Oxindole derivatives: Synthesis and antiglycation activity

Medicinal Chemistry

Volumn 9, Issue 5, 2013, Pages 681-688

  Khan, Khalid Mohammed ^a   Khan, Momin ^a,b   Ambreen, Nida ^a   Taha, Muhammad ^a   Rahim, Fazal ^a   Rasheed, Saima ^a   Saied, Sumayya ^a   Shafi, Humaira ^a   Perveen, Shahnaz ^c   Choudhary, Muhammad Iqbal ^a,d  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b ABDUL WALI KHAN UNIVERSITY   (Pakistan)

^c PCSIR LABORATORIES COMPLEX   (Pakistan)

^d KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

AGEPs; Antiglycation; Benzaldehydes; Oxindole; Rutin

Indexed keywords

3 [(1,1 BIPHENYL) 4 YL METHYLIDINE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(2 FLUOROPHENYL)METHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(2 HYDROXY 3 METHOXYPHENYL)METHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(2 HYDROXY 5 METHYLPHENYL)METHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(2 HYDROXYPHENYL)METHYLIDINE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(2 METHOXYPHENYL)METHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(2,4 DICHLOROPHENYL)METHYLIDINE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(3 CHLOROPHENYL)METHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(3 ETHOXY 2 HYDROXYPHENYL)METHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(3 HYDROXYPHENYL)METHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(3 NITROPHENYL)METHYLIDINE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(3,4 DICHLOROPHENYL)METHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(4 CHLOROPHENYL)METHYLIDINE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(4 ETHOXYPHENYL)METHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(4 FLUOROPHENYL)METHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(4 HYDROXYPHENYL)METHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(4 NITROPHENYL)METHYLIDINE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [(5 CHLORO 2 HYDROXYPHENYL)METHYLIDINE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [2 NAPHTHYLMETHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [9 ANTHRYLMETHYLIDENE] 1,3 DIHYDRO 2H INDOL 2 ONE; 3 [[4 (METHYLSULFANYL)PHENYL]METHYLIDENE) 1,3 DIHYDRO 2H INDOL 2 ONE; ADVANCED GLYCATION END PRODUCT; OXINDOLE; RUTOSIDE; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTEIN GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SCANNING ELECTRON MICROSCOPY; STRUCTURE ACTIVITY RELATION;

DOSE-RESPONSE RELATIONSHIP, DRUG; GLYCOSYLATION; INDOLES; MOLECULAR STRUCTURE;

EID: 84883413388     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/1573406411309050007     Document Type: Article

References (42)

1. Stefan, B.; Ratan, B.; Philip, E.; Sven, H. Preparation of 2-oxindole derivatives as glycogen synthase kinase-3 (GSK3) inhibitors for use in pharmaceutical compositions for treatment of neurodegenerative diseases, Patent 2003055877, 2003
2. Heidi, S-K.; Olivier, T. D. B.; Valerie, T. D. B.; Laura, C.; Pierfausto, S.; Hans-Wolfgang, K.; Tobias, B.; Silvia, M.; Barbara, F. W. M.; Sandra, G.; Hanno, R., Preparation of N-carbacycle monosubstituted indolocarbazoles for therapeutic use as protein kinase inhibitors. Patent WO 2003051887, 2003
3. Anne, B. J.; Gerd, R.; Jon, S. D.; Theo, S. Preparation of 3-substituted oxindole derivatives as 3- adrenergic receptor agonists, Patent WO 2003044016, 2003
4. John, S. R.; Anthony, A. M.; Claude, P. J.; Ronald, S. W.; Martin, M. E. Substituted 2-(S)-hydroxy-3-[(piperidin-4-ylmethyl) amino]propyl ethers and substituted 2-aryl-2-(R)-hydroxy-1-(piperidin-4-yl-methyl)ethylamines as β-3 adrenergic receptor agonists, antidiabetics, and antiobesity agents, Patent WO 2002006255, 2002
5. Susumu, M.; Akiko, I. Preparation of phenol or phenyl acetate derivatives as therapeutic drugs for prevention or treatment of diabetes and/or diabetes complications, Patent WO 2003103648, 2003
6. Noriaki, S.; Jun, S.; Masataka, K; Takao, M. Preparation of hydroxyindole derivatives as Pim-1 kinase inhibitors, Patent WO 2008056634, 2008
7. Bacon, E. R.; Bailey, T.; Becknell, N. C.; Gingrich, D. E.; Hostetler, G.; Hudkins, R. L.; Learn, K. S.; Wagner, J. C. Preparation of substituted pyrazolopyrimidines as inhibitors of glycogen synthase kinase 3 and cyclin dependent kinase 5, Patent WO 2008063232, 2007
8. Xialing, G.; Zhen, Z.; Malone, T. C.; Julie, W. Patent WO 2007087419, 2007
9. Stefan, B.; Ratan, B.; Philip, E.; Sven, H. Preparation of substituted 3-(5-membered unsaturated heterocyclyl)-1,3-dihydro-indol-2-one's and derivatives thereof as kinase inhibitors, Patent WO 2003055877
10. Cho, T. P.; Sun, Li, S.; Anthony, M. T.; Congxin, L.; My, T. N.; Thi, N. A.; Asaad, N. 3- Methylidenyl-2-indolinone modulators of protein kinase, Patent WO 2000008202, 2000
11. Cho, T. P.; Sun, Li; Gerald, M.; Peter, H. K.; Kay, S. L. et al. Indolinone combinatorial libraries and related products and methods for the treatment of disease, Patent WO 9807695, 1998
12. Showell, H. J. 3-Substituted-2-oxindole-1- carboxamides for suppressing T-cell function, Patent US 4853409, 1989.
13. Zaveri, N. T.; Jiang, F.; Olsen, C. M.; Deschamps, J. R.; Parrish, D.; Polgar, W.; Toll, L. A novel series of piperidin-4-yl-1,3- dihydroindol-2-ones as agonist and antagonist ligands at the nociceptin receptor. J. Med. Chem. 2004, 47, 2973-2976.
14. Alcaraz, M.; Atkinson, S.; Cornwall, P.; Foster, A. C.; Gill, D. M.; Humphries, L. A.; Keegan, P. S.; Kemp, R.; Merifield, E.; Nixon, R. A.; Noble, A. J.; O'Beirne, D.; Patel, Z. M.; Perkins, J.; Rowa, P.; Sadler, P.; Singleton, J. T.; Tornos, J.; Watts, A. J.; Woodland, I. A. Efficient syntheses of AZD4407 via thioether formation by nucleophilic attack of organometallic species on sulphur. Org. Process Res. Dev. 2005, 9, 555-569.
15. 7 receptor. Bioorg. Med. Chem. Lett. 2002, 12, 2549-2552.
16. Gallagher, R. Jr.; Patricia, G. L.; James, W. W.; Hieble, J. P.; De-Marinis, R. M. 4-[2-(Di-n-propylamino)ethyl]-2(3H)-indolone: a prejunctional dopamine receptor agonist. J. Med. Chem. 1985, 28, 1533-1536.
17. Koguchi, Y.; Kohno, J.; Nishio, M.; Takahashi, K.; Okuda, T.; Ohnuki, T.; Komatsubara, S. TMC-95A, B, C, and D, novel proteasome inhibitors produced by Apiospora montagnei Sacc. TC 1093. Taxonomy, production, isolation, and biological activities. J. Antibiot. 2000, 53, 105-109.
18. Smith, C. D.; Zilfou, J. T.; Stratmann, K.; Patterson, G. M. L.; Moore, R. E. Welwitindolinone analogues that reverse Pglycoprotein-mediated multiple drug resistance. Mol. Pharmacol. 1995, 47, 241-247.
19. Pajaoshesh, H.; Parson, R.; Popp, F. D. Potential anticonvulsants VI: condensation of isatins with cyclohexanone and other cyclic ketones. J. Pharm. Sci.1983, 72, 318-321.
20. Moilanen, E.; Alanko, J.; Asmawi, M. Z.; Vapaatalo, H.; Asmawi, M. Z.; Moilanen, E.; Alanko, J.; Vapaatalo, H. CP-66,248, A new antiinflammatoryagent, is a potent inhibitor of leukotriene B4 and prostanoid synthesis in human polymorphonuclear leucocytes in vitro. Eicosanoids 1988, 1, 35-39.
21. Mokrosz, M. J.; Duszyńska, B.; Misztal, S.; Kłodziń ska, A.; Tatarczyńska, E.; Chojnacka-Wójcik E.; Dziedzicka-Wasylewska M. A search for new 5-HT1A/5-HT2A receptor ligands. in vitro and in vivo studies of 1-[omega-(4-aryl-1-piperazinyl)alkyl]indolin-2(1H)- ones. Arch. Pharm. 1998, 331, 325-330.
22. Kornet, M. J.; Thio, A. P. Oxindole-3-spiropyrrolidines and - piperidines. Synthesis and local anesthetic activity. J. Med. Chem. 1976, 19, 892-898.
23. Khan, K. M.; Mughal, U. R.; Ambreen, N.; Khan, A.; Perveen, S.; Choudhary, M. I. Schiff Bases of istain: antiglycation activity. Lett. Drug Desig. Discov. 2009, 6, 358-362.
24. Khan, K. M.; Khan, M.; Ali, M.; Taha, M.; Rasheed, S.; Perveen, S.; Choudhary, M. I. Synthesis of Bis-Schiff bases of isatins and their antiglycation activity. Bioorg. Med. Chem. 2009, 17, 7795-7801.
25. Ahmed, N. Advanced glycation endproducts-role in pathology of diabetic complications. Diabeties Res. Clin. Pract. 2005, 67, 3-21.
26. Rahbar, S.; Figarola, J.L. Novel inhibitors of advanced glycation endproducts. Arch. Biochem. Biophys. 2003, 419, 63-79.
27. Brownlee, M. Glycation and diabetic complications. Diabetes 1994, 43, 836-841.
28. Peppa, M.; Uribarri, J.; Vlassara, H. Advanced glycation end products, and diabetes complications: what is new and what works. Clinical Diabetes 2003, 21, 186-187.
29. Monnier, V. M. Intervention against the Maillard reaction in vivo. Arch. Biochem. Biophys. 2003, 419, 1-15.
30. Vasan, S.; Foiles, P.; Founds, H. Therapeutic potential of breakers of advanced glycation end product-protein crosslinks. Arch. Biochem. Biophys. 2003, 419, 89-96.
31. Hunt, J. V.; Bottoms, M. A.; Mitchinson, M. J. Oxidative alterations in the experimental glycation model of diabetes mellitus are due to protein-glucose adduct oxidation. Some fundamental differences in proposed mechanisms of glucose oxidation and oxidant production. Biochem. J. 1993, 291, 529-535.
32. Ahmed, M. S.; Ahmed, N. Antiglycation properties of aged garlic extract: possible role in prevention of diabetic complications. Amer. Soc. Nutrit. 2006, 136, 796S-799S.
33. Gugliucci, A. Glycation as the glucose link to diabetic complications, J. Amer. Osteopath. Associ. 2000, 100, 621-634
34. Singh, R.; Barden, A.; Mori, T.; Beilin, L. Advanced glycation endproducts: A review. Diabetologia 2001, 44, 129-146.
35. Degenhardt, T. P.; Anderson, N. L.; Arrington, D. D.; Beattie, R. J.; Basgen, J. M. Pyridoxamine inhibits early renal disease and dyslipidemia in the streptozotocin-diabetic rat. Kidney International, 2002, 61, 939-950
36. Forbes, J. M.; Soulis, T.; Thallas, V.; Panagiotopoulos, S.; Long, D. M. Renoprotective effects of a novel inhibitor of advanced glycation. Diabetologia 2001, 44, 108
37. Lehman, T. D.; Ortwerth, B. J. Inhibitors of advanced glycation end product-associated protein cross-linking. Biochim. Biophys. Acta 2001, 1535, 110-119
38. Price, D. L.; Rhett, P. M.; Thorpe, S. R.; Baynes, J. W. Chelating activity of advanced glycation endproduct inhibitors. J. Biol. Chem. 2001, 276, 48967-48972
39. Khan, K. M.; Mughal, U. R.; Khan, A.; Naz, F.; Perveen, S.; Choudhary, M. I. N-Arylated isatins antiglycation activity. Lett. Drug Des. Disc., 2010, 7, 188-193.
40. Gugliucci, A.; Menini, T. The polyamines spermine and spermidine protect proteins from structural and functional damage by AGE precursors: A new role for old molecules?. Life Sciences 2003, 72, 2603-2616.
41. Quallich, G.; Morrissey, P. A general oxindole synthesis. Synthesis 1993, 51-67.
42. Sun, L.; Liang, C.; Shirazian, S.; Zhou, Y.; Miller, T.; Cui, J.; Fukuda, J. Y.; Chu, J.; Nematalla, A.; Wang, X.; Chen H.; Sistla, A.; Luu, T. C.; Tang, F.; Wei, J.; Tang, C. Discovery of 5-[5-fluoro-2- oxo-1,2-dihydroindol-(3Z)- ylidenemethyl]-2,4-dimethyl-1Hpyrrole-3-carboxylic acid (2-diethylaminoethyl) amide, a novel tyrosine kinase inhibitor targeting vascular endothelial and plateletderived growth factor receptor tyrosine tinase. J. Med. Chem. 1998, 41, 2588-2603.