Synthesis and docking studies of thiophene scaffolds in COX-2

Abstract

A series of new thiophene compounds 6a-6l was synthesized from the reactions of in situ generated cross-conjugated enaminothiones 2 and α-bromoketones/ethyl bromoacetate. Moreover, the synthesis of 1,3-thiazine 12 and functionalized thiopyran 18 heterocycles from the cycloaddition reactions of N,N'-bis[(dimethylamino)methylene]thiourea 9, is also described. Additionally, the binding conformations of these compounds 6a-6l and some anti-inflammatory drugs (NSAIDs) were determined by their docking in the active site of the Cyclooxygenase-2 (COX-2) enzyme.

Thiophene-Based Compounds with Potential Anti-Inflammatory Activity

“…Singh et al [ 70 ] synthesized a series of novel thiophene derivatives, and performed molecular docking studies with COX-2 (PDB id: 1CX2) using QUANTUM 3.3.0 software. Compound 24 (a-l) ( Figure 6 ) presented binding energy values comparable to conventional NSAIDs, with values ranging between −6.23 and −6.32 kcal/mol.…”

Isoxazole derivatives as new nitric oxide elicitors in plants

“…The benzo[1,3]dioxole framework is a constituent of some fragrances and flavors [ 44 ], and several bioactive compounds with a broad spectrum of applications [ 45 – 48 ]. The thiophene is a core system of a large number of bioactive molecules such as antineoplastic agents [ 49 ], non-steroidal anti-inflammatory drugs [ 50 ] or compounds with antibacterial activities against several Gram-positive strains [ 51 ]. Thus, 3,5-disubstituted isoxazole derivatives were obtained by regioselective 1,3-dipolar cycloaddition reactions of aromatic nitrile oxides to non-symmetrical activated alkyne derivatives in the presence of catalytic amounts of copper(I) iodide.…”