Synthesis and SAR studies of urea and thiourea derivatives of Gly/Pro conjugated to piperazine analogue as potential AGE inhibitors

Protein and Peptide Letters

Volumn 20, Issue 8, 2013, Pages 888-897

  Vardhan, Doddahindaiah M Suyoga ^a   Shantharam, Chavalmane S ^a   Suhas, Ramesh ^a   Sridhara, Malavalli B ^a   Gowda, D Channe ^a  

^a UNIVERSITY OF MYSORE   (India)

Author keywords

Amino acids; Antiglycation; Conjugation; Piperazine; Urea thiourea

Indexed keywords

ADVANCED GLYCATION END PRODUCT; GLYCINE; PIPERAZINE DERIVATIVE; PROLINE; RUTOSIDE; TERT BUTYL 2 [4 (2,3 DICHLOROPHENYL)PIPERAZIN 1 YL 2 OXOETHYLCARBAMATE]THIOUREA DERIVATIVE; TERT BUTYL 2 [4 (2,3 DICHLOROPHENYL)PIPERAZIN 1 YL 2 OXOETHYLCARBAMATE]UREA DERIVATIVE; TERT BUTYL 2 [4 (2,3 DICHLOROPHENYL)PIPERAZINE 1 CARBONYL PYRROLIDINE 1 CARBOXYLATE]THIOUREA DERIVATIVE; TERT BUTYL 2 [4 (2,3 DICHLOROPHENYL)PIPERAZINE 1 CARBONYL PYRROLIDINE 1 CARBOXYLATE]UREA DERIVATIVE; UNCLASSIFIED DRUG; CARBANILAMIDE DERIVATIVE; THIOUREA;

ANTIGLYCATION ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CONJUGATION; DRUG DETERMINATION; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROSCOPY; PROTEIN GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; SYNTHESIS;

GLYCINE; GLYCOSYLATION END PRODUCTS, ADVANCED; HUMANS; MOLECULAR STRUCTURE; PHENYLUREA COMPOUNDS; PIPERAZINES; PROLINE; STRUCTURE-ACTIVITY RELATIONSHIP; THIOUREA;

EID: 84882354567     PISSN: 09298665     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929866511320080005     Document Type: Article

References (31)

1. Wild, S.; Roglic, G.; Green, A.; Sicree, R.; King, H. Global prevalence of diabetes: estimates for the year 2000 and projections for 2030. Diabetes Care, 2004, 27, 1047-1053.
2. Mohan, V.; Sandeep, S.; Deepa, R.; Shah, B.; Varghese, C. Epidemeology of type 2 diabetes. Indian J. Med. Res., 2007, 125, 217-230.
3. Giancarlo, V.; Thiazolidinediones-benefits on microvascular complications of type 2 diabetes. J. Diabetes Complicat., 2005, 19, 168-177.
4. Rahbar, S.; Figarola, J. L. Novel inhibitors of advanced glycation end products. Arch. Biochem. Biophys., 2003, 419, 63-79.
5. Puppala, M.; Chandrasekhar, A.; Reddy, B. Elagic acid, a new antiglycating agent: its inhibition of N.-(Carboxymethyl)lysine. Biochem. J., 2012, 442, 221-230.
6. Frederic, R.; Bihan, G. L.; Xuan, W; Aazdine, L.; Estera, T.; Georges, D. Design and synthesis of imidazoline derivatives active on glucose homeostasis in a rat model of type II diabetes. 1. Synthesis and biological activities of N.-benzyl-N'-(arylalkyl)-2-(4',5'-dihydro-1'H.-imidazol-2'-yl)piperazines. J. Med. Chem., 1997, 40, 3793-3803.
7. Chaudhary, P.; Kumar, R.; Verma, A. K.; Singh. D. Synthesis and antimicrobial activity of N.-Alkyl and N.-Aryl piperazine derivatives. Bioorg. Med. Chem., 2006, 14, 1819-1826.
8. Hachiro, S.; Hiroo, O.; Yasuo, A.; Youichi, I.; Yoshiharu, Y. Research and development of Donepezil Hydrochloride, a new type of Acetylcholinesterase inhibitor. Japanese J. Pharmacol., 2002, 89, 7-20.
9. Rebecca, D. P.; Patricia. The fractionation of t-RNA on N,Nbis(3-Aminopropyl)-piperazine substituted-Sepharose. Com. Chem. High. T. Scr., 2005, 8, 39-48.
10. Makoto, K.; Tomoko, M.; Koji, Y.; Masaki, M.; Nobuo, K.; Nobuyuki, K. Novel Diphenylalkyl piperazine derivatives with high affinities for the dopamine transpoter. Bioorg. Med. Chem., 2003, 11, 3953-3963.
11. He Zhao; Xiaoshu He; Andrew, T.; Diane, H.; Andrzej, K.; Robbin. B. Indoline and piperazine containing derivatives as a novel class of mixed D2/D4 receptors antagonists. Part 2 Asymmetric synthesis and biological evaluation. Bioorg. Med. Chem. Lett., 2002, 12, 3111-3115.
12. Brian, D.; Jessica, P.; Teresa, P.; Lee, C.; Brian, M.; Robin, S. Aryl piperazine melanocortin MC4 receptor Agonists. Bioorg. Med. Chem. Lett., 2003, 13, 3793-3796.
13. Rossen, K.; Steven, A. W.; Sager, J.; Reamer, R. A.; Askin, D.; Volante, R. P. Indole, azaindole and related heterocyclic Nsubstituted piperazine derivatives. Tetrahedron Lett., 1995, 36, 6419-6422.
14. Lee, L. F.; Schleppnik, F. M.; Schneider, R. W.; Campbell, D. H. Synthesis and 13C NMR of (trifluromethyl)hydroxypyrazoles. J. Heterocycl. Chem., 1990, 27, 243-245.
15. Rose, T. E.; Morisseau, C.; Jun-Yan Liu; Inceoglu, B.; Jones, P. D.; James R. S.; Hammock, B. D. 1-Aryl-3-(1-Acylpiperidin-4-yl)urea inhibitors of human and murine soluble epoxide hydrolase: structure-Activity relationships, pharmacokinetics, and reduction of inflammatory pain. J. Med. Chem., 2010, 53, 7067-7075.
16. Rachael, A. H.; Christopher, J. M. Free amino acids to heteroaromatics-Thiopeptide antibiotics natures heterocyclic peptides. Angew. Chem., 2007, 46, 7930-7954.
17. Ten Hoeve, W.; Wynberg, H. Substituted pyrimidinone and pyridone compounds and methods of use. Synth. Commun., 1994, 24, 2215-2221.
18. Khan, S. A.; Singh, N.; Saleem. K. Synthesis, characterization and in vitro antibacterial activity of thiourea and urea derivatives of steroids. Eur. J. Med. Chem., 2008, 43, 2272-2277.
19. Jung, Y.S.; Joe, B.Y.; Chob, S.J.; Konishi, Y. 2,3-Dimethoxy-5-methyl-1, 4-benzoquinones and 2-methyl-1,4-naphthoquinones: glycation inhibitors with lipid peroxidation activity. Bioorg. Med. Chem. Lett., 2005, 15, 1125-1129.
20. Khan, K. M.; Saeed, S.; Ali, M.; Gohar, M.; Zahid, J.; Khan, A.; Perveen, S.; Choudhary, M. I. Unsymmetrically disubstituted urea derivatives: A potent class of antiglycating agents. Bioorg. Med. Chem., 2009, 17, 2447-2451.
21. 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.
22. Khan, K.M.; Mughal, U.R.; Khan, A.; Naz, F.; Perveen, S.; Choudhary, M.I. N-Aroylated Isatins: Antiglycation Activity. Lett. Drug Des. Discov., 2010, 7, 188-193.
23. Khan, K.M.; Karim, A.; Ambreen, N.; Saied, S.; Rasheed, S.; Perveen, S.; Choudhary, M.I. Synthesis of benzoxazoles derivatives: Antiglycation activity. J. Pharm. Res., 2012, 5, 664-665.
24. Suhas, R.; Chandrashekar, S.; Gowda, D. C. A new family of highly potent inhibitors of microbes: Synthesis and conjugation of elastin based peptides to piperazine derivative. Int. J. Pept. Res. Thera., 2012, 18, 89-98.
25. Suresha, G. P.; Prakasha, K. C.; Shivakumara, K. N.; Wethroe K.; Gowda, D. C. Design and synthesis of heterocyclic conjugated peptides as novel antimicrobial agents. Int. J. Pept. Res. Thera., 2009, 15, 25-30.
26. Suhas, R.; Chandrashekar, S.; Gowda, D. C. Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials -A novel approach to enhance biocompatibility. Eur. J. Med. Chem., 2011, 46, 704-711.
27. Suresha, G. P.; Suhas, R.; Wethroe, K.; Gowda, D. C. Urea/thiourea derivatives of quinazolinone-lysine conjugates: Synthesis and structure activity relationships of a new series of antimicrobials. Eur. J. Med. Chem., 2011, 46, 2530-2540.
28. Suhas, R.; Chandrashekar, S.; Gowda. D. C. Synthesis of uriedo and thiouriedo derivatives of peptides conjugated heterocycles -A new class of promising antimicrobials. Eur. J. Med. Chem., 2012, 48, 179-191.
29. Suhas, R.; Gowda, D. C. Structure based rationale design and synthesis of aurantiamide acetate analogues -Towards a new class of potent analgesics and anti-inflammatory agents. Chem. Biol. Drug Des., 2012, 79, 850-862.
30. Oshiro Y.; Tokushima S.; Sato and Itana. US Patent, 1991, 5,006,528
31. Nakagawa, T.; Yokozawa, T.; Terasawa, K.; Shu, S.; Juneja, L.R. Protective Activity of Green Tea against Free Radical-And Glucose-Mediated Protein Damage. J. Agric. Food Chem., 2002, 50, 2418-2422.