Synthesis of hybrid perillyl‐4H‐pyrans. Cytotoxicity evaluation against hepatocellular carcinoma HepG2/C3A cell line

Abstract

A series of 15 new hybrid perillyl‐4H‐pyrans compounds was straightforwardly synthesized by a strategy combining the multicomponent reaction and the copper‐catalyzed alkyne‐azide cycloaddition (CuAAC). The 2‐amino‐4H‐pyrans‐3‐carbonitrile containing the alkyne moiety was prepared via multicomponent reaction between 1,3‐dicarbonyl, a propargyloxy aromatic aldehyde and malononitrile or ethyl α‐cyanoacetate. The alkyne derivative was sequentially reacted with the perillyl azide component through the copper‐catalyzed [3+2] Huisgen cycloaddition reaction. The antiproliferative activity of hybrid compounds were evaluated against the human hepatoma HepG2/C3A cell line.

Chromene-dihydropyrimidinone and xanthene-dihydropyrimidinone hybrids: design, synthesis, and antibacterial and antibiofilm activities

“…The 6-azidomethyldihydropyrimidin-2-ones 14a-d were prepared directly from the 6-chloromethyldihydropyrimidin-2-ones 12a-d by the reaction with NaN 3 . Thus, the Biginelli-like multicomponent reaction of ethyl 4-chloroacetoacetate (9), urea (10), and aromatic aldehydes 11a-d in acetic acid as the solvent produced the 6-cloromethyldihydropyrimidin-2-ones 12a-d (Cl-DHPM) in 68-74% yield after recrystallization (entries 1-4, Table 4). 29 The azidation reaction was carried out in the acetone : water solvent system, in the presence of sodium azyde (13), for 8 h. 30 The 6-azido-methyldihydropyrimidin-2-ones 14a-d (N 3 -DHPMs) were obtained in 78-92% yield after purification (see entries 5-8, Table 4).…”

“…3 Thus, changing from the sole to the multitarget paradigm has paved, in an unlimited way, drug discovery by the conjugation of different ligands for multiple medicinal targets challenging imagination and creativity. 4 From a plethora of hybrid compounds, our research has been focused on the design and synthesis of privileged molecules such as dihydropyridines-benzoxazoles, 5 dihydropyrimidinones-fatty acids, 6 -perillyl alcohol, 7 -benzoxazoles 8 and 4H-pyran-perillyl alcohol derivatives, 9 mainly targeting anticancer activity. Now, this work reports the design and synthesis of eleven chromene-dihydropyrimidinone (Chro-DHPM) and eleven xanthene-dihydropyrimidinone hybrids (Xanth-DHPM) aiming at the investigation of antibacterial and antibiofilm properties.…”

Greener organic synthetic methods: Sonochemistry and heterogeneous catalysis promoted multicomponent reactions

“…Pyrans have been extensively studied for their biological properties, such as antibacterial [197] , antioxidant [198] , antitumor [199] , as well as against Hep G2/C3A [200] . This scaffold can also be found in natural products [201] .…”

Synthesis and antiproliferative activity of 1H-1,2,3-triazole-4H-chromene-d-glucose hybrid compounds with dual inhibitory activity against EGFR/VEGFR-2 and molecular docking studies

“…4 H -Chromene is an important class of heterocyclic compounds with versatile biological profiles, a simple structure, and mild adverse effects. It has numerous exciting biological activities, such as anticancer, 17,18 anticonvulsant, 18 antimicrobial, 19 antituberculosis, 20 and antidiabetic activities. 21 Alternatively, 1 H -1,2,3-triazole is a nitrogen-containing heterocycle with three nitrogen atoms.…”