Spiroindolone analogues bearing benzofuran moiety as a selective cyclooxygenase COX-1 with TNF-α and IL-6 inhibitors

Plants as Sources of Anti-Inflammatory Agents

“…Free radicals induced by peroxidation are implicated in the pathogenesis of chronic inflammation that can trigger various pathological conditions such as arthritis and cancer, among others [ 121 ]. It is important to mention that inflammation has been linked to an increased risk for the development of different types of tumors such as gastric mucosal lymphoma, colon cancer, gastric cancer, and prostate cancer.…”

Synthesis, Anticancer Activity, and Molecular Modeling of New Halogenated Spiro[pyrrolidine-thiazolo-oxindoles] Derivatives

“…One of the most privileged aza-heterocyclic scaffolds is spiro[pyrrolidine-oxindole] [2], which is present in natural products and useful as a building block for the synthesis of significant biologically active compounds. This class of aza-heterocyclic compounds has gained great interest, owing to several reports of its pharmaceutical potency, including anticancer [3], antitumor [4], 5-HT3 receptor antagonist [5], acetylcholinesterase-inhibitory [6], antibacterial [7], antibiotic [8], and MDM2-p53 inhibitor [9] effects; selective cyclooxygenase COX-1 with TNF-α and IL-6 inhibitors [10]; and potential hypoglycemic dual inhibitory activity against α-amylase and α-glucosidase [11] (Figure 1). To date, prolonged efforts have been exerted to expand divergent complexity and to develop efficient synthetic routes for these valuable privileged aza-heterocyclic scaffolds, which would remarkably enhance their bioactivity [1,12].…”

“…Sci. 2020, 10, x FOR PEER REVIEW 2 of 10 antagonist [5], acetylcholinesterase-inhibitory [6], antibacterial [7], antibiotic [8], and MDM2-p53 inhibitor [9] effects; selective cyclooxygenase COX-1 with TNF-α and IL-6 inhibitors [10]; and potential hypoglycemic dual inhibitory activity against α-amylase and α-glucosidase [11] (Figure 1). To date, prolonged efforts have been exerted to expand divergent complexity and to develop efficient synthetic routes for these valuable privileged aza-heterocyclic scaffolds, which would remarkably enhance their bioactivity [1,12].…”

Synthesis of a New Class of Spirooxindole–Benzo[b]Thiophene-Based Molecules as Acetylcholinesterase Inhibitors

“…In particular, a series of spiro-oxindole-tethered benzo[ b ]thiophene scaffolds consisting of a single regio- and diastereo-selective isomer were synthesized from benzo[ b ]thiophene-based chalcones ( 2a – e ), which were in turn prepared through an aldol condensation of the corresponding substituted acetophenones ( 1a – e ) with benzo[ b ]thiophene-2-carboxaldehyde. Following the 1,3-dipolar cycloaddition reaction protocol [ 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ], 2a – e reacted with 5-substituted isatins ( 3a – c ) and secondary amino acids, such as thioproline ( 4a ) and octahydro-1 H -indole-2-carboxylic acid ( 4b ), forming the corresponding spiro-oxindole analogs IIa–n in high yields after purification by short column chromatography. The chemical features of the target compounds were assigned based on the NMR spectrum.…”

“…The chalcone derivatives 2a – e were synthesized based on a reported procedure [ 27 , 28 ] using benzo[ b ]thiophene-2-carboxaldehyde (1.0 eq.) in ethanol and the corresponding substituted acetophenone (acetopehnone, p -Cl- acetopehnone, p -Br-acetopehnone, p -F-acetopehnone and p -CF 3 -acetopehnone) (1.0 eq.)…”