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3-(1,3-thiazol-2-yl)-1H-indole

CAS No.: 135531-86-1

  • Molecular Formula: C₁₁H₈N₂S
  • Molecular Weight: 200.26 g/mol

Chemical type

  • Indole-type phytoalexin (indolic phytoalexins/alkaloids)
[1]
  • Indole phytoalexin (Plant-derived secondary metabolite)
[2]

Key properties

  • Synthesized from tryptophan via indole-3-acetaldoxime (IAOx)
  • Broad antimicrobial activity against fungi and bacteria
  • Induced by pathogen-triggered immunity (PTI/ETI)
  • Regulated by WRKY TFs and SA/JA signaling
[1]
  • Antiproliferative and cancer chemopreventive effects
  • Induces oxidative stress (Reactive Oxygen Species - ROS) in cancer cells
  • Promotes lysosomal membrane permeabilization (LMP) and cathepsin D (CD) release
  • Selectively more cytotoxic towards aggressive/metastatic prostate cancer cell lines (e.g., C4-2, ARCaPM) compared to less aggressive ones (e.g., LNCaP, ARCaPE)
[2]
  • Antimicrobial defense in Arabidopsis and crucifers
  • Inhibits pathogen growth and contributes to innate immunity
[1]
  • Potential novel therapeutic agent for the treatment of metastatic prostate cancer
  • Research tool for studying ROS-induced and lysosome-mediated apoptosis pathways
[2]

Classification by use

  • Phytoalexins used in fungal and bacterial resistance
  • Inducible secondary metabolites for biotic stress response
[1]
  • Chemicals with potential therapeutic use in cancer treatment
  • Chemicals used in biological/mechanistic research (apoptosis, oxidative stress)
[2]
  1. [1] Redefining phytoalexins as engineered defenses for plant disease resistance, Current Plant Biology, Volume 45, January 2026, 100577
  2. [2] Camalexin-Induced Apoptosis in Prostate Cancer Cells Involves Alterations of Expression and Activity of Lysosomal Protease Cathepsin D, Molecules, 2014, 19(4), 3988-4005