Synthesis and Antimicrobial Studies of Some 4-(Substituted)-Ethanoylamino-3-Mercapto-5- (4-Substituted) Phenyl-1,2,4-Triazoles

Upmanyu, Neeraj; Kumar, Sanjay; Shah, Kamal; Mishra, Pradeep

doi:10.3329/dujps.v11i1.12481

Cited by 10 publications

(10 citation statements)

References 22 publications

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“…One of the observed resonances is found to be at higher chemical shift region due to deshielding effect of neighbouring C=O moiety [23]. In the range of δ H 7.95-6.78 ppm, roofing effect due to para substituted phenyl group can be observed in T2 and T3 [24]. However, different pattern at δ H 8.02-7.52 ppm is observed due to presence of tri-substituted phenyl in T1.…”

Section: V(c-h) V(c=o) V(c=n)mentioning

confidence: 87%

Synthesis and Molecular Docking of 2,4,5-Trisubstituted-1,3-Thiazole Derivatives as Antibacterial Agents

2019

MJAS

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The emergence of antibiotic resistance against bacterial strains has attracted great interest in the discovery and development of new antibacterial agents. Thiazole derivatives have been widely used in the biological as well as pharmacological fields and their efficiency as pharmaceutical drugs are well established. In this study, a series of thiazole derivatives were synthesized in reaction between 3-chloroacetyl acetone and ammonium thiocyanate followed by incorporating selected amines in one-pot synthesis manner. The compounds were structurally characterized by Fourier Transform Infrared (FTIR), Proton Nuclear Magnetic Resonance ( 1 H NMR), Ultraviolet-Visible (UV-Vis) and Gas Chromatography-Mass Spectrometry (GC-MS). Their antibacterial properties were screened using disc diffusion technique against selected Gram-positive (Bacillus cereus and Staphylococcus epidermidis) as well as Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) with T3 exhibited the most potent antibacterial activity. Molecular docking studies were also performed against Glucosamine-6-phosphate (GlcN-6-P) synthase which is known as the essential building block of most bacteria. The docking result displayed that T3 exhibited the minimum binding energy of -7.09 kcal mol -1 as compared to T1 and T2 with -6.49 and -6.76 kcal mol -1 , respectively which is in agreement with antibacterial result. The output of this preliminary study will contribute in structural enhancement in drug discovery. AbstrakKewujudan rintangan terhadap bakteria telah menarik minat dalam penemuan dan perkembangan agen antibakteria yang terkini. Terbitan tiazol telah digunakan dengan meluas dalam bidang biologi dan farmakologi di mana keberkesanannya sebagai ubat farmaseutikal telah ditemui. Dalam kajian ini, terbitan tiazol telah disintesis dengan menindakbalaskan α-haloketon (3-kloroasetil aseton), ammonium tiosianat dan beberapa sebatian amina terpilih secara sintesis satu pot. Produk tindak balas yang terhasil telah dicirikan dengan Transformasi Fourier-Inframerah (FTIR), Proton Resonans Magnet Nukleus ( 1 H NMR), Ultralembayung-Sinar Nampak (UV-Vis) serta Kromatografi Gas-Spektrometer Jisim (GC-MS). Sifat antibakteria sebatian ini telah disaring menggunakan teknik serapan cakera terhadap bakteria Gram-positif (Bacillus cereus dan Staphylococcus epidermidis) dan Gram-negatif (Escherichia coli dan Pseudomonas aeruginosa) dengan T3 menunjukkan aktiviti antibakteria yang paling berkesan. Penyatuan molekul telah dilakukan terhadap enzim Glukosamina-6-fosfat sintase (GlcN-6-P) yang merupakan unsur binaan penting bagi kebanyakan bakteria. Merujuk kepada keputusan penyatuan molekul, T3 menunjukkan tenaga pengikatan yang paling minima iaitu -7.09 kcal mol -1 berbanding T1 dan T2 masing-masing pada -6.49 dan -6.76 kcal mol -1 , menunjukkan nilai-nilai ini bersetuju dengan keputusan saringan antibakteria. Keputusan kajian awal ini akan menyumbang kepada penambahbaikan struktur untuk penghasilan ubat.

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Section: V(c-h) V(c=o) V(c=n)mentioning

confidence: 87%

Synthesis and Molecular Docking of 2,4,5-Trisubstituted-1,3-Thiazole Derivatives as Antibacterial Agents

2019

MJAS

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“…Previous studies showed that 1,2,4-triazole derivatives are important group in the field of medicinal chemistry due to their diverse biological properties [23]. The biological activity of triazoles is highly dependent on the chemical side groups that may enhance their activity.…”

Section: Discussionmentioning

confidence: 99%

Synthesis, characterization and evaluation of antibacterial activity of six novel 1,2,4-triazole derivatives against standard and medical bacteria

Jacob

Irshaid²,

Al‐Soud³

et al. 2013

asb

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1,2,4-triazoles have been reported to possess a wide range of biological activities, including anticancer, antifungal, antiviral and antibacterial activities. Therefore, the current investigation is intended to synthesize six novel 1,2,4-triazole derivatives (designated as 2aa, 2ab, 2ac, 2bb, 2bd, and 2be). These derivatives were screened for their antibacterial activity against two Gram-negative bacteria isolated from clinical specimens (stool and ear exudates of infected patients) and two Gram-positive standard bacteria (Staphylococcus aureus ATCC29213 and Bacillus cereus ATCC11778) using both well diffusion and broth dilution methods. The chemical structures of the new 1,2,4-triazole derivatives were characterized by 1 H and 13 C-NMR spectra, in addition to elemental analysis. The bacterial strains designated as GN1 and GN2 were identified by biochemical and molecular methods and confirmed as new strains of Shigella sp., and Pseudomonas aeruginosa, respectively. All triazole derivatives were found to be active against bacteria with varying degrees. Some derivatives were found to have the same antibacterial activity as penicillin G (the positive control) against certain strains, for instance, 2ab, 2bd, and 2be against B. cereus ATCC11778. Interestingly, some compounds were more active than penicillin G against certain strains. The activity of 2aa against B. cereus ATCC11778 was higher than the activity of penicillin G, whereas 2ab and 2ac were more active than penicillin G against the clinical isolate P. aeruginosa. The variation seen in antimicrobial activity could be attributed to the difference in the substituent groups attached to the 1,2,4-triazole nucleus. In conclusion, these findings might hold promise for development of a new class of a novel expanded spectrum antibiotics against clinically important bacteria that are highly resistant to current antibacterial agents and associated with serious and life-threatening infections.

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“…Hydrazinolysis of compounds IIa-IIb gave the corresponding acetohydrazides (IIIa-IIIb) in good yields [30,32]. One mole of the compound IIa or IIb in ethanol was heated for 4-6 h with hydrazine hydrate (two moles).…”

Section: Mechanism Of the Pechmann Condensationmentioning

confidence: 99%

“…The reaction of the acid hydrazides (4-methyl/propyl-2-oxo-2H-benzopyran-7oxyacetic acid hydrazide) with CS 2 in ethanol containing KOH at room temperature has been presented in Figure 6. The corresponding potassium dithiocarbazate derivatives, IVa-IVb, are obtained [32].…”

Section: Mechanism Of the Pechmann Condensationmentioning

confidence: 99%

Coumarin Derivatives with Antimicrobial and Antioxidant Activities

Tătărîngă¹,

Zbancioc²

2020

Phytochemicals in Human Health

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Coumarin derivatives are structurally interesting compounds for synthesizing antimicrobial and antioxidant agents. Starting from 4-methyl-7-hydroxycoumarin, several derivatives with these properties have been obtained through different reaction steps. Their molecular structures were established by Fourier-transform infrared spectroscopy and nuclear magnetic resonance spectroscopy. The synthesized coumarin derivatives exerted meaningful activities against Gram-positive and Gram-negative bacteria as well as strains of Candida spp. All compounds also exhibited high and moderate antioxidant activity in assays for DPPH inhibition, total reducing power, and nitric oxide (NO) inhibition when compared to ascorbic acid.

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Synthesis and Antimicrobial Studies of Some 4-(Substituted)-Ethanoylamino-3-Mercapto-5- (4-Substituted) Phenyl-1,2,4-Triazoles

Cited by 10 publications

References 22 publications

Synthesis and Molecular Docking of 2,4,5-Trisubstituted-1,3-Thiazole Derivatives as Antibacterial Agents

Synthesis and Molecular Docking of 2,4,5-Trisubstituted-1,3-Thiazole Derivatives as Antibacterial Agents

Synthesis, characterization and evaluation of antibacterial activity of six novel 1,2,4-triazole derivatives against standard and medical bacteria

Coumarin Derivatives with Antimicrobial and Antioxidant Activities

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