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Synthesis, Reactions, and Anti-inflammatory Activity of Heterocyclic Systems Fused to a Thiophene Moiety Using Citrazinic Acid As Synthon

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Summary.

A series of pyridines, pyrimidinones, and oxazinones were synthesized as anti-inflammatory agents using citrazinic acid (2,6-dihydroxyisonicotinic acid) as a starting material. Acryloyl pyridine was treated with cyanothioacetamide to give cyano pyridine-thione, which was reacted with ethyl chloroacetate to yield the corresponding amino ester. The ester was hydrolysed to the sodium salt, which was treated with acetic anhydride to afford 2-methyloxazinone, which was treated with ammonium acetate to afford 2-methylpyrimidinone followed by methylation with methyl iodide to yield 2,3-dimethylpyrimidinone. In addition, the oxazinone derivative was reacted with aniline or hydrazine hydrate to give 3-phenyl- or 3-aminopyrimidinones. The latter reacted with thiophene-2-carboxaldehyde or phenylisothiocyanate to afford Schiff’s bases or thiosemicarbazides. 3-Aminopyrimidinone was treated with phthalic anhydride or 1,2,4,5-benzenetetracarboxylic acid dianhydride or toluene-3,5-diisocyanate to afford the corresponding imide, bis-imide, and bis-semicarbazide derivatives. The pharmacological screening showed that many of these compounds have good anti-inflammatory activity comparable to Prednisolone® as reference drug.

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References

  • A Attia OI Abdel-Salam MH Abo-Ghalia AE Amr (1995) Egypt J Chem 38 543 Occurrence Handle1:CAS:528:DyaK28Xitl2jt7o%3D

    CAS  Google Scholar 

  • AE Amr MM Ashraf FM Salwa AA Nagla AG Hammam (2006) Bioorg Med Chem 14 5481 Occurrence Handle10.1016/j.bmc.2006.04.045 Occurrence Handle1:CAS:528:DC%2BD28Xmslyru74%3D

    Article  CAS  Google Scholar 

  • AE Amr NA Abdel-Latif MM Abdalla (2006) Acta Pharm 56 203 Occurrence Handle1:CAS:528:DC%2BD28XltValsLw%3D

    CAS  Google Scholar 

  • AE Amr MM Abdalla (2006) Bioorg Med Chem 14 4341 Occurrence Handle10.1016/j.bmc.2006.02.045 Occurrence Handle1:CAS:528:DC%2BD28XltVGqsro%3D

    Article  CAS  Google Scholar 

  • MH Abo-Ghalia AE Amr (2004) Amino Acids 26 283 Occurrence Handle10.1007/s00726-003-0042-8 Occurrence Handle1:CAS:528:DC%2BD2cXkvF2ms74%3D

    Article  CAS  Google Scholar 

  • AE Amr OI Abdel-Salam A Attia I Stibor (1999) Collect Czech Chem Commun 64 288 Occurrence Handle10.1135/cccc19990288 Occurrence Handle1:CAS:528:DyaK1MXitFyqt7g%3D

    Article  CAS  Google Scholar 

  • A Attia OI Abdel-Salam AE Amr (2000) Egypt J Chem 43 297 Occurrence Handle1:CAS:528:DC%2BD3cXptFSnsr4%3D

    CAS  Google Scholar 

  • MF Brana JM Castellano M Moran MJ Perez de Vega XD Qian CA Romerdahl G Keihauer (1995) Eur J Med Chem 30 235 Occurrence Handle10.1016/0223-5234(96)88230-4 Occurrence Handle1:CAS:528:DyaK2MXls1Srs74%3D

    Article  CAS  Google Scholar 

  • JK Chakrabarti L Horsman TM Hotten IA Pullar DE Tupper FC Wright (1980) J Med Chem 23 878 Occurrence Handle10.1021/jm00182a013 Occurrence Handle1:CAS:528:DyaL3cXls1Sqtrk%3D

    Article  CAS  Google Scholar 

  • VJ Ram HK Pandey AJ Vlietinck (1981) J Heterocycl Chem 18 1277 Occurrence Handle1:CAS:528:DyaL38Xht1aksbw%3D

    CAS  Google Scholar 

  • HH Fahmy W El-Eraqy (2001) Arch Pharm Res 24 171 Occurrence Handle1:CAS:528:DC%2BD38XitlCmsrY%3D Occurrence Handle10.1007/BF02978252

    Article  CAS  Google Scholar 

  • E DeClercq (1986) Anticancer Res 6 549 Occurrence Handle1:CAS:528:DyaL28Xls1Cht7c%3D

    CAS  Google Scholar 

  • E DeClercq (1986) J Med Chem 29 156

    Google Scholar 

  • AG Hammam M Sharaf NA Abdel-Hafez (2001) Ind J Chem 40B 213 Occurrence Handle1:CAS:528:DC%2BD3MXit1ejtL0%3D

    CAS  Google Scholar 

  • AG Hammam AFM Fahmy AE Amr AM Mohamed (2003) Ind J Chem 42B 1985 Occurrence Handle1:CAS:528:DC%2BD3sXms1Wgt7c%3D

    CAS  Google Scholar 

  • AE Amr MI Hegab AA Ibrahiem MM Abdulla (2003) Monatsh Chem 134 1395 Occurrence Handle1:CAS:528:DC%2BD3sXnvVWrurs%3D

    CAS  Google Scholar 

  • Nehad AA, Amr AE, Alhusain AI (2006) Monatsh Chem (Accepted 23-11-2006)

  • AE Amr NA Abdel-Latif MM Abdalla (2006) Bioorg Med Chem 14 273 Occurrence Handle10.1016/j.bmc.2005.08.023 Occurrence Handle1:CAS:528:DC%2BD2MXht1egsLvI

    Article  CAS  Google Scholar 

  • AE Amr HH Sayed MM Abdulla (2005) Arch Pharm Chem Life Sci 338 433 Occurrence Handle10.1002/ardp.200500982 Occurrence Handle1:CAS:528:DC%2BD2MXhtV2hu73J

    Article  CAS  Google Scholar 

  • AE Amr (2005) Z Naturforsch 60b 90

    Google Scholar 

  • AE Amr MH Abou-Galia MM Abdulla (2006) Z Naturforsch 61b 1335

    Google Scholar 

  • AE Amr MM Abdulla (2006) Arch Pharm Chem Life Sci 339 88 Occurrence Handle10.1002/ardp.200500209 Occurrence Handle1:CAS:528:DC%2BD28XitFCjtLs%3D

    Article  CAS  Google Scholar 

  • AE Amr (2000) Ind J Heterocycl Chem 10 49

    Google Scholar 

  • CA Winter EA Risely GW Nuss (1962) Proc Soc Exp Bio Med 111 541

    Google Scholar 

  • F Herrmann A Lindemann J Gamss R Mertelsmann (1999) Eur J Immunol 20 2513 Occurrence Handle10.1002/eji.1830201124

    Article  Google Scholar 

  • KF Austen WE Brocklehurst (1961) J Exp Med 113 521 Occurrence Handle10.1084/jem.113.3.521 Occurrence Handle1:CAS:528:DyaF3MXotF2qtA%3D%3D

    Article  CAS  Google Scholar 

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Correspondence to Abd El-Galil E. Amr.

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Amr, AG., Sabry, N. & Abdulla, M. Synthesis, Reactions, and Anti-inflammatory Activity of Heterocyclic Systems Fused to a Thiophene Moiety Using Citrazinic Acid As Synthon. Monatsh. Chem. 138, 699–707 (2007). https://doi.org/10.1007/s00706-007-0651-0

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