1. Competition between inter and intramolecular hydrogen bond evidenced by vibrational circular dichroism spectroscopy: the case of (1s,2r)-(-)-cis-1-amino-2-indanol.
Katia Le Barbu-Debus, Anne Zehnacker. Chirality. 2021 Dec; 33(12): 858-874. DOI: 10.1002/chir.23362. PMID: 34570370.
The infrared (IR) absorption and vibrational circular dichroism (VCD) spectra of an intramolecularly hydrogen-bonded chiral amino-alcohol, (1S,2R)-(-)-cis-1-amino-2-indanol, are studied in DMSO-d6. The spectra are simulated at the density functional theory (DFT) level within the frame of the cluster-in-the-liquid model. Both IR and VCD spectra show a clear signature of the formation of intermolecular hydrogen bonds at the detriment of the intramolecular OH … N interaction present in the isolated molecule. Two solvent molecules are necessary to reproduce the experimental spectra. Whereas the first DMSO molecule captures the main spectral modifications due to hydrogen bond formation between the solute and the solvent, the second DMSO molecule is necessary for a good description of the Boltzmann contribution of the different complexes, based on their Gibbs free energy.
2. Synthesis and biological evaluation of novel homochiral carbocyclic nucleosides from 1-amino-2-indanols.
Beatriz Lantaño, Esteban A Ugliarolo, Rodolfo H Campos, Albertina G Moglioni, Lucía V Cavallaro, Dolores Gagey, Graciela Y Moltrasio. Bioorg Med Chem. 2012 Oct 1; 20(19): 5986-91. DOI: 10.1016/j.bmc.2012.07.028. PMID: 22944333.
New chiral purinyl and 8-azapurinyl carbanucleoside derivatives based on indanol were synthesized from commercial available (1S,2S)-trans-1-amino-2-indanol and (1R,2R)-trans-1-amino-2-indanol using a linear methodology. The antiviral activity and cytotoxicity of these compounds were evaluated against herpes simplex virus type 1 (HSV-1) in Vero cells, bovine viral diarrhea virus (BVDV) in Mardin-Darby bovine kidney (MDBK) cells and hepatitis B virus (HBV) in HepG2 2.2.15 cell line. Three compounds, showed an inhibition of the HBsAg levels similar to reference drug lamivudine. One chloropurinyl nucleoside, derived from the cis-1-amino-2-indanol, was cytotoxic on MDBK cells and it could be a lead for developing anticancer agents.
