What question did this study set out to answer?

The study aims to synthesize new dipyrromethanes from natural aldehydes and evaluate their anticholinesterase activity.

March 30, 2026

In situ hemisynthesis of new meso -substituted dipyrromethanes using natural aldehydes: in vitro anticholinesterase activity and in silico study

Key Points

The study aims to synthesize new dipyrromethanes from natural aldehydes and evaluate their anticholinesterase activity.
Synthesized dipyrromethanes using double Friedel-Crafts reactions with different catalysts.
Compounds were characterized using various NMR techniques and HR-MS.
Assessments of anticholinesterase activity were conducted in vitro.
In silico analysis was performed to explore the compounds' potential as anti-Alzheimer's agents.
DPM-2 exhibited a stronger inhibitory effect on AChE (IC50 = 22.6 μM) compared to DPM-1 (IC50 = 51 μM).
Both DPM-1 and DPM-2 showed significant activity against BChE, with DPM-2 being more potent (IC50 = 115 μM).
DPM-2's activity was comparable to Galantamine for both AChE and BChE inhibition.

Abstract

This study reports the in situ hemisynthesis of two novel dipyrromethanes (DPM-1 and DPM-2) from ethyl 1,2-dimethyl-1H-pyrrole-3-carboxylate and natural aldehydes: perillaldehyde from Ammodaucus leucotrichus and cuminaldehyde from cumin seed essential oil. The compounds were synthesized via a double Friedel-Crafts reaction under two catalytic systems: (i) water/ethanol (1:1 v/v) with 0.18 M HCl, and (ii) iodine-catalyzed chloroform. Structural elucidation was achieved using 1H NMR,13C NMR, HSQC, HMBC, and HR-MS. Both derivatives showed significant inhibitory activity against AChE and BChE. DPM-2 was more active against AChE (IC50 = 22.6 ± 0.06 μM) than DPM-1 (IC50 = 51 ± 1.74 μM), and comparable to Galantamine (IC50 = 21.81 ± 1.15 μM). Regarding BChE, DPM-2 (IC50 = 115 ± 1.91 μM) exhibited greater inhibitory potency than DPM-1 (IC50 = 230.41 ± 0.75 μM), and remained close to Galantamine (IC50 = 120.93 ± 1.99 μM). In silico analysis supported their potential as anti-Alzheimer's agents.

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Cite This Study

Maadadi et al. (Fri,) studied this question.

synapsesocial.com/papers/69ca12d4883daed6ee0950a5 https://doi.org/https://doi.org/10.1080/14786419.2026.2648132

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