Synthesis, Antiviral and Cytotoxic Activity of 6-Bromo-2,3-disubstituted-4(3H)-quinazolinones(Medicinal Chemistry)

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概要

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• In the present study, a series of 6-bromo-2,3-disubstitued-4(3H)-quinazolinones was synthesized by condensation of 6-bromo-2-substituted-benzoxazin-4-one with trimethoprim, pyrimethamine and lamotrigine. The chemical structures of the synthesized compounds were confirmed by means of IR, ^1H-NMR and mass spectral and elemental analysis. The antiviral activity and cytotoxicity of the compounds were tested in E_6SM (Herpes simplex-1 KOS, Herpes simplex-1 TK-KOS ACV, Herpes simplex-2 G, Vaccinia virus, Vesicular stomatitis virus, Parainfluenza-3 virus, Reovirus-1, Sindbis virus, Coxsackie virus B4 and Punta Toro virus) and HeLa cell culture (Vesicular stomatitis virus, Coxsackie virus B4 and Respiratory syncyticla virus). Investigation of anti-HIV activity was done against replication of HIV-1 (HTLV-III B LAI) in MT-4 cells. 6-Bromo-2-phenyl-3-[(4-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-2-yl]-4(3H)-quinazolinone (4) exhibited the most potent antiviral activity with a MIC of 1.92μg/ml against vaccinia virus in E_6SM cell culture. The other compounds did not exhibit antiviral activity nor afford significant cytoprotection to the E_6SM and HeLa cell culture when challenged with the viruses. The study implies that 4 may possess activity against Pox viruses including variola. In the anti-HIV study, 6-bromo-2-methyl-3-[(4-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-2-yl]-4(3H)-quinazolinone (3) and 6-bromo-2-phenyl-3-[(4-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-2-yl]-4(3H)-quinazolinone (4) exhibited the least cytotoxic concentration (0.424, 0.461 μg/ml) which is an index of the infective viability of mock infected MT-4 cells with HIV-1. None of the compounds exhibited significant anti-HIV activity.

• 公益社団法人日本薬学会の論文
• 2003-09-01

著者

• Selvam Periyaswamy

  Department Of Pharamaceutical Chemistry Periyar College Of Pharmaceutical Science

• SRIDHAR Seshaiah

  Department of Pharmaceutical Chemistry and Pharmacology, Vel's College of Pharmacy

• Dinakaran Murugesan

  Department Of Pharamaceutical Chemistry Periyar College Of Pharmaceutical Science

• DECLERCQ Erik

  Rega Institute of Medical Research, Katholieke University

• Sridhar Seshaiah

  Department Of Pharmaceutical Chemistry C. L. Baid Metha College Of Pharmacy

• Declercq Erik

  Rega Institute Of Medical Research Katholieke University

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