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Synthesis and evaluation of cytotoxic activities of some substituted isoxazolone derivatives

Year 2011, Volume: 15 Issue: 3, 94 - 99, 07.03.2014

Sevim Rollas Şila Kokyan Bedia Koçyiğit Kaymakçıoğlu , Suna Özbaş Turan , Jülide Akbuğa

Abstract

References

  • 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.
  • 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.
  • 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.
  • Ergenç N, Çapan G, Ötük G. New arylhydrazono-5(4H)- isoxazolone derivatives as possible antibacterial and an- ticonvulsant agents. Pharmazie 1993; 48: 780-782.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Abbiati G, Beccalli EG, Broggini G, Zoni CA. Valuable heterocyclic ring transformation: from isoxazolin-5(2H)- ones to quinolines. Tetrahedron 2003; 59: 9887-9893.
  • Frydenvang K, Brehm L, Dı Biase R, Falch E. 2-Ethyl- 3-(3-piridinil)-5(2H)-isoxazolone. Acta Cryst 1996; 52: 2102-2105.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Kokyan Ş. Synthesis and evaluation of cytotoxic activi- ties of some substituted isoxazolone derivatives. MU In- stitute of Health Sciences MSc thesis 2010; İstanbul.
  • Mossman T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxic- ity assays. J Immunol Methods 1983; 65: 55-63.
  • Beekman AC, Barentsen AR, Woerdenbag HJ, Uden WV, Pras N. Stereochemistry-dependent cytotoxicity of some artemisinin derivatives. J Nat Prod 1997; 60: 325-330.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.

Synthesis and evaluation of cytotoxic activities of some substituted isoxazolone derivatives

Year 2011, Volume: 15 Issue: 3, 94 - 99, 07.03.2014

Sevim Rollas Şila Kokyan Bedia Koçyiğit Kaymakçıoğlu , Suna Özbaş Turan , Jülide Akbuğa

Abstract

Keywords

1 2 4-Triazole-3-thione 1 3 4-thiadiazole isoxazolone hydrazone cytotoxic activity

References

  • 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.
  • 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.
  • 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.
  • Ergenç N, Çapan G, Ötük G. New arylhydrazono-5(4H)- isoxazolone derivatives as possible antibacterial and an- ticonvulsant agents. Pharmazie 1993; 48: 780-782.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Abbiati G, Beccalli EG, Broggini G, Zoni CA. Valuable heterocyclic ring transformation: from isoxazolin-5(2H)- ones to quinolines. Tetrahedron 2003; 59: 9887-9893.
  • Frydenvang K, Brehm L, Dı Biase R, Falch E. 2-Ethyl- 3-(3-piridinil)-5(2H)-isoxazolone. Acta Cryst 1996; 52: 2102-2105.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Kokyan Ş. Synthesis and evaluation of cytotoxic activi- ties of some substituted isoxazolone derivatives. MU In- stitute of Health Sciences MSc thesis 2010; İstanbul.
  • Mossman T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxic- ity assays. J Immunol Methods 1983; 65: 55-63.
  • Beekman AC, Barentsen AR, Woerdenbag HJ, Uden WV, Pras N. Stereochemistry-dependent cytotoxicity of some artemisinin derivatives. J Nat Prod 1997; 60: 325-330.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
There are 35 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Sevim Rollas This is me

Şila Kokyan This is me

Bedia Koçyiğit Kaymakçıoğlu

Suna Özbaş Turan

Jülide Akbuğa This is me

Publication Date March 7, 2014
Published in Issue Year 2011 Volume: 15 Issue: 3

Cite

APA Rollas, S., Kokyan, Ş., Koçyiğit Kaymakçıoğlu, B., Özbaş Turan, S., et al. (2014). Synthesis and evaluation of cytotoxic activities of some substituted isoxazolone derivatives. Marmara Pharmaceutical Journal, 15(3), 94-99. https://doi.org/10.12991/mpj.62173
AMA Rollas S, Kokyan Ş, Koçyiğit Kaymakçıoğlu B, Özbaş Turan S, Akbuğa J. Synthesis and evaluation of cytotoxic activities of some substituted isoxazolone derivatives. J Res Pharm. March 2014;15(3):94-99. doi:10.12991/mpj.62173
Chicago Rollas, Sevim, Şila Kokyan, Bedia Koçyiğit Kaymakçıoğlu, Suna Özbaş Turan, and Jülide Akbuğa. “Synthesis and Evaluation of Cytotoxic Activities of Some Substituted Isoxazolone Derivatives”. Marmara Pharmaceutical Journal 15, no. 3 (March 2014): 94-99. https://doi.org/10.12991/mpj.62173.
EndNote Rollas S, Kokyan Ş, Koçyiğit Kaymakçıoğlu B, Özbaş Turan S, Akbuğa J (March 1, 2014) Synthesis and evaluation of cytotoxic activities of some substituted isoxazolone derivatives. Marmara Pharmaceutical Journal 15 3 94–99.
IEEE S. Rollas, Ş. Kokyan, B. Koçyiğit Kaymakçıoğlu, S. Özbaş Turan, and J. Akbuğa, “Synthesis and evaluation of cytotoxic activities of some substituted isoxazolone derivatives”, J Res Pharm, vol. 15, no. 3, pp. 94–99, 2014, doi: 10.12991/mpj.62173.
ISNAD Rollas, Sevim et al. “Synthesis and Evaluation of Cytotoxic Activities of Some Substituted Isoxazolone Derivatives”. Marmara Pharmaceutical Journal 15/3 (March 2014), 94-99. https://doi.org/10.12991/mpj.62173.
JAMA Rollas S, Kokyan Ş, Koçyiğit Kaymakçıoğlu B, Özbaş Turan S, Akbuğa J. Synthesis and evaluation of cytotoxic activities of some substituted isoxazolone derivatives. J Res Pharm. 2014;15:94–99.
MLA Rollas, Sevim et al. “Synthesis and Evaluation of Cytotoxic Activities of Some Substituted Isoxazolone Derivatives”. Marmara Pharmaceutical Journal, vol. 15, no. 3, 2014, pp. 94-99, doi:10.12991/mpj.62173.
Vancouver Rollas S, Kokyan Ş, Koçyiğit Kaymakçıoğlu B, Özbaş Turan S, Akbuğa J. Synthesis and evaluation of cytotoxic activities of some substituted isoxazolone derivatives. J Res Pharm. 2014;15(3):94-9.

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