Synthesis and evaluation of cytotoxic activities of some substituted isoxazolone derivatives

Abstract

References

1. Flores AFC, Zanatta N, Rosa A, Brondani S, Martins MAP. Synthesis of hydroxypyrazoles and 1-methyl-3- isoxazolones via haloform reactions. Tetrahedron Lett 2002; 43: 5005-5008.
2. Ishioka T, Tanatani A, Nagasawa K, Hashimoto Y. Anti- Androgens with full antagonistic activity toward human prostate tumor LNCaP cells with mutated androgen re- ceptor. Bioorg Med Chem 2003; 13: 2655–2658.
3. Demers J, Hageman W, Johnson S, Klaubert D, Look R, Moore J. Selective inhibitors of protein kinase C in a model of graft-vs-host disease. Bioorg Med Chem 1994; 4: 2451–2456.
4. Ergenç N, Çapan G, Ötük G. New arylhydrazono-5(4H)- isoxazolone derivatives as possible antibacterial and an- ticonvulsant agents. Pharmazie 1993; 48: 780-782.
5. Tamura N, Matsushta Y, Iwana T, Harada S, Kıshımoto S, Itoh K. Synthesis and biological activity of (S)-2-ami- no-3-(2,5-dhydro-5-oxo-4-isoxazolyl)propanoic acid (TAN-950 A) derivatives. Chem Pharm Bull 1991; 39: 1199-1212.
6. Tamura N, Iwama T, Itoh K. Synthesis and glutamate- agonistic activity of (S)-2-amino-3-(2,5-dihydro-5-oxo- 3-isoxazolyl)-propanoic acid derivatives. Chem Pharm Bull 1992; 40: 381-386.
7. Oral B. Synthesis and biological activities of hydrazones derived from five membered heterocylic rings. M U In- stitute of Health Sciences PhD thesis 2007; İstanbul.
8. Chande MS, Verma RS, Barve PA, Khanwelkar RR, Vai- dya RB, Ajaikumar KB. Facile synthesis of active antitu- bercular, cytotoxic and antibacterial agents: A Michael addition approach. Eur J Med Chem 2005; 40: 1143-1148.

9. Zhang J, Didierlaurent S, Fortin M, Lefrancois D, Uridat E, Vevert JP. Nonpeptide endothelin antagonists: from lower affinity pyrazol-5-ols to higher affinity pyrazole-5- carboxylic acids. Bioorg Med Chem Lett 2000; 10: 1351– 1355.
10. Selwood DL, Brummell DG, Glen RC, Goggin MC, Reynolds K, Tatlock MA, Wishart G. Solution-phase parallel synthesis of 5-carboxamido 1-benzyl-3-(3- dimethylaminopropyloxy)-1H-pyrazoles as activators of soluble guanylate cyclase with improved oral bioavail- ability. Bioorg Med Chem Lett 2001; 11: 1089–1092.
11. Abbiati G, Beccalli EG, Broggini G, Zoni CA. Valuable heterocyclic ring transformation: from isoxazolin-5(2H)- ones to quinolines. Tetrahedron 2003; 59: 9887-9893.
12. Frydenvang K, Brehm L, Dı Biase R, Falch E. 2-Ethyl- 3-(3-piridinil)-5(2H)-isoxazolone. Acta Cryst 1996; 52: 2102-2105.
13. Kömürcü ŞG, Rollas S, Yılmaz N, Çevikbaş A. Synthesis of 3-methyl-4-[(2,4-dihydro-4-substituted-3H-1,2,4-tria- zole-3-thione-5-yl)phenylhydrazono]-5-isoxazolone and evaluation of their antimicrobial activities. Drug Metab Drug Inter 1995; 12: 161-168.
14. Khan I, Sajid A, Hameed S, Rama NH, Hussain MT, Wa- dood A, Udin R, Ul-Haq Z, Khan A, Ali S, Choudhary MI. Synthesis, antioxidant activities and urease inhibi- tion of some new 1,2,4-triazole and 1,3,4-thiadiazole de- rivatives. Eur J Med Chem 2010; 45: 5200-5207.
15. Holla B S, Veerenda B, Shivananda K, Boja P. Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles. Eur J Med Chem 2003; 38: 759-767.
16. Abdel-Megeed AM, Abdel-Rahman HM, Alkaramany GE, El-Gendy MA. Design, synthesis and molecular modeling study of acylated 1,2,4-triazole-3-acetates with potential anti-inflammatory activity. Eur J Med Chem 2009; 44: 117-123.
17. Kumar H, Javed SA, Khan SA, Amir M. 1,3,4-Oxadia- zole/thiadiazole and 1,2,4-triazole derivatives of biphe- nyl-4-yloxy acetic acid: Synthesis and preliminary evalu- ation of biological properties. Eur J Med Chem 2008; 43: 2688-2698.
18. Kaplancikli ZA, Turan-Zitouni G, Ozdemir A, Revial G. New triazole and triazolothiadiazine derivatives as pos- sible antimicrobial agents. Eur J Med Chem 2008; 43: 155- 159.
19. Küçükgüzel İ, Küçükgüzel G, Rollas S, Otük-Saniş G, Ozdemir O, Bayrak I, Altuğ T, Stables, JP. Synthesis of some 3-(arylalkylthio)-4-alkyl/aryl-5-(4-aminophenyl)- 4H-1,2,4-triazole derivatives and their anticonvulsant activity. Farmaco 2004; 59: 893-901.
20. Küçükgüzel İ, Tatar E, Küçükgüzel ŞG, Rollas S, Clercq ED. Synthesis of some novel thiourea derivatives ob- tained from 5-[(4-aminophenoxy)methyl]-4- alkyl/aryl- 2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti- HIV and antituberculosis agents. Eur J Med Chem 2008; 43: 381-392.
21. Tozkoparan B, Küpeli E, Yeşilada E, Ertan M. Prepara- tion of 5-aryl-3-alkylthio-1,2,4-triazoles and correspond- ing sulfones with antiinflammatory-analgesic activity. Bioorg Med Chem 2007; 15: 1808-1814.
22. Doğan HN, Duran A, Rollas S. Synthesis and preliminary anticancer activity of new 1H-4,5-dihydro-3-(3-hydroxy- 2-naphthyl)-4-substituted-1,2,4-triazole-3-thiones. Indi- an J Chem Sec B 2005; 44: 2301-2307.
23. Ashok M, Holla BS, Boja P. Convenient one pot synthesis and antimicrobial evaluation of some new Mannich bas- es carrying 4-methylthiobenzyl moiety. Eur J Med Chem 2007; 42: 1095-1101.
24. Rollas S, Kalyoncuoğlu N, Sür-Altıner D, Yeğenoğlu Y. 5-(4-Aminophenyl)-4-substituted-2,4-dihydro-3H-1,2,4- triazole-3-thiones:Synthesis and antibacterial and anti- fungal activities. Pharmazie 1993; 48: 308-309.
25. Schenone S, Brullo C, Bruno O, Bondavalli F, Ranise A, Flippelli W, Rinaldi B, Capuano A, Falcone G. New 1,3,4-thiadiazole derivatives endowed with analgesic and anti-inflammatory activities. Bioorg Med Chem 2006; 14: 1698-1705.
26. Rzeski W, Matysiak J, Szerszén MK. Anticancer, neu- roprotective activities and computational studies of 2-amino-1,3,4-thiadiazole based compound. Bioorg Med Chem 2005; 15: 3201-3207.
27. Mavrova AT, Wesselinova D, Tsenov YA, Denkova P. Synthesis, cytotoxicity and effects of some 1,2,4-triazole and 1,3,4-thiadiazole derivatives on inmunocompetent cells. Eur J Med Chem 2009; 44: 63-69.
28. Kokyan Ş. Synthesis and evaluation of cytotoxic activi- ties of some substituted isoxazolone derivatives. MU In- stitute of Health Sciences MSc thesis 2010; İstanbul.
29. Mossman T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxic- ity assays. J Immunol Methods 1983; 65: 55-63.
30. Beekman AC, Barentsen AR, Woerdenbag HJ, Uden WV, Pras N. Stereochemistry-dependent cytotoxicity of some artemisinin derivatives. J Nat Prod 1997; 60: 325-330.
31. Srivastava V, Negi AS, Kumar JK, Faridi U, Sisodia BS, Darokar MP, Luqman S, Khanuja SPS. Synthesis of 1-(3’,4’,5’-trimethoxy)phenyl naptho[2,1b]furan as a novel anticancer agent. Bioorg Med Chem 2006; 16: 911- 914.
32. Karakuş S, Rollas S. Synthesis and antituberculosis ac- tivity of new N-phenyl-N’-[4-(5 alkyl/ arylamino-1,3,4- thiadiazole-2-yl)phenyl]thioureas. Farmaco 2002; 57: 577-581.
33. Solak N, Rollas S. Synthesis and antituberculosis activity of 2-(aryl/alkylamino)-5-(4-aminophenyl)-1,3,4-thiadia- zoles and their schiff bases. Arkivoc 2006; 12: 173-181.
34. Karakuş S, Çoruh U, Barlas-Durgun B, Vázquez-López EM, Özbaş-Turan S, Akbuğa J, Rollas S. Synthesis and cytotoxic activity of some 1,2,4-triazoline-3-thione and 2,5-disubstituted- 1,3,4-thiadiazole derivatives. Marma- ra Pharm J 2010; 14: 84-90.
35. Küçükgüzel G, Rollas S, Erdeniz H, Kiraz M, Ekinci CA, Vidin A. Synthesis, characterization and pharmacologi- cal properties of some 4-arylhydrazono-2-pyrazoline-5- one derivatives obtained from heterocyclic amines. Eur J Med Chem 2000; 35: 761-771.