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Volumn 79, Issue 6, 2012, Pages 897-906

Synthesis, Structure-Activity Relationship, and Pharmacophore Modeling Studies of Pyrazole-3-Carbohydrazone Derivatives as Dipeptidyl Peptidase IV Inhibitors

Author keywords

Dipeptidyl peptidase IV; Inhibitors; Molecular docking; Pharmacophore modeling; Synthesis

Indexed keywords

DIPEPTIDYL PEPTIDASE IV; DIPEPTIDYL PEPTIDASE IV INHIBITOR; N' [1 [2,4 DIHYDROXYPHENYL]ETHYLIDENE] 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; N' [3,4 DIHYDRO 1[2H] NAPHTHALEN 1 YL] 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; N' [[1 METHYL 1H PYRROL 2 YL]METHYLENE] 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; N' [[2 HYDROXY NAPHTHALEN 1 YL]METHYLENE] 1,4,5,6 TETRAHYDRO CYCLOPENTA[C]PYRAZOLE 3 CARBOHYDRAZONE; N' [[2 HYDROXY NAPHTHALEN 1 YL]METHYLENE] 1,4,5,6,7,8 HEXAHYDRO CYCLOPENTA[C]PYRAZOLE 3 CARBOHYDRAZONE; N' [[2 HYDROXY NAPHTHALEN 1 YL]METHYLENE] 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; N' [[2 HYDROXY NAPHTHALEN 1 YL]METHYLENE] 5 [3 METHOXYPHENYL] 1H PYRAZOLE 3 CARBOHYDRAZOLE; N' [[2 HYDROXY PHENYL]METHYLENE] 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; N' [[2,4 DIHYDROXYPHENYL]METHYLENE] 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; N' [[3 CHLORO 4 HYDROXY 5 METHOXYPHENYL]METHYLENE] 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; N' [[4 CHLORO 3 FLUOROPHENYL]METHYLENE] 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; N' [[4 CHLORO 3 NITROPHENYL]METHYLENE] 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; N' [[4 CYANO PHENYL]METHYLENE] 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; N' [[4 METHOXY NAPHTHALEN 1 YL]METHYLENE] 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; N' [[NAPHTHALEN 1 YL]METHYLENE] 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; N' CYCLOHEPTYLIDENE 4,5,6,7 TETRAHYDRO 1H INDAZOLE 3 CARBOHYDRAZONE; PYRAZOLE 3 CARBOHYDRAZONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84862796538     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2012.01365.x     Document Type: Article
Times cited : (29)

References (17)
  • 1
    • 0035723325 scopus 로고    scopus 로고
    • CD26: a multifunctional integral membrane and secreted protein of activated lymphocytes
    • Gorrell M.D., Gysbers V., McCaughan G.W. (2001) CD26: a multifunctional integral membrane and secreted protein of activated lymphocytes. Scand J Immunol;54:249-264.
    • (2001) Scand J Immunol , vol.54 , pp. 249-264
    • Gorrell, M.D.1    Gysbers, V.2    McCaughan, G.W.3
  • 3
    • 0027215348 scopus 로고
    • Dipeptidylpeptidase IV hydrolyses gastric inhibitory polypeptide, glucagon-like peptide-1 (7-36) amide, peptide histidine methionine and is responsible for their degradation in human serum
    • Mentlein R., Gallwitz B., Schmidt W.E. (1993) Dipeptidylpeptidase IV hydrolyses gastric inhibitory polypeptide, glucagon-like peptide-1 (7-36) amide, peptide histidine methionine and is responsible for their degradation in human serum. Eur J Biochem;214:829-835.
    • (1993) Eur J Biochem , vol.214 , pp. 829-835
    • Mentlein, R.1    Gallwitz, B.2    Schmidt, W.E.3
  • 4
    • 0029118049 scopus 로고
    • Degradation of glucose-dependent insulinotropic polypeptide and truncated glucagon-like peptide 1 in vitro and in vivo by dipeptidyl peptidase IV
    • Kieffer T.J., McIntosh C.H., Pederson R.A. (1995) Degradation of glucose-dependent insulinotropic polypeptide and truncated glucagon-like peptide 1 in vitro and in vivo by dipeptidyl peptidase IV. Endocrinology;358:5-3596.
    • (1995) Endocrinology , vol.358 , pp. 5-3596
    • Kieffer, T.J.1    McIntosh, C.H.2    Pederson, R.A.3
  • 5
    • 19944427998 scopus 로고    scopus 로고
    • (2R)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-α]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine: a potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes
    • Kim D., Wang L.P., Beconi M., Eiermann G.J., Fisher M.H., He H.B., Hickey G.J. et al. (2005) (2R)-4-Oxo-4-[3-(trifluoromethyl)-5, 6-dihydro[1, 2, 4]triazolo[4, 3-α]pyrazin-7(8H)-yl]-1-(2, 4, 5-trifluorophenyl)butan-2-amine: a potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. J Med Chem;48:141-151.
    • (2005) J Med Chem , vol.48 , pp. 141-151
    • Kim, D.1    Wang, L.P.2    Beconi, M.3    Eiermann, G.J.4    Fisher, M.H.5    He, H.B.6    Hickey, G.J.7
  • 6
    • 0037777695 scopus 로고    scopus 로고
    • 1-[[(3-hydroxy-1-adamantyl)amino] acetyl]-2-cyano-(S)-pyrrolidine: a potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties
    • Villhauer E.B., Brinkman J.A., Naderi G.B., Burkey B.F., Dunning B.E., Prasad K., Mangold B.L., Russell M.E., Hughes T.E. (2003) 1-[[(3-hydroxy-1-adamantyl)amino] acetyl]-2-cyano-(S)-pyrrolidine: a potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties. J Med Chem;46:2774-2789.
    • (2003) J Med Chem , vol.46 , pp. 2774-2789
    • Villhauer, E.B.1    Brinkman, J.A.2    Naderi, G.B.3    Burkey, B.F.4    Dunning, B.E.5    Prasad, K.6    Mangold, B.L.7    Russell, M.E.8    Hughes, T.E.9
  • 7
    • 22744449063 scopus 로고    scopus 로고
    • Discovery and preclinical profile of saxagliptin (BMS-477118): a highly potent, long-acting, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes
    • Augeri D.J., Robl J.A., Betebenner D.A., Magnin D.R., Khanna A., Robertson J.G., Wang A.Y. et al. (2005) Discovery and preclinical profile of saxagliptin (BMS-477118): a highly potent, long-acting, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. J Med Chem;48:5025-5037.
    • (2005) J Med Chem , vol.48 , pp. 5025-5037
    • Augeri, D.J.1    Robl, J.A.2    Betebenner, D.A.3    Magnin, D.R.4    Khanna, A.5    Robertson, J.G.6    Wang, A.Y.7
  • 9
    • 37349073397 scopus 로고    scopus 로고
    • 8-(3-(R)-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydropurine-2,6-dione (BI 1356), a highly potent, selective, long-acting, and orally bioavailable DPP-4 inhibitor for the treatment of type 2 diabetes
    • Eckhardt M., Langkop E., Mark M., Tadayyon M., Thomas L., Nar H., Pfrengle W., Guth B., Lotz R., Sieger P., Fuchs H., Himmelsbach F. (2007) 8-(3-(R)-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3, 7-dihydropurine-2, 6-dione (BI 1356), a highly potent, selective, long-acting, and orally bioavailable DPP-4 inhibitor for the treatment of type 2 diabetes. J Med Chem;50:6450-6453.
    • (2007) J Med Chem , vol.50 , pp. 6450-6453
    • Eckhardt, M.1    Langkop, E.2    Mark, M.3    Tadayyon, M.4    Thomas, L.5    Nar, H.6    Pfrengle, W.7    Guth, B.8    Lotz, R.9    Sieger, P.10    Fuchs, H.11    Himmelsbach, F.12
  • 10
    • 34249280590 scopus 로고    scopus 로고
    • Rational design of a novel, potent, and orally bioavailable cyclohexylamine DPP-4 inhibitor by application of molecular modeling and X-ray crystallography of sitagliptin
    • Biftu T., Scapin G., Singh S., Feng D., Becker J.W., Eiermann G., He H. et al. (2007) Rational design of a novel, potent, and orally bioavailable cyclohexylamine DPP-4 inhibitor by application of molecular modeling and X-ray crystallography of sitagliptin. Bioorg Med Chem Lett;17:3384-3387.
    • (2007) Bioorg Med Chem Lett , vol.17 , pp. 3384-3387
    • Biftu, T.1    Scapin, G.2    Singh, S.3    Feng, D.4    Becker, J.W.5    Eiermann, G.6    He, H.7
  • 13
    • 84862780587 scopus 로고
    • 1-(3-Indazolecarbonyl)-hydrazines and their preparation. Patent No. US3007938
    • Kirchner F.K., Bethlehem N.Y. (1961) 1-(3-Indazolecarbonyl)-hydrazines and their preparation. Patent No. US3007938.
    • (1961)
    • Kirchner, F.K.1    Bethlehem, N.Y.2
  • 14
    • 22744442874 scopus 로고    scopus 로고
    • Type 2 diabetes-therapy with dipeptidyl peptidase IV inhibitors
    • Demuth H.U., McIntosh C.H., Pederson R.A. (2005) Type 2 diabetes-therapy with dipeptidyl peptidase IV inhibitors. Biochim Biophys Acta;1751:33-44.
    • (2005) Biochim Biophys Acta , vol.1751 , pp. 33-44
    • Demuth, H.U.1    McIntosh, C.H.2    Pederson, R.A.3
  • 15
    • 79955708969 scopus 로고    scopus 로고
    • Possible ligand release pathway of dipeptidyl peptidase IV investigated by molecular dynamics simulations
    • Li C., Shen J., Li W.H., Lu C.H., Liu G.X., Tang Y. (2011) Possible ligand release pathway of dipeptidyl peptidase IV investigated by molecular dynamics simulations. Proteins;79:1800-1809.
    • (2011) Proteins , vol.79 , pp. 1800-1809
    • Li, C.1    Shen, J.2    Li, W.H.3    Lu, C.H.4    Liu, G.X.5    Tang, Y.6
  • 17
    • 34547626099 scopus 로고    scopus 로고
    • 3D-QSAR studies on fluoropyrrolidine amides as dipeptidyl peptidase IV inhibitors by CoMFA and CoMSIA
    • Zeng J., Liu G.X., Tang Y., Jiang H.L. (2007) 3D-QSAR studies on fluoropyrrolidine amides as dipeptidyl peptidase IV inhibitors by CoMFA and CoMSIA. J Mol Model;13:993-1000.
    • (2007) J Mol Model , vol.13 , pp. 993-1000
    • Zeng, J.1    Liu, G.X.2    Tang, Y.3    Jiang, H.L.4


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