Synthesis of phenyl thiazole hydrazones and their activity against glycation of proteins

Medicinal Chemistry Research

Volumn 24, Issue 7, 2015, Pages 3077-3085

  Khan, Khalid Mohammed ^a   Irfan, Muhammad ^a   Ashraf, Mahwish ^a   Taha, Muhammad ^b   Saad, Syed Muhammad ^a   Perveen, Shahnaz ^c   Choudhary, M Iqbal ^a,d  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b UNIVERSITI TEKNOLOGI MARA   (Malaysia)

^c PCSIR LABORATORIES COMPLEX   (Pakistan)

^d KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

AGEPs; Antiglycation; Glycation of protein; Phenyl thiazole hydrazones; Schiff bases

Indexed keywords

2 METHOXY 5 [[2 (4 PHENYLTHIAZOL 2 YL)HYDRAZONO]METHYL]PHENOL; 2 METHOXY 6 [[2 (4 PHENYLTHIAZOL 2 YL)HYDRAZONO]METHYL]PHENOL; 2 [[2 (2 BROMOBENZYLIDENE)HYDRAZINYL]] 4 PHENYLTHIAZOLE; 2 [[2 (2 CHLORO 5 NITROOBENZYLIDENE)HYDRAZINYL]] 4 PHENYLTHIAZOLE; 2 [[2 (2 NITROBENZYLIDENE)HYDRAZINYL]] 4 PHENYLTHIAZOLE; 2 [[2 (2,4 DICHLOROBENZYLIDENE)HYDRAZINYL]] 4 PHENYLTHIAZOLE; 2 [[2 (2,6 DICHLOROBENZYLIDENE)HYDRAZINYL]] 4 PHENYLTHIAZOLE; 2 [[2 (3 CHLOROBENZYLIDENE)HYDRAZINYL]] 4 PHENYLTHIAZOLE; 2 [[2 (3 NITROBENZYLIDENE)HYDRAZINYL]] 4 PHENYLTHIAZOLE; 2 [[2 (3,4 DIMETHOXYBENZYLIDENE)HYDRAZINYL]] 4 PHENYLTHIAZOLE; 2 [[2 (4 BROMOBENZYLIDENE)HYDRAZINYL] 4 PHENYLTHIAZOLE; 2 [[2 (4 CHLOROBENZYLIDENE)HYDRAZINYL]] 4 PHENYLTHIAZOLE; 2 [[2 (4 ETHOXYBENZYLIDENE)HYDRAZINYL]] 4 PHENYLTHIAZOLE; 2 [[2 (4 NITROBENZYLIDENE)HYDRAZINYL]] 4 PHENYLTHIAZOLE; 2 [[2 (4 PHENYLTHIAZOL 2 YL)HYDRAZONO]METHYL]BENZENE 1,3,5 TRIOL; 2 [[2 (4 PHENYLTHIAZOL 2 YL)HYDRAZONO]METHYL]BENZENE 1,4 DIOL; 2 [[2 [1 (4 NITROPHENYL)ETHYLIDENE]HYDRAZINYL]] 4 PHENYLTHIAZOLE; 3 [[2 (4 PHENYLTHIAZOL 2 YL)HYDRAZONO]METHYL]PHENOL; 4 [1 [2 (4 PHENYLTHIAZOL 2 YL)HYDRAZONO]ETHYL]PHENOL; 4 [[2 (4 PHENYLTHIAZOL 2 YL)HYDRAZONO]METHYL]BENZENE 1,2 DIOL; 4 [[2 (4 PHENYLTHIAZOL 2 YL)HYDRAZONO]METHYL]BENZENE 1,3 DIOL; BOVINE SERUM ALBUMIN; HYDRAZONE DERIVATIVE; PHENOL DERIVATIVE; RUTOSIDE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

3T3 CELL LINE; ANIMAL CELL; ANTIGLYCATION ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FIBROBLAST; FIBROBLAST CULTURE; IC50; IN VITRO STUDY; NONHUMAN; PROTEIN GLYCOSYLATION; RAT; STRUCTURE ACTIVITY RELATION;

EID: 84940045270     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-015-1349-1     Document Type: Article

References (32)

1. AL-Garawi ZSM, Tomi IHR, AL-Daraji AHR (2012) Synthesis and characterization of new amino acid-Schiff bases and studies their effects on the activity of ACP, PAP and NPA enzymes (in vitro). Eur J Chem 9:962-969
2. Amanullah M, Sadozai SK, Rehman W, Hassan Z, Rauf A, Iqbal M (2011) Cytotoxic, antibacterial activity and physico-chemical properties of some acid catalyzed Schiff bases. African J Biotechnol 10:209-213
3. Anouar EH, Raweh S, Bayach I, Taha M, Baharudin MS, Meo FD, Hasan MH, Adam A, Ismail NH, Weber JF, Trouillas P (2013) Antioxidant properties of phenolic Schiff bases: structure-activity relationship and mechanism of action. J Comput Aided Mol Des 27:951-964
4. Bharti SK, Nath G, Tilak R, Singh SK (2010) Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring. Eur J Med Chem 45:651-660
5. Brewster CM (1924) Schiff's bases from 3,5-dibromo-salicylaldehyde. J Am Chem Soc 46:2463-2468
6. Campbell KN, Sommers AH, Campbell BK (1944) The preparation of unsymmetrical secondary aliphatic amines. J Am Chem Soc 66:82-84
7. Dimas K, Demetzos C, Marsellos M, Sotiriadou R, Malamas M, Kokkinopolos D (1998) Cytotoxic activity of labdane type diterpenes against human leukemic cell lines in vitro. Planta Med 64:208-211
8. Elhassan GOM, Adhikari A, Yousuf S, Rahman MH, Khalid A, Omer H, Fun H-K, Jahan H, Choudhary MI, Yagi S (2012) Phytochemistry and antiglycation activity of Aloe sinkatana Reynolds. Phytochem Lett 5:725-728
9. Kadhum MY (2011) Synthesis, identification and study of some new schiff bases as inhibitors for brass corrosion and bacterial growth. J Basrah Res Sci 37:87-112
10. Kazeem MI, Akanji MA, Hafizur RM, Choudhary MI (2012) Antiglycation, antioxidant and toxicological potential of polyphenol extracts of alligator pepper, ginger and nutmeg from Nigeria. Asian Pac J Trop Biomed 2:727-732
11. Khan KM, Khan M, Ali M, Taha M, Rasheed S, Perveen S, Choudhary MI (2009) Synthesis of bis-schiff bases of istain and their antiglycation activity. Bioorg Med Chem 17:7795-7801
12. Khan KM, Shah Z, Ahmad VU, Khan M, Taha M, Rahim F, Jahan H, Perveen S, Choudhary MI (2011a) Synthesis of 2,4,6-trichlorophenyl hydrazones and their inhibitory potential against glycation of protein. Med Chem 7:572-580
13. Khan KM, Rahim F, Halim SA, Taha M, Khan M, Perveen S, Zaheer-Ul-Haq Mesaik MA, Choudhary MI (2011b) Synthesis of novel inhibitors of β-glucuronidase based on benzothiazole skeleton and study of their binding affinity by molecular docking. Bioorg Med Chem 19:4286-4294
14. Khan KM, Shah Z, Ahmad VU, Khan M, Taha M, Ali S, Perveen S, Choudhary MI, Voelter W (2012a) 2,4,6-Trichlorophenylhydrazine Schiff bases as DPPH radical and super oxide anion scavengers. Med Chem 8:452-461
15. Khan KM, Taha M, Naz F, Ali S, Perveen S, Choudhary MI (2012b) Synthesis of acylhydrazide schiff bases and their anti-oxidant activity. Med Chem 8:705-710
16. Khan KM, Taha M, Rahim F, Fakhari MI, Choudhary MI (2013a) Acylhydrazide Schiff bases: synthesis and antiglycation activity. J Chem Soc Pak 35:929-937
17. Khan KM, Khan M, Ambreen N, Taha M, Rahim F, Rasheed S, Saied S, Shafi H, Perveen S, Choudhary MI (2013b) Oxindole derivatives: synthesis and antiglycation activity. Med Chem 9:681-688
18. Mahmud T, Rehman R, Abbas A, Anwar J (2012) Synthesis, analytical and antibacterial studies of N-[4-(phenyliminomethyl) phenyl] acetamide 0.67-hydrate and its complexes with Manganese (II), Cobalt (II) and Nickel (II). J Chem Soc Pak 34:67-71
19. Mohamed ME, Ishak CY, Wahbi HI (2011) Restricted Hartree-Fock (RHF) study of Schiff base (N-[(Z)-furan-2-ylmethylidene]- 4-methoxyaniline) formation between aromatic amine and furaldehyde. Der Chem Sin 2:133-139
20. Monnier VM, Sell DR, Dai Z, Nemet I, Collard F, Zhang J (2008) The role of the amadori product in the complications of diabetes. Ann N Y Acad Sci 1126:81-88
21. Munir C, Yousaf SM, Ahmad N (1985) Synthesis, characterization and pharmacological properties of a cobalt (II) complex of antibiotic ampicillin. J Chem Soc Pak 7:301-307
22. Musharraf SG, Bibi A, Shahid N, Najam-ul-Haq Khan M, Taha M, Mughal UR, Khan KM (2012) Acylhydrazide and Isatin Schiff bases as alternate UV-laser desorption ionization (LDI) matrices for low molecular weight (LMW) peptides analysis. Am J Anal Chem 3:779-789
23. Mustapha M, Thorat BR, Sawant S, Atram RG, Yamgar R (2011) Synthesis of novel Schiff bases and its transition metal complexes. J Chem Pharm Res 3:5-9
24. Pandey V, Chawla V, Saraf SK (2012) Comparative study of conventional and microwave-assisted synthesis of some Schiff bases and their potential as antimicrobial agents. Med Chem Res 21:844-852
25. Patil R, Donde KJ, Raut SS, Patil VR, Lokhande RS (2011) Synthesis, spectral and antimicrobial studies on mixed ligand Cu (II) complexes of Schiff base 2-amino-4-nitrophenol-N-salicylidene and some amino acids. J Pharm Res 4:2256-2260
26. Perez-Gutierrez RM, Muniz-Ramirez A, Gomez YG, Ramirez EB (2010) Antihyperglycemic, antihyperlipidemic and antiglycation effects of Byrsonima crassifolia Fruit and seed in normal and streptozotocin-induced diabetic rats. Plant Foods Hum Nutr 65:350-357
27. Sidambaram R, Jisha J, Mary NL (2011) Antibacterial studies of Schiff base complexes and polymer supported Schiff base complexes. Int J Inst Pharm Life Sci 1:49-56
28. Taha M, Baharudin MS, Ismail NH, Khan KM, Jaafar FM, Samreen Siddiqui S, Choudhary MI (2013a) Synthesis of 2-methoxybenzoylhydrazone and evaluation of their antileishmanial activity. Bioorg Med Chem Lett 23:3463-3466
29. Taha M, Ismail NH, Jamil W, Yousuf S, Jaafar FM, Ali MI, Kashif SM, Hussain E (2013b) Synthesis, evaluation of antioxidant activity and crystal structure of 2,4-dimethylbenzoylhydrazones. Molecules 18:10912-10929
30. Taha M, Ismail NH, Jamil W, Rashwan H, Kashif SM, Sain AA, Adenan MI, Anouar EH, Ali M, Rahim F, Khan KM (2014) Synthesis of novel derivatives of 4-methylbenzimidazole and evaluation of their biological activities. Eur J Med Chem 84:731-738
31. Vennilaa JP, Thiruvadigalb DJ, Kavitha HP (2012) Antibacterial evaluation of some organic compounds as potential inhibitors for glucosamine-6-phospate synthase. J Pharm Res 5:1963-1966
32. Wu JW, Hsieh CL, Wang HY, Chen HY (2009) Inhibitory effects of guava (Psidium guajava L.) leaf extracts and its active compounds on the glycation process of protein. Food Chem 113:78-84