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<p>In this study, indeno[1,2-b]indolone scaffolds were assembled through an operationally simple, aqueous Cu(OAc)₂ catalyzed three-component domino reaction furnishing mono-, bis- and tris-analogues in 68–95% isolated yields under mild conditions (60–85 °C, ≤ 150 min). Antimicrobial profiling (MIC &amp; IC₅₀, 125 µg disc) against six clinically relevant strains revealed a steep electronic gradient: electron-withdrawing (EW) substituents usually drive sub-μg mL⁻¹ potency, whereas electron-donating (ED) groups abolish activity (&gt;100 μg mL⁻¹). The meta-chloro mono-derivative <b>19g</b> reaches 0.06 μg mL⁻¹ against <i>(Bacillus subtilis) B. subtilis</i> and <i>(Escherichia coli) E. coli</i> (equipotent to gentamicin, 2-fold above ampicillin), while the tris-expanded <b>23</b> breaches 0.015 μg mL⁻¹ 9-fold superior to ampicillin and the first indeno-indolone to match reference antibiotics without surpassing them. Mechanistic cues (ROS burst &amp; DNA-gyrase docking) support a dual-mode action: membrane disruption plus topoisomerase inhibition. The scalable, metal-light protocol and clear EW &gt; push–pull &gt; ED ranking offer immediate lead-optimization handles to close the remaining 4–8-fold fungal gap versus <i>Amphotericin B</i> and to attenuate Gram-negative efflux, positioning <b>23</b> as a credible next-generation antibiotic candidate.</p>

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Preparation and antimicrobial activity of Mono-, Bis, and Tris-4,9-Dihydroxy-7,7-Dimethyl-5-(mono-substituted-aryl)-Hexahydro-Indeno[1,2-b]Indole-9,10-Dione derivatives

  • 期刊论文

  • 发表日期：

    2026年1月27日

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  • Ali Kadhim Rashid,
  • Hadeel Majed Ahmed,
  • Zainab Naeif Mageed,
  • Zaid Hameed Mahmoud,
  • Raed Muslim Mhaibes

摘要

In this study, indeno[1,2-b]indolone scaffolds were assembled through an operationally simple, aqueous Cu(OAc)₂ catalyzed three-component domino reaction furnishing mono-, bis- and tris-analogues in 68–95% isolated yields under mild conditions (60–85 °C, ≤ 150 min). Antimicrobial profiling (MIC & IC₅₀, 125 µg disc) against six clinically relevant strains revealed a steep electronic gradient: electron-withdrawing (EW) substituents usually drive sub-μg mL⁻¹ potency, whereas electron-donating (ED) groups abolish activity (>100 μg mL⁻¹). The meta-chloro mono-derivative 19g reaches 0.06 μg mL⁻¹ against (Bacillus subtilis) B. subtilis and (Escherichia coli) E. coli (equipotent to gentamicin, 2-fold above ampicillin), while the tris-expanded 23 breaches 0.015 μg mL⁻¹ 9-fold superior to ampicillin and the first indeno-indolone to match reference antibiotics without surpassing them. Mechanistic cues (ROS burst & DNA-gyrase docking) support a dual-mode action: membrane disruption plus topoisomerase inhibition. The scalable, metal-light protocol and clear EW > push–pull > ED ranking offer immediate lead-optimization handles to close the remaining 4–8-fold fungal gap versus Amphotericin B and to attenuate Gram-negative efflux, positioning 23 as a credible next-generation antibiotic candidate.