Facile Synthesis of a New Class of Pyrazolone Attached Chromene Derivatives Showing Good Binding with β‐Lactoglobulin

Abstract

A new class of compounds having both chromene and pyrazolone moieties in the structural motif has been developed starting from 2-hydroxychalcones and pyrazolones using amberlyst-15 as a heterogeneous catalyst. The methodology involves a domino sequence of Michael addition, cyclisation, dehydration and aerial oxidation. Most of the compounds thus synthesised show good binding with the carrier protein blactoglobulin. Molecular docking study of the compound showing best binding with the protein has been carried out.

Synthesis of 4‐Alkenylated Pyrazolinones by 2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ)‐Mediated Oxidative Coupling Reaction

“…[3] Compound III, alkenylated pyrazolinone with a terene structure is able to bind to β-Lactoglobulin and its binding constant is calculated to be 16.3 × 10 5 M À 1 . [4] Compounds IV-VII, 4-benzylene pyrazolinones show antifungal (IC 50 = 10.05 μM), anti-methicillin-susceptible strains of staphylococcus aureus (MSSA) (MIC = 4 mg/mL) and methicillinresistant strains of staphylococcus aureus (MRSA) (MIC = 8 mg/ mL), anti-tumor (IC 50 = 0.84 μM), and SARS-CoV 3CL protease inhibition activities (IC 50 = 5.5 μM), respectively. [5] Alkenylated pyrazolinones are also valuable intermediates and applied for the construction of diverse bioactive spirocyclics [6] Therefore, the development of efficient and convenient tactics for the preparation of alkenylated pyrazolinones is a highly desirable synthetic task.…”

“…[2] Compound II, alkenylated pyrazolinone with tetrazole‐substituted on the 1‐ position is evaluated for a HIV‐1 integrase inhibitor (IC 50 =14±7 μM) [3] . Compound III, alkenylated pyrazolinone with a terene structure is able to bind to β‐Lactoglobulin and its binding constant is calculated to be 16.3×10 5 M −1 [4] . Compounds IV–VII, 4‐benzylene pyrazolinones show antifungal (IC 50 =10.05 μM), anti‐methicillin‐susceptible strains of staphylococcus aureus (MSSA) (MIC=4 mg/mL) and methicillin‐resistant strains of staphylococcus aureus (MRSA) (MIC=8 mg/mL), anti‐tumor (IC 50 =0.84 μM), and SARS‐CoV 3CL protease inhibition activities (IC 50 =5.5 μM), respectively [5] .…”