Many terpenes exhibit various biological activities. In a series of articles it has been reported on the appearance of a new activity or the intensification of the original activity that accompanies the introduction of nitrogen in the molecules of native terpenoids.
The present communication put into discussion the recently elaborated methods for preparation of the new nitrogen-containing drimane and homodrimane compounds.
A series of dihomodrimane sesquiterpenoids containing an NH2 group were synthesized. 11-Dihomodriman-8-ol-12-one and its dehydration products, ketones with double bonds in the C7-C8 and C8-C9 positions were prepared from sclareolide. The oximes of the ketones were reduced by LiAlH4 to the corresponding amines.
The synthesis of new nitrogen-containing drimane and homodrimane sesquiterpenoids in cycle B is reported. A comparative study of the microwave (MW) assisted synthesis of drimenone versus classical conditions has been done. The drimane and homodrimane oximes were prepared on the base of ketones derived from commercially available sclareolide. The drimane amine was obtained by reduction of corresponding oxime with LiAlH4 .
The synthesis of new drimane and homodrimane lactams, derivatives of octahydro-1H-benzo[d]azepine and octahydro-1H-benzo[c]azepine, from norambreinolide is reported. Those compounds were prepared by the Beckmann rearrangement of the corresponding ketoximes.
We herein describe the synthesis of guanidine derivatives of 12-amino-11-dihomodrimane-8α-ol and 13-amino-14,15-dinorlabd-8(9)-ene.
A key step in the synthesis of these compounds is the reaction of the corresponding amines with sodium hydrogencyanamide in ethanol/water solution, which was neutralized with acetic acid. We describe also the preparation of 8,9-bicyclohomofarnesenic acid guanidine derivatives.
New dihomodrimane sesquiterpenoids containing azine, hydrazide, and dihydrazide fragments were synthesized.
All the newly-obtained compounds were identified and characterized by IR- and 1H, 13C NMR- spectroscopic methods, their structures being confirmed by single crystal X-ray diffraction.
All compounds were tested for antibacterial and antifungal activity, some of them have shown quite pronounced activity against gram positive and gram negative bacteria and fungal strains.