3a0i › Citations

Discovery of novel 3,6-disubstituted 2-pyridinecarboxamide derivatives as GK activators.

Mitsuya M, Kamata K, Bamba M, Watanabe H, Sasaki Y, Sasaki K, Ohyama S, Hosaka H, Nagata Y, Eiki J, Nishimura T
Bioorg Med Chem Lett 19 2718-21 (2009)
Cited: 23 times
EuropePMC logo PMID: 19362831

Abstract

A novel class of 3,6-disubstituted 2-pyridinecarboxamide derivatives was designed based on X-ray analysis of the 2-aminobenzamide lead class. Subsequent chemical modification led to the discovery of potent GK activators which eliminate potential toxicity concerns associated with an aniline group of the lead structure. Compound 7 demonstrated glucose lowering effect in a rat OGTT model.

Articles - 3a0i mentioned but not cited (2)

  1. Strain analysis of protein structures and low dimensionality of mechanical allosteric couplings. Mitchell MR, Tlusty T, Leibler S. Proc Natl Acad Sci U S A 113 E5847-E5855 (2016)
  2. Development of antidiabetic drugs from benzamide derivatives as glucokinase activator: A computational approach. Ali A. Saudi J Biol Sci 29 3313-3325 (2022)


Reviews citing this publication (2)

  1. Homotropic allosteric regulation in monomeric mammalian glucokinase. Larion M, Miller BG. Arch Biochem Biophys 519 103-111 (2012)
  2. Identification of YH-GKA, a novel benzamide glucokinase activator as therapeutic candidate for type 2 diabetes mellitus. Park K. Arch Pharm Res 35 2029-2033 (2012)

Articles citing this publication (19)

  1. Order-disorder transitions govern kinetic cooperativity and allostery of monomeric human glucokinase. Larion M, Salinas RK, Bruschweiler-Li L, Miller BG, Brüschweiler R. PLoS Biol 10 e1001452 (2012)
  2. The active conformation of human glucokinase is not altered by allosteric activators. Petit P, Antoine M, Ferry G, Boutin JA, Lagarde A, Gluais L, Vincentelli R, Vuillard L. Acta Crystallogr D Biol Crystallogr 67 929-935 (2011)
  3. Discovery of novel 2-(pyridine-2-yl)-1H-benzimidazole derivatives as potent glucokinase activators. Ishikawa M, Nonoshita K, Ogino Y, Nagae Y, Tsukahara D, Hosaka H, Maruki H, Ohyama S, Yoshimoto R, Sasaki K, Nagata Y, Eiki J, Nishimura T. Bioorg Med Chem Lett 19 4450-4454 (2009)
  4. Discovery and structure-activity relationships of a novel class of quinazoline glucokinase activators. Iino T, Sasaki Y, Bamba M, Mitsuya M, Ohno A, Kamata K, Hosaka H, Maruki H, Futamura M, Yoshimoto R, Ohyama S, Sasaki K, Chiba M, Ohtake N, Nagata Y, Eiki J, Nishimura T. Bioorg Med Chem Lett 19 5531-5538 (2009)
  5. The design and optimization of a series of 2-(pyridin-2-yl)-1H-benzimidazole compounds as allosteric glucokinase activators. Takahashi K, Hashimoto N, Nakama C, Kamata K, Sasaki K, Yoshimoto R, Ohyama S, Hosaka H, Maruki H, Nagata Y, Eiki J, Nishimura T. Bioorg Med Chem 17 7042-7051 (2009)
  6. Discovery of 3-(4-methanesulfonylphenoxy)-N-[1-(2-methoxy-ethoxymethyl)-1H-pyrazol-3-yl]-5-(3-methylpyridin-2-yl)-benzamide as a novel glucokinase activator (GKA) for the treatment of type 2 diabetes mellitus. Park K, Lee BM, Hyun KH, Lee DH, Choi HH, Kim H, Chong W, Kim KB, Nam SY. Bioorg Med Chem 22 2280-2293 (2014)
  7. Discovery of a novel phenylethyl benzamide glucokinase activator for the treatment of type 2 diabetes mellitus. Park K, Lee BM, Kim YH, Han T, Yi W, Lee DH, Choi HH, Chong W, Lee CH. Bioorg Med Chem Lett 23 537-542 (2013)
  8. The use of docking-based comparative intermolecular contacts analysis to identify optimal docking conditions within glucokinase and to discover of new GK activators. Taha MO, Habash M, Khanfar MA, Khanfar MA. J Comput Aided Mol Des 28 509-547 (2014)
  9. Design and Synthesis of Acetylenyl Benzamide Derivatives as Novel Glucokinase Activators for the Treatment of T2DM. Park K, Lee BM, Hyun KH, Han T, Lee DH, Choi HH. ACS Med Chem Lett 6 296-301 (2015)
  10. Metabolic activation of N-thiazol-2-yl benzamide as glucokinase activators: Impacts of glutathione trapping on covalent binding. Iino T, Hashimoto N, Hasegawa T, Chiba M, Eiki J, Nishimura T. Bioorg Med Chem Lett 20 1619-1622 (2010)
  11. Discovery of orally active hepatoselective glucokinase activators for treatment of Type II Diabetes Mellitus. Xu J, Lin S, Myers RW, Trujillo ME, Pachanski MJ, Malkani S, Chen HS, Chen Z, Campbell B, Eiermann GJ, Elowe N, Farrer BT, Feng W, Fu Q, Kats-Kagan R, Kavana M, McMasters DR, Mitra K, Tong X, Xu L, Zhang F, Zhang R, Addona GH, Berger JP, Zhang B, Parmee ER. Bioorg Med Chem Lett 27 2063-2068 (2017)
  12. Small-Molecule Allosteric Activation of Human Glucokinase in the Absence of Glucose. Bowler JM, Hervert KL, Kearley ML, Miller BG. ACS Med Chem Lett 4 (2013)
  13. Structural insight into the glucokinase-ligands interactions. Molecular docking study. Ermakova E. Comput Biol Chem 64 281-296 (2016)
  14. Discovery and hit-to-lead optimization of novel allosteric glucokinase activators. Lang M, Seifert MH, Wolf KK, Aschenbrenner A, Baumgartner R, Wieber T, Trentinaglia V, Blisse M, Tajima N, Yamashita T, Vitt D, Noda H. Bioorg Med Chem Lett 21 5417-5422 (2011)
  15. N-pyridin-2-yl benzamide analogues as allosteric activators of glucokinase: Design, synthesis, in vitro, in silico and in vivo evaluation. Grewal AS, Kharb R, Prasad DN, Dua JS, Lather V. Chem Biol Drug Des 93 364-372 (2019)
  16. Design, synthesis and evaluation of novel 3,5-disubstituted benzamide derivatives as allosteric glucokinase activators. Grewal AS, Kharb R, Prasad DN, Dua JS, Lather V. BMC Chem 13 2 (2019)
  17. Discovery of cycloalkyl-fused N-thiazol-2-yl-benzamides as tissue non-specific glucokinase activators: Design, synthesis, and biological evaluation. Wang Z, Shi X, Zhang H, Yu L, Cheng Y, Zhang H, Zhang H, Zhou J, Chen J, Shen X, Duan W. Eur J Med Chem 139 128-152 (2017)
  18. Novel, highly potent systemic glucokinase activators for the treatment of Type 2 Diabetes Mellitus. Xu J, Lin S, Myers RW, Addona G, Berger JP, Campbell B, Chen HS, Chen Z, Eiermann GJ, Elowe NH, Farrer BT, Feng W, Fu Q, Kats-Kagan R, Kavana M, Malkani S, McMasters DR, Mitra K, Pachanski MJ, Tong X, Trujillo ME, Xu L, Zhang B, Zhang F, Zhang R, Parmee ER. Bioorg Med Chem Lett 27 2069-2073 (2017)
  19. ¹⁹F nuclear magnetic resonance screening of glucokinase activators. Assemat O, Antoine M, Fourquez JM, Wierzbicki M, Charton Y, Hennig P, Perron-Sierra F, Ferry G, Boutin JA, Delsuc MA. Anal Biochem 477 62-68 (2015)


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