Design, synthesis and biological evaluation of novel arylidine-malononitrile derivatives as non-carboxylic inhibitors of protein tyrosine phosphatase 1B

Bhattarai BR, Kafle B, Hwang JS, Khadka D, Lee SM, Kang JS, Ham SW, Han IO, Park H, Cho H (2009) Thiazolidinedione derivatives as PTP1B inhibitors with antihyperglycemic and antiobesity effects. Bioorg Med Chem Lett 19:6161–6165

Cheon HG, Kim SM, Yang SD, Ha JD, Choi JK (2004) Discovery of a novel protein tyrosine phosphatase-1B inhibitor, KR61639: potential development as an antihyperglycemic agent. Eur J Pharmacol 485:333–339

Cho SY, Baek JY, Han SS, Kang SK, Ha JD, Ahn JH, Lee JD, Kim KR, Cheon HG, Rhee SD, Yang SD, Yon GH, Pak CS, Choi JK (2006) PTP1B inhibitors: Cyclopenta[d][1,2]-oxazine derivatives. Bioorg Med Chem Lett 16:499–502

Dixit M, Tripathi BK, Tamrakar AK, Srivastava AK, Kumar B, Goel A (2007) Synthesis of benzofuran scaffold-based potential PTP1B inhibitors. Bioorg Med Chem 15:727–734

Douty B, Wayland B, Ala PJ, Bower MJ, Pruitt J, Bostrom L, Wei M, Klabe R, Gonneville L, Wynn R, Burn TC, Liu PCC, Combs AP, Yue EW (2008) Isothiazolidinone inhibitors of PTP1B containing imidazoles and imidazolines. Bioorg Med Chem Lett 18:66–71

Egede LE, Ellis C (2010) Diabetes and depression: global perspectives. Diabetes Res Clin Pract 87:302–312

Forghieri M, Laggner C, Paoli P, Langer T, Manao G, Camici G, Bondioli L, Prati F, Costantino L (2009) Synthesis, activity and molecular modeling of a new series of chromones as low molecular weight protein tyrosine phosphatase inhibitors. Bioorg Med Chem Lett 17:2658–2672

Johnson TO, Ermolieff J, Jirousek MR (2002) Protein tyrosine phosphatase 1B inhibitors for diabetes. Nat Rev Drug Discov 1:696–709

Joshi P, Deora GS, Rathore V, Tanwar OP, Rawat AK, Srivastava AK, Jain D (2012a) Identification of ZINC02765569: a potent inhibitor of PTP1B by vHTS. Med Chem Res. doi:10.1007/s00044-012-0007-0

Joshi P, Deora GS, Rathore V, Rawat AK, Srivastava AK, Jain D (2012b) Molecular modeling and synthesis of ZINC02765569 derivatives as protein tyrosine phosphatase 1B inhibitors: lead optimization study. Med Chem Res. doi:10.1007/s00044-012-0165-0

Kafle B, Bhattarai BR, Cho H (2011) Barbituric acid derivatives as protein tyrosine phosphatase inhibitors. Bull Korean Chem Soc 32:31–32

Kumar R, Mittal A, Ramachandran U (2007) Design and synthesis of 6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid derivatives as PPARγ activators. Bioorg Med Chem Lett 17:4613–4618

Liljebris C, Martinsson J, Tedenborg L, Williams M, Barker E, Duffy JES, Nygren A, James S (2002) Synthesis and biological activity of a novel class of pyridazine analogues as non-competitive reversible inhibitors of protein tyrosine phosphatase 1B (PTP1B). Bioorg Med Chem Lett 10:3197–3212

Maestro (2011) version 9.2, Schrödinger, LLC, New York, NY

Nicholas K (2003) PTP1B: from the sidelines to the front lines! FEBS Lett 546:140–148

Pei Z, Li X, Liu G, Bad-Zapatero C, Lubben T, Zhang T, Ballaron SJ, Hutchins CW, Trevillyan JM, Jirousek MR (2003) Discovery and SAR of novel, potent and selective protein tyrosine phosphatase 1B inhibitors. Bioorg Med Chem Lett 13:3129–3132

Puius YA, Zhao Y, Sullivan M, Lawrence DS, Almo SC, Zhang ZY (1997) Identification of a second aryl phosphate-binding site in protein-tyrosine phosphatase 1B: a paradigm for inhibitor design. Proc Natl Acad Sci 94:13420–13425

Shaw JE, Sicree RA, Zimmet PZ (2010) Global estimates of the prevalence of diabetes for 2010 and 2030. Diabetes Res Clin Pract 87:4–14

Simpson RW, Shaw JE, Zimmet PZ (2003) The prevention of type 2 diabetes—lifestyle change or pharmacotherapy? A challenge for the 21st century. Diabetes Res Clin Pract 59:165–180

Wan ZK, Lee J, Xu W, Erbe DV, Joseph-McCarthy D, Follows BC, Zhang YL (2006) Monocyclic thiophenes as protein tyrosine phosphatase 1B inhibitors: capturing interactions with Asp48. Bioorg Med Chem Lett 16:4941–4945

Xin Z, Liu G, Bad-Zapatero C, Pei Z, Szczepankiewicz BG, Li X, Zhang T, Hutchins CW, Hajduk PJ, Ballaron SJ, Stashko MA, Lubben TH, Trevillyan JM, Jirousek MR (2003) Identification of a monoacid-Based, cell permeable, selective inhibitor of protein tyrosine phosphatase 1B. Bioorg Med Chem Lett 13:3947–3950

Zarghi A, Hamedi S, Tootooni F, Amini B, Sharifi B, Faizi M, Abbas Tabatabai S, Shafiee A (2008) Synthesis and pharmacological evaluation of new 2-substituted-5-{2-[(2-halobenzyl)thio)phenyl}-1,3,4-oxadiazoles as anticonvulsant agents. Sci Pharm 76:185–201

Zhang P, Zhang X, Brown J, Vistisen D, Sicree R, Shaw J, Nichols G (2010) Global healthcare expenditure on diabetes for 2010 and 2030. Diabetes Res Clin Pract 87:293–301

Zhao H, Liu G, Xin Z, Serby MD, Pei Z, Szczepankiewicz BG, Hajduk PJ, Bad-Zapatero C, Hutchins CW, Lubben TH, Ballaron SJ, Haasch DL, Kaszubska W, Rondinone CM, Trevillyan JM, Jirousek MR (2004) Isoxazole carboxylic acids as protein tyrosine phosphatase 1B (PTP1B) inhibitors. Bioorg Med Chem Lett 14:5543–5546