Document Type : Original Article


Department of Biochemistry, College of Medicine, University of Misan, Misan, Iraq


In this study, new Chalcones was prepared from reaction of 4-hydroxy acetophenone with different aldehydes in a basic medium, then new pyrimidine derivatives were synthesized from reaction of prepared Chalcones with urea and thiourea, the physical and chemical properties of synthesized compounds were studied using FT-IR, 1H-NMR, melting points. Likewise, the possible biological and antioxidant activity of prepared compounds was studied.

Graphical Abstract

Antimicrobial and Antioxidant Activity of Heterocyclic Compounds Derived from New Chalcones


Main Subjects


Chalcone compounds, which derived from 1,3-diphenyl-2-propene-1-one, are possessing chromophore moiety in their structures such as ketoethylenic group (–CO–CH=CH-), usually exhibiting different colors [1]. Their abundance in edible plants and is considered as the flavonoids and iso-flavonoids precursors, give the chalcones their importance. This type of compound might be synthesized via the Claisen-Schmidt condensation reaction. They have various applications in terms of biological activities and industrial uses. The chalcones synthesis can be carried out by following the standard methods and microwave aided approach [2, 3]. On the other hand, pyrimidine heterocyclic compounds possess in their structures an unsaturated-six-membered ring with two nitrogen atoms located at the first and the third locations of the ring [4, 5]. The derivatives of pyrimidine play a significant role in medicinal chemistry as it is reported that they exhibit a wide range of biological activities, including anthelmintic, antimicrobial, and anti-inflammatory activities. Many other biological applications are shown in the literature belonged to this class of organic compounds such as being anti-tubercular, antimalarial, antiviral, anticancer, and analgesic. These reports and previous studies encourage the current research for synthesizing the novel derivatives of pyrimidine and investigating their biological activities such as analgesic and anti-inflammatory activities [6].

Materials and Methods

The solvents and reagents employed in this study were used with no further purification. The open-glass capillaries method was used to record the melting points of the prepared compounds with no correction. In addition, Affinity-1 Shimadzu model of FT-IR spectrometer was used to record the Infrared spectra in forms of KBr pellets. However, Brucker model of NMR instrument with spectrospin ultrashield magnet 300 MHz was used to scan the 1H-NMR spectra. The internal reference was TMS and the solvent was DMSO-d6 for identifying the organic inhibitor.

The Synthesis of Chalcones (Ia-c) [7]

5 mmol of 4-hydroxyacetophenone and 5 mmol of aldehyde derivatives were mixed in 20 mL of EtOH in a round bottom flask, and then 6 mL of 40% NaOH solution was added dropwise and the reacting mixture was kept stirring and temperature under 10 °C for 12 hours. Thereafter, the mixture was kept for 24 hours at room temperature. Next, 1.5mL of 10% HCI was added dropwise to the mixture. The produced compound was then subjected to filtration and recrystallization from CH3CH2OH.

Synthesis of compounds (IId-i) [8]

A mixture of Chalcones (Ia-c) (0.6 g, 0.01 mol), with NH2CONH2 and NH2CSNH2 (0.6 g, 0.01 mol) were dissolved in EtOH (10 mL). 40% aqueous NaOH (10 mL) was added slowly with constant stirring. The reaction mixture was stirred for 4 hours, and then 100 mL of cold H2O was added with continuous stirring for two hours. After that, the mixture was kept in a cold place for 12 hours, and the product recrystallized was using C2H5OH as a solvent.

Biological activity [9]

The disk diffusion method was used to test the biological activity of the prepared compounds. The test was carried out against one strain of (E.coli), gram-negative bacteria, and one (Staphylococcus Aurous), gram-positive bacteria, as well as (Aspergillus niger), the fungi. The sterilization of the Petri dishes and prepared agar was conducted by autoclaving at 121 °C and for 15 min. The agar plates were uniformly surface inoculated from the broth culture of the tested microorganisms. 6 mm in diameter spaced apart holes were suitably made for the solidified medium and 100 μl of the synthesized compounds (0.025 mg of the produced material dissolved in DMSO solvent (1 mL)) was filled in. The prepared plates were subjected to 37 °C incubation for 24 hours to examine the inhibition zones that the compounds are causing on the bacteria. Table 1 presents the results of the preliminary screening test.

Antioxidant activity [10]

The solution was prepared by dissolving 4 g of DPPH in 100 mL of MeOH. Different concentrations were prepared from the some of the synthesized compounds, including 25, 50 and 100 ppm, by dissolving 1 milligram of the compound in 10 mL of MeOH to achieve the 100 parts per million, followed by diluting the solution to 25 and 50 parts per million. The same way was used for the concentrations, 1 mL of normal, or diluted solution such as 25, 50, and 100 ppm was poured to the solution in the test-tube that contains 1 mL DPPH. Each solution was measured in terms of the absorbance using spectrophotometer at wavelength 517 nm after incubation for 1 hour and at 37 °C.

(Blank absorption - sample absorption/blank absorption) × 100 = 1 %

Results and discussion

In the current study, the new chalcones (Ia-c) was synthesized from reaction of 4-hydroxyacetophnone with aldehyde derivatives, and then from reaction of prepared chalcones with urea and thiourea prepared compounds (Id-I), as indicated in Scheme 1. The vibration band of the (OH) group (stretch) appeared at (3458-3348) cm-1 and at (1315-1335) cm-1 for the (C=S) group, whereas, the (C=N) pyrimidine ring at (1610-1630) cm-1 [11]. The infrared spectra of compounds (Ia-c) and (Id-i) are depicted in Figures 1, 2 and 3. 1H-NMR spectrum compound (IC), δ 3.4 (s, 3H, OCH3), 5.2 (s, 1H, CH‚N), 6.6-8.3 (m, 8H, Harom), 7.4 (s, 1H, H pyrimidine ring), and 9.2 (s, 1H, OH). [12]. The compounds (Ib), (Ie), and (Ih) gives the best biological and antioxidant activity, as provided in Table 1 and Figure 4.

Scheme 1: Synthesis compounds Ia-c and Id-i


Compound (Ia)

Brown solid, yield 80%, mp 110-112 °C, IR (KBr) (νmax/ cm-1): 3358, 3109, 2927, 2854, 1620, 1577, 1517, 1348. v(OH), v(C-H) aromatic, v(C-H) aliphatic, v(C=C) aromatic, v(C=C) Chalcone and v(NO2) respectively. 1H-NMR (300 MHz, DMSO): δ 8.4 (d, 2H, CH=CH), 7.6-8.3 (d, J=12 Hz, 8H, aromatic rings), and 9.5 (S, 1H, OH).

Compound (Ib)

Brown solid, yield 90%, mp 120-122 °C, IR (KBr) (νmax/ cm-1): 3458, 3100, 2927, 2854, 1654, 1600, 1577, 1560. v(OH), v(C-H) aromatic, v(C-H) aliphatic,v(CHO),v(C=C) aromatic and Chalcone  respectively.

Compound (Ic)

White solid, yield 70%, mp 170-172 °C, IR (KBr) (νmax/ cm-1): 3348, 3090, 2945, 2837, 1662, 1583, 1232. v(OH), v(C-H) aromatic, v(C-H) aliphatic, v(C=C) chalcone, v(C-O-C)  respectively.

Compound (Id)

Yellow solid, yield 70%, mp 205-207 °C, IR (KBr) (νmax/ cm-1): 3360, 3080, 2955, 2850, 1645, 1625, 1580, 1507, 1350. v(OH), v(C-H) aromatic, v(C-H) aliphatic, v(C=O)amid, v(C=N)and v(NO2) respectively .  1H NMR (300 MHz, DMSO): δ 3.30 (s, 1H, -CH of pyrimidine ring), 7.5-8.28 (m, 9H, Ar-H), 8.4 (s, 1H, NH), and 10.5 (s, 1H, OH).

Compound (Ie)

Yellow solid, yield 60%, mp 220-222 °C, IR (KBr) (νmax/ cm-1): 3340, 3065, 2959, 2870, 1650, 1630, 1615, 1600. v(OH), v(C-H) aromatic, v(C-H) aliphatic, v(CHO),v(C=O)amide, v(C=N) and v(C=C) chalcone  respectively.

Compound (If)

White solid, yield 65%, mp 210-212 °C, IR (KBr) (νmax/ cm-1): 3420, 3050, 2970, 2840, 1640, 1620, 1570, 1240. v(OH), v(C-H) aromatic, v(C-H) aliphatic, v(C=O)amide, v(C=N), v(C=C) Chalcone  and v(C-O-C)  respectively.

Compound (Ig)

Brown solid, yield 55%, mp 260-262 °C, IR (KBr) (νmax/ cm-1): 3380, 3040, 2980, 2850, 1630, 1510, 1345, 1320. v(OH), v(C-H) aromatic, v(C-H) aliphatic,v(C=N), v(NO2 and v(C=S)  respectively.

Compound (Ih)

Green solid, yield 70%, mp 280-282 °C, IR (KBr) (νmax/ cm-1): 3360, 3080, 2950, 2866, 1625, 1620, 1600, 1315. v(OH), v(C-H) aromatic, v(C-H) aliphatic, v(C=N), v(CHO), v(C=C) chalcone  and v(C=S)  respectively.

Compound (Ii)

Milky solid, yield 80%, mp 270-272 °C, IR (KBr) (νmax/ cm-1):  3420, 3050, 2945, 2838, 1670, 1610, 1595, 1335. v(OH), v(C-H) aromatic, v(C-H) aliphatic, v(CHO), v(C=N), v(C=C) chalcone  and v(C=S)  respectively. 1H NMR (300 MHz, DMSO): δ 3.50 (s, 1H, -OCH3), 7.0-8.20 (m, 9H, Ar-H), 8.5 (s, 1H, NH), and 10 (s, 1H, OH).


Figure 1: FT-IR spectrums of chalcones (Ia)

Figure 2: FT-IR spectrums of chalcones (Ib)

Figure 3: FT-IR Spectrums of Chalcones (Ic)

Table 1: Biological study of prepared compounds



Staphylococcus aureus

Aspergillus niger




25 mm


14 mm

19 mm

25 mm


10 mm

15 mm

20 mm




25 mm


16 mm

22 mm

22 mm


5 mm

15 mm

20 mm


5 mm

10 mm

15 mm


13 mm

18 mm

27 mm


10 mm

15 mm

15 mm


29 mm





27 mm





28 mm

Figure 4: Antioxidant activity Ib, Ie and Ih



The new prepared compounds were synthesized from reaction of Chalcones with urea, thiourea, and the new prepared Chalcones have a lot of an electron-donating group. This donating group gave more activity for the prepared compounds against ant-bacterial and anti-fungal. The prepared compounds were characterized using spectroscopic techniques (FT-IR and 1H-NMR). The biological and antioxidant activity of three prepared compounds Ib, Ie, and Ih were better than another prepared compounds because they have more an electron donating groups.


This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.

Authors' contributions

All authors contributed to data analysis, drafting, and revising of the paper and agreed to be responsible for all the aspects of this work.

Conflict of Interest

The author declared that they have no conflict of interest.


Raed Muslim Muhiebes


Raed Muslim Mhaibes. Antimicrobial and Antioxidant Activity of Heterocyclic Compounds Derived from New Chalcones. J. Med. Chem. Sci., 2023, 6(4) 931-937



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