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Structure-based drug design of tricyclic 8H-indeno[1,2-d][1,3]thiazoles as potent FBPase inhibitors.

Tsukada T, Takahashi M, Takemoto T, Kanno O, Yamane T, Kawamura S, Nishi T
Bioorg Med Chem Lett 20 1004-7 (2010)
Related entries: 3kbz, 3kc0

Cited: 12 times
EuropePMC logo PMID: 20045638

Abstract

With the goal of improving metabolic stability and further enhancing FBPase inhibitory activity, a series of tricyclic 8H-indeno[1,2-d][1,3]thiazoles was designed and synthesized with the aid of structure-based drug design. Extensive SAR studies led to the discovery of 19a with an IC(50) value of 1nM against human FBPase. X-ray crystallographic studies revealed that high affinity of 19a was due to the hydrophobic interaction arising from better shape complementarity and to the hydrogen bonding network involving the side chain on the tricyclic scaffold.

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  2. Design, synthesis and biological evaluation of indeno[1,2-d]thiazole derivatives as potent histone deacetylase inhibitors. Zhou M, Ning C, Liu R, He Y, Yu N. Bioorg Med Chem Lett 23 3200-3203 (2013)
  3. Modeling the metabolic interplay between a parasitic worm and its bacterial endosymbiont allows the identification of novel drug targets. Curran DM, Grote A, Nursimulu N, Geber A, Voronin D, Jones DR, Ghedin E, Parkinson J. Elife 9 e51850 (2020)
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  6. Discovery of novel indole derivatives as allosteric inhibitors of fructose-1,6-bisphosphatase. Bie J, Liu S, Li Z, Mu Y, Xu B, Shen Z. Eur J Med Chem 90 394-405 (2015)
  7. Structures of Leishmania Fructose-1,6-Bisphosphatase Reveal Species-Specific Differences in the Mechanism of Allosteric Inhibition. Yuan M, Vásquez-Valdivieso MG, McNae IW, Michels PAM, Fothergill-Gilmore LA, Walkinshaw MD. J Mol Biol 429 3075-3089 (2017)
  8. Quadruple space-group ambiguity owing to rotational and translational noncrystallographic symmetry in human liver fructose-1,6-bisphosphatase. Ruf A, Tetaz T, Schott B, Joseph C, Rudolph MG. Acta Crystallogr D Struct Biol 72 1212-1224 (2016)
  9. Discovery of Novel Indole Derivatives as Fructose-1,6-bisphosphatase Inhibitors and X-ray Cocrystal Structures Analysis. Wang X, Zhao R, Ji W, Zhou J, Liu Q, Zhao L, Shen Z, Liu S, Xu B. ACS Med Chem Lett 13 118-127 (2022)
  10. Discovery of potent and orally active tricyclic-based FBPase inhibitors. Tsukada T, Kanno O, Yamane T, Tanaka J, Yoshida T, Okuno A, Shiiki T, Takahashi M, Nishi T. Bioorg Med Chem 18 5346-5351 (2010)
  11. Protein-based alignment in 3D-QSAR of FBPase inhibitors. Yi P, Di YT, Liu W, Hao XJ, Ming Y, Huang DS, Yang J, Yi ZZ, Li ZJ, Yang RD, Zhang JC. Eur J Med Chem 46 885-892 (2011)


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