Antioxidant and antitumor activities of new synthesized aromatic c-nucleoside derivatives

Molecules

Volumn 19, Issue 4, 2014, Pages 5163-5190

  Sadek, Mohamed M El ^a   El Dayem, Nagwa S Abd ^a   Hassan, Seham Y ^a   Mostafa, Mohamed A ^a   Yacout, Galila A ^a  

^a Alexandria University Faculty Of Science   (Egypt)

Author keywords

Antioxidant; Indole; Isoindole; Isopropylidene; Oxadiazole; Oxoindoline; Pyrazole; Pyrrole

Indexed keywords

2,2-DIPHENYL-1-PICRYLHYDRAZYL; ANTINEOPLASTIC AGENT; ANTIOXIDANT; BIPHENYL DERIVATIVE; CARBOHYDRAZIDE; HYDRAZINE DERIVATIVE; NUCLEOSIDE; OXADIAZOLE DERIVATIVE; PICRIC ACID; THIOSEMICARBAZONE DERIVATIVE; TRIAZOLE DERIVATIVE;

ANTAGONISTS AND INHIBITORS; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; BIPHENYL COMPOUNDS; CELL LINE, TUMOR; CELL SURVIVAL; HUMANS; HYDRAZINES; MOLECULAR STRUCTURE; NUCLEOSIDES; OXADIAZOLES; PICRATES; STRUCTURE-ACTIVITY RELATIONSHIP; THIOSEMICARBAZONES; TRIAZOLES;

EID: 84899567895     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19045163     Document Type: Article

References (28)

1. El-Sadek, M.M.; El-Dayem, N.S.A.; Hassan, S.Y.; Yacout, G.A. 1,3,4-oxadiazole and selenadiazole derivatives as new C-glycosyl analogs with MAO-B, antibacterial and antifungal activities. Int. Res. J. Microbiol. 2013, 4, 204-219.
2. El-Sadek, M.M.; Hassan, S.Y.; El-Dayem, N.S.A.; Yacout, G.A. 5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and new cyclic C-glycoside analogues from carbohydrate precursors with MAO-B, antimicrobial and antifungal activities. Molecules 2012, 17, 7010-7027.
3. Nicolaou, K.C.; Ellery, S.P.; Rivas, F.; Saye, K.; Rogers, E.; Workinger, T.J.; Schallenberger, M.; Tawatao, R.; Montero, A.; Hessell, A.; et al. Synthesis and biological evaluation of 2',4'-and 3',4'-bridged nucleoside analogues. Bioorg. Med. Chem. 2011, 19, 5648-5669.
4. Popsavin, M.; Torovic, L.; Spaic, S.; Stankov, S.; Kapor, A.; Tomic, Z.; Popsavin, V. Synthesis and biological evaluation of new pyrazole-and tetrazole-related C-nucleosides with modified sugar moieties. Tetrahedron 2002, 58, 569-580.
5. Kamel, M.M.; Ali, H.I.; Anwar, M.M.; Mohamed, N.A.; Soliman, A.M. Synthesis, antitumor activity and molecular docking study of novel sulfonamide-schiff's bases, thiazolidinones, benzothiazinones and their C-nucleoside derivatives. Eur. J. Med. Chem. 2010, 45, 572-580.
6. Cho, A.; Saunders, O.L.; Butler, T.; Zhang, L.; Xu, J.; Vela, J.E.; Feng, J.Y.; Ray, A.S.; Kim, C.U. Synthesis and antiviral activity of a series of 1'-substituted 4-aza-7,9-dideazaadenosine C-nucleosides. Bioorg. Med. Chem. Lett. 2012, 22, 2705-2707.
7. Cho, A.; Zhang, L.; Xu, J.; Babusis, D.; Butler, T.; Lee, R.; Saunders, O.L.; Wang, T.; Parrish, J.; Perry, J.; et al. Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors. Bioorg. Med. Chem. Lett. 2012, 22, 4127-4132.
8. Wang, Q.; Li, Y.; Song, C.; Qian, K.; Chen, C.H.; Lee, K.H.; Chang, J. Synthesis and anti-HIV activity of 2'-deoxy-2'-fluoro-4'-C-ethynyl nucleoside analogs. Bioorg. Med. Chem. Lett. 2010, 20, 4053-4056.
9. Kifli, N.; Clercq, E.D.; Balzarini, J.; Simons, C. Novel imidazo[1,2-c]pyrimidine base-modified nucleosides: Synthesis and antiviral evaluation. Bioorg. Med. Chem. 2004, 12, 4245-4252.
10. Chen, H.; Zhao, J.; Li, Y.; Shen, F.; Li, X.; Yin, Q.; Qin, Z.; Yan, X.; Wang, Y.; Zhang, P.; et al. Synthesis and biological activity of novel 5'-arylamino-nucleosides by microwave-assisted one-pot tandem Staudinger/aza-Wittig/reduction. Bioorg. Med. Chem. Lett. 2011, 21, 574-576.
11. Wu, J.; Yu, W.; Fu, L.; He, W.; Wang, Y.; Chai, B.; Song, C.; Chang, J. Design, synthesis, and biological evaluation of new 2'-deoxy-2'-fluoro-4'- triazole cytidine nucleosides as potent antiviral agents. Eur. J. Med. Chem. 2013, 63, 739-745.
12. Rao, J.R.; Schinazib, R.F.; Chua, C.K. Enantioselective synthesis and antiviral activity of purine and pyrimidine cyclopentenyl C-nucleosides. Bioorg. Med. Chem. 2007, 15, 839-846.
13. Zemlicka, J. Enantioselectivity of the antiviral effects of nucleoside analogues. Pharmacol. Ther. 2000, 85, 251-266.
14. Jin, Y.L.; Hong, J.H. Synthesis and antiviral activity of novel 4'-branched carbocyclic C-nucleoside. Bull. Korean Chem. Soc. 2005, 26, 1366-1368.
15. El-Gazzar, A.R.B.A.; Hafez, H.N.; Hebat-Allah, S.A. S-and C-nucleosidoquinazoline as new nucleoside analogs with potential analgesic and anti-inflammatory activity. Eur. J. Med. Chem. 2009, 44, 4249-4258.
16. Hu, W.; Wang, P.; Song, C.; Pan, Z.; Wang, Q.; Guo, X.; Yu, X.; Shen, Z.; Wang, S.; Chang, J. Synthesis and anti-HCV activity of a new 2'-deoxy-2'-fluoro-2'-C-methyl nucleoside analogue. Bioorg. Med. Chem. Lett. 2010, 20, 7297-7298.
17. Bisht, S.S.; Jaiswal, N.; Sharma, A.; Fatima, S.; Sharma, R.; Rahuja, N.; Srivastava, A.K.; Bajpai, V.; Kumar, B.; Tripathi, R.P. A convenient synthesis of novel pyranosyl homo-C-nucleosides and their antidiabetic activities. Carbohydr. Res. 2011, 346, 1191-1201.
18. Wang, J.F.; Yang, X.D.; Zhang, L.R.; Yang, Z.J.; Zhang, L.H. Synthesis and biological activities of 5'-ethylenic and acetylenic modified L-nucleosides and isonucleosides. Tetrahedron 2004, 60, 8535-8546.
19. El-Sadek, M.M.; Zagzoug, N.B.; El-Soccary, N.N. Reactions of 2-methyl-5-(D-arabinotetrahydroxybutyl)-3-furoylhydrazine. Carbohydr. Res. 1993, 250, 323-326.
20. El-Sadek, M.M.; Yacout, G.A.; El-Soccary, N.N. Synthesis and MAO activity of 3-substituted-5-(5'-aryl-1',3',4'-oxadiazol-5-yl)-1,2-dimethyl-pyrroles. Pak. J. Sci. Ind. Res. 1989, 32, 649-654.
21. Sallam, M.A.; Ibrahim, E.S.I.; El-Eter, K.A.A.; Cassady, J.M. Synthesis and anomeric configuration of 2-(erythrofuranosyl)benzimidazole C-nucleoside analogues. Carbohydr. Res. 1997, 298, 93-104.
22. Sable, H.Z.; Ritchey, W.M.; Nordlander, J.E. Studies on cyclic polyols part IV. Nuclear magnetic resonance spectra and configurational assignments of polyhydroxycyclopentanes. Carbohydr. Res. 1965, 1, 10-21.
23. Amin, M.A.; Ibrahim, H.K.; Soliman, E.S.A.; Gaad, E.M. Synthesis and some reactions of [(4-arylphthalazine-1-yl) oxy]acetohydrazides. Mens. Agitat. 2009, 4, 55-70.
24. Hassan, S.Y.; Faidallah, H.M.; El-Massry, A.M.; El-Sadek, M.M. Synthesis and reactions of 5-(D-arabino-tetrahydroxybutyl)-3-(2,3-dihydro-1,3,4- oxadiazole-2-thion-5-yl)-2-methylfuran and 5-(D-arabino-tetrahydroxybutyl)-3(2- substituted amino-1,3,4-oxadiazol-5-yl)-2-methylfuran. Carbohydr. Res. 1997, 298, 123-126.
25. Abdel-Aziz, H.A.; Hamdy, N.A.; Farag, A.M.; Fakhr, I.M.I. Synthesis and reactions of 3-methylthiazolo[3,2-a]benzimidazole-2-carboxylic acid hydrazide: Synthesis of some new pyrazole, 1,3-thiazoline, 1,2,4-triazole and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives pendant to thiazolo[3,2-a]benzimidazole moiety. J. Chin. Chem. Soc. 2007, 54, 1573-1582.
26. Shahwar, D.; Raza, M.A.; Mirza, A.S.M.; Abbasi, M.; Ammad, V. Comparative study of antioxidant and antimicrobial activities of stembark extracts of Litchi chinensis and its organic fractions. J. Chem. Soc. Pak. 2010, 32, 357-362.
27. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
28. Vijayan, P.; Raghu, C.; Ashok, G.; Dhanaraj, S.A.; Suresh, B. Antiviral activity of medicinal plants of Nilgiris. Ind. J. Med. Res. 2004, 120, 24-29.