Synthesis of New Drimane and Homodrimane Lactams by Beckmann Rearrangement of Some Ketoximes

Secara, Elena

doi:10.19261/cjm.2016.11(1).06

Cited by 2 publications

References 14 publications

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Synthesis of Antimicrobial Norlabdane Compounds with Rearranged Cycle B and Molecular Docking Studies

Ciocarlan,

Lungu,

Shova

et al. 2024

Molecules

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The synthesis of tetra- and pentanorlabdane compounds with rearranged cycle B based on commercially available (+)-sclareolide is reported. Desired compounds were prepared from intermediate ketones via Baeyer–Villiger oxidation. The structures of synthesized compounds were confirmed by spectral IR, 1D (1H, 13C, and DEPT), and 2D (H-COSY, H,C-HSQC, H,C-HMBC, H,N-HMBC, NOESY) NMR analyses, mass-spectrometry and single crystal X-rays diffraction. Two out of the four synthesized compounds showed high antifungal and antibacterial activities comparable to and exceeding standard antifungal (caspofungin) and antibacterial (kanamycin) agents. DFT calculations show that in gas and DCM, compound 4 is more stable than 3 with a difference in the Gibbs free energy of 23.3 kJ/mol and 20.7 kJ/mol, respectively. In water and methanol, compound 3 is slightly more stable, by 2.4 kJ/mol and 2.78 kJ/mol, respectively. Molecular docking to four targets DNA gyrase from E. coli (1KZN), Fabz from P. aeruginosa (1U1Z), dihydrofolate reductase from C. albicans (3QLS) and MurB from E. coli (2Q85) showed good agreement with the results of in vitro evaluation and confirmed the biological activity of compounds 3 and 4, with binding affinities comparable and for some targets exceeding that of Caspofungin and Kanamycin.

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Synthesis of Antimicrobial Norlabdane Compounds with Rearranged Cycle B and Molecular Docking Studies

Ciocarlan,

Lungu,

Shova

et al. 2024

Molecules

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Synthesis of Biologically Active Nitrogen and Sulfur-Containing Terpenoids

Aricu

Ciocârlan

Lungu

et al. 2023

Fundamental and Biomedical Aspects of Redox Processes

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New, original, and ecologically pure methods for the synthesis of compounds with hybrid terpene and heteroatomic functional groups or fragments have been developed, starting from accessible (+)-sclareolide, obtained from (-)-sclareol, well-known labdane diterpenoid diol extracted from the waste of Clary sage (Salvia sclarea L.) remaining after extracting the essential oil. The natural origin of terpene compounds supposes biocompatibility, selective biological activity, and low toxicity. The compounds with combined skeleton were obtained by coupling some terpene derivatives (acids, chloroanhydrides, bromides) with azaheterocyclic compounds or heterocyclization of some intermediates such as hydrazides, hydrazincarbothioamides, or thiosemicarbazones. A series of over 120 newly obtained substances were subjected to biological testing, of which 10 showed pronounced antifungal and antibacterial activity, two amides showed pronounced antioxidant activity, and two derivatives with guanidine fragments showed high antitumor activity.

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Synthesis of New Drimane and Homodrimane Lactams by Beckmann Rearrangement of Some Ketoximes

Abstract: Abstract. 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.

Cited by 2 publications

References 14 publications

Synthesis of Antimicrobial Norlabdane Compounds with Rearranged Cycle B and Molecular Docking Studies

Synthesis of Antimicrobial Norlabdane Compounds with Rearranged Cycle B and Molecular Docking Studies

Synthesis of Biologically Active Nitrogen and Sulfur-Containing Terpenoids

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