In order to find new biologically active compounds and in continuation of our work on the synthesis of the novel compounds containing both terpenic and heterocyclic fragments, herein we report the synthesis and assessment of the in vitro antifungal and antibacterial activities of some new drimane sesquiterpenoids with azaheterocyclic fragments. The structures of the synthesized compounds were confirmed using nuclear magnetic resonance spectroscopy, mass-spectrometry, gas-chromatography, and single-crystal X-ray diffraction analyses. A comparative study of microwave assisted transformations vs. classical conditions has been done. The in vitro antifungal and antibacterial activities of the drimane sesquiterpenoids with azaheterocyclic skeleton have been evaluated. One of the tested compounds has an excellent activity against five strains of fungi and two species of bacteria at minimum inhibitory concentration values of 5 × 10⁻³ and 3.2 × 10⁻² µg/ml, respectively, and another good antifungal activity at the MIC value of 1.5 µg/ml. Structure-activity relationship correlations concerning the biological activity mentioned are also reported.