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Synthesis and characterization of triazenes derived from sulfonamides

Year 2011, Volume: 15 Issue: 1, 11 - 17, 06.03.2014

Seda Ünsalan Pelin Çıkla , Ş. Küçükgüzel , Sevim Rollas Fikrettin Şahin Ömer Bayrak

Abstract

Keywords

Triazene sulfonamide prontosil azo reduction

References

  • Scozzafava A, Supuran. CT. Carbonic anhydrase and matrix metalloproteinase inhibitors. Sulfonylated amino acid hydroxamates withMMP inhibitory properties act as efficient inhibitors of carbonic anhydrase isozymes I, II and IV, and N-hydroxy sulfonamides inhibit both these zinc enzymes. J Med Chem, 43: 3677-3687, 2000.
  • Wilkinson BL, Bornaghi LF, Wright, AD, Houston TTA, Poulsen A. Anti-mycobacterial activity of a bis-sulfona- mide. Bioorg Med Chem Lett, 17: 1355-1357, 2007.
  • Güzel Ö, Temperini C, Innocenti A, Scozzafava A, Sal- man A, Supuran CT. Carbonic anhydrase inhibitors. In- teraction of 2-(hydrazinocarbonyl)-3-phenyl-1H-indole- 5-sulfonamide with 12 mammalian isoforms: Kinetic and X-ray crystallographic studies. Bioorg Med Chem Lett, 18: 152- 158, 2008.
  • Kim J.S, Jung M, Ho Yoo K, Cho J, Hyun Ho C Synthesis and antibacterias activities of novel oxazolidinones hav- ing cyclic sulfonamides moities. Bioorg Med Chem Lett, 18: 5815-5818, 2008.
  • Crocetti L, Maresca A, Temperini C, Hall RA, Scozza- fava A, Mühlschlegel FA, Supuran CT. A thiabendazole sulfonamide shows potent inhibitory activity against mammalian and nematode alpha-carbonic anhydrases. Bioorg Med Chem Lett, 19:1371-1375, 2009.
  • Ghorab MM, Ragab FA, Hamed MM. Design, synthesis and anticancer evaluation of novel tetrahydro-quinoline derivatives containig sulfonamide moiety. Eur J Med Chem, 44: 4211-4217, 2009.
  • Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Anticancer and antiviral sulfonamide. Curr Med Chem, 10:925-953, 2003.
  • Rollas S, Küçükgüzel ŞG. Hydrazone, amide, carbamate, macromolecular and other prodrugs of doxorubicin. The Open Drug Deliv J, 2: 77-85, 2008.
  • Perry MJ, Carvolho E, Rosa E, Iley J. Towards an efficient prodrug of the alklating metabolite monomethyltria- zene: synthesis and stability of N-acylamino acid deriva- tives of triazene. Eur J Med Chem, 44:1049-1056, 2008.
  • Perry MJ, Mendes E, Simplicio AL, Coelho A, Soares RV, Iley J, Moreira R, Francisco AP Dopamine and tyramine- based derivatives of triazenes: activation by tyrosinase and implications for prodrug design. Eur J Med Chem, 44: 3228-3234, 2009.
  • Smith RH Jr, Scudiero DA, Michejda CJ. 1,3-dialkyl-3- acyltriazenes, a novel class of antineoplastic alkylating agents. J Med Chem, 33: 2579-2583, 1990.
  • Sanada M, Takagi Y, Ito R, Sekiguchi M. Killing and mutogenic actions of dacarbazine, a chemotherapeutic alkylating agent, on human and mouse cells: effects of Mgmt and Mıh1 mutations. DNA Repair, 3: 413-420, 2004.
  • Gescher A, Threadgill MD. The metabolism of triazene antitumor drugs. Pharmacol Ther, 32: 191-205, 1987.
  • Gibson NW, Erickson LC, Hickman JA. Effects of the antitumor agent 8-carbamoyl-3-(2-chloroethyl) imidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one on the DNA of mouse L1210 cells. Cancer Res, 44: 1767-1771, 1984.
  • Cheng CC, Elslager EF,Werbel LM, Priebe SR, Leopold WR Pyrazole derivatives. 5. Synthesis and antine- oplastic activity of 3-(2-chloroethyl)3,4-dihydro-4- oxopyrazolo[5,1-d]-1,2,3,5-tetrazine-8-carboxamide and related compounds. J Med Chem, 29: 1455-1547, 1986.
  • Tsang LLH, Quarterman CP, Gescher A, Slack JA Com- parison of the cytotoxicity in vitro of temozolomide and dacarbazine, prodrugs of 3-methyl-(triazen-1-yl)imida- zole-4-carboxamide. Cancer Chemother Pharmacol, 27: 342-346, 1991.
  • Clark AS, Deans B, Stevens MFG, Tisdale MJ, Wheelhouse RT, Denny BJ, Hartley JA. Antitumor imidazotetrazines. 32. Synthesis of novel imidazoteteazines and related bicy- clic heterocycles to probe the mode of action of the antitu- mor drug temozolomide. J Med Chem, 38: 1493-1504, 1995.
  • Kouroussis C, Vamvakas L, Vardakis N, Kotsakis A, Ka- lykaki A, Kalbakis K, Saridaki Z, Kentepozidis N, Gias- sas S, Georgoulias V. Continous administration of daily low-dose temozolomide in pretreated patients with ad- vanced non-small cell lung cancer: a phase II study. On- cology, 76: 112-117, 2009.
  • McConnaughie AW, Jenkins TC. Novel acridine-tria- zenes as protype combilexins:synthesis, DNA binding and biological activity. J Med Chem, 38: 3488-3501, 1995.
  • Coates L, Ikpeazu EV, Chen Y, Valenzuela MS. Inhibi- tion of DNA replication by berenil in plasmids containig poly(dA)poly(dT) sequences. Plasmid, 47: 120-128, 2002.
  • Burr SJ, Mselati A, Thomas EW. Photochemical DNA cleavage by a berenil analog. Tetrahedron Lett, 44: 7307- 7309, 2003.
  • Unsalan S, Rollas S. Synthesis and primary cytotoxic evaluation of new diaryltriazenes. Indian J Chem Sec B, 46: 185-191, 2007.
  • Çıkla P, Rollas S. Synthesis of some new triazene and di- azene derivatives and in vitro evaluation of preliminary antitumor activities. FABAD. J Pharm Sci, 32: 33-40, 2007.
  • Mathews JM, Costa KS Absorption, metabolism and dis- position of 1,3-diphenyl-1-triazene in rats and mice after oral, i.v. and dermal administration. Drug Metab Dispos, 27: 1499-1504, 1999.
  • Matheson SL, McNamee JP, Wang T, Alaoui-Jamali MA, Jean-Claude BJ. The combi-targeting concept: dissection of the binary mechanism of action of the combi-triazene SMA41 in vitro and antitumor activity in vivo. J Pharm Exp Ther, 311: 1163-1170, 2004.
  • Brahimi F, Rachid Z, McNamee JP, Alaoui-Jamali MA, Tari AM, Jean-Claude BJ. Mechanism of action of a novel “combi-triazene” engineered to possess a polar function- al group on the alkylating moiety: Evidence for enhance- ment of potency. Biochem Pharmacol, 70: 511-519, 2005.
  • Manolov I, Machullam HJ, monekov G. Synthesis, physi- cochemical characterization and preliminary pharmaco- logical in vitro evaluation of two novel cytotoxic benz- ophenone-linked 3,3-dimethyltriazenes. Pharmazie, 61: 511-516, 2006.
  • Daidone G, Raffa D, Maggio B, Raimondi MV, Plescia F, Schillaci D. Synthesis and antiproliferative activity of triazenoindazoles and triazenopyrazoles: a comparative study. Eur J Med Chem, 39: 219-224, 2004.
  • Vaughan K, Gamage Nicholas KUK, Singer RD, Roy M, Gibson NW. Triazene metabolism VI. 3-azidomethyl-3- alkyl-1-aryltriazenes, a new class of anti-tumour triazene with potential pro-drug applications. Anti-Cancer Drug Design, 2: 279-287, 1987.
  • Carvalho E, Francisco AP, Iley J, Rosa E. Triazene drug metabolites. Part 17: synthesis and plasma hydrolysis of acyloxymethyl carbamate derivatives of antitumor tria- zenes. Bioorg Med Chem, 8: 1719-1725, 2000.
  • Pages T, Langlois BR, Bars DL, Landais P. Fluorination of aromatic compounds from 1-aryl-3,3-dimethyltriazenes and fluoride anions in acidic medium: 2. Synthesis of (S)- [18F]-3-fluoro-α-methylphenylalanine. J Fluorine Chem, 107: 329-335, 2001.
  • Burui ana EC, Niculescu V, Buruiana T. Synthesis and properties of new polyurethane ionomers. I. Photosensi- tive cationomers with triazene units. J Appl Polym Sci, 88: 1203-1210, 2003.
  • Rachid Z, Katsoulas A, Brahimi F, Jean-Claude BJ. Syn- thesis of pyrimidinopyridine-triazene conjugates tar- geted to abl tyrosine kinase. Bioorg Med Chem Lett, 13: 3297-3300, 2003.
  • Kumar A, Mukarjee SK, Bhattacharya SK. Synthesis of N3-4-substituted-aryl-N1-(alkyl/aryl)substituted aryl) triazene-n1-oxides as potential anticonvulsant agents. Pharmazie, 38:66-67, 1983.
  • Buruiana EC, Melinte V, Buruiana T, Lippert T, Yoshikawa H, Mashuhara H. Synthesis and characteriza- tion of new hard polyurethanes with triazene pendants. J Photochem Photobiol A Chem, 171:261-267, 2005.
  • Burui ana EC, Niculescu V, Buruiana T. New poly- urethane cationemers with naphthyl and phenyltriazene pendants:synthesis and properties J Appl Polym Sci, 92:2599-2605, 2004.
  • Kaupp G, Herrmann A, Schmeyers J. Waste-free chemis- try of diazonium salts and benign separation of coupling products in solid salt reactions. Chem Eur J, 8:1395-1406, 2002.
  • Masoud MS, Ali AE, Shaker MA, Ghani MA. Solvent and substituent effects on spectroscopical changes of some diazoaminobenzene derivatives. Spectrochim Acta A Mol Biomol Spectrosc, 61: 3102-3107, 2005.
  • Dabbagh HA, Teimouri A, Chermahini AN, Shiasi R. DFT and ab initio calculations of the vibrational frequen- cies and visible spectra of triazenes derived from cyclic amines. Spectrochim Acta A Mol Biomol Spectrosc, 67: 437-443, 2007.
  • Prikryl J, Černý M, Bĕlohlavová H, Macháček V, Lyčka A. Structure of azo coupling products of 5-nitro-2,1-ben- zisothiazole-3-diazonium hydrogensulphate with aro- matic amines. Dyes and Pigments, 72:392-402, 2007.
  • Ding W, Liu B, Vought JL, Yamauchi H, Lind SE Anti- cancer activity of the antibiotic clioquinol. Cancer Res, 65:3389-3395, 2005.

Synthesis and characterization of triazenes derived from sulfonamides

Year 2011, Volume: 15 Issue: 1, 11 - 17, 06.03.2014

Seda Ünsalan Pelin Çıkla , Ş. Küçükgüzel , Sevim Rollas Fikrettin Şahin Ömer Bayrak

Abstract

References

  • Scozzafava A, Supuran. CT. Carbonic anhydrase and matrix metalloproteinase inhibitors. Sulfonylated amino acid hydroxamates withMMP inhibitory properties act as efficient inhibitors of carbonic anhydrase isozymes I, II and IV, and N-hydroxy sulfonamides inhibit both these zinc enzymes. J Med Chem, 43: 3677-3687, 2000.
  • Wilkinson BL, Bornaghi LF, Wright, AD, Houston TTA, Poulsen A. Anti-mycobacterial activity of a bis-sulfona- mide. Bioorg Med Chem Lett, 17: 1355-1357, 2007.
  • Güzel Ö, Temperini C, Innocenti A, Scozzafava A, Sal- man A, Supuran CT. Carbonic anhydrase inhibitors. In- teraction of 2-(hydrazinocarbonyl)-3-phenyl-1H-indole- 5-sulfonamide with 12 mammalian isoforms: Kinetic and X-ray crystallographic studies. Bioorg Med Chem Lett, 18: 152- 158, 2008.
  • Kim J.S, Jung M, Ho Yoo K, Cho J, Hyun Ho C Synthesis and antibacterias activities of novel oxazolidinones hav- ing cyclic sulfonamides moities. Bioorg Med Chem Lett, 18: 5815-5818, 2008.
  • Crocetti L, Maresca A, Temperini C, Hall RA, Scozza- fava A, Mühlschlegel FA, Supuran CT. A thiabendazole sulfonamide shows potent inhibitory activity against mammalian and nematode alpha-carbonic anhydrases. Bioorg Med Chem Lett, 19:1371-1375, 2009.
  • Ghorab MM, Ragab FA, Hamed MM. Design, synthesis and anticancer evaluation of novel tetrahydro-quinoline derivatives containig sulfonamide moiety. Eur J Med Chem, 44: 4211-4217, 2009.
  • Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Anticancer and antiviral sulfonamide. Curr Med Chem, 10:925-953, 2003.
  • Rollas S, Küçükgüzel ŞG. Hydrazone, amide, carbamate, macromolecular and other prodrugs of doxorubicin. The Open Drug Deliv J, 2: 77-85, 2008.
  • Perry MJ, Carvolho E, Rosa E, Iley J. Towards an efficient prodrug of the alklating metabolite monomethyltria- zene: synthesis and stability of N-acylamino acid deriva- tives of triazene. Eur J Med Chem, 44:1049-1056, 2008.
  • Perry MJ, Mendes E, Simplicio AL, Coelho A, Soares RV, Iley J, Moreira R, Francisco AP Dopamine and tyramine- based derivatives of triazenes: activation by tyrosinase and implications for prodrug design. Eur J Med Chem, 44: 3228-3234, 2009.
  • Smith RH Jr, Scudiero DA, Michejda CJ. 1,3-dialkyl-3- acyltriazenes, a novel class of antineoplastic alkylating agents. J Med Chem, 33: 2579-2583, 1990.
  • Sanada M, Takagi Y, Ito R, Sekiguchi M. Killing and mutogenic actions of dacarbazine, a chemotherapeutic alkylating agent, on human and mouse cells: effects of Mgmt and Mıh1 mutations. DNA Repair, 3: 413-420, 2004.
  • Gescher A, Threadgill MD. The metabolism of triazene antitumor drugs. Pharmacol Ther, 32: 191-205, 1987.
  • Gibson NW, Erickson LC, Hickman JA. Effects of the antitumor agent 8-carbamoyl-3-(2-chloroethyl) imidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one on the DNA of mouse L1210 cells. Cancer Res, 44: 1767-1771, 1984.
  • Cheng CC, Elslager EF,Werbel LM, Priebe SR, Leopold WR Pyrazole derivatives. 5. Synthesis and antine- oplastic activity of 3-(2-chloroethyl)3,4-dihydro-4- oxopyrazolo[5,1-d]-1,2,3,5-tetrazine-8-carboxamide and related compounds. J Med Chem, 29: 1455-1547, 1986.
  • Tsang LLH, Quarterman CP, Gescher A, Slack JA Com- parison of the cytotoxicity in vitro of temozolomide and dacarbazine, prodrugs of 3-methyl-(triazen-1-yl)imida- zole-4-carboxamide. Cancer Chemother Pharmacol, 27: 342-346, 1991.
  • Clark AS, Deans B, Stevens MFG, Tisdale MJ, Wheelhouse RT, Denny BJ, Hartley JA. Antitumor imidazotetrazines. 32. Synthesis of novel imidazoteteazines and related bicy- clic heterocycles to probe the mode of action of the antitu- mor drug temozolomide. J Med Chem, 38: 1493-1504, 1995.
  • Kouroussis C, Vamvakas L, Vardakis N, Kotsakis A, Ka- lykaki A, Kalbakis K, Saridaki Z, Kentepozidis N, Gias- sas S, Georgoulias V. Continous administration of daily low-dose temozolomide in pretreated patients with ad- vanced non-small cell lung cancer: a phase II study. On- cology, 76: 112-117, 2009.
  • McConnaughie AW, Jenkins TC. Novel acridine-tria- zenes as protype combilexins:synthesis, DNA binding and biological activity. J Med Chem, 38: 3488-3501, 1995.
  • Coates L, Ikpeazu EV, Chen Y, Valenzuela MS. Inhibi- tion of DNA replication by berenil in plasmids containig poly(dA)poly(dT) sequences. Plasmid, 47: 120-128, 2002.
  • Burr SJ, Mselati A, Thomas EW. Photochemical DNA cleavage by a berenil analog. Tetrahedron Lett, 44: 7307- 7309, 2003.
  • Unsalan S, Rollas S. Synthesis and primary cytotoxic evaluation of new diaryltriazenes. Indian J Chem Sec B, 46: 185-191, 2007.
  • Çıkla P, Rollas S. Synthesis of some new triazene and di- azene derivatives and in vitro evaluation of preliminary antitumor activities. FABAD. J Pharm Sci, 32: 33-40, 2007.
  • Mathews JM, Costa KS Absorption, metabolism and dis- position of 1,3-diphenyl-1-triazene in rats and mice after oral, i.v. and dermal administration. Drug Metab Dispos, 27: 1499-1504, 1999.
  • Matheson SL, McNamee JP, Wang T, Alaoui-Jamali MA, Jean-Claude BJ. The combi-targeting concept: dissection of the binary mechanism of action of the combi-triazene SMA41 in vitro and antitumor activity in vivo. J Pharm Exp Ther, 311: 1163-1170, 2004.
  • Brahimi F, Rachid Z, McNamee JP, Alaoui-Jamali MA, Tari AM, Jean-Claude BJ. Mechanism of action of a novel “combi-triazene” engineered to possess a polar function- al group on the alkylating moiety: Evidence for enhance- ment of potency. Biochem Pharmacol, 70: 511-519, 2005.
  • Manolov I, Machullam HJ, monekov G. Synthesis, physi- cochemical characterization and preliminary pharmaco- logical in vitro evaluation of two novel cytotoxic benz- ophenone-linked 3,3-dimethyltriazenes. Pharmazie, 61: 511-516, 2006.
  • Daidone G, Raffa D, Maggio B, Raimondi MV, Plescia F, Schillaci D. Synthesis and antiproliferative activity of triazenoindazoles and triazenopyrazoles: a comparative study. Eur J Med Chem, 39: 219-224, 2004.
  • Vaughan K, Gamage Nicholas KUK, Singer RD, Roy M, Gibson NW. Triazene metabolism VI. 3-azidomethyl-3- alkyl-1-aryltriazenes, a new class of anti-tumour triazene with potential pro-drug applications. Anti-Cancer Drug Design, 2: 279-287, 1987.
  • Carvalho E, Francisco AP, Iley J, Rosa E. Triazene drug metabolites. Part 17: synthesis and plasma hydrolysis of acyloxymethyl carbamate derivatives of antitumor tria- zenes. Bioorg Med Chem, 8: 1719-1725, 2000.
  • Pages T, Langlois BR, Bars DL, Landais P. Fluorination of aromatic compounds from 1-aryl-3,3-dimethyltriazenes and fluoride anions in acidic medium: 2. Synthesis of (S)- [18F]-3-fluoro-α-methylphenylalanine. J Fluorine Chem, 107: 329-335, 2001.
  • Burui ana EC, Niculescu V, Buruiana T. Synthesis and properties of new polyurethane ionomers. I. Photosensi- tive cationomers with triazene units. J Appl Polym Sci, 88: 1203-1210, 2003.
  • Rachid Z, Katsoulas A, Brahimi F, Jean-Claude BJ. Syn- thesis of pyrimidinopyridine-triazene conjugates tar- geted to abl tyrosine kinase. Bioorg Med Chem Lett, 13: 3297-3300, 2003.
  • Kumar A, Mukarjee SK, Bhattacharya SK. Synthesis of N3-4-substituted-aryl-N1-(alkyl/aryl)substituted aryl) triazene-n1-oxides as potential anticonvulsant agents. Pharmazie, 38:66-67, 1983.
  • Buruiana EC, Melinte V, Buruiana T, Lippert T, Yoshikawa H, Mashuhara H. Synthesis and characteriza- tion of new hard polyurethanes with triazene pendants. J Photochem Photobiol A Chem, 171:261-267, 2005.
  • Burui ana EC, Niculescu V, Buruiana T. New poly- urethane cationemers with naphthyl and phenyltriazene pendants:synthesis and properties J Appl Polym Sci, 92:2599-2605, 2004.
  • Kaupp G, Herrmann A, Schmeyers J. Waste-free chemis- try of diazonium salts and benign separation of coupling products in solid salt reactions. Chem Eur J, 8:1395-1406, 2002.
  • Masoud MS, Ali AE, Shaker MA, Ghani MA. Solvent and substituent effects on spectroscopical changes of some diazoaminobenzene derivatives. Spectrochim Acta A Mol Biomol Spectrosc, 61: 3102-3107, 2005.
  • Dabbagh HA, Teimouri A, Chermahini AN, Shiasi R. DFT and ab initio calculations of the vibrational frequen- cies and visible spectra of triazenes derived from cyclic amines. Spectrochim Acta A Mol Biomol Spectrosc, 67: 437-443, 2007.
  • Prikryl J, Černý M, Bĕlohlavová H, Macháček V, Lyčka A. Structure of azo coupling products of 5-nitro-2,1-ben- zisothiazole-3-diazonium hydrogensulphate with aro- matic amines. Dyes and Pigments, 72:392-402, 2007.
  • Ding W, Liu B, Vought JL, Yamauchi H, Lind SE Anti- cancer activity of the antibiotic clioquinol. Cancer Res, 65:3389-3395, 2005.
There are 41 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Seda Ünsalan This is me

Pelin Çıkla

Ş. Küçükgüzel

Sevim Rollas This is me

Fikrettin Şahin This is me

Ömer Bayrak This is me

Publication Date March 6, 2014
Published in Issue Year 2011 Volume: 15 Issue: 1

Cite

APA Ünsalan, S., Çıkla, P., Küçükgüzel, Ş., Rollas, S., et al. (2014). Synthesis and characterization of triazenes derived from sulfonamides. Marmara Pharmaceutical Journal, 15(1), 11-17. https://doi.org/10.12991/mpj.95844
AMA Ünsalan S, Çıkla P, Küçükgüzel Ş, Rollas S, Şahin F, Bayrak Ö. Synthesis and characterization of triazenes derived from sulfonamides. J Res Pharm. March 2014;15(1):11-17. doi:10.12991/mpj.95844
Chicago Ünsalan, Seda, Pelin Çıkla, Ş. Küçükgüzel, Sevim Rollas, Fikrettin Şahin, and Ömer Bayrak. “Synthesis and Characterization of Triazenes Derived from Sulfonamides”. Marmara Pharmaceutical Journal 15, no. 1 (March 2014): 11-17. https://doi.org/10.12991/mpj.95844.
EndNote Ünsalan S, Çıkla P, Küçükgüzel Ş, Rollas S, Şahin F, Bayrak Ö (March 1, 2014) Synthesis and characterization of triazenes derived from sulfonamides. Marmara Pharmaceutical Journal 15 1 11–17.
IEEE S. Ünsalan, P. Çıkla, Ş. Küçükgüzel, S. Rollas, F. Şahin, and Ö. Bayrak, “Synthesis and characterization of triazenes derived from sulfonamides”, J Res Pharm, vol. 15, no. 1, pp. 11–17, 2014, doi: 10.12991/mpj.95844.
ISNAD Ünsalan, Seda et al. “Synthesis and Characterization of Triazenes Derived from Sulfonamides”. Marmara Pharmaceutical Journal 15/1 (March 2014), 11-17. https://doi.org/10.12991/mpj.95844.
JAMA Ünsalan S, Çıkla P, Küçükgüzel Ş, Rollas S, Şahin F, Bayrak Ö. Synthesis and characterization of triazenes derived from sulfonamides. J Res Pharm. 2014;15:11–17.
MLA Ünsalan, Seda et al. “Synthesis and Characterization of Triazenes Derived from Sulfonamides”. Marmara Pharmaceutical Journal, vol. 15, no. 1, 2014, pp. 11-17, doi:10.12991/mpj.95844.
Vancouver Ünsalan S, Çıkla P, Küçükgüzel Ş, Rollas S, Şahin F, Bayrak Ö. Synthesis and characterization of triazenes derived from sulfonamides. J Res Pharm. 2014;15(1):11-7.

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