New nitroindazole-porphyrin conjugates: synthesis, characterization and antibacterial properties

The synthesis of new porphyrin-indazole hybrids by a Knoevenagel condensation of 2-formyl-5,10,15,20-tetraphenylporphyrin and N-methyl-nitroindazolylacetonitrile derivatives is reported. The target compounds were isolated in moderate to good yields (32-57%) and some of the isolated porphyrin-indazole conjugates showed good performance in the generation of singlet oxygen when irradiated with visible light. Their efficiency as photosensitizers in the photoinactivation of methicillin resistant Staphylococcus aureus-MRSA was evaluated. All derivatives showed to be able to photoinactivate the MRSA bacteria. Compound 3a appears to be the most promising photosensitiser (PS) in the photoinactivation of these bacteria, despite being the least efficient in singlet oxygen generation. The addition of potassium iodide (KI) significantly potentiated the antimicrobial Photodynamic Therapy (aPDT) process mediated by all the analysed porphyrin-indazole conjugates. The combined action of nitroindazole-porphyrins with potassium iodide (KI) action appears to be promising in the photoinactivation of MRSA.publishe

Exploring the Use of Iris Species: Antioxidant Properties, Phytochemistry, Medicinal and Industrial Applications

The genus Iris from the Iridaceae family consists of more than 262 recognized species. It is an ornamental and medicinal plant widely distributed in the Northern Hemisphere. Iris species convey a long history as valuable traditional drugs with a wide variety of applications in various cultures, having been recorded since medieval times. Currently, Iris spp. still find application in numerous fields, including cosmetics, pharmaceutics and the food industry. Moreover, many of their empirical uses have been validated by in vitro and in vivo studies, showing that Iris spp. exhibit potent antioxidant, anticancer, anti-inflammatory, hepatoprotective, neuroprotective and anti-microbial properties. Phytochemicals investigations have revealed that the plant extracts are rich in phenolic compounds, especially flavonoids and phenolic acids. As such, they constitute a promising lead for seeking new drugs with high susceptibilities towards various health issues, particularly oxidative-stress-related diseases such as cancers, neurodegenerative diseases, cardiovascular diseases, diabetes, etc. Herein, we present a literature review of the genus Iris intending to determine the plant’s chemical profile and establish a coherent overview of the biological applications of the plant extracts with reference to their traditional uses

Sydnone: Synthesis, reactivity and biological activities

: Sydnones are among the most well-known mesoionic compounds. Since their synthesis in 1935 by Earl and Mecknay, numerous researches have shown that the chemical behavior, physical and biological properties of sydnones make them among the most useful compounds in organic chemistry. Sydnones undergo thermal 1,3-dipolar cycloaddition reaction with dipolarophiles (alkynes or alkenes) to give exclusively derivatives containing a pyrazole moiety exhibiting numerous applications such as pharmaceuticals and agrochemicals. However, the sydnone cycloaddition reaction with alkynes requires harsh conditions like high temperatures and long reaction times giving poor regioselectivity on the resulting products. To overcome these constraints, new reactions named CuSAC (Copper-Catalyzed Sydnone-Alkyne Cycloaddition) and SPSAC (Strain-Promoted Sydnone-Alkyne Cycloaddition) and have been developed, leading to pyrazoles with interesting constant kinetics

Carvacrol and Thymol Content Affects the Antioxidant and Antibacterial Activity of <i>Origanum compactum</i> and <i>Thymus zygis</i> Essential Oils

Essential oils are of great interest due to their potent pharmaceutical and biological activities. In this study, essential oils extracted from Origanum compactum and Thymus zygis originating from the Middle Atlas of Morocco were investigated. Their chemical compositions were analyzed using gas chromatography and mass spectrometry, while the assessment of the trapping power of the radical (DPPH: 1,1-diphenyl-2-picrylhydrazyl) and the reducing antioxidant potential of ferric ions (FRAP: Ferric Reducing Antioxidant Power) were performed in order to evaluate the antioxidant activity. Their antibacterial potency was tested against six bacterial strains through the disk diffusion method. The chromatography analyses of the extracted essential oils highlighted the presence of two main components, namely carvacrol at 75.70% in O. compactum and thymol at 40.67% in T. zygis. The antioxidant activity tests showed that both essential oils demonstrated a significant antioxidant activity comparable to the positive control (e.g., ascorbic acid). The antibacterial activity results showed a strong antimicrobial effect for both essential oils, compared to synthetic antibiotics. This study affirms the presence of bioactive components with interesting antioxidant and antibacterial activities in the essential oils extracted from Origanum compactum and Thymus zygis, which could find several applications in the food and pharmaceutical industries through the substitution of synthetic antioxidants and antibiotics

N-(1H-Indazol-5-yl)-4-methoxybenzenesulfonamide

In the title compound, C14H13N3O3S, the fused ring system is almost planar, the largest deviation from the mean plane being 0.023&#8197;(2)&#8197;&#197;, and makes a dihedral angle of 47.92&#8197;(10)&#176; with the benzene ring of the benzenesulfonamide moiety. In the crystal, molecules are connected through N&#8212;H...O hydrogen bonds and weak C&#8212;H...O contacts, forming a two-dimensional network which is parallel to (010)

N-(3-Chloro-1H-indazol-5-yl)-4-methoxybenzenesulfonamide

In the title compound, C14H12ClN3O3S, the fused five- and six-membered rings are folded slightly along the common edge, forming a dihedral angle of 3.2&#8197;(1)&#176;. The mean plane through the indazole system makes a dihedral angle of 30.75&#8197;(7)&#176; with the distant benzene ring. In the crystal, N&#8212;H...O hydrogen bonds link the molecules, forming a two-dimensional network parallel to (001)

Tetraclinis articulata (Vahl) Mast.: Volatile constituents, antioxidant, antidiabetic and wound healing activities of its essential oil

Type 2 diabetes mellitus (T2DM) is a metabolic syndrome known to contribute to impaired wound healing. This condition can be further worsened by excessive melanin production, elastin degradation, and chronic infections at the wound site, potentially leading to melasma and diabetic dermopathy. The purpose of this study was to investigate the phytochemical profile and inhibitory effects of Tetraclinis articulata essential oil (TAEO) on target enzymes involved in diabetes pathogenesis and chronic wound remodeling, namely α-amylase, α-glucosidase, tyrosinase, and elastase, as well as its in vitro antibacterial activity. Gas chromatography and mass spectrometry (GC-MS) analysis of TAEO led to the identification of 46 volatile compounds, representing 96.61 % of TAEO. The major metabolites were bornyl acetate (29.48 %), α-pinene (8.96 %), germacrene D (7.70 %), and d-limonene (5.90 %). TAEO exhibited limited scavenging activity against DPPH free radicals, whereas the FRAP and ABTS assays indicated a relatively higher antioxidant activity. Remarkably, TAEO disclosed a promising in vitro antidiabetic activity against α-glucosidase with an IC50 value of 178 ± 1.6 μg/mL, which is comparable to the standard inhibitor acarbose (IC50 = 143 ± 1.1 μg/mL). In silico, molecular docking analysis against α-glucosidase identified 15 compounds that interacted with the enzyme's active site, whereas skin permeability and sensitization assessments indicated that 26 out of the 44 identified volatile compounds were predicted to be free from any skin sensitivity risk. On the other hand, moderate inhibitory activity was recorded against α-amylase, tyrosinase, and elastase. Notably, TAEO at 5 % significantly suppressed biofilm formation by P. aeruginosa, S. aureus, and E. faecalis, common skin pathogens associated with wound infections, and reduced their swarming motility. Our findings suggest that TAEO may hold the potential as a natural remedy for type 2 diabetes and its associated co-morbidities, especially chronic wounds

N-(1-Allyl-3-chloro-4-ethoxy-1H-indazol-5-yl)-4-methylbenzenesulfonamide

In the title compound, C19H20ClN3O3S, the benzene ring is inclined to the indazole ring system by 51.23 (8)°. In the crystal, molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers which stack in columns parallel to [011]. The atoms in the allyl group are disordered over two sets of sites with an occupancy ratio of 0.624 (8):0.376 (8)