86106-18-5Relevant academic research and scientific papers
Thiazolidinone-peptide hybrids as dengue virus protease inhibitors with antiviral activity in cell culture
Nitsche, Christoph,Schreier, Verena N.,Behnam, Mira A. M.,Kumar, Anil,Bartenschlager, Ralf,Klein, Christian D.
, p. 8389 - 8403 (2013/12/04)
The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide-hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with Ki values between 1.5 and 1.8 μM and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.
Design, synthesis, and biological activity of a novel series of 2,5-disubstituted furans/pyrroles as HIV-1 fusion inhibitors targeting gp41
Jiang, Shibo,Tala, Srinivasa R.,Lu, Hong,Zou, Peng,Avan, Ilker,Ibrahim, Tarek S.,Abo-Dya, Nader E.,Abdelmajeid, Abdelmotaal,Debnath, Asim K.,Katritzky, Alan R.
supporting information; experimental part, p. 6895 - 6898 (2011/12/22)
Based on molecular docking analysis of earlier results, we designed a series of 2,5-disubstituted furans/pyrroles (5a-h) as HIV-1 entry inhibitors. Compounds were synthesized by Suzuki-Miyaura cross coupling, followed by a Knoevenagel condensation or Witt
THIA-ACYLIMINIUM - OLEFIN CYCLIZATIONS
Hamersma, J. A. M.,Speckamp, W. N.
, p. 3255 - 3266 (2007/10/02)
Regioselective NaBH4/H(1+)-reduction of thiazolidine-diones 3 - 8 substituted at the nitrogen atom with different ?-nucleophiles affords hydroxylactams 9 - 14 in good yields.The latter compounds are excellent precursors for the α-acyliminium ion 16 and ca
