Introduction

Heterocyclic composites play a crucial role in biochemical processes because the side groups of the most prevalent and significant components of living cells are based on heterocyclic [1]. Heterocyclic units can be found in large number of compounds which display manufacturing requests. The activity of the most compounds is mostly dependent on their molecular buildings [2-9]. As an importance of growth of systems suitable for the meeting of molecules containing heterocyclic models continues to be a focus for the attention of both the learning and manufacturing communities [10]. Furthermore, N-heterocyclic compounds exhibit biological properties such herbicidal activity, anti-inflammatory, antibacterial, anti-oxidative, anti-allergic, anti-convulsant, enzyme inhibitors, herbicidal activity, anti-HIV, anti-diabetic, anticancer activity and insecticidal agents [11, 12]. Treatment of infectious diseases brought on by viruses is a challenge regardless of the existence of several antiviral drugs. 1,2,4-triazines and their fused derivatives important in medicinal chemistry due to their high biological activity. Triazine is an aromatic heterocyclic ring analog to benzene in which three carbon atoms are substituted with nitrogen, giving it the chemical formula C₃H₃N₃ [13]. According to the location of the nitrogen atoms; namely, 1,2,3-triazine(I), 1,2,4-triazine(II), and 1,3,5-triazine(III) are the three isomeric forms. Due to their great biological activity, 1,2,4-triazines and their fused derivatives are significant compounds in medicinal chemistry [14]. Since compounds with a 1,2,4-triazine nucleus have received the greatest attention in term of their pharmacological and therapeutic potential, some of their derivatives are currently in the final stages of clinical research [15, 16].

Materials and Methods

The entire chemicals were purchased from BDH, Sigma Aldrich, CDH, and Merck. Melting point determinations were performed by the open capillary method using a SMP30 melting point apparatus and are reported uncorrected. The FT-IR spectra (KBr-discs) were recorded with IRAFFINITY-1CE Shimadzu spectrometer. ¹H-NMR spectra were recorded on a Jeol-500HZ- NMR spectrophotometer operating at 500MHz for ¹H-measurements.

Synthesis of 5,6-diphenyl-1,2,4-triazine-3-(2H)-one (S1) 5 ,6-diphenyl-1,2,4-triazine-3-(2H)-thione (S2) [17]

Benzil (0.5 mmol, 0.10 g) was combined with semicarbazide or thiosemicarbazide (1 mmol, 0.11 g, 0.09 g), respectively, in ethanol for 30 hours. The mixture was refluxed. Under vacuum, the solvent was extracted. These were extracted with dichloromethane, and then the organic layer was washed three times with water (3 × 10 mL), dried over magnesium sulphate, filtered, and the solvent was removed under vacuum to produce the crude products, recrystallization from ethanol.

Compounds S1

IR (KBr) (ν_max/ cm^-1): 1645(C=O, amide), 3198 (N-H, str), 1635(C=N), 1558 (C=C), 3000 (C-H aromatic), 12000 (N-N), 1026 (C-C), 1369 (C-N). ¹H-NMR (500 MHz, DMSO): δ 10.88 (s, H, NH), 7.18-8.38 (m, 5H, C-H aromatic), 13.56 (s, 1H, OH). ¹³C-NMR (125 MHz, DMSO): δ 153.88 (C=O amide), 128.5-136.23 (Car), 166.88 (C=N).

Compounds S2

IR (KBr) (ν_max/ cm^-1): 3126 (N-H Str), 1537 (C=C), 1367 (C=N), 1556 (C=S), 3000 (C-H aromatic), 1217 (N-N), 1057 (C-C), 1367(C-N). ¹H-NMR (500 MHz, DMSO): δ 10.05 (s, H, NH), 7.19-7.57 (m, 5H, C-H aromatic), 12.13 (s, 1H, SH). ¹³C-NMR (125 MHz, DMSO): δ 184.22(C-S), 126.84-142.22 (Car), 162.80 (C=N).

Synthesis of 2-(hydroxy methyl)-5,6-di phenyl-1,2,4-triazin-3(2H)–one (S3), 2-(hydroxymethyl)-5,6-di phenyl-1,2,4-triazin-3(2H)-thione (S4) [18]

Equal volume of 37% aqueous solution of formaldehyde was added to a suspension of (1 mmol, 0.24 g, 0.26 g) of compound S1 and S2, respectively, in 3-4 mL of EtOH and the mixture was refluxed during 3-5 min. The product which was crystallized from the formed light red solution was filtered off, washed with cold EtOH and dried. Analytical-pure compounds were obtained.

Compound S3

IR (KBr) (ν_max/ cm^-1): 3385 (O-H Stretch), 1658 (C=O, amide), 2900 (C-H alpha), 1084 (C-O, Str), 3000 (C-H aromatic), 1556 (C=C), 1369 (C-N), 1200 (N-N), 1000 (C-C), 1658 (C=N). ¹H-NMR (500 MHz, DMSO): δ 5.42 (t, 2H, N-CH₂), 7.09-7.46 (m, 5H, CH aromatic), 4.52 (s, 1H, OH). ¹³C-NMR (125 MHz, DMSO): δ 155.55 (C=O amide), 75.62 (CH₂ aliphatic), 166.55 (C=N), 128.55-131.49 (C aromatic).

Compound S4

IR (KBr) (ν_max/ cm^-1): 3360 (O-H, Str), 1057 (C-O, Str), 2978 (C-H alpha), 1489 (C=C), 1599 (C=S), 1114 (N-N), 3061 (C-H aromatic), 1340 (C-N), 1085 (C-C), 1599 (C=N). ¹H-NMR (500 MHz, DMSO): δ 4.78 (s, H, OH), 7.20-7.95 (m, 5H, CH aromatic), 5.82 (t, 2H, N-CH₂). ¹³C-NMR (125 MHz, DMSO): δ 179.59 (C=S), 80.67 (N-CH₂), 126.84-134.79 (C aromatic), 158.59 (C=N).                                 

Synthesis of (3-oxo-5,6-diphenyl-1,2,4-triazin-2(3H)-yl)methyl benzenesulfonate (S5), (5,6-diphenyl-3-thioxo-1,2,4-triazin-2(3H)-yl)methyl benzenesulfonate (S6) [18]

Benzene sulfonyl chloride (5.57 mmol, 0.97 g) was gradually added to a compound (S3, S4) (1.85 mmol, 0.50 g, 0.52 g), respectively, in 15 mL of pyridine while stirring at 0 °C. The solution was diluted with 6N. HCl after stirring at 0 °C for 10 hours. With the aid of CHCl₃, the reaction mixture was extracted. The extract was washed in brine and dried over anhydrous MgSO₄. After the solvent evaporation, chromatography on silica gel (eluent: CHCl₃) gave the product.

Compound S5                                                             

IR (KBr) (ν_max/ cm^-1): 1653 (C=O, amide), 1182 (S=O), 2928 (C-H, str), 1050 (C-O), 1489 (C=C), 1691 (C=N), 3063 (C-H aromatic), 1200 (N-N), 1100 (C-C), 1300 (C-N), 1631 (C-S). ¹H-NMR (500 MHz, DMSO): δ 5.40 (t, 2H, N-CH₂), 6.53-9.25 (m, 5H, C-H aromatic). C¹³-NMR (125 MHz, DMSO): δ 158.12 (C=O amide), 77.67 (N-CH₂), 167.59 (C=N), 126.84-134.59 (C aromatic).                           

Compound S6                                                            

IR (KBr) (ν_max/ cm^-1): 1182 (C-O, Str), 2845 (C-H stretch), 1483 (C=C), 1662 (C=N), 3059 (C-H aromatic), 1125 (S=O), 1506 (C=S), 1097 (C-C), 1211 (N-N), 1330 (C-N). ¹H-NMR (500 MHz, DMSO): δ 7.85-9.42 (m, 5H, CH aromatic), 5.53 (t, 2H, N-CH₂).

Synthesis of 2-(azidomethyl)-5,6-diphenyl-1,2,4-triazin-3(2H)-one (S7), 2-(azidomethyl)-5,6-diphenyl-1,2,4-triazine-3(2H)-thione (S8) [19]

The compound (S5 and S6) (1.1 mmol, 0.45 g, 0.477 g), respectively was dissolved in dry DMF (5 mL) and added to a solution of dry DMF (5 mL) and NaN₃ (7.66 mmol, 0.48 g). Prior to use, the solvent has been dried 1 hour on molecular sieves under Argon. The reaction was heated to 100 °C while being stirred beneath a blast shield and heating lasted for 6 hours at 100 °C. The precipitate was removed by filtration through a plug of silica under suction after cooling to room temperature and the solvent was evaporated to dryness. The solid was filtered. 

Compound S7 

IR (KBr) (ν_max/ cm^-1): 2123 (N=N=N), 1658 (C=O, amide), 2900 (C-H, str), 1500 (C=C), 1300 (C-N), 3086 (C-H aromatic), 1215 (N-N), 1000 (C-C), 1674 (C=N). ¹H-NMR (500 MHz, DMSO): δ 5.77 (S, 2H, N-CH₂), 7.28-7.34 (m, 5H, CH aromatic).

Compound S8

IR (KBr) (ν_max/ cm^-1): 2114 (N=N=N), 2900 (C-H str), 1500 (C=C), 1301 (C-N), 3000 (C-H ar), 1523 (C=S), 1100 (C-C), 1689 (C=N), 1100(N-N). ¹H-NMR (500 MHz, DMSO): δ 5.89 (s, 2H, N-CH₂), 7.45-7.86 (m, 5H, CH aromatic).

Synthesis of 2-((4-butyl-1H-1,2,3-triazol-1-yl)methyl)-5,6-diphenyl-1,2,4-triazin-3(2H)-one (S27), 2-((4-butyl-1H-1,2,3-triazol-1-yl)methyl)-5,6-diphenyl-1,2,4-triazine-3(2H)-thione (S28), N-((1-((3-oxo-5,6-diphenyl-1,2,4-triazin-2(3H)-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-5-((3aR,4R,6aS)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide (S31), N-((1-((5,6-diphenyl-3-thioxo-1,2,4-triazin-2(3H)-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-5-((3aR,4R,6aS)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide (S32) , 2-amino-3-(1-((3-oxo-5,6-diphenyl-1,2,4-triazin-2(3H)-yl)methyl)-1H-1,2,3-triazol-4-yl)propanoic acid (S33), 2-amino-3-(1-((5,6-diphenyl-3-thioxo-1,2,4-triazin-2(3H)-yl)methyl)-1H-1,2,3-triazol-4-yl)propanoic acid (S34) [20, 21]

 To the mixture of  benzyl azide (S7, S8) (1.00 mmol, 0.30 g, 0.32 g), respectively, and hex-l-yne (1.1 mmol, 0.09 g), biotin alkyne (1.1 mmol, 0.58 g), propargyl-glycine  (1.1 mmol, 0.12 g), respectively in THF/water (1:1) were added CuSO₄-5H₂O (5 mL, 0.2 mole, 0.04 g) and  sodium  ascorbate (0.2  mole, 0.03 g) at  room temperature. The reaction mixture was stirred at room temperature for 5-6 hours. After completion of the reaction which was monitored by TLC, the reaction mixture was extracted with ethyl acetate (210 mL) and water (5 mL). The organic layer was separated and dried over anhydrous Na₂SO₄, concentrated under reduced pressure and the remaining material was then flash column chromatography purified to provide the desired tri-azole.

Compound S27

IR (KBr) (ν_max/ cm^-1): 1651 (C=O, amide), 2870 (C-H, str), 1550 (C=C), 1689 (C=N), 2953 (C-H aromatic), 1111 (N-N), 1000 (C-C), 1462 (C-N). ¹H-NMR (500 MHz, DMSO): δ 0.65 (t, 3H, CH₃), 1.032-1.34 (m, 4H, CH₂), 7.085-7.136 (m, 5H, C-H aromatic), 2.33 (t, 2H, CH₂), 5.52 (s, 2H, N-CH₂-N).

Compound S28

IR (KBr) (ν_max/ cm^-1): 1550 (C=C), 2926 (C-H str), 1523 (C=S), 1687 (C=N), 3059 (C-H aromatic, str), 1379 (C-N), 1000 (C-C), 1100 (N-N). ¹H-NMR (500 MHz, DMSO): δ 7.233-7.565 (m, 5H, CH aromtic), 0.84 (t, 3H, CH₃), 1.23, 1.65 (t, 4H, CH₂), 2.51 (t, 2H, CH₂), 5.50 (s, 2H, N-CH₂-N).   

Compound S31

IR (KBr) (ν_max/ cm^-1): 3381 (NH), 1653 (C=O, amide), 2922 (C-H, str), 1456 (C=N), 3000 (C-H aromatic), 1500 (C-S), 1136 (N-N), 1369 (C-N), 1000 (C-C), 1600 (C=C). ¹H-NMR (500 MHz, DMSO): δ 8.07 (s, H, NH, amide), 7.28-7.37 (m, 5H, C-H aromatic), 5.78 (S, 1H, NH-C=O), 5.57 (s, 2H, N-CH₂-N), 4.23 (d, 2H, CH₂NH), 4.56 (m, 2H, CH-N), 2.76 (d, 4H, CH₂-S), 0.95, 1.25 (m, 6H, CH₂-CH₂-CH₂), 2.25 (t, 2H, O=C-CH₂).

Compound S32

IR (KBr) (ν_max/ cm^-1): 3383 (NH), 2924 (C-H stretch), 1550 (C=C), 1627 (C=N), 3000 (C-H aromatic), 1653 (C=O, amide), 1525 (C=S), 1126 (N-N), 1000 (C-C), 1516 (C-S), 1300 (C-N). ¹H-NMR (500 MHz, DMSO): δ 7.99 (s, H, NH, amide), 5.68 (s, 2H, NH-C=O-NH), 5.57 (s, 2H, N-CH₂-N), 0.95, 1.35 (m, 6H, CH₂–CH₂-CH₂), 2.15 (t, 2H, O=C-CH₂), 4.66 (m, 2H, CH-NH), 7.28-7.96 (m, 5H, CH aromatic), 4.23 (d, 2H, CH₂-NH), 3.27 (d, 4H, CH₂-S).

Compound S33

IR (KBr) (ν_max/ cm^-1): 2960-3392 (OH, carboxylic acid), 1700 (C=O, Carboxyl), 1635 (C=O, amide), 3298-3200 (NH₂, amine), 1606 (C=C), 1120 (N-N), 1051 (C-C), 1190 (C-N), 2900 (C-H, Str), 3000 (C-H aromatic). ¹H-NMR (500 MHz, DMSO): δ 10.71 (S, 1H, OH-carboxylic acid), 5.80 (s, 2H, NH₂, amine), 7.33-7.65 (m, 5H, C-H aromatic), 5.14 (S, 2H, N-CH₂-N), 4.04 (t, H, CH-NH₂), 2.76 (d, 2H, CH₂-C-NH₂).

Compound S34

IR (KBr) (ν_max/ cm^-1): 2856-3300 (OH, carboxylic acid), 1710 (C=O, Carboxyl), 1640 (C=O, amide), 3184-3200 (NH₂, amine), 2922 (C-H alp), 1066 (C-C), 1286 (N-N), 1516 (C=S), 1379 (C-N), 3055 (C-H aromatic), 1456 (C=C). ¹H-NMR (500 MHz, DMSO): δ 11.11 (s, H, OH-carboxylic acid), 5.80 (s, 2H, NH₂, amine), 7.68 CH (1,2,3-triazole), 5.17 (s, 2H, 2H, N-CH₂-N), 4.12 (t, H, CH-NH₂), 7.34-7.99 (m, 5H, C-H aromatic), 2.76 (d, 2H, CH₂-C-NH₂.

Synthesis of 2-(3-oxo-5,6-diphenyl-1,2,4-triazin-2(3H)-yl)quinazolin-4(3H)-one (S29), 2-(5,6-diphenyl-3-thioxo-1,2,4-triazin-2(3H)-yl)quinazolin-4(3H)-one (S30) [22]

Potassium tert-butoxide 1 mmol in 4 mL of DMSO, was added to the mixture of benzyl azide (S7 and S8) (1 mmol, 0.0032 g, 0.0031 g), respectively and isatoic anhydride (1 mmol, 0.006 g). After 4 hours of stirring at 100 °C for 4 hours, and then the reaction mixture was cooled to room temperature, H₂O (4 mL) was added and DCM (2 × 4 mL) was used to extract it.   

Compound S29

IR (KBr) (ν_max/ cm^-1): 3392 (NH), 1651 (C=O, amide), 1508 (C=C), 1689 (C=N), 3068 (C-H aromatic), 1238 (N-N), 1381 (C-N), 1000 (C-C). ¹H-NMR (500 MHz, DMSO): δ 7.34-8.21 (m, 5H, CH aromatic). ¹³C-NMR (125 MHz, DMSO): δ 161.17-168.71 (C=O amide), 147.07-152.71 (C=N), 125.98-135.35 (C aromatic).

Compound S30

IR (KBr) (ν_max/ cm^-1): 3389 (NH), 1575 (C=C), 1383 (C-N), 3063 (C-H aromatic), 1516 (C=S), 1257 (N-N), 1026 (C-C), 1689 (C=N), 1610 (C=O), ¹H-NMR (500 MHz, DMSO): δ 6.35-7.79 (m, 5H, CH aromatic). ¹³C-NMR (125 MHz, DMSO): δ 162.81 (C=O, amide), 114.19-150.62 (C aromatic), 164.81 (C=N), 173.81 (C=S).  

Results and Discussion

Triazine derivatives were produced as a result of benzil's reaction with smecarbazide or thiosemicarbazide respectively and then with formaldehyde. We first obtained the hydroxymethylation derivative, we carried out multiple reactions to produce the azide compounds, Scheme 1 (S1-S8).

The reaction the azide compounds with different alkynes we obtained the triazole, triazine, quinazoline, imidazoldine derivatives, in the Scheme 2 (S27-S34).

We prepared S1 by the reaction of benzil with semicarbazid. The IR spectrum of the S1 indicated by disappearance of broad bands at 3309-3433 cm^-1 of NH₂ group of semicarbazide. The ¹H-NMR spectrum showed the appearance of singlet peak at 10.88 ppm of NH group. The ¹³C-NMR spectrum showed the appearance of peak at 153.88 ppm (C=O, amide) and 166.88 ppm (C=N). Compound S2 has been identified by IR spectroscopy through the disappearance of bands at 3306 cm^-1 of NH₂ group of thiosemicarbazid and appearance bands at 3126 cm^-1 of NH group. Also, the appearance of band at 1367 cm^-1related to C=N group, compound S2 has been identified by ¹H-NMR spectroscopy. The ¹H-NMR spectrum showed the appearance of singlet peak at 10.05 ppm of NH group. The ¹³C-NMR spectrum showed the appearance of peak at 184.22 ppm (C=S, thioamide) and 162.80 ppm (C=N). Compound S3 has been identified by IR spectroscopy through the disappearance of bands at 3198 cm^-1 of NH group and appearance of bands at 3385 cm^-1 of OH group and the appearance of band at 2945 related to (C-H alpha). Likewise, the appearance of band at 1367 cm^-1 related to C=N group. The ¹H-NMR spectrum showed the appearance of singlet peak at 10.45 ppm of OH group and appearance of triplet peak at 5.42ppm of N-CH₂. The ¹³C-NMR spectrum showed the appearance of (C=O) at 155.55 ppm and appearance of (C=N) at 166.55 ppm and appearance of (CH₂) at 75.62 ppm. The IR spectrum of compound S4 showed the disappearance of bands at 3126 cm^-1 of NH group and appearance of bands at 3360 cm^-1 of OH group. The ¹H-NMR spectrum showed the appearance of singlet peak at 4.78 ppm of OH group and the appearance of triplet peak at 5.82 ppm to N-CH₂. The infrared spectrum of compound S5 showed the disappearance of band at 3385 cm^-1 of OH group. The ¹H-NMR spectrum showed the disappearance of triplet peak at 4.52 ppm of OH group and appearance of doublet peak at 5.40 ppm of N-CH₂. The ¹³C-NMR spectrum showed the appearance of S5 158.12 ppm due to (C=O) and appearance of 77.67 ppm due to (N-CH₂). The IR spectrum of compound S6 showed the disappearance of band at 3360 cm^-1 of OH group. The ¹H-NMR spectrum showed the disappearance of triplet peak at 4.78 ppm of OH group and appearance of doublet peak at 5.53ppm of N-CH₂. The IR spectrum of compound S7 showed the appearance of band at 2123 cm^-1 of g (N=N=N) group. The ¹H-NMR spectrum showed the appearance of singlet peak at 5.77 ppm to CH₂-N. The IR spectrum of compound S8 showed the appearance of band at 2114 cm^-1 of (N=N=N) and the appearance of band at 1674 of (C=N). The ¹H-NMR spectrum showed the appearance of singlet peak at 5.89 ppm to CH₂-N. The IR spectrum of compound S27 showed the disappearance of band at 2123 cm^-1 of (N=N=N) group. The ¹H-NMR spectrum showed the appearance of triplet peak at 0.659 ppm of CH₃ alpha and appearance of multiplet peak at 1.34 ppm to CH₂ and singlet peak at 5.52 ppm of N-CH2-N group. The IR spectrum of compound S28 showed the disappearance of bands at 2114.05 cm^-1 of (N=N=N) and appearance of band at (1523 cm^-1) of C=S group. The ¹H-NMR spectrum of compound S28 showed the appearance of triplet peak at 0.84-0.94 ppm of CH₃ alpha and the appearance of singlet peak at 5.50 ppm to N-CH₂-N. The IR spectrum of compound S29 showed the disappearance of band at 2123 cm^-1 of (N=N=N) group and appearance of bands of 3392 cm^-1 of NH group. The ¹H-NMR spectrum of compound S29 showed the disappearance of singlet peak at 5.77 ppm related to CH₂-N₃. The ¹³C-NMR spectrum showed the appearance of 161 and 168.71ppm due to (C=O) and appearance of 147,152.71 ppm due to (C=N). The IR spectrum of compound S30 showed the disappearance of band at 2114 cm^-1 of (N=N=N) and appearance of band at 3389 cm^-1 of NH group. The ¹H-NMR spectrum showed the disappearance of singlet peak to CH₂-N₃. The ¹³C-NMR spectrum showed the appearance of 162.8-164.8 ppm due to (C=O) and appearance of 173.8 ppm due to (C=S) and appearance of 147-150.6ppm due to (C=N). The IR spectrum of compound S31 showed the disappearance of band at 2123 cm^-1 of (N=N=N) group appearance of band at 3381 cm^-1 of NH group and 1620 cm^-1 and 1653 cm^-1 of amide group. The ¹H-NMR spectrum showed the appearance of singlet peak at 8.0 7ppm of NH group and appearance of singlet peak at 5.78 ppm related to NH-C=O group, and appearance of doublet peak at 3.3 ppm of CH₂-S. The IR spectrum of compound S32 showed the disappearance of bands at 2114 cm^-1 of (N=N=N) and appearance of band at 3352cm^-1 of NH group and 1653 cm^-1 and 1627cm^-1 of C=O. The ¹H-NMR spectrum showed the appearance of singlet peak at 7.8-7.9 ppm of NH group, and appearance of singlet peak at 5.65 ppm related to NH-C=O and appearance of doublet peak at 3.1-3.2 ppm of CH₂-S. The IR spectrum of compound S33 showed the appearance of band at 2960 cm^-1 of OH carboxylic acid group and 3298 and 3392 cm^-1 of NH₂ group. The ¹H-NMR spectrum showed the appearance of doublet peak at 5.8 ppm of NH₂ group and appearance of singlet peak at 10.7 ppm related to OH group and appearance of singlet peak at 5.14 ppm of N-CH₂-N. The IR spectrum of compound S34 showed the appearance of band at 3318 cm^-1 of NH₂ group and 2922 cm^-1 of OH carboxylic acid. The ¹H-NMR spectrum showed the appearance of singlet peak at 5.8 ppm of NH₂ group and appearance of singlet peak at 11.11 ppm related to OH group and appearance of singlet peak at 5.17 ppm of N-CH₂-N.

Biological activity

Antibacterial activity

 Escherichia coli, and Staphylococcus aurous. These bacteria were selected due to the importance in the field of medicine. These types of bacteria caused many diseases. The method used to calculate the inhibitory effect of compounds prepared on these types of bacteria is Agar diffusion method. It includes the following:

1. Work of several drilling in the dishes planted with bacteria.

2. (0.1 mL) of (25 mg/1 mL) of some derivatives prepared in the excavation of cultivars planted with bacteria.

3. Place the dishes in an incubator at a temperature of (37 °C) for 24 hours.

4. The inhibition zone was measured and the results are shown in Table 2.

These types of bacteria were selected because one of them (Staphylococcus aurous) is positive for the Graham stain, while the other (Escherichia coli) is negative. The inhibition extent of bacterial growth was studied according to the method of (agar diffusion method), where it was observed that most of the prepared compounds have biological effective as inhibitors to the growth of these two bacteria. Especially the (Escherichia coli) trend, where it was shown that the compounds S4, S8, S7, S27, S28, S29, S30, S31, S32, S33, and S34 have a high efficacy towards inhibiting their growth, and also it was discovered that the compound S4 and S8 has a stronger activity preventing the growth of bacteria (Staph.) If weighed against the other produced derivatives. Discovered that some additional compounds have a higher level of activity inhibiting Asp.niger growth if compared with the rest of the prepared derivatives.

Conclusion

1- New compounds were prepared and identified for the two compounds 5,6-diphenyl-1,2,4-triazine-3-(2H)-one and 5,6-diphenyl-1,2,4-triazine-3-(2H)-thione.                         

 2- Important heterocyclic compounds such as triazine, triazole, imidazolidine and quinazoline were prepared and diagnosed.

 3- Most of the compounds have high stability in weather conditions.   

4- The possibility of using some of the prepared compounds as antibacterials as they have high susceptibility to inhibit the growth of bacteria such as E.coli and Staphylococcus aureus after completing the necessary medical studies.

Funding

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.

ORCID:

Safaa Thamer Ahmed

https://orcid.org/0000-0001-8098-0085

HOW TO CITE THIS ARTICLE

Safaa Thamer Ahmed, Shireen Ridha Rasool. Synthesis, Characterization and Study Biological Activity of Some 1,2,4-Triazin Heterocyclic Derivatives.  J. Med. Chem. Sci., 2023, 6(7) 1537-1547

https://doi.org/10.26655/JMCHEMSCI.2023.x.x

URL: http://www.jmchemsci.com/article_161005.html