Thiazole, triazole, thio- and semicarbazone derivatives - Promising moieties for drug development for the treatment of tuberculosis

Pavan, Fernando Rogério

doi:10.1016/j.ejmcr.2021.100002

Cited by 10 publications

(4 citation statements)

References 110 publications

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“…Specifically, the derivative 3 demonstrated the strongest antioxidant activity through reduced UVB-induced ROS generation and, subsequently, induced a marked reduction in MDA levels, being the most antioxidant compound. Thereby, semicarbazone moiety resulted in an effective pharmacophore that improves the antioxidant potential in cells [36].…”

Section: Discussionmentioning

confidence: 99%

Photoprotective Effects of Two New Morin-Schiff Base Derivatives on UVB-Irradiated HaCaT Cells

García-Gil,

Rodríguez-Luna,

Ávila-Román

et al. 2024

Antioxidants

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Ultraviolet (UV) radiation harms the skin, causing oxidative damage, inflammation, and disruption of the skin’s barrier function. There is considerable interest in identifying new natural ingredients with antioxidant and anti-inflammatory properties to serve as adjuvants in sunscreens. The flavonoid morin (1) can undergo structural modifications to enhance its biological properties. The aim of this study was to synthesize two new morin-Schiff base derivatives, morin oxime (2) and morin semicarbazone (3), comparing their photoprotective effects with that of the parent compound on UVB-exposed HaCaT keratinocytes. The chemical structure of the novel compounds was revealed based on spectroscopic data analysis. Our findings demonstrated that derivatives 2 and 3 enhanced the light absorption capability in the UV–visible (vis) range compared to 1. Tested compounds exhibited a higher scavenger capacity than Trolox. Moreover, pre-treatment with all compounds protected HaCaT cells from UVB-induced cell death. Compound 3 demonstrated the strongest antioxidant effect, reducing reactive oxygen species (ROS) generation and, subsequently, malondialdehyde (MDA) levels. Additionally, compounds 2 and 3 exhibited greater anti-inflammatory effects than compound 1, significantly reducing interleukin (IL)-6 production levels at all tested concentrations. These findings have demonstrated, for the first time, a promising photoprotective activity of two new Schiff base derivatives and suggest their use as natural sunscreen ingredients.

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Section: Discussionmentioning

confidence: 99%

Photoprotective Effects of Two New Morin-Schiff Base Derivatives on UVB-Irradiated HaCaT Cells

García-Gil,

Rodríguez-Luna,

Ávila-Román

et al. 2024

Antioxidants

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“…Triazole has been recognized as an indispensable pharmacophoric feature for anti-TB activity. [58] Prashanth et al have reported novel 1,2,3-triazole based imidazoles (29, Figure 12) with MIC of 1.47 μM against Mtb H 37 Rv and non-cytotoxic activity against mammalian Vero cell lines. [59] Molecular docking of the present compound against enoyl acyl carrier protein (InhA, PDB ID: 1QXM) revealed better binding of these compounds with the proposed target as compared to isoniazid.…”

Section: Triazolementioning

confidence: 99%

Comprehensive Coverage on Anti‐mycobacterial Endeavour Reported in 2021

et al. 2022

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Tuberculosis (TB) has been the highly contagious airborne disease caused by Mycobacterium tuberculosis and the major leading infectious disease with the higher upsurge of morbidity and mortality. Owing to problems in the current regimen for TB and emergence of drug resistance strains, there is a strong necessity for development of new anti-TB drugs with better efficacy, reduced duration of action, along with improved patient compliance. Towards this, the scaffolds reported in 2021 with anti-tubercular activity such as benzofuran, benzothiazinone, benzimidazoles, indole, piperidine, piperazine, pyrazole, pyridine, pyrimidine, pyrrolidine, quinoxaline, triazole, etc. have been critically reviewed along with their structureactivity relationships, mode of actions with anticipations of intuitions to design the newer anti-mycobacterial scaffolds.The present work provide the organized coverage of diversified scaffolds with anti-tubercular profile reported in 2021 along with the insightful discussion on their merits and demerits. The mode of anti-tubercular action against Mycobacterium tuberculosis strains have been presented keeping in mind the novel drug candidates against drug resistant strains [a] Dr.

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“…These thiophene, thiazole, and pyridine-containing compounds show anticancer [4][5][6][7][8], anti-inflammatory [9][10][11], antibacterial [12][13][14], antioxidant [15], anti-oxidant [16], anti-fungal [17,18], anti-coronavirus [19,20] properties. Thiazoles were also found to act as anti-Alzheimer [21], anti-tubercular [22], and anti-diabetic [23]. While pyridone as well exhibits antimalarial [24], anti-hepatitis B [25], cardiotonic [26], and anti-fibrosis [27] properties.…”

Section: Introductionmentioning

confidence: 99%

New thiazole, thiophene and 2-pyridone compounds incorporating dimethylaniline moiety: synthesis, cytotoxicity, ADME and molecular docking studies

Metwally,

Younis,

Abdel-Latif

et al. 2024

BMC Chemistry

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Various sets of thiazole, thiophene, and 2-pyridone ring structures containing a dimethylaniline component were synthesized. Substituted thiazoles 2–3 and thiophenes 5–7 were produced by reacting thiocarbamoyl compound 4 with α-halogenated reagents in different basic conditions. Also, a series of 2-pyridone derivatives 9a–f substituted with dimethylaniline was synthesized through Michael addition of malononitrile to α,β-unsaturated nitrile derivatives 8a–f. The synthesized products were structurally proven by spectroscopic methods such as IR, 1H NMR, 13C NMR, and MS data. Furthermore, the anti-cancer efficacy of the compounds was assessed using the MTT assay on two cell lines: hepatocellular carcinoma (HepG-2) and breast cancer (MDA-MB-231). The results showed the highest growth inhibition for derivatives 2, 6, 7, and 9c, which were further examined for their IC50 values. The IC50 for compound 2 showed equipotent activity (IC50 = 1.2 µM) against the HepG-2 cell line compared to Doxorubicin (IC50 = 1.1 µM). Compounds 2, 6, 7 and 9c showed very good ADME assessments for further drug administration. Moreover, the PASS theoretical prediction for the compounds showed high antimitotic and antineoplastic activities for compounds 2, 6, 7, and 9c, as well as potent inhibition activity for the insulysin enzyme (IDE). Molecular docking stimulations were performed on CDK1/CyclinB1/CKS2 (PDB ID: 4y72) and BPTI (PDB ID: 2ra3). When docked into (PDB ID: 4y72), all of the tested compounds showed considerable inhibition, and the 2-pyridone derivative 9d had the maximum binding affinity (− 8.1223 kcal/mol). While thiophene derivative 6 offered the maximum binding affinity (− 7.5094 kcal/mol) when docked into (PDB ID: 2ra3). Graphical Abstract

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Thiazole, triazole, thio- and semicarbazone derivatives - Promising moieties for drug development for the treatment of tuberculosis

Cited by 10 publications

References 110 publications

Photoprotective Effects of Two New Morin-Schiff Base Derivatives on UVB-Irradiated HaCaT Cells

Photoprotective Effects of Two New Morin-Schiff Base Derivatives on UVB-Irradiated HaCaT Cells

Comprehensive Coverage on Anti‐mycobacterial Endeavour Reported in 2021

New thiazole, thiophene and 2-pyridone compounds incorporating dimethylaniline moiety: synthesis, cytotoxicity, ADME and molecular docking studies

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