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Proceeding Paper

Synthesis and Evaluation of Novel 5-Arylidene-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) Thiazolidin-4-Ones as Anti-Microbial Agents †

by
Pritam N. Dube
1,* and
Yogita B. Thombare
2
1
Sandip Foundation’s Sandip Institute of Pharmaceutical Sciences, Mahiravani, Nashik 422213, Maharashtra, India
2
Department Pharm D, MGVs Pharmacy College, Panchavati, Nashik 422003, Maharashtra, India
*
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), 51; https://doi.org/10.3390/ecsoc-28-20120
Published: 14 November 2024
(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)
Browse Figure
Versions Notes

Abstract

:
The development of combination chemotherapeutic drugs, each with distinct mechanisms and minimal side effects, is crucial in combating antimicrobial resistance. Discovering novel drugs with diverse mechanisms is laborious and time-consuming. Alternatively, combining multiple pharmacophores into a single molecule offers a promising strategy to develop more effective treatments. In this study, we synthesized and assessed the antimicrobial activity of novel 5-arylidene-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) thiazolidin-4-ones.

1. Introduction

Antibiotics have long served as humanity’s primary weapon against pathogenic microorganisms [1,2,3]. However, decades after their discovery, microbes have resiliently developed novel survival strategies, leading to significant challenges. It is humanity that has borne the brunt of this battle. We urgently require new drugs with mechanisms of action distinct from those of current antibiotics to effectively combat pathogenic microorganisms [2,3,4,5,6].
Development of successful novel antimicrobial agents targeting pathogens would decrease the demand for antibiotics and thereby lower the pressure that leads to antibiotic-resistant mutations. Heterocyclic chemistry is one of the most important branches of chemistry from the medicinal point of view [7,8]. Many heterocyclic compounds having hetero atoms such as N, O and S have shown biological activities that are important from the pharmaceutical perspective. Drug-resistant bacteria cause the deaths of more than a million people across the globe each year. In the US alone, more than 23,000 people die every year because of drug-resistant pathogens. The current pace of drug development is inadequate to alleviate the global health threat of drug-resistant organisms [9,10,11,12,13].
The pyrimidine moiety is a crucial heterocyclic compound widely present in the human body, exhibiting diverse biological activities such as antimicrobial, anti-inflammatory, anti-coagulant, antihypertensive, and antitubercular properties. It is integral to nucleic acids and enzymes in living organisms, offering potential as both antagonist and agonist drugs [14,15,16].
The rise of resistance to antibiotics and other antimicrobial agents poses a significant global challenge today [3,5,8]. As microbes develop resistance to current treatments, the battle between bacteria and humans intensifies, often resulting in adverse outcomes for human health. Addressing these challenges requires controlling the overuse of antibiotics, which exacerbates resistance, and developing novel antibiotics with enhanced potency and efficacy [11,12,13,14,15].
To mitigate these challenges and improve treatment outcomes, discovering new antimicrobial agents with improved safety profiles remains paramount. This study focused on the synthesis and evaluation of novel pyrimidine derivatives as potential antimicrobial agents, aiming to contribute to the ongoing efforts against microbial resistance [17,18,19,20].

2. Materials and Methods

For the determination of structures of newly synthesized compounds, we used sophisticated techniques including IR, 1H NMR, 13C NMR and mass spectra. Aluminum-coated TLC plates 60F254 (E. Merck, Mumbai, Maharashtra, India) were used for reaction monitoring and checking the purity of all compounds. Ultraviolet (UV) light, or iodine vapor, was used for visualization purposes. Elemental analysis (% C, H, N) was carried out with a Perkin-Elmer 2400 CHN analyzer (Bengaluru, Karnataka, India). IR spectra of all compounds were recorded on a Perkin-Elmer FTIR spectrophotometer in KBr (Bengaluru, Karnataka, India). The mass spectrum was scanned on a Schimadzu LC-MS 2010 spectrophotometer (New Delhi, India). 1H NMR and 13C NMR spectra were recorded on a Bruker (400 MHz) and (100 MHz) spectrometer (Mumbai, Maharashtra, India), respectively, using DMSO-d6 as a solvent and TMS as an internal standard. Parts per million (ppm) was used as a unit to express the chemical shifts.
  • Preparation of 7-chloroquinoline-6-carbaldehyde (I)
7-Chloroquinoline-6-carbaldehyde I was prepared as per the method given in the literature [21,22].
  • Preparation of 1-(7-chloroquinolin-6-yl)-N-(pyrimidin-2-yl)methanimine (II)
Compound I (0.01 mol) was dissolved in ethanol (95%) (20 mL) and pyrimidin-2-amine A (0.01 mol) was added to it. After adding CH3COOH in a catalytic amount, the reaction mixture was stirred at 80 °C for 4 h. The reaction mixture was then allowed to cool at room temperature and the product formed as crystals was filtered [21,22,23,24]. The product was washed with cold ethanol (95%), dried and recrystallized from the same solvent to obtain compound II.
Yield: 69%; m.p.: 163 °C; FTIR (cm−1): 3462 (CH stretching), 1647 (C=O), 1541 (C=N), 846 (=CH), 659 (C-S); anal. calcd. for C14H9ClN4: C-62.58, H-3.38, N-20.85; Found: C-62.67, H-3.29, N-20.77%.
  • Preparation of 2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl)thiazolidin-4-one (III)
Compound II (0.01 mol) was dissolved in 1,4-dioxane (20 mL) and thioglycolic acid (0.03 mol) was added to it. After adding ZnCl2 in a catalytic amount, the reaction mixture was stirred at 110 °C for 5.5 h. The reaction mixture was then allowed to cool at room temperature and poured into cooled dil.NaHCO3 solution. The product obtained, which was a dark cream color, was filtered and washed with the same solution, followed by cold methanol, then dried and recrystallized from methanol to obtain compound III.
Yield: 59%; m.p.: 182 °C; FTIR (cm−1): 3307 (CH stretching), 1602 (C=O), 1495 (C=N), 883 (=CH), 655 (CH), 584 (C-Cl); anal. calcd. for C16H11ClN4OS: C-56.06, H-3.23, N-16.34; Found: C-56.13, H-3.15, N-16.27%.
  • Preparation of 5-arylidene-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) thiazolidin-4-ones (IV)
Compound III (0.01 mol) was dissolved in ethanol (95%) (20 mL) and benzaldehyde (0.01 mol) was added to it. After the addition of NaOH in a catalytic amount, the reaction mixture was stirred at 50 °C for 80 min [21,22,23,24]. The reaction mixture was then allowed to cool at room temperature. Theproduct was filtered and washed with cold methanol, dried and recrystallized from dimethyl formaldehyde to obtain compound IV.
Yield: 62%; m.p.: 217 °C; FTIR (cm−1): 3391(-CH stretching), 1655 (C=O), 1539 (C=N), 851 (=CH), 663 (C-S), 516 (C-Cl); 1H NMR (ppm): 2.4 (s, 1H, -CH), 6.7 (s, 1H, C-H thiazolidinone), 6.9–7.8 (m, 13H, aromatic); 13C NMR:37.5 (CH2), 66.7 (thhiazolidine), 111.8 (p-benzene), 121.4 (CH=CH), 126.8, 126.9, 127.4, 127.8, 128.2, 128.4, 128.6, 128.8, 128.9, 129.0, 129.1 (CH-Ar), 133.5 (Ar-C-Cl), 135.9 (Ar-CH=C), 139.1 (Ar-C-phenyl), 143.2 (=C-Ar), 151.2 (N=C-Ar), 167.5 (C=O); anal. calcd. for C23H15ClN4OS: C-59.36, H-3.03, N-12.04; Found: C-59.45, H-3.12, N-12.13%.
The progress of reaction was monitored by TLC (aluminum sheet silica gel 60 F254 (E. Merck)) plates using CHCl3:CH3OH (8.5:1.5) as an irrigator and the plates were visualized with ultraviolet (UV) light, or iodine vapor. All the compounds of the series were prepared using the same method. Chemical Structures of the synthesized compounds was depicted in Table 1.

2.1. Biological Evaluation

2.1.1. Antimicrobial Assay

The synthesized compounds were evaluated against E. coli, P. aeruginosa, S. aureus, S. pyogenes and strains of fungi C. albicans, A. niger and A. clavatus. The results of antibacterial and antifungal activities for the synthesized compounds are depicted. Minimum inhibition concentration (MIC) values of standard drugs for the comparison of antimicrobial activity of the synthesized compounds are reported.

2.1.2. Antibacterial Assay

The Mueller–Hinton broth dilution method (Becton Dickinson, Franklin Lakes, NJ, USA) was used for antibacterial assays of synthesized compounds. The strains obtained from the Institute of Microbial Technology were used for antibacterial activity. The compounds were tested in triplicate sets for antibacterial activity with different concentrations. The drugs, which were found to be active in primary analysis, were further diluted and evaluated; 10 μg/mL suspensions were further inoculated on appropriate media and the growth was noted after one or two days. The minimum inhibitory concentration was the lowest concentration, which showed no growth of microbes after spot subculture for each drug. The test mixture contained 108 cells/mL. In this study, gentamicin, chloramphenicol, ciprofloxacin and norfloxacin were the standard drugs used for evaluating the antibacterial activity [21,22,23,24].

2.1.3. Antifungal Assay

Antifungal activity of the bioactive molecules under investigation was tested in six sets and the strains reported. The concentrations used for experimentation were 1000, 500 and 250 μg/mL. The compounds that were active in primary screening underwent secondary testing with the fungal strains diluted to obtain 200, 125, 62.5, 50, 25, 12.5. The fungal activity of each compound was compared with that of nystatin and griseofulvin as standard drugs. Sabouraud’s dextrose broth method was used for the fungal growth at 28 °C in aerobic conditions for 48 h. Dimethyl sulphoxide and sterilized distilled water were used as negative controls while nystatin and griseofulvin (1U strength) were used as a positive controls [25,26,27,28].

3. Result and Discussion

3.1. Chemistry

For the construction of the desired 5-arylidene-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) thiazolidin-4-ones, the synthetic method of forming the targeted compound is depicted in Scheme 1.

3.2. Biological Evaluation

The synthesized derivatives were screened for their antibacterial and antifungal activity using various strains. The results are depicted in Table 2.
Compound 1 showed prominent activity against E. coli and P. aeruginosa with MIC values of 12.5 and 62.5 µg/mL, respectively, due to the presence of a hydrogen group at the third position of the benzene ring. It was found to be more active than the standard drugs. Compound 2, with an electron-donating group at the third position of the phenyl ring, exhibited potent antibacterial activity with an MIC value of 12.5 µg/mL.
The electron-withdrawing chloro group (-Cl) at the fourth position of the phenyl ring in the compound exhibited potent antifungal activity with an MIC value of 100 µg/mL for C. albican and A. niger, while a value of 62.5 µg/mL was shown for A. clavatus compared to standard drugs griseofulvin and nystatin. The tested compound showed potent antibacterial activity due to the presence of the electron-withdrawing group –OH at the fourth position of the phenyl ring with an MIC value of 12.5 µg/mL, compared to standard drugs, against E. coli. It also showed potent antifungal activity with an MIC value of 100 µg/mL for C. albicans compared to the standard drug griseofulvin.

4. Conclusions

All the synthesized derivatives were meticulously characterized and their structures confirmed through spectroscopic analysis. These compounds exhibited significant activity against both bacterial and fungal agents, highlighting their potential as effective antimicrobial agents. As we continue to face evolving challenges in microbial resistance, these findings underscore the importance of exploring novel therapeutic strategies to safeguard public health.

Author Contributions

P.N.D.: Writing—original draft, Visualization, Validation, Resources, Investigation, Formal analysis, Data curation. Y.B.T.: Writing—review & editing, Validation, Supervision, Resources, Project administration, Methodology, Investigation, Conceptualization. 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

Data is unavailable due to privacy.

Conflicts of Interest

The authors declare no conflict of interest.

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Chemproc 16 00051 sch001
Scheme 1. Synthesis of designed compounds (IV).
Scheme 1. Synthesis of designed compounds (IV).
Chemproc 16 00051 sch001
Table 1. Chemical structures of the newly synthesized compounds.
Table 1. Chemical structures of the newly synthesized compounds.
Sr. No.RChemical NameStructure
1.H5-(benzylidene)-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) thiazolidin-4-oneChemproc 16 00051 i001
2.4-OCH35-(4-methoxybenzylidene)-2-(7-
chloroquinolin-6-yl)-3-(pyrimidin-2-yl) thiazolidin-4-one		Chemproc 16 00051 i002
3.4-Cl5-(4-chlorobenzylidene)-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) thiazolidin-4-oneChemproc 16 00051 i003
4.4-OH5-(4-hydroxybenzylidene)-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) thiazolidin-4-oneChemproc 16 00051 i004
Table 2. Antimicrobial activity of synthesized compounds.
Table 2. Antimicrobial activity of synthesized compounds.
Sr. No.RMinimum Inhibitory Concentration (MIC)
Bacteria (µg/mL)Fungi (µg/mL)
E.c.P.a.S.a.S.p.C.a.A.n.A.c.
1.-H12.562.51002001000250250
2.4-OCH320012.5500500>100010001000
3.4-Cl25020020020010010062.5
4.4-OH12.5200500500250100100
5.Gentamicin0.0510.250.5---
6.Chloramphenicol50505050---
7.Ciprofloxacin25255050---
8.Nystatin----100100100
9.Griseofulvin----500100100
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MDPI and ACS Style

Dube, P.N.; Thombare, Y.B. Synthesis and Evaluation of Novel 5-Arylidene-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) Thiazolidin-4-Ones as Anti-Microbial Agents. Chem. Proc. 2024, 16, 51. https://doi.org/10.3390/ecsoc-28-20120

AMA Style

Dube PN, Thombare YB. Synthesis and Evaluation of Novel 5-Arylidene-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) Thiazolidin-4-Ones as Anti-Microbial Agents. Chemistry Proceedings. 2024; 16(1):51. https://doi.org/10.3390/ecsoc-28-20120

Chicago/Turabian Style

Dube, Pritam N., and Yogita B. Thombare. 2024. "Synthesis and Evaluation of Novel 5-Arylidene-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) Thiazolidin-4-Ones as Anti-Microbial Agents" Chemistry Proceedings 16, no. 1: 51. https://doi.org/10.3390/ecsoc-28-20120

APA Style

Dube, P. N., & Thombare, Y. B. (2024). Synthesis and Evaluation of Novel 5-Arylidene-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) Thiazolidin-4-Ones as Anti-Microbial Agents. Chemistry Proceedings, 16(1), 51. https://doi.org/10.3390/ecsoc-28-20120

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