Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5, 120-135 2025 Publisher: Learning Gate DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate © 2025 by the authors; licensee Learning Gate History: Received: 19 February 2025; Revised: 10 April 2025; Accepted: 14 April 2025; Published: 3 May 2025 * Correspondence: zainabdh9977@gmail.com Design, synthesis and antimicrobial activity screening of new dimethyl maleimidyl heterocyclic derivatives based on 4-(N-dimethyl maleimidyl) phenyl hydrazide Zainab Majid Sadiq1*, Ahlam Marouf Al-Azzawi2 1,2Department of Chemistry, College of Science, University of Baghdad, Baghdad. Iraq; zainabdh9977@gmail.com (Z.M.S.) ahlammarouf24@gmail.com (A.M.A.A.). Abstract: The research involved the design and synthesis of a collection of innovative dimethyl maleimide heterocyclic derivatives through a multistep synthesis process. The synthesis of compound [1] ethyl-4-(N-dimethyl maleimidyl) benzoate was achieved through the reaction of dimethyl maleic anhydride with ethyl-4-amino benzoate. In the second stage, molecule [1] was reacted with hydrazine hydrate to provide compound [2] 4-(N-dimethyl maleimidyl)phenyl hydrazide. Compound [2] is the crucial precursor from which all objectives compounds were produced. In the third step, compound [2] was subjected to a condensation reaction with aromatic aldehydes, yielding Schiff base derivatives [3-5] which were subsequently reacted with acid to produce target compounds [6-8] specifically dimethyl maleimides featuring dihydroquinazoline cycles. Meanwhile, the treatment of compounds [3-5] with acetic anhydride resulted in additional target compounds [9-11] namely dimethyl maleimides containing oxadiazole cycles. Furthermore , the introduction of compound [2] in a reaction with CS2 in a medium that is basic, followed by treatment with hydrazine hydrate, resulted in the formation of the target compound [12] while the condensation of compound [2] with pyrrole carbaldehyde produced the target compound [13]. The results of the antimicrobial efficacy research of the target compounds against four species of bacteria and fungi are quite encouraging. Keywords: Dihydroquinazoline, Dimethyl Maleimide, Oxadiazole, Schiff Base, Triazole. 1. Introduction Cyclic imides and their derivatives represent a valuable group of bioactive compounds with wide range of various important applications [1, 2]. Besides cyclic imide moiety is an important core present in many drugs and medicines because to their extensive array of biological activities inclualing antimicrobial [3] antifungal analgesic [4] antioxidants [5] antinflammatory [6] and anticancer activity [7]. On the other hand heterocyclic compounds are very important moieties in organic chemistry and since they exhibit a broad range of biological actions, including anticancer and antiviral properties, analgesic and anti-inflammatory they are used as pharmaceuticals, in drug synthesis, veterinary products , agrochemicals , antioxidants and as corrosion inhibitors [8, 9]. Depending all these points we thought that it was too worthy on to design new molecules that contain these two active components (imide rings and hetero cycles together). Consequently, the current study entailed the synthesis of novel dimethyl maleimide derivatives containing different heterocycles based on 4-(N-dimrthyl maleimidul )phenyl hyrazide [14], through applying of different synthetic methods with high expectations that these new compounds will exhibit high biological activity and give promising results. 121 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate 2. Experimental The melting temperatures of the synthesized compounds were determined using a Gallen Kamp melting point equipment and were reported uncorrected. FTIR spectra were acquired using a Shimadzu FTIR-8400 Fourier Transform spectrophotometer. The Ultrashield 400MHz Bruker apparatus was employed to record both 1H-NMR spectra in the presence of the solvent DMSO-d6 and the internal standard tetramethyl silane. Figure 1. Synthetic steps of compounds [1-12]. 122 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate 2.1. Synthesis of Ethyl-4-(N-Dimethyl Maleimidyl) Benzoate [1] To the solution of dimethyl maleic anhydride (0.01mol, 1.26g) dissolved in (15mL) acetone a solution of (0.01mol, 1.65g) ethyl-4-aminobenzonte dissolved in (15 mL) acetone was added drop by drop with good stirring and cooling (10). After completion of the addition, the amalgamation was agitated at ambient temperature for two hours. Subsequently, the resultant precipitate was then put to filtration,dried, and purified through recrystallization using ethanol. 2.2. Synthesis of 4-(N-dimethyl maleimidyl)phenyl hydrazide [2] The chemical [2] was synthesized via the reaction of compound [1] (0.01 mol, 2.73 g) with hydrazine hydrate (0.015 mol, 0.75 g) over a period of four hours. Subsequently, 20 mL of ethanol was introduced, and reflux conditions were sustained for an additional eight hours (11). Following the reflux process, the mixture was allowed to cool. The resultant precipitate was thereafter filtered and rinsed with distilled water, dried, and subsequently underwent recrystallization using dioxane. 2.3. Synthesis of 4-(N-dimethyl maleimidyl)-N-benzylidene benzamide [3-5] The designated Schiff bases [3-5] were produced by refluxing a mixture of compound [2] (0.01 mol, 2.59 g) and 0.01 mol of aromatic aldehyde (benzaldehyde, p-anisaldehyde, p-tolualdehyde) in 25 mL of pure ethanol, with a few drops of glacial acetic acid as a catalyst [12, 15] for eight hours. Upon completion of the reflux, This mixture was cooled, and the resultant material was filtered, dried, and subsequently recrystallized using a suitable solvent [16, 17]. 2.4. Synthesis of 2-(Substituted Phenyl)-3-[N-(4-(N-dimethyl Maleimidyl) Benzamido]-Dihydroquinazoline-4- One [6-8] The titled compounds [6-8] were synthesized through reaction of anthranilic acid (0.01mol,1.37g) with (0.01mol) of schiff bases [3-5] in dioxane with few drops of triethylamine with stirring and cooling in ice bath (20 min ) [11, 18]. The resulting mixture underwent reflux for ten hours, followed by cooling, subsequently, the precipitate underwent filtration, drying, and recrystallization using a suitable solvent. 2.5. Synthesis of 5-(4-(N-Dimethyl Maleimidyl)Phenyl-3-Acetyl-2- (Substituted Phenyl)-1,3,4-Oxadiazole [9- 11] The titled compounds [9-11] were synthesized via refluxing the mixture of schiff bases [3-5] (0.01 mole) and (15mL) of acetic anhydride for six hours .The resultant mixture after reflux was permitted to cool to the ambient temperature before being introduced into chilled water while stirring, which continued for thirty minutes [9]. The precipitate underwent filtration, was washed once more with water, dried, and subsequently recrystallized using a suitable solvent. 2.6. Synthesis of N-[4-(4-Amino-5-Mercapto-1,2,4-Triazole-3-y1) Phenyl Dimethyl Maleimide [12] The designated compound [2] (0.01 mol, 2.59 g) was dissolved in 20 mL of absolute ethanol containing( 0.01 mol ,0.56 g) of KOH, to which (0.02 mol ,1.52 g) of quantity of carbon disulfide was introduced while stirring vigorously. The mixture underwent reflux for one hour, following which the resultant solid was filtered. Following drying, it was refluxed with (5 mL) of distilled water and( 0.01 mol ,0.48 mL) of hydrazine hydrate for eight hours [11, 19]. Upon completion of the reflux, the resulting mixture was permitted to cool, subsequently neutralized with HCl, The resulting powder was subjected to filters, followed by washing with distilled water, drying, and recrystallization from ethanol. 2.7. Synthesis of 4-(N-Dimethyl Maleimcidyl)-N-(2-Imino Pyrrol) Benzamide [9]. The melding of compound [2] (0.01 mol, 2.59 g) and Pyrrol-2-aldehyde (0.01 mol, 0.95 g) in (20 mL) of absolute ethanol, along with a few drops of glacial acetic acid as a catalyst, was subjected to 123 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate reflux for eight hours while being stirred [12]. After the reflux was completed, the resulting mixture was permitted to cool. The resulting solid was then filtered, dried, and recrystallized using chloroform. 3. Results and Discussion The current study focused on the synthesis of a range of novel dimethylmaleimide heterocyclic derivatives.Synthesis of the new derivatives was based on 4-CN-dimethyl maleimidyl) phenyl hydrazide and the new compounds contain 1,2,4-triazole, 1, 3, 4-oxadiazole, different heterocycles including [10]. Dimethyl maleimide is a well known bioactive molety and the mentioned hetero cycles are also biologically active components this means combination of these two components in the newly synthesized compounds producing important bioactive new molecules leading to important applications. Synthesis of the chosen compounds was conducted through multiple processes, as outlined in Scheme (1). As indicated in scheme (1) different synthetic stratgies are followed in performing synthesis of the target compounds [10]. In the first step compound [1] ethyl-4-(N-dimethyl maleimidyl) benzoate was synthesized via reaction between ethyl-4-aminobenzoate and dimethyl maleic anhydride, in the second stage, compound [1] was subjected to a reaction with hydrazine hydrate, resulting in compound [2] via a nucleophilic substitution reaction 4-(N-dimethyl maleimidy1) phenyl hydrazide [10-12]. The FTIR spectra of chemical [1] displayed distinctive absorption bands at (1762 ) cm⁻¹ and (1280, 1124 )cm⁻¹, attributed to ʋ(C=O) ester and ʋ(C-O) ester, respectively. In contrast, these absorption bands were absent in the spectrum of compound [2] which instead displayed distinct absorption bands at(3236-3429 ) cm⁻¹, corresponding to ʋ(NH2) and ʋ(NH). This point serves as compelling evidence of the successful production of hydrazide. The 1H-NMR spectra of compound [1] exhibited signals at( δ=1.34) ppm and( 1.95-2 )ppm, pertaining to the protons of the CH3 group and two CH3 groups within the imide ring. Signals corresponding to COCH2 protons and aromatic protons were observed at (δ=4.2-4.3) and (6.59-8.08) ppm, respectively [20]. Conversely 1H-NMR spectrum of chemical [2] exhibited signals at (δ=1.91-2), (5.59-5.68), (6.51- 7.59) and (9.1-9.28) ppm which are belong to protons of two CH3 groups (NH2), aromatic protons and (NH) proton respectively. It is noticable that the spectrum showed dis appearance of (OCH₂) signal and this is a secondary validation for the successful synthesis of hydrazide.The physical characteristics of chemicals [1] and [2] are presented in table (1), while their FTIR and 1H-NMR spectral data are detailed in tables (6) and (11). Compound [2] serves as the crucial precursor from which the target compounds were synthesized. We are pleased to present The introduction of compound [2] in a condensation reaction with three aromatic aldehydes resulted in the formation of three new dimethyl maleimidyl Schiff bases [3-5, 12, 21]. The FTIR spectra of compounds [3-5] demonstrated absorption spectra at (1770-1782) cm-1, (1689-1722) cm-1, (1654-1691) cm-1, (1602-1623) cm-1, and (1377-1386) cm-1, corresponding to asymmetrical (C=O) imide, symmetrical ʋ (C=O) imide, ʋ(C=O) amide, ʋ(C=N), and ʋ(C-N) imide, respectively. Conversely, the 1H-NMR spectra of chemical [4] exhibit signals at (δ=1.99-2.16) and (6.65-8.3) ppm, essential to the protons of two (CH3) groups and aromatic protons. Additional signals are observed at (δ=8.64-8.65) and (8.9-11.42) ppm,attributed to the (N=CH-) proton and the (NH) proton, respectively. The physical characteristics of the chemicals are presented in table (2), while their FTIR and 1H-NMR spectral information are presented in tables (7) and (11). Compounds [3-5] serve as the initial materials in the synthesis of the target. In the fourth step, compounds [3-5] are reacted with anthranilic acid to yield compounds [6-8] which are dimethyl maleimides featuring a dihydroquinazoline cycle. The FTIR spectra of chemicals [6-8] exhibited absorption bands at (1710-1720) cm-1, (1620-1681) cm-1, and (1361-1373) cm-1, corresponding to ʋ(C=O) imide, ʋ(C=O) amide, and ʋ(C-N) imide, this order [12]. 1H-NMR spectrum of chemical [7] showed signals at( δ= 1.99), (3.05) and (3.60-3-81) ppm which are belong to protons of two CH3, (CH-N-) proton and (OCH3) protons while other signals appeared at 124 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate (δ=4.9-5.2), (6.5-8.3) and (8.63-8.84) ppm which correspond to (NH) protons, aromatic protons, and (NH) amide protons, respectively [9, 22]. The compounds' physical characteristics are displayed in table (3), and their FTIR and 1H-NMR spectrum data are outlined in tables (8) and (11). Compounds [3-5] are also utilized in the synthesis of additional target compounds [9-11] by introducing them into a reaction with acetic anhydride under reflux, resulting in the formation of new dimethyl maleimides that incorporate a 1,3,4-oxadiazole cycle [9-11]. The FTIR spectra of the chemicals [9-11] exhibited absorption bands at (1772 )cm-1, along with bands in the ranges of (1681- 1733) cm-1, (1654-1670) cm-1, (1602-1627) cm-1, and (1369-1371 )cm-1. The bands translate to the asymmetric (C=O) imide, symmetric ʋ(C=O) imide, ʋ(C=O) amide, (C=N), and (C-N) imide functionalities, this order [23]. The 1H-NMR spectra of chemical [9] displayed signals at (δ=1.99 and 2.20 )ppm, indicative of the protons from two (CH3) groups and (CH3-C) protons. Furthermore, signals at (δ=3.75 )and within the range of (6.22-8.2 )ppm were ascribed to the proton in the heterocyclic ring and the aromatic protons. The compounds' physical parameters are displayed in table 4, and their FTIR and 1H-NMR spectrum data are outlined in tables (9) and (11). The procedure entailed the synthesis of a new dimethyl morleimide [12] which integrates a 1,2,4- triazole ring through the reaction of compound [2] with CS2 in an alkaline environment, subsequently treated with hydrazine hydrate [11, 24] . The FTIR spectra of chemical [12] exhibited absorption spectra at (1716 , 1701 ) cm⁻¹, (1629) cm⁻¹, and (1377) cm⁻¹, corresponding to asymmetric ʋ (C=O) imide, symmetric ʋ (C=O) imide, ʋ(C=N), and ʋ (C-N) imide, this order .The 1H-NMR spectrum of this compound [12] displayed signals at ( δ = 1.95- 2.0), (7.45), and (8.4) ppm, attributed to the protons of two CH3 groups, (NH2) protons, and aromatic protons, respectively [25]. Ultimately, molecule [2] was synthesized through a condensation reaction with the heterocyclic aldehyde pyrrole-2-carbaldehyde, yielding compound [13] dimethylmaleimide, which incorporates a pyrrole ring. The FTIR spectra of chemical [13] absorption bands were observed at (1778) cm-1, (1706) cm-1, (1625) cm-1, (1610) cm-1, and (1334) cm-1, that correspond to asymmetrical ʋ(C=O) imide, symmetrical ʋ(C=O) imide, ʋ(C=O) amide, ʋ(C=N), and ʋ(C-N) imide, this order . The 1H-NMR spectra of chemical [13] exhibited signals at (δ = 2.0-2.13 )ppm and (6.13 )ppm, corresponding to the protons of two (CH3) groups and the (NH) amine proton. Additionally, signals at ( δ = 6.44-8.3) ppm, (9.8 )ppm, and (10.8 )ppm were ascribed to aromatic protons, the (-N=CH-) proton, and the (NH) amide proton, respectively. The physical parameters of compounds Yassen and AL-Azzawi [12] and Jaber [13] are presented in Table (5), while their FTIR and 1H-NMR spectrum data are detailed in Tables (10 ) and (11), respectively [12]. 125 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate Table 1. Shows the physical characteristics of the chemicals [1, 2]. Recryst. Solvent Melting point OC Yield % Colour Compound Structure Comp. No. Ethanol 269-272 90 Off white 1 Dioxane 254-256 88 white 2 Table 2. Shows the physical characteristics of the compounds [3-5]. Recryst. Solvent Melting point OC Yield % Colour Compound Structure Comp. No. Chloroform 234-236 90 Off white 3 Ethanol 248-250 88 brown 4 Chloroform 278-280 70 bige 5 Table 3. Shows the physical characteristics of the chemicals [6-8]. Recryst. Solvent Melting point OC Yield % Colour Compound Structure Comp. No. Hexan >300 80 brown 6 Dioxan >300 76 Drak brown 7 Hexan >300 68 brown 8 126 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate Table 4. Shows the physical characteristics of the chemicals [9-11]. Recryst. Solvent Melting point OC Yield % Colour Compound Structure Comp. No. Acetone >300 59 Yellow light 9 Ethanol 290-292 54 brown 10 Acetone 244-246 60 brown 11 Table 5. Shows the physical characteristics of the chemicals [12, 13]. Recryst. Solvent Melting point OC Yield % Colour Compound Structure Comp. No. Dioxane 218-220 55 Off white 12 Chloro form 284-286 95 Yellow 13 Table 6. Shows FTIR spectra (cm-1) of chemicals [1, 2]. Comp. No. ʋ (N-H , NH2) ʋ (C-H) Aromatic ʋ (C-H) Aliphatic ʋ (C=O) Ester ʋ (C=O) Imide ʋ (C=O) Amide ʋ (C=C) ʋ (C-N) Imide ʋ (C-O) Ester 1 _____ 3068 2983 2898 1762 1791 1683 _____ 1598 1392 1280 1124 2 3429 3346 3305 3234 3031 2977 2879 _____ 1670 1625 1604 1560 1350 _____ 127 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate Table 7. Shows FTIR spectra (cm-1) of chemicals [3-5]. Comp. No. ʋ (N-H ) ʋ (C-H) Aromatic ʋ (C-H) Aliphatic ʋ (C=N) ʋ (C=O) Imide ʋ (C=O) Amide ʋ (C=C) ʋ (C-N) Imide others 3 3203 3151 3055 3029 2952 2839 1623 1770 1689 1654 1556 1379 ____ 4 3153 3080 2977 2904 2877 1602 1782 1704 1691 1512 1386 ʋ (C-O) ether 1166 1026 5 3321 3145 3020 2960 2931 2875 1618 1772 1722 1658 1560 1377 _____ Table 8. Shows FTIR spectra (cm-1) of chemicals [6-8]. Comp. No. ʋ (N-H ) ʋ (C-H) Aromatic ʋ (C-H) Aliphatic ʋ (C=O) Imide ʋ (C=O) Amide ʋ (C=C) ʋ (C-N) Imide others 6 3471 3371 3224 3058 2933 2860 1770 1718 1654 1620 1595 1361 ____ 7 3407 3355 3224 3020 2937 2881 2840 1710 1681 1604 1512 1373 ʋ (C-O) ether 1168 1027 8 3440 3402 3234 3029 2920 2852 1720 1670 1623 1608 1512 1367 _____ Table 9. Shows FTIR spectra (cm-1) of chemicals [9-11]. Comp.No. ʋ (C-H) Aromatic ʋ (C-H) Aliphatic ʋ (C=O) Imide ʋ (C=O) Amide ʋ (C=N) ʋ (C=C) ʋ (C-N) Imide others 9 3064 2979 2933 2881 1772 1712 1658 1627 1606 1552 1371 ____ 10 3068 3006 2970 2840 1772 1681 1654 1602 1577 1512 1369 ʋ (C-O) ether 1163 1024 11 3040 2927 2856 2817 1733 1670 1620 1589 1371 _____ Table 10. Shows FTIR spectra (cm-1) of chemicals [12, 13]. Comp. No. ʋ (N-H , NH2) ʋ (C-H) Aromatic ʋ (C-H) Aliphatic ʋ (C=O) Imide ʋ (C=O) Amide ʋ (C=N) ʋ (C=C) ʋ (C-N) Imide 12 3407 3377 3346 3236 3060 2964 2929 2860 1716 1701 _____ 1629 1606 1587 1377 13 3350 3301 3218 3068 2979 2856 1778 1708 1625 1610 1558 1334 128 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate Table 11. Shows 1HNMR spectral data (ppm) of the prepared chemicals. (ppm) δ Comp. No. δ = 1.34 ( CH3 protons) , δ=1.95-2.02 (protons of two CH3 in imide ring), δ=4.2-4.3 (OCH₂), δ=6.59-8.08 (aromatic protons) 1 δ=1.95-2.02 (protons of two CH3),δ=5.59-5.68 (NH₂ protons), δ=6.51-7.59 (aromatic protons) , δ=9.1-9.28 (NH proton) 2 , δ = 3.83-3.86 ( OCH3 proton) (protons of two CH3) δ = 2.0-2.16 aromatic protons) , δ = 8.64( -N=CH-) , δ = 8.9 ( NH) ) δ = 6.67-8. 0 4 δ=1.99-2.0 (protons of two CH3),δ = 2.34 ( CH3 protons) , δ=6.65-8.3 (aromatic protons) , δ = 8.65 ( -N=CH- ), δ=11.42(NH proton) 5 δ=1.99 (protons of two CH3),δ = 3.05 (-CH-N-,) δ = 3.6-3.81( OCH3 protons) , δ = 4.9-5.2 ( NH proton) , δ=6.6-8.3 (aromatic protons) , δ=8.63-8.84 (NH amide) 7 δ=1.99 (protons of two CH3),δ = 2.2( CH3 -CO) ,δ = 3.37 (proton in hetro ring ), δ=6.22-8.2 (aromatic protons 9 , δ = 7.45 ( NH2 proton) (protons of two CH3) δ = 1.95-2.0 aromatic protons) ) δ = 8.40 12 = 2.0- 2.13 ( proton of two CH3 ) δ = 6.13 ( NH amine ) δ = 6.44 – 8.3 δ ( vinylic and aromatic protons ) , δ = 9.8 ( -N=CH-) ,δ = 10.8 ( NH amide ) 13 4. Examination of Biological Activity The cup plate method was utilized to investigate the antibacterial and antifungal properties of the synthesized chemicals against four bacterial strains: Escherichia coli, Staphylococcus aureus, Streptococcus pyogenes, and Klebsiella pneumoniae, in addition to against the fungus Candida albicans, using Amoxicillin and Fluconazole as reference agents, with DMSO serving as the sample solution (23). The zones of inhibition generated by the substances under investigation were quantified, and the outcomes are detailed in table 12. Table 12. Inhibition zones of chemicals [6-13]. Comp.no Staphylococcus aureus Staphylococcus pyogenes Escherichia Coli Klebsiella Candida albicans pneumoniae 6 14 12 - - 19 7 14 12 - - 18 8 12 13 - - 29 9 18 17 17 20 21 10 14 17 17 17 23 11 26 26 23 24 34 12 24 27 - - 43 13 17 14 18 15 25 Amoxicillin 15 18 17 15 0 Fluconazole 0 0 0 0 19 Table 12 demonstrates that compounds [11, 12] had significant action against Staphylococcus aureus and Streptococcus. Compounds [6, 7, 9, 10, 13] derived from pyogenes bacteria shown significant efficacy against Staphylococcus aureus, while compounds [9, 10] demonstrated pronounced activity against Streptococcus pyogenes. Compounds [6-8, 13] displayed moderate activity against Streptococcus pyogenes, and compound [11] revealed exceptional action against Escherichia coli. Compounds [9, 10, 13] had significant action, whereas compounds [6-8, 12] demonstrated no activity against this bacterium (17). Compounds [9, 11] had significant efficacy against Klebsiella pneumoniae, while compounds [10, 13] shown considerable activity. Compounds [6-8, 12] shown no action against this bacterium. Conversely, substances [8, 11, 12] had significant efficacy against Candida fungus, whilst other examined compounds shown considerable effectiveness against this fungi. 129 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate Figure 1. FTIR spectrum of of chemical [1]. 130 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate Figure 2. FTIR spectrum of of chemical [2]. 131 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate Figure 3. FTIR spectrum of of chemical [4]. 132 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate Figure 4. FTIR spectrum of of chemical [6]. 133 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate Figure 5. 1H-NMR spectrum of of chemical [2]. 134 Edelweiss Applied Science and Technology ISSN: 2576-8484 Vol. 9, No. 5: 120-135, 2025 DOI: 10.55214/25768484.v9i5.6806 © 2025 by the authors; licensee Learning Gate Figure 6. 1H-NMR spectrum of chemical [4]. Transparency: The authors confirm that the manuscript is an honest, accurate, and transparent account of the study; that no vital features of the study have been omitted; and that any discrepancies from the study as planned have been explained. This study followed all ethical practices during writing. 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