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Proceeding Paper

Synthesis and In Vitro Antibacterial Studies of Two New Hydrazone Derivatives †

by
Hamza Karimatu
1,*,
Idris Abdullahi Yunusa
1,
Muhammad Aliyu Musa
1,
Hamza Asmau Nasiru
1,
Hamza Sa’adatu Auwal
2 and
Abdullahi Maryam
1
1
Department of Pharmaceutical and Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Ahmadu Bello University Zaria, Zaria 810107, Nigeria
2
Department of Chemistry, Faculty of Physical Science, Ahmadu Bello University Zaria, Zaria 810107, Nigeria
*
Author to whom correspondence should be addressed.
Presented at the 28th International Electronic Conference on Synthetic Organic Chemistry (ECSOC-28), 15–30 November 2024; Available online: https://sciforum.net/event/ecsoc-28.
Chem. Proc. 2024, 16(1), 118; https://doi.org/10.3390/ecsoc-28-20138
Published: 14 November 2024

Abstract

Throughout history to the present day, infectious diseases have been a persistent global threat, causing significant harm to public health and economic stability. To address these challenges, the development of novel antimicrobial drugs is crucial. Hydrazones have gained significant attention in the scientific literature as promising candidates for developing new antimicrobial drugs. Two new hydrazones (H3 and H4) incorporating moieties that are known to enhance antimicrobial activity were synthesized. Methods: Hydrazone derivatives were synthesized through a condensation reaction of substituted acetophenone and nitro phenyl hydrazine. The compounds were characterized by their melting points and spectral analyses, including FT-IR, 1H NMR, 13C NMR, and 2D NMR. Their antibacterial effects on Escherichia coli and Staphylococcus aureus were assessed in-vitro using the agar diffusion and broth dilution methods. Results: In-vitro testing demonstrated the compounds’ good activity against the tested organisms, particularly Gram-positive bacteria. At a concentration of 50 mg/mL, H3 produced a zone of inhibition (19 mm) comparable to that of the standard ciprofloxacin (20 mm) at 0.05 mg/mL. Only H3 was able to kill both Staphylococcus aureus and Escherichia coli at a concentration of 50 mg/mL. In all cases, H3 was found to be the most effective with optimum bactericidal and bacteriostatic activity against staphylococcus aureus and Escherichia coli. Conclusions: All the synthesized compounds were proven to possess promising antibacterial activity in vitro against the tested organisms.

1. Introduction

Infectious diseases significantly impact human health, causing widespread death and suffering, particularly among vulnerable groups [1]. In 2017, infections were responsible for over 20% of global deaths, including more than 10 million deaths linked to sepsis [2]. Antimicrobials are crucial for treating infections in humans, animals, and plants [3]. Antimicrobial resistance is a growing concern, making infections harder to manage and increasing the risk of severe illness and death [4,5,6,7]. Researchers are exploring novel antimicrobial agents, such as plant and microbial extracts, essential oils, and synthetic molecules, to combat resistant strains and address healthcare system limitations [8]. Over the past two decades, organic compounds containing hydrazone have shown promise due to their antimicrobial properties and diverse biological activities [9]. Hydrazones, formed by reacting hydrazine with carbonyl compounds [10,11], exhibit a wide range of biological effects including anticancer [12,13,14], antibacterial [15,16,17,18,19], anti-inflammatory [15,20], antiviral [12,21], antiprotozoal [22], antitubercular [15], and antidepressant activities [23]. Their antimicrobial activity makes them potential candidates for new antimicrobial agents against pathogenic bacteria and fungi [22]. The hydrazone function is also critical in various antibiotic drugs [24]. Our research yielded two hydrazone derivatives incorporating functional moieties (NO2 and OCH3) that have been documented to enhance the antimicrobial activity of hydrazones [25]. Notably, the two hydrazone compounds H3 and H4 (Figure 1) exhibit distinct substitution patterns on the ring. It is noteworthy that all the synthesized compounds are entirely novel, with no prior mention in the existing literature or chemical databases (www.scifinder.com, accessed on 2 March 2021).

2. Methods

2.1. Synthesis and Characterization

2.1.1. Reagents and Equipment Used for Synthesis

All reagents were purchased from Sigma-Aldrich, Darmstadt, Germany. All the starting reagents and solvents used for the experiments were of analytical grade and were used without further purification. IR spectra were recorded on a 400 MHz Agilent FT-IR spectrometer, Santa Clara, CA, USA. 1H NMR spectra were recorded in chloroform on a 500 MHz Bruker NMR spectrometer using TMS as a reference, Billerica, MA, USA.

2.1.2. The General Procedure for the Synthesis of Hydrazone Derivatives (H3 and H4)

The synthetic pathways adopted to prepare the new hydrazone compounds are depicted in Figure 2. Compounds H3 and H4 were obtained via the reaction of an equimolar amount of 2,4,5-trimethoxyacetophenone/2,4-dimethoxyacetophenone and 4-nitrophenylhydrazine dissolved in 30 mL of ethanol in a round-bottom flask to which 5 mL of 40% NaOH was added. The reaction mixture was refluxed for 4 hours, while being continuously stirred using a magnetic stirrer. The product was filtered and air-dried. The resulting residue was then purified by recrystallization in ethanol to give the pure product.

2.2. Evaluation of Antibacterial Activity

The in vitro antibacterial activity of the test compounds H3 and H4 was assessed against 24 h cultures of clinical isolates of Escherichia coli and Staphylococcus aureus obtained from the department of microbiology, Ahmadu Bello University Teaching Hospital, Shika, Nigeria. The antibiotic ciprofloxacin was used as a standard. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of the synthesized compounds were determined by employing the agar diffusion method and broth dilution method.

2.2.1. Procedure for Agar Diffusion Method

To determine the MICs of the test compounds against S. aureus and E. coli, the agar diffusion method as described by Weigand et al. 2008 was employed [20]. Mueller-Hinton agar (MHA) was used as the growth medium and was prepared according to the manufacturer’s instructions. The freshly prepared liquid agar medium (20 mL) was poured into each Petri dish. About 0.1 mL of a standard inoculum of test microorganisms was evenly spread onto the surface of the solid medium using a sterile swab. The seeded Petri dishes were dried in an incubator at 37 °C for a duration of 1 h. Cups of approximately 6 mm diameter were made in the center of the Petri dishes using a sterile cork borer and were labeled. Prepared solutions (0.1 mL) of the test compounds (in a mixture of dimethylsulfoxide and methanol) were added to each cup in Petri dishes and were kept aside in an aseptic area for 1 h to allow for the diffusion of the drug/sample, followed by incubation at 37 °C for 18 h. Each plate of the medium was observed for the appearance of the zone of inhibition.

2.2.2. Procedure for Broth Dilution Method

To determine the MBCs of the test compounds against S. aureus and E. coli, Mueller–Hinton broth (MHB) was prepared according to the manufacturer’s instructions and was sterilized at 121 °C for 15 min, and the broth was allowed to cool. The broth was inoculated with a standardized inoculum of the test microorganisms. The dilution of the test microorganisms was conducted using normal saline until the turbidity matched that of McFarland standard number 0.5 by visual comparison; at this point, the test microbes had a concentration of about 5 × 105 cfu/mL. A two-fold serial dilution of the test compounds was conducted to obtain the concentrations of 50 mg/mL, 25 mg/mL, 12.5 mg/mL, 6.25 mg/mL, 3.125 mg/mL, 1.56 mg/mL, 0.78 mg/mL, 0.39 mg/mL, 0.2 mg/mL, and 0.1 mg/mL for the test compounds. Each concentration of the test compounds was inoculated with a standardized inoculum of the test microorganisms and then incubated at 37 °C for 20 h, after which each test tube was observed for turbidity (growth). The lowest concentration in the sterile broth which showed no turbidity was recorded as the minimum inhibitory concentration. The minimum bactericidal concentrations (MBCs) were determined by sub-culturing broth dilutions that inhibited the growth of the tested organisms. The broth dilutions were streaked onto agar and incubated for 48 hours. The lowest concentration in the sterile broth which prevented the growth of the organisms was recorded as the minimum bactericidal concentration.

3. Results and Discussions

3.1. Synthesis and Characterization

3.1.1. (E)-1-(4-nitrophenyl)-2-(1-(2,4,5-trimethoxyphenyl)ethylidene) Hydrazine (H3)

Yield: 90% obtained as deep red powder; MP 148.5–149.8 °C; FT-IR (KBr) vMax/cm−13300 1591(C=N), 3108(C-H atom), 2840 (C-H Aliph), 3317(N-H); 1H δ(ppm) 2.29 (s) (C2), 6.55(s) (C3′), 7.09(s) (C6′), 7.14(d) (C2″), 8.17(d) (C3″), 81.5(d) (C5″), 7.12(s) (C6″); 13C NMR (CCl4) δ (ppm) 150 ppm–164 pm (1C=N 16.36(C2), 120.66 (C1′), 152.44(C2′), 98.22(C3′), 151.16(C4′), 150.49 (C5′), 113.24 (C6′) 144.08 (C1″), 112.33 (C2″), 126.36 (C3″), 139.79 (C4″), 126.36 (C5″), 112.33 (C6″).

3.1.2. (E)-1-(4-nitrophenyl)-2-(1-(2,4,-dimethoxyphenyl)ethylidene) Hydrazine (H3)

Yield: 92% obtained as orange crystals; MP 149.5–151.2 °C; FT-IR (KBr) vMax/cm−1 3300 1599(C=N), 3004(C-H atom), 2832 (C-H Aliph), 3309(N-H); 1H δ(ppm) 2.26(s) (C2), 6.49(s) (C3′), 6.54(d) (C5′), 6.74(d) (C6′), 7.14(d) (C2″), 8.17(d) (C3″), 81.5(d) (C5″), 7.12(d) (C6″); 13C NMR (CCl4) δ (ppm) 164.78 (1C=N 16.38 (C2), 104.97 (C1′), 157.39 (C2′), 99.62 (C3′), 162.29 (C4′), 105.77 (C5′), 129.46 (C6′), 150.25 (C1″), 111.54 (C2″), 139.77 (C3″), 139.79 (C4″), 126.38 (C5″), 111.54 (C6″).
The synthesis of hydrazones produced pure compounds in excellent yield. The use of a strong base (NAOH) as the catalyst for hydrazone synthesis promoted the deprotonation of the hydrazine derivatives, creating a more reactive nucleophile. This enhanced the attack on carbonyl carbon, facilitating hydrazone formation. The increased nucleophilicity in basic conditions might have contributed to the high reaction yield of the hydrazones.
1H NMR showed resonances due to aromatic protons that appeared in the region of 6.49–8.2 ppm for H3 and H4. For H3, two doublets at 7.14/7.18 ppm and 8.14/8.17 ppm were assigned to protons on carbon 2″/6″ and carbon 3″/5″, respectively. These protons (2″/6 and 3″/5″) appeared on the same/or almost same chemical shift because they belong to the same chemical environment. A distinguishing feature from the 1H NMR spectra of H3 and H4 is the appearance of the proton on carbon 6″ as a singlet and doublet in H3 and H4, respectively. Other noticeable resonances are the methoxy proton as a singlet in the region of 3.83–4.25 ppm integrating into nine and six protons for H3 and H4, respectively. The rest of the protons appeared in their expected regions. Additional support for the structures comes from the 13C NMR spectra of H3 and H4 which showed resonance in the range 150–164 ppm due to the carbons (C1) of the azomethine(C=N) providing evidence that hydrazones were formed [11,14]. The two-dimensional (COSY, HSQC, and HMBC) NMR spectroscopic data confirm the tentative structural assignment that was made using 1H and 13C NMR for H3 and H4. The correlation between each carbon atom and the attached hydrogen atom(s) was unambiguously established using HSQC, and long-range correlation between protons and carbon was established using HMBC, which led to the linking of sub-structural fragments. Protons at C3″–C5″, C2″–C6′, and C5″–C6″ showed COSY correlation for both H3 and H4.

3.2. Antibacterial Studies

The antibacterial studies revealed that H3 and H4 were able to hinder the growth of Staphylococcus aureus and Escherichia coli. At a concentration of 50 mg/mL, H3 produced a zone of inhibition comparable to that of the standard ciprofloxacin at 0.02 mg/mL (Table 1); however, only H3 was able to kill both Staphylococcus aureus and Escherichia coli at a concentration of 50 mg/mL (Table 2). In all cases, H3 was found to be the most effective antibacterial agent synthesized with optimum bactericidal and bacteriostatic activity against Staphylococcus aureus and Escherichia coli. The optimum antimicrobial activity produced by hydrazones may be attributed to the presence of electron-withdrawing groups like NO2 or OCH3 on the aromatic ring [21,26], and the superior activity of H3 to H4 could be due to the presence of three OCH3 substitutions as compared to the two of H4.

4. Conclusions

The synthesized phenylhydrazones [(E)-1-(1-(2,4,5-trimethoxyphenyl)ethylidene)-2-(4-nitrophenyl) hydrazine] and [(E)-1-(1-(2,4-dimethoxyphenyl)ethylidene)-2-(4-nitrophenyl)hydrazine] are promising candidates as antimicrobial agents.

Author Contributions

Conceptualization, methodology, writing—review and editing, software, validation and formal analysis and investigation, H.K. and H.A.N.; resources, I.A.Y. and M.A.M.; data curation, A.M.; writing—original draft preparation, H.K.; writing—review and editing, H.S.A.; visualization, H.K. and H.A.N.; supervision, I.A.Y. and M.A.M.; project administration I.A.Y. and M.A.M. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

The raw data supporting the reported results in this article will be made available by the Authors on request.

Acknowledgments

We extend our hand in gratitude to Almighty Allah, the Exalted, most Beneficent, and most Merciful. Our heartfelt appreciation goes to the staff of the Pharmaceutical and Medicinal Chemistry department of A.B.U, Zaria, especially Atiku and Mal Nafi’u, whose guidance and support have been invaluable to us. We would also like to acknowledge the contribution of Ezikiel of the pharmaceutical microbiology laboratory for assisting in antibacterial screening.

Conflicts of Interest

The authors declare no conflict of interest.

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Figure 1. Chemical structure of H3 and H4.
Figure 1. Chemical structure of H3 and H4.
Chemproc 16 00118 g001
Figure 2. Reaction scheme for hydrazones.
Figure 2. Reaction scheme for hydrazones.
Chemproc 16 00118 g002
Table 1. Zone of inhibition of hydrazones.
Table 1. Zone of inhibition of hydrazones.
OrganismCompoundConcentrations of Compounds
(mg/mL)
Cipro
(mg/mL)
502512.56.250.05
S. aureusH31915121120
H4171411020
E. coliH3181311024
H4161412024
Table 2. Minimum inhibitory concentration of synthesized compounds against E. coli and S. aureus.
Table 2. Minimum inhibitory concentration of synthesized compounds against E. coli and S. aureus.
OrganismCompoundConcentrations (mg/mL)
502512.56.253.1251.560.780.390.20.1
S. aureusH3+++++++++
H4++++++++++
E. coliH3+++++++++
H4++++++++++
+ = growth of the test organism observed, and − = no growth of the test organism observed.
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MDPI and ACS Style

Karimatu, H.; Yunusa, I.A.; Musa, M.A.; Nasiru, H.A.; Auwal, H.S.; Maryam, A. Synthesis and In Vitro Antibacterial Studies of Two New Hydrazone Derivatives. Chem. Proc. 2024, 16, 118. https://doi.org/10.3390/ecsoc-28-20138

AMA Style

Karimatu H, Yunusa IA, Musa MA, Nasiru HA, Auwal HS, Maryam A. Synthesis and In Vitro Antibacterial Studies of Two New Hydrazone Derivatives. Chemistry Proceedings. 2024; 16(1):118. https://doi.org/10.3390/ecsoc-28-20138

Chicago/Turabian Style

Karimatu, Hamza, Idris Abdullahi Yunusa, Muhammad Aliyu Musa, Hamza Asmau Nasiru, Hamza Sa’adatu Auwal, and Abdullahi Maryam. 2024. "Synthesis and In Vitro Antibacterial Studies of Two New Hydrazone Derivatives" Chemistry Proceedings 16, no. 1: 118. https://doi.org/10.3390/ecsoc-28-20138

APA Style

Karimatu, H., Yunusa, I. A., Musa, M. A., Nasiru, H. A., Auwal, H. S., & Maryam, A. (2024). Synthesis and In Vitro Antibacterial Studies of Two New Hydrazone Derivatives. Chemistry Proceedings, 16(1), 118. https://doi.org/10.3390/ecsoc-28-20138

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