A series of tetrachloroquinazolin-2,4-dione derivatives were synthesized using appropriate synthetic route and characterized by IR, 1H NMR, MS, and elemental analysis. The synthesized compounds were evaluated for their preliminary in vitro antibacterial activity towards
Pyrimidine and quinazoline derivatives have occupied a unique position in medicinal chemistry; the pyrimidine ring is present in a large number of biological important compounds [
The reaction sequences employed for synthesis of the target compounds are shown in Scheme
Physical properties and elemental analysis data.
Comp. | Molecular formula | Molecular weight | Elemental analysis (%) | |
---|---|---|---|---|
Anal calcd. | Found | |||
|
C8H3Cl4N3O2 | 314.94 | C-30.52; H-0.96; N-13.34; Cl-45.03 | C-30.75; H-0.97; N-13.52; Cl-45.01 |
|
C10H4Cl5N3O3 | 391.43 | C-30.69; H-1.03; N-10.73; Cl-45.29 | C-30.81; H-1.02; N-10.90; Cl-45.31 |
|
C11H4Cl4N4O3S | 414.06 | C-31.91; H-0.97; N-13.53; Cl-34.25 | C-32.15; H-0.98; N-13.72; Cl-34.27 |
|
C11H4Cl4N4O4 | 397.99 | C-33.20; H-1.01; N-14.08; Cl-35.63 | C-33.45; H-1.07; N-14.18; Cl-35.65 |
|
C11H4Cl4N4O3S | 414.06 | C-31.91; H-0.97; N-13.53; Cl-34.25 | C-32.02; H-0.99; N-13.56; Cl-34.30 |
|
C15H14Cl4N4O3 | 440.12 | C-40.94; H-3.20; N-12.73; Cl-32.22 | C-41.21; H-3.21; N-12.94; Cl-32.25 |
The reaction of compound
Formation of compounds
The two most active compounds tested are compounds
Antibacterial activity of some resulted compounds.
Compound no. ( |
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|
|
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Zone of inhibition (mm) | |||
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−ve | 8 | 15 |
|
7 | 9 | 18 |
|
7 | 10 | 16 |
Melting points were uncorrected and determined on an electric melting point apparatus (Kofler). The IR spectra (KBr) were recorded on a Shimadzu 408 spectrometer. The 1H-NMR spectra were recorded using 200 MHz varian EM 390 spectrometer; chemical shifts are reported in ppm with TMS as an internal standard and are given in
To a stirred solution of 3-aminotetrachloroquinazolin-2,4-dione
3-(2-Chloromethylcarbonylamino)tetrachloroquinazolin-2,4-dione
To a solution of 3-(2-chloromethylcarbonylamino)tetrachloroquinazolin-2,4-dione
Pale yellow crystals (0.27 gm, 67% yield), m.p. 306–308 C. FT.IR (KBr) (cm−1): 3211 (NH), 3021 (CH aliph.), 1751 and 1695 (C=O’s). 1HNMR (200 MHz, DMSO-d6)
White crystalline material (0.27 gm, 66% yield), m.p. 300–302 C. FT.IR (KBr) (cm−1): 3308 (NH), 1746 and 1669 (C=O’s), 1200 (C=S). 1HNMR (200 MHz, DMSO-d6)
A mixture of 3-(2-chloromethylcarbonylamino)tetrachloroquinazolin-2,4-dione
The authors are thankful to Dr. W. M. Salem, Lecturer of microbiology, Faculty of Science at Qena, South Valley University for his help, advice, and guidance in the microbiological studies in this work.