Synthesis, structure and antimicrobial activity of new homodrimane sesquiterpenoids with oxa- and thiadiazole units

Aricu Aculina; Lungu Lidia; Ciocarlan Alexandru; Barba Alic; Vornicu Nicoleta; Mangalagiu Ionel

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2022-06-06 08:54

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ARICU, Aculina, LUNGU, Lidia, CIOCARLAN, Alexandru, BARBA, Alic, VORNICU, Nicoleta, MANGALAGIU, Ionel. Synthesis, structure and antimicrobial activity of new homodrimane sesquiterpenoids with oxa- and thiadiazole units. In: Romanian Chemistry Conference, 2-5 octombrie 2018, Călimăneşti-Căciulata, Vâlcea . Călimăneşti-Căciulata, Vâlcea, România: Centrul de Cercetare Oltchim, 2018, Ediția a XXXV-a, p. 94.

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Romanian Chemistry Conference
Ediția a XXXV-a, 2018

Conferința "Romanian Chemistry Conference"
Călimăneşti-Căciulata, Vâlcea , Romania, 2-5 octombrie 2018

Synthesis, structure and antimicrobial activity of new homodrimane sesquiterpenoids with oxa- and thiadiazole units

Pag. 94-94

Aricu Aculina¹, Lungu Lidia¹, Ciocarlan Alexandru¹, Barba Alic¹, Vornicu Nicoleta², Mangalagiu Ionel³

¹ Institute of Chemistry,
² Metropolitan Center of Research TABOR, The Metropolitanate of Moldavia and Bukovina,
³ Alexandru Ioan Cuza University of Iaşi

Disponibil în IBN: 19 iunie 2020

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Teza

Homodrimane sesquiterpenoids constitute an interesting class of compounds with a broad range of
biological activities including antibacterial, antifungal, anticancer activity, etc. With the aim of improving
therapeutic potential of homodrimane sesquiterpenoids, we combined homodrimanepharmacophoric moieties
with a biologically active oxa- and thiadiazole skeletons. A series of novel hybrid homodrimane
sesquiterpenoids with a substituted oxa- and thiadiazole units has been synthesized (Scheme).

Scheme Synthesis of new oxa- and thiadiazoles
Reagents and conditions: a. TMTD (1 eq.) or TMTD (1.5 eq.), DMF, 90˚C, 1,5h; b. CNBr, NaHCO3, aqueous dioxane, 1h, 80%; c.
CDI, Et3N, THF, 0˚C, 74%; d. Br-acetophenone, Et3N, acetone, 3h, 80%;e. R-NCS, Et3N, H2O, Δ, 18 h, 70-78%; f. R-NCS, EtOH, r.t., 4-5 h,
83-91%, or MW, 5 min., 85-92%; g. DCC, Acetone, MeOH, Δ, 5 h, 76-81%.
The structure of all compounds was proven by NMR spectroscopy, mass-spectrometry, gas chromatography,
and single-crystal X-ray diffraction. Hybrid homodrimane compounds demonstrated promising in vitro
antibacterial and antifungal activity.