182153-34-0Relevant academic research and scientific papers
Synthesis and evaluation of 9,9-dimethylxanthene tricyclics against trypanothione reductase, Trypanosoma brucei, Trypanosoma cruzi and Leishmania donovani
Chibale, Kelly,Visser, Mark,Yardley, Vanessa,Croft, Simon L.,Fairlamb, Alan H.
, p. 1147 - 1150 (2007/10/03)
Derivatives of 9,9-dimethylxanthene was synthesised and evaluated against trypanothione reductase (TR) and in vitro against parasitic trypanosomes and leishmania. High in vitro antiparasitic activity was observed for some derivatives with one compound showing high activity against all three parasites (ED50 values of 0.02, 0.48 and 0.32 μM, for Trypanosoma brucei, Trypanosoma cruzi, and Leishmania donovani, respectively). The lack of correlation between inhibitory activity against TR and ED50 values suggests that TR is not the target. (C) 2000 Elsevier Science Ltd. All rights reserved.
Synthesis and conformational preferences of a potential β-sheet nucleator based on the 9,9-dimethylxanthene skeleton
McWilliams, Kurt,Kelly, Jeffery W.
, p. 7408 - 7414 (2007/10/03)
A 4,5-disubstituted-9,9-dimethylxanthene-based amino acid (10) has been synthesized for incorporation into peptide sequences which have a propensity to adopt β-sheet structure. Molecular dynamics studies support the FT-IR and NMR results which demonstrate that amides based on this residue utilize the NH and the C=O from the xanthene residue to form an intramolecular hydrogen bond (13-membered ring), unlike the previously studied dibenzofuran-based amino acid residues in which the NH and the C=O of the attached amide groups participate in intramolecular hydrogen bonding (15-membered ring). Interestingly, residue 10 derivatized as a simple amide prefers to adopt a trans conformation where the aliphatic side chains are placed on opposite sides of the plane of the 9,9-dimethylxanthene ring system. This is different than the conformational preferences of the dibenzofuran-based amino acids which adopt a cis conformation that is preorganized to nucleate β-sheet formation. It will be interesting to see how these conformational differences effect nucleation in aqueous solution.
