycotic drug.…”

Section: Introductionmentioning

confidence: 99%

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

Eleamen¹,

Costa²,

Lima-Neto³

et al. 2016

Journal of the Brazilian Chemical Society

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This study aimed to prepare a complex of 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) and 6CN10, a poorly water soluble 2-aminothiophene derivative with antifungal properties, by freeze-drying technique. The complex was characterized by thermal analysis, infrared/Raman spectroscopy, X-ray diffraction and scanning electron microscopy. In addition, we used the data of the phase solubility study, 1 H, and 2D NMR spectroscopy and molecular modeling in order to investigate the interactions between 6CN10 and HP-β-CD. The apparent solubility of 6CN10 with HP-β-CD increased more than 29 fold. The phase solubility assay in water at 25 ºC showed an A P -type curve, with an apparent stability constant K 1:1 and K 1:2 of 96 and 0.1989 M -1 , respectively. The results of IR, NMR and docking indicate that 6CN10 is able to form complexes with HP-β-CD (1:1 and 1:2 stoichiometric ratios), generating the formation of inclusion and preferably, non-inclusion complexes. The antifungal activity against Cryptococcus neoformans demonstrated the superior performance of the complex (46.66 μg mL -1 ) when compared with the free drug (166.66-333.33 μg mL -1 ). The present study provides useful information for the potential application of complexation with low soluble compounds and about the type of complex formation between 6CN10 and HP-β-CD.

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“…In the pharmaceutical industry, thiophene and its derivatives are used to impart pharmacological properties such as the anti-inflammatory, the antimicrobial, and the antianxiety. (Souza et al, 2012) Oligo and polythiophene are utilized as an indicator to recognize DNA or protein. (Barbarella & Sotgiu, 2005) Azo thiophene is used in the dye manufacturing industry, where its heterocyclic nature allows excellent sublimation rapidity on the dyed fiber.…”

Section: Introductionmentioning

confidence: 99%

One Step Synthesis of Polythiophenes from the Partially Purified Crude Extract of the Roots of Tagetes Erecta

Kodithuwakku

Alwis²,

Prashantha³

et al. 2016

IJC

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Polythiophene and its derivatives are valuable conjugated polymers due to their physical properties and applications in various fields. Precursors of polythiophenes were conventionally obtained from petrochemical byproducts, which are non-renewable. Thiophene and its derivatives had been found naturally in Tagetes species such as Tagetes erecta, Tagetes tenuifolia, etc. Tagetes species produce 2, 2':5', 2''-terthienyl (Alpha-T), 5-(3-buten-1-ynyl)-2, 20-bithienyl (BBT), 5-(4-hydroxy-1-butynyl)-2, 20-bithienyl (BBTOH), and 5-(4-acetoxy-1-butynyl)-2, 20-bithienyl (BBTOAc), which are accumulated in different parts, specifically in the roots of the plants. These thiophene derivatives were extracted and identified by GC-MS, Uv-vis, FTIR and TLC analysis. The partially purified plant extract is polymerized through one step oxidative free radical polymerization to obtain polythiophenes. Product characterization has revealed that the selective polymerization of thiophene derivatives results in the phase-separated end product from the rest of the materials in the plant-extract.

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Preliminary antifungal and cytotoxic evaluation of synthetic cycloalkyl[b]thiophene derivatives with PLS-DA analysis

Cited by 35 publications

References 17 publications

Synthesis, Structure-Activity Relationships (SAR) and in Silico Studies of Coumarin Derivatives with Antifungal Activity

Synthesis, Structure-Activity Relationships (SAR) and in Silico Studies of Coumarin Derivatives with Antifungal Activity

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

One Step Synthesis of Polythiophenes from the Partially Purified Crude Extract of the Roots of Tagetes Erecta

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