A high-order multicomponent reaction involving a six-component reaction to obtain the novel linked 1,5-disubstituted tetrazole-1,2,3-triazole hybrids in low to moderate yield is described. This one-pot reaction is carried out under a cascade process consisting of three sequential reactions: Ugi-azide, bimolecular nucleophilic substitution (S2), and copper-catalyzed alkyne-azide reaction (CuAAC), with high atom and step-economy due the formation of six new bonds (one C-C, four C-N, and one N-N). Thus, the protocol developed offers operational simplicity, mild reaction conditions, and structural diversity. Finally, to evaluate the antitumoral potential of the synthetized molecules, a proliferation study was performed in the breast cancer (BC) derived cell line MCF-7. The hybrid compounds showed several degrees of cell proliferation inhibition with a remarkable effect in those compounds with cyclohexane and halogens in their structures. These compounds represent potential drug candidates for breast cancer treatment. However, additionally assays are needed to elucidate their complete effect over the cellular hallmarks of cancer.
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http://dx.doi.org/10.3390/molecules26206104 | DOI Listing |
Chem Commun (Camb)
July 2024
Center of Micro and Nanochemistry and (Bio)Technology, Organische Chemie I, School of Science and Technology, University of Siegen, Adolf-Reichwein-Str. 2, D-57068 Siegen, Germany.
ACS Omega
January 2024
Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Leuven 3000, Belgium.
In this study, a homogeneous acid-catalyzed reaction of a series of benzaldehydes, benzylamines, and Meldrum's acid was presented, allowing the novel one-pot and multicomponent synthesis of hexahydroquinolines with high stereoselectivity. The current strategy has advantages including high regioselectivity, good efficiency, reasonable diversity, utilization of an inexpensive and safe catalyst, and easy purification of products by simple recrystallization. The current reaction utilizes 2 equiv of Meldrum's acid, 3 equiv of benzaldehyde derivatives, and one equiv of amine derivatives to yield (4'S,5'S,7'S)-1'-benzyl-2,2-dimethyl-4',5',7'-triphenyl-3',4',7',8'-tetrahydro-1'-spiro[[1,3]dioxane-5,6'-quinoline]-2',4,6(5')-trione derivatives.
View Article and Find Full Text PDFCommun Chem
June 2023
University of Zurich, Department of Chemistry, Winterthurerstrasse 190, CH-8057, Zurich, Switzerland.
Dual-modality imaging agents featuring both a radioactive complex for positron emission tomography (PET) and a fluorophore for optical fluorescence imaging (OFI) are crucial tools for reinforcing clinical diagnosis and intraoperative surgeries. We report the synthesis and characterisation of bimodal mechanically interlocked rotaxane-based imaging agents, constructed via the cucurbit[6]uril CB[6]-mediated alkyne-azide 'click' reaction. Two synthetic routes involving four- or six-component reactions are developed to access asymmetric rotaxanes.
View Article and Find Full Text PDFFront Chem
September 2022
Department of Chemistry, Firoozkooh Branch, Islamic Azad University, Firoozkooh, Iran.
rhizome water extract was used as green media for the preparation of Ag/FeO/CdO@multi-walled carbon nanotubes magnetic nanocomposites (Ag/FeO/CdO@MWCNTs MNCs), and its activity was evaluated by using in the one-pot multicomponent reaction of isatins, acetyl chloride, secondary amines, vinilidene Meldrum's acid, primary amines, and malononitrile in an aqueous medium at room temperature for the generation of spiropyridoindolepyrrolidine as new derivatives with tremendous output. In addition, organic pollutant reduction of 4-nitrophenol (4-NP) was carried out by generated Ag/FeO/CdO@MWCNTs in water at room temperature. The results displayed that Ag/FeO/CdO@MWCNTs were reduced as pollutants of organic compounds in a short time.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2022
Center of Micro and Nanochemistry and (Bio)Technology, Organische Chemie I, University of Siegen, Adolf-Reichwein Str. 2, 57068, Siegen, Germany.
The heteroleptic multi-component double slider-on-deck system DS3 exhibits tight coupling of motional speed of two distinct nano-circular sliders (k =77 and 41 kHz) despite a 2.2 nm separation. In comparison, the single sliders in DS1 and DS2 move at vastly different speed (k =1.
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