113899-36-8Relevant articles and documents
Design of novel N-(2,4-dioxo-1,2,3,4-tetrahydro-thieno[3,2-d]pyrimidin-7-yl)-guanidines as thymidine phosphorylase inhibitors, and flexible docking to a homology model.
Price, Melissa L P,Guida, Wayne C,Jackson, Tara E,Nydick, Jason A,Gladstone, Patricia L,Juarez, Jose C,Donate, Fernando,Ternansky, Robert J
, p. 107 - 110 (2003)
A novel class of thymidine phosphorylase (TP) inhibitors has been designed based on analogy to the enzyme substrate as well as known inhibitors. Flexible docking studies, using a homology model of human TP, of the designed N-(2,4-dioxo-1,2,3,4-tetrahydro-thieno[3,2-d]pyrimidin-7-yl)-guanidines as well as their synthetic precursors provide insight into the observed experimental trends in binding affinity.
Distamycin-NA: A DNA Analog with an Aromatic Heterocyclic Polyamide Backbone: Part 1 - Synthesis and Structural Analysis of Monomers and Dimers Containing the Nucleobase Uracil
Sauter, Guido,Stulz, Eugen,Leumann, Christian
, p. 14 - 34 (1998)
The synthesis of the monomeric building block 13 and its constitutional isomer 12 of a new type of DNA analog, distamycin-NA, is presented (Schemes 1 and 2). This building block consists of a uracil base attached to a thiophene core unit via a biaryl-like axis. Next to the biaryl-like axis on the thiophene chromophore, a carboxy and an amino substituent are located allowing for oligomerization via peptide coupling. The proof of constitution and the conformationsl preferences about the biaryl-like axis were established by means of X-ray analyses of the corresponding nitro derivatives 10 and 11. Thus, the uracil bases are propeller-twisted relative to the thiophene core, and bidentate H-bonds occur between two uracil bases in the crystals. The two amino-acid building blocks 12 and 13 were coupled to give the dimers 15 and 16 using dicyclohexylcarbodiimide (DCC) in THF/LiCl and DMF, respectively. While the dimer 15 showed no atropisomerism on the NMR time scale at room temperature, its isomer 16 occurred as distinct diastereoisomers due to the hindered rotation around its biaryl-like axis. Variable-temperature 1H-NMR experiments allowed to determine a rotational barrier of 19 ± 1 kcal/mol in 16. The experimental data were complemented by AM1 calculations.
Potent selective thienoxazinone inhibitors of herpes proteases
Jarvest, Richard L.,Connor, Susan C.,Gorniak, Joselina G.,Jennings, L. John,Serafinowska, Halina T.,West, Andrew
, p. 1733 - 1738 (2007/10/03)
Thieno[3,2-d]oxazinones are potent, selective, mechanism-based inhibitors of the herpes proteases with good aqueous stability. Specificity between the HSV and CMV proteases varies across the series: compounds 14b and 14c are submicromolar HSV protease inhibitors with modest CMV protease inhibition, 14g is a selective CMV protease inhibitor, and 32 inhibits both enzymes with an IC50 of about 1 μM.
