Antimicrobial, Structural, Optical, and Redox Profiling of 7H‑Benzo[c]carbazol-10-ol Derivatives - An Integrated Experimental and Computational Study

Sep 29, 2026

Carbazoles represent a versatile class of heterocycles with wide-ranging applications in medicinal and materials chemistry. However, their functionalized derivatives remain underexplored due to challenges in synthesis and derivatization. This study evaluates, for the first time, integrated antimicrobial, photophysical, and redox properties of novel 7H-benzo[c]carbazol-10-ol derivatives. Hydroxylated and naphthyl-substituted scaffolds were accessed via one-pot annulation and C−C coupling. In vitro agar well diffusion showed strong activity, especially for compounds 3a and 3c against P. aeruginosa (MIC = 8 μg/mL), supported by SEM and docking. TD-DFT revealed distinct redox and UV/vis absorption features, highlighting antimicrobial potential and organophotocatalysis.

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Abstract

Introduction

This article is licensed under CC-BY 4.0 [http://pubs.acs.org/journal/acsodf](http://pubs.acs.org/journal/acsodf) Article Antimicrobial, Structural, Optical, and Redox Profiling of 7H‑Benzo[c]carbazol-10-ol Derivatives: An Integrated Experimental and Computational Study Mohamed S. H. Salem, * Manar El Samak, Yasmine M. Abdel Aziz, Mohamed H. Aboutaleb, Sharvari Patil, Tin Zar Aye, Tarek S. Ibrahim, and Shinobu Takizawa * Cite This: ACS Omega 2025, 10, 59183−59199 Read Online | | | | | | | | --- | --- | --- | --- | --- | --- | | ACCESS | Metrics & More | | Article Recommendations | | *sı Supporting Information | ABSTRACT: Carbazoles represent a versatile class of heterocycles with wide-ranging applications in medicinal and materials chemistry. However, their functionalized derivatives remain underexplored, largely due to challenges in synthesis and derivatization. This study investigates, for the first time, the integrated antimicrobial, photophysical, and redox properties of structurally novel 7H-benzo[c]carbazol-10-ol derivatives. These derivatives, distinct from parent carbazoles, were synthesized via a one-pot annulation and C−C coupling approach, enabling access to hydroxylated and naphthyl-substituted scaffolds with enhanced bioactivity and optoelectronic features. The target compounds were initially screened for their in vitro antimicrobial activity using the agar well diffusion assay. Compounds 3a and 3c exhibited superior activity over amoxicillin and ceftazidime against P. aeruginosa with (MIC = 8 μg/mL). Scanning electron microscopy (SEM) and molecular docking studies provided insights into the mode of antibacterial action and morphological changes. Moreover, these compounds exhibited unique redox and UV/vis absorption behavior, characterized by high absorption coefficients and distinct electronic transitions, as demonstrated by time-dependent density functional theory (TD-DFT) calculations. This dual profiling underscores their potential as antimicrobial agents and sustainable organophotocatalysts, offering new horizons in both medicinal and materials chemistry. 1. INTRODUCTION Carbazoles are a versatile class of heterocyclic compounds with a rich history and broad applicability in both medicinal chemistry and materials science. 1−7 The core structure of carbazoles consists of a tricyclic system, formed by two benzene rings fused to a nitrogen-containing five-membered ring (Figure 1). This highly conjugated π-system endows carbazoles with exceptional electronic, optical, and chemical properties, making them a key scaffold in the development of bioactive compounds and advanced materials.8−10 The parent compound, 9H-carbazole, was first isolated from coal tar in 1872 by Graebe and Glaser.11 Since then, carbazoles have evolved from chemical curiosities into indispensable molecules, influencing drug discovery, electronics, and energy materials. 12, 13 Notably, naturally occurring carbazole-containing molecules such as murrayanine, clausenal, clausenine, olivacin, and others exemplify the biological significance of these compounds (Figure 1A). For instance, murrayanine exhibits potent antimicrobial activity, 14, 15 while olivacin has demonstrated antiviral effects.16 These natural products highlight the therapeutic potential of carbazole derivatives, particularly in addressing infections.17 In addition to naturally occurring compounds, several carbazole-based drugs have received FDA approval for clinical use. Midostaurin (Rydapt), approved in 2017 for treating acute myeloid leukemia (AML) and systemic mastocytosis, 18 and carvedilol (Coreg), approved in 1995 for hypertension and heart failure, are prime examples of the medicinal applications of carbazoles.19 Other notable FDA-approved drugs include ondansetron (Zofran) for nausea and vomiting,20 frovatriptan (Frova) for migraines,21 and alectinib (Alecensa) for advanced nonsmall cell lung cancer (NSCLC) (Figure 1B).22 These examples u

FAQs

What is the purpose of the integrated study in this paper?

The study investigates antimicrobial, photophysical, and redox properties together to characterize structurally novel 7H-benzo[c]carbazol-10-ol derivatives and relate them to bioactivity and optoelectronic behavior.

How were the target derivatives synthesized?

The derivatives were synthesized using a one-pot annulation and C−C coupling approach, enabling access to hydroxylated and naphthyl-substituted scaffolds.

Which compounds showed the strongest antimicrobial performance and how was it measured?

Compounds 3a and 3c showed superior activity against P. aeruginosa, measured by the agar well diffusion assay, with MIC reported as 8 μg/mL.

Sep 29, 2026

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