Synthesis and evaluation of new pirfenidone derivatives as anti-fibrosis agents

Pirfenidone, an oral anti‐fibrotic and anti‐inflammatory medication used for the treatment of idiopathic pulmonary fibrosis (IPF), has been proposed to treat post‐COVID pneumonia pulmonary fibrosis (PF). However, pirfenidone displays side effects which include hepatotoxicity and anorexia. Cubane and cyclooctatetraene (COT) derivatives of pirfenidone were prepared as bioisostere/biomotif replacements of the phenyl ring to explore potential changes in activity. The key intermediate, aminocubane, enabled the synthesis of both the cubane and cyclooctatetraene (COT) derived pirfenidone analogues in 6 steps. The COT derivative was observed to display similar activity and cytotoxicity with pirfenidone in an anti‐virus and ACE2 inhibition assay, although limited effect was observed from pirfenidone and the analogues described herein.

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Cubane and Cyclooctatetraene Pirfenidones – Synthesis and Biological Evaluation

Liu

Liang

Modhiran

et al. 2023

Asian J Org Chem

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Pirfenidone microcrystals for pulmonary delivery: Regulation of the precipitation behavior in the supercooled droplet

Lu,

Yan,

et al. 2025

International Journal of Pharmaceutics

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The current landscape of antifibrotic therapy across different organs: A systematic approach

Fuster-Martínez,

Calatayud

2024

Pharmacological Research

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Synthesis and evaluation of new pirfenidone derivatives as anti-fibrosis agents

Abstract: Two series of new pirfenidone derivatives were synthesized and evaluated as anti-fibrosis agents. Among them, compound 9d give 35 μM of the IC50 against the human fibroblast cell line HFL1.

Cited by 4 publications

References 27 publications

Cubane and Cyclooctatetraene Pirfenidones – Synthesis and Biological Evaluation

Cubane and Cyclooctatetraene Pirfenidones – Synthesis and Biological Evaluation

Pirfenidone microcrystals for pulmonary delivery: Regulation of the precipitation behavior in the supercooled droplet

The current landscape of antifibrotic therapy across different organs: A systematic approach

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