The present review presents an overview of antitumor pyrazoles of natural or bioinspired origins. Pyrazole compounds are relatively rare in nature, the first ones having been reported in 1966 and being essentially used as somniferous drugs. Cytotoxic pyrazoles of natural sources were first isolated in 1969, and a few others have been reported since then, most of them in the last decade. This paper presents a perspective on the current knowledge on antitumor natural pyrazoles, organized into two sections. The first focuses on the three known families of cytotoxic pyrazoles that were directly isolated from plants, for which the knowledge of the medicinal properties is in its infancy. The second section describes pyrazole derivatives of natural products, discussing their structure–activity relationships.

Bio-based ionic liquids (ILs) are being increasingly sought after, as they are more sustainable and eco-friendly. Purines are the most widely distributed, naturally occurring N-heterocycles, but their low water-solubility limits their application. In this work, four purines (theobromine, theophylline, xanthine, and uric acid) were combined with the cation tetrabutylammonium to synthesize bio-based ILs. The physico–chemical properties of the purine-based ILs were characterized, including their melting and decomposition temperatures and water-solubility. The ecotoxicity against the microalgae Raphidocelis subcapitata was also determined. The ILs show good thermal stability (>457 K) and an aqueous solubility enhancement ranging from 53- to 870-fold, in comparison to their respective purine percursors, unlocking new prospects for their application where aqueous solutions are demanded. The ecotoxicity of these ILs seems to be dominated by the cation, and it is similar to chloride-based IL, emphasizing that the use of natural anions does not necessarily translate to more benign ILs. The application of the novel ILs in the formation of aqueous biphasic systems (ABS), and as solubility enhancers, was also evaluated. The ILs were able to form ABS with sodium sulfate and tripotassium citrate salts. The development of thermoresponsive ABS, using sodium sulfate as a salting-out agent, was accomplished, with the ILs having different thermosensitivities. In addition, the purine-based ILs acted as solubility enhancers of ferulic acid in aqueous solution.

This paper describes the Koenigs–Knorr reaction of (E)-3(5)-(2-hydroxyphenyl)-4-styryl-1H-pyrazoles 1a–d with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide, using silver carbonate (Ag₂CO₃) as base and silver triflate (AgOTf) as a promoter/activator in dry dichloromethane. Four per-O-acetylated pyrazole-coupled glucosides 2a–d, the target products of the reaction, were obtained in low yields (11–30%). Surprisingly, the main products of the reaction were new structures with the glucoside forming a dioxolo-bridge with the N-1 of the styrylpyrazole. These compounds 3a–d were obtained in moderate to good yields (39–52%). Compounds 2a–d and 3a–d were deacetylated, in mild conditions, using Amberlite® IRA-400(OH) in methanol, yielding deprotected pyrazole-glucoside conjugates 4a–d and 5b and 5c. The structures of the new compounds were assigned by 1D (¹H and ¹³C) and 2D (COSY, HSQC, HMBC and NOESY) NMR experiments, as well as by MS and HRMS. The cytotoxicity of compounds 1a–d, 4a–d and 5b and 5c against AGS gastric adenocarcinoma cells and MRC-5 lung fibroblasts was evaluated.

This paper proposes an automated system integrating infrared thermography (IRT) and computer vision for air leak detection and localization in end-of-line (EOL) testing stations. This system consists of (1) a leak tester for detection and quantification of leaks, (2) an infrared camera for real-time thermal image acquisition; and (3) an algorithm for automatic leak localization. The python-based algorithm acquires thermal frames from the camera’s streaming video, identifies potential leak regions by selecting a region of interest, mitigates environmental interferences via image processing, and pinpoints leaks by employing pixel intensity thresholding. A closed circuit with an embedded leak system simulated relevant leakage scenarios, varying leak apertures (ranging from 0.25 to 3 mm), and camera–leak system distances (0.2 and 1 m). Results confirmed that (1) the leak tester effectively detected and quantified leaks, with larger apertures generating higher leak rates; (2) the IRT performance was highly dependent on leak aperture and camera–leak system distance, confirming that shorter distances improve localization accuracy; and (3) the algorithm localized all leaks in both lab and industrial environments, regardless of the camera–leak system distance, mostly achieving accuracies higher than 0.7. Overall, the combined system demonstrated great potential for long-term implementation in EOL leakage stations in the manufacturing sector, offering an effective and cost-effective alternative for manual inspections.