Fused polycyclic indoles represent a privileged class of scaffolds with broad therapeutic utility. The synthetic accessibility of diversely substituted indoles — particularly at the 4- to 7-positions — renders them valuable starting materials for drug discovery programs. Our group has previously reported the synthesis and bioactivity evaluation of polycyclic indoles as kinase inhibitors (1) and cannabinoid receptor modulators (2), and more recently extended this work to cipargamin analogs with antiplasmodial activities. Ongoing efforts to incorporate these scaffolds into proximity-induced protein degraders and fluorescent probes will be presented.