Tyrosyl-DNA phosphodiesterase 1 (TDP1) is a perspective target-enzyme for creating drugs used in oncological desease therapy for fighting against drug-resistant tumors. Natural compounds are important and renewable sources in modern medicine development. Earlier, it has been found that compounds containing monoterpenoid fragments possess inhibiting activity in relation to TDP1. In this work, we have synthesized several thiazolidinones and thiazolidinediones containing different terpenoids (cyclic, acyclic, and bicyclic) at different positions in the thiazolidine ring. Some of them have been found to possess inhibiting activity in relation to TDP1 at micromolar concentration range.