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

Ramzi Maadadi; Chafai Boukentoucha; Ismahene Bazine; Rafik Menacer; Chawki Bensouici; Leonid Pevzner; Mikhail Petrov; Alexander V. Stepakov; Anthony Abou Dib; Dominique Harakat

doi:10.1080/14786419.2026.2648132

March 27, 2026Natural Product Research

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

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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.

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Implication

In situ synthesis creates dipyrromethanes with anticholinesterase effects, indicating potential for Alzheimer's treatment.

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. (2026) studied this question.

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

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

Key Points

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Implication

Abstract

Discussion

Cite This Study

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

Key Points

Ask about this paper

Implication

Abstract

Discussion

Cite This Study

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