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Article

Stereoselective Synthesis, Synthetic and Pharmacological Application of Monoterpene-Based 1,2,4- and 1,3,4-Oxadiazoles

1
Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös utca 6, Hungary
2
Department of Pharmacodynamics and Biopharmacy, University of Szeged, H-6720 Szeged, Eötvös utca 6, Hungary
3
Interdisciplinary Centre of Natural Products, University of Szeged, H-6720 Szeged, Eötvös utca 6, Hungary
4
Stereochemistry Research Group of the Hungarian Academy of Sciences, H-6720 Szeged, Eötvös utca 6, Hungary
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2018, 19(1), 81; https://doi.org/10.3390/ijms19010081
Received: 12 December 2017 / Revised: 21 December 2017 / Accepted: 22 December 2017 / Published: 28 December 2017
(This article belongs to the Special Issue Molecular Transformations of Natural Products)
Stereoselective synthesis of monoterpene-based 1,2,4- and 1,3,4-oxadiazole derivatives was accomplished starting from α,β-unsaturated carboxylic acids, obtained by the oxidation of (−)-2-carene-3-aldehyde and commercially available (−)-myrtenal. 1,2,4-Oxadiazoles were prepared in two steps via the corresponding O-acylamidoxime intermediates, which then underwent cyclisation induced by tetrabutylammonium fluoride (TBAF) under mild reaction conditions. Stereoselective dihydroxylation in highly stereospecific reactions with the OsO4/NMO (N-methylmorpholine N-oxide) system produced α,β-dihydroxy 1,2,4-oxadiazoles. Pinane-based 1,3,4-oxadiazoles were obtained similarly from acids by coupling with acyl hydrazines followed by POCl3-mediated dehydrative ring closure. In the case of the arane counterpart, the rearrangement of the constrained carane system occurred with the loss of chirality under the same conditions. Stereoselective dihydroxylation with OsO4/NMO produced α,β-dihydroxy 1,3,4-oxadiazoles. The prepared diols were applied as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes. All compounds were screened in vitro for their antiproliferative effects against four malignant human adherent cell lines by means of the MTT assay with the O-acylated amidoxime intermediates exerting remarkable antiproliferative action. View Full-Text
Keywords: terpenoid; stereoselective; 1,2,4-oxadiazole; 1,3,4-oxadiazole; chiral catalyst; diethyl zinc; antiproliferative activity terpenoid; stereoselective; 1,2,4-oxadiazole; 1,3,4-oxadiazole; chiral catalyst; diethyl zinc; antiproliferative activity
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MDPI and ACS Style

Gonda, T.; Bérdi, P.; Zupkó, I.; Fülöp, F.; Szakonyi, Z. Stereoselective Synthesis, Synthetic and Pharmacological Application of Monoterpene-Based 1,2,4- and 1,3,4-Oxadiazoles. Int. J. Mol. Sci. 2018, 19, 81. https://doi.org/10.3390/ijms19010081

AMA Style

Gonda T, Bérdi P, Zupkó I, Fülöp F, Szakonyi Z. Stereoselective Synthesis, Synthetic and Pharmacological Application of Monoterpene-Based 1,2,4- and 1,3,4-Oxadiazoles. International Journal of Molecular Sciences. 2018; 19(1):81. https://doi.org/10.3390/ijms19010081

Chicago/Turabian Style

Gonda, Tímea, Péter Bérdi, István Zupkó, Ferenc Fülöp, and Zsolt Szakonyi. 2018. "Stereoselective Synthesis, Synthetic and Pharmacological Application of Monoterpene-Based 1,2,4- and 1,3,4-Oxadiazoles" International Journal of Molecular Sciences 19, no. 1: 81. https://doi.org/10.3390/ijms19010081

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