Synthetic modifications in ethyl 2-amino-4-methylthiazole-5-carboxylate: 3D QSAR analysis and antimicrobial study

Desai, N. C.; Bhatt, Nayan; Joshi, Surbhi B.

doi:10.1080/00397911.2019.1587777

Cited by 7 publications

(20 citation statements)

References 24 publications

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“…Molecule 1 was synthesized according to the reported procedure by Meng 26 . Furthermore, the reaction of molecule 1 with hydrazine hydrate was carried out using the reported procedure 27 .…”

Section: Resultsmentioning

confidence: 99%

Untitled

2023

IJPSR

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A series of novel (Z)-3-((5-(2-((E)-arylidene) hydrazine-1carbonyl)-4-methylthiazol-2-yl)amino)-2-cyano-3-(methylthio) acrylate 4a-t molecules have been synthesized and characterized by 1 H NMR, 13 C NMRand mass spectral analysis. Starting from ethyl 2-amino-4methylthiazole-5-carboxylate 1 was reacted with hydrazine hydrate to obtain carbohydrazide molecule 2. Furthermore, reaction of molecule 2 with various aldehyde and the adduct 3a-t formed was reacted with ethyl 2-cyano-3,3-bis(methylthio) acrylate to get novel thiazole derivatives 4at, furthermore it was reacted with lithium hydroxide to form acid containing novel thiazole molecule 5a. The significant features of this reaction procedure are novel, easy and less time consuming with analytically pure product formation. INTRODUCTION:Thiazole moiety is present in several medicinal compounds and natural sources. The first widely used antibiotic penicillin, also have thiazole moiety in its core structure. Numerous medicinal drugs available for various types of illness also hold thiazole moiety, as shown in Fig. 1. Thiazoles and their derivatives also play a significant role in the field of medicinal chemistry where they found to exhibit a wide variety of activities such as, antiviral 1 , antioxidant 2 , antituberculosis 3 , antimicrobial 4 , anticancer 5 , anticonvulsant 6 , anti-inflammatory 7 , anti-infective 8 , antidiabetic 9 , anticonvulsant 10 , antifungal 11 , antiepileptic 12 , antidepressant 13 . Some of the thiazole molecules also showed inhibition against SARS-CoV-2 virus disease 14,15 . Several procedures for synthesizing thiazole derivatives are described in the literature [16][17][18][19][20][21][22][23] .

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Section: Resultsmentioning

confidence: 99%

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2023

IJPSR

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“…Some series of 2-thiazolyl-5-mercapto-1,3,4-oxadiazoles, either linked through a methylene linker between the fourth position of the thiazole ring and the second position of the 1,3,4-oxadiazole ring, or directly linked between the fifth position of the thiazole ring and the second position of the 1,3,4-oxadiazole ring, were synthesized [ 62 , 63 ].…”

Section: Structure–activity Relationships In Antimicrobial Thiazole-b...mentioning

confidence: 99%

“…Existing data [ 64 ] show that the thione tautomer ( II ) is more stable in the solid state, while, in a solution, the thiol tautomer ( I ) is predominant. The existence of thiol–thione tautomerism was valorized by obtaining the corresponding thioether derivatives and Mannich bases [ 62 , 63 ].…”

Section: Structure–activity Relationships In Antimicrobial Thiazole-b...mentioning

confidence: 99%

“…and Aspergillus sp. strains [ 63 ]. Compounds 199 , 200 , and 203 showed superior activity against E. coli MTCC 443, P. aeruginosa MTCC 1688, and S. pyogenes MTCC 442, compared to ampicillin (MICs = 100–250 µg/mL) [ 63 ].…”

Section: Structure–activity Relationships In Antimicrobial Thiazole-b...mentioning

confidence: 99%

“…Concerning antifungal activity, compounds 201 and 202 showed superior activity (MICs = 25–50 µg/mL) against C. albicans (MTCC 227) and A. niger (MTCC 282), compared to griseofulvin (MICs = 100–500 µg/mL) [ 63 ].…”

Section: Structure–activity Relationships In Antimicrobial Thiazole-b...mentioning

confidence: 99%

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An Overview of the Structure–Activity Relationship in Novel Antimicrobial Thiazoles Clubbed with Various Heterocycles (2017–2023)

Ungureanu,

Tiperciuc,

Nastasă

et al. 2024

Pharmaceutics

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Antimicrobial resistance is an increasing problem for global public health. One of the strategies to combat this issue is the synthesis of novel antimicrobials through rational drug design based on extensive structure–activity relationship studies. The thiazole nucleus is a prominent feature in the structure of many authorized antimicrobials, being clubbed with different heterocycles. The purpose of this review is to study the structure–activity relationship in antimicrobial thiazoles clubbed with various heterocycles, as reported in the literature between 2017 and 2023, in order to offer an overview of the last years in terms of antimicrobial research and provide a helpful instrument for future research in the field.

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Synthesis, molecular docking, DFT study, and in vitro antimicrobial activity of some 4‐(biphenyl‐4‐yl)‐1,4‐dihydropyridine and 4‐(biphenyl‐4‐yl)pyridine derivatives

Malani

Makwana

Monapara

et al. 2021

J Biochem & Molecular Tox

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The evolution of microbial resistance necessitates the development of new antimicrobial drugs that are more effective than those currently on the market. To address this problem, we have prepared a series of novel 4‐(biphenyl‐4‐yl)‐1,4‐dihydropyridine and 4‐(biphenyl‐4‐yl)pyridine derivatives via Hantzsch reaction using nine different compounds containing active methylene group. IR, NMR, and mass spectra were used to determine the structures. Using ampicillin and griseofulvin as standards, the titled compounds were investigated for their antibacterial activity against different bacteria and fungi. Compounds 1f, 1g, 2f, and 2g have the best antibacterial activity against Gram‐negative bacteria (minimum inhibitory concentration = 50 μg/ml), while 1f, 1h, 2g, and 2h have high antifungal activity against Candida albicans (minimum inhibitory concentration = 100 μg/ml). To gain a better understanding of the binding process and affinity for the bacterial Staphylococcus epidermidis protein, researchers used molecular docking and molecular mechanics, as well as the generalized Born model and solvent accessibility‐based binding free energy. The active compounds 1g, 1h, and 2f have good docking scores of −5.575, −5.949, and −5.234, respectively, whereas compound 2c has the greatest docking score (−6.23). The HOMO‐LUMO energy gap and molecular electrostatic potential were used to evaluate the reactivity of promising compounds, which were then associated with antibacterial efficacy.

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Synthetic modifications in ethyl 2-amino-4-methylthiazole-5-carboxylate: 3D QSAR analysis and antimicrobial study

Cited by 7 publications

References 24 publications

Untitled

Untitled

An Overview of the Structure–Activity Relationship in Novel Antimicrobial Thiazoles Clubbed with Various Heterocycles (2017–2023)

Synthesis, molecular docking, DFT study, and in vitro antimicrobial activity of some 4‐(biphenyl‐4‐yl)‐1,4‐dihydropyridine and 4‐(biphenyl‐4‐yl)pyridine derivatives

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