JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 61 No 2 (2016): Journal of the Chilean Chemical Society
Original Research Papers

DESIGN, SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF 1-(4-OXO-3-(4-FLUOROPHENYL)-3HQUINAZOLIN- 2-YL)-4-(SUBSTITUTED) THIOSEMICARBAZIDE DERIVATIVES

V. Alagarsamy
Medicinal Chemistry Research Laboratory, MNR College of Pharmacy, Sangareddy, Gr.Hyderabad -502 294
Ramgopal Appan
Medicinal Chemistry Research Laboratory, MNR College of Pharmacy, Sangareddy, Gr.Hyderabad -502 294
M. T. Sulthana
Medicinal Chemistry Research Laboratory, MNR College of Pharmacy, Sangareddy, Gr.Hyderabad -502 294
B. Narendar
Medicinal Chemistry Research Laboratory, MNR College of Pharmacy, Sangareddy, Gr.Hyderabad -502 294
V. Raja Solomon
Medicinal Chemistry Research Laboratory, MNR College of Pharmacy, Sangareddy, Gr.Hyderabad -502 294
Vol 61, No 2 (2016): Journal of the Chilean Chemical Society
Published June 10, 2016
Keywords
  • Quinazolinone,
  • Substituted thiosemicarbazide,
  • Anti-bacterial,
  • Antitubercular activity
How to Cite
Alagarsamy, V., Appan, R., Sulthana, M. T., Narendar, B., & Raja Solomon, V. (2016). DESIGN, SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF 1-(4-OXO-3-(4-FLUOROPHENYL)-3HQUINAZOLIN- 2-YL)-4-(SUBSTITUTED) THIOSEMICARBAZIDE DERIVATIVES. Journal of the Chilean Chemical Society, 61(2). Retrieved from https://www.jcchems.com/index.php/JCCHEMS/article/view/2

Abstract

A new series of 1-(4-oxo-3-(4-fluorophenyl)-3H-quinazolin-2-yl)-4-(substituted) thiosemicarbazides (AR1-AR10) were obtained by the reaction of 2-hydrazino-3-(4-fluorophenyl) quinazolin-4(3H)-one (6) with different dithiocarbamic acid methyl ester derivatives. The key intermediate 3-(4-fluorophenyl)- 2-thioxo-2,3-dihydro-1H-quinazolin-4-one (4) was obtained by reacting 4-fluoroaniline (1) with carbon disulphide and sodium hydroxide in dimethyl sulphoxide to give sodium dithiocarbamate, which was methylated with dimethyl sulfate to yield the dithiocarbamic acid methyl ester (2) and condensed with methyl anthranilate (3) in ethanol yielded the desired compound (4) via the thiourea intermediate. The SH group of compound (4) was methylated for the favorable nucleophilic displacement reaction with hydrazine hydrate, which afford 2-hydrazino-3-(4-fluorophenyl)-3H-quinazolin-4-one (6). All synthesized compounds (AR1-AR10) were also screened for their antimicrobial activity against selective gram positive and gram negative by agar dilution method. In the present study compounds AR8 and AR9 were emerged as the most active compounds of the series.

  Fig. 1. Hybrid approach design of 1-(4-oxo-3-(4-fluorophenyl)-3H-quinazolin-2-yl)-4-(substituted)thiosemicarbazide analogs.

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