Synthesis and antibacterial activity of Schiff bases of 5-substituted isatins

Tehrani, Kamaleddin Haj Mohammad Ebrahim; Hashemi, Maryam; Hassan, Maryam; Kobarfard, Farzad; Mohebbi, Shohreh

doi:10.1016/j.cclet.2015.10.027

Cited by 65 publications

(12 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Haj Mohammad Ebrahim Tehrani et al [ 36 ] have described the antibacterial evaluation of fluorinated ketimine-type Schiff bases 83 – 88 ( Figure 21 ) obtained by a condensation/dehydration reaction of 1-aminohydantoin, semicarbazide or thiosemicarbazide and variously substituted isatines (stoichiometric amounts). The synthetic process has been carried out in refluxing ethanol for 5 h, with the assistance of small amount of glacial acetic acid as an efficient catalyst.…”

Section: Fluorinated Ketimine-type Schiff Basesmentioning

confidence: 99%

“…Haj Mohammad Ebrahim Tehrani et al [ 36 ] have described the antibacterial evaluation of fluorinated hydrazide-hydrazones 190 – 191 ( Figure 51 ) obtained from stoichiometric ratios of benzohydrazide or isonicotinic acid hydrazide and 5-fluoro-1 H -indole-2,3-dione, in refluxing ethanol for 4–6 h, with assistance of small amount of glacial acetic acid as an efficient catalyst. The authors have reported that microwave irradiation at 110 °C for 5 min was an alternative method of their synthesis.…”

Section: Fluorinated Hydrazide-hydrazonesmentioning

confidence: 99%

See 1 more Smart Citation

An Insight into Fluorinated Imines and Hydrazones as Antibacterial Agents

Sztanke,

Wilk,

Sztanke

2024

IJMS

View full text Add to dashboard Cite

Fluorinated imines (Schiff bases) and fluorinated hydrazones are of particular interest in medicinal chemistry due to their potential usefulness in treating opportunistic strains of bacteria that are resistant to commonly used antibacterial agents. The present review paper is focused on these fluorinated molecules revealing strong, moderate or weak in vitro antibacterial activities, which have been reported in the scientific papers during the last fifteen years. Fluorinated building blocks and reaction conditions used for the synthesis of imines and hydrazones are mentioned. The structural modifications, which have an influence on the antibacterial activity in all the reported classes of fluorinated small molecules, are highlighted, focusing mainly on the importance of specific substitutions. Advanced research techniques and innovations for the synthesis, design and development of fluorinated imines and hydrazones are also summarized.

show abstract

Section: Fluorinated Ketimine-type Schiff Basesmentioning

confidence: 99%

Section: Fluorinated Hydrazide-hydrazonesmentioning

confidence: 99%

An Insight into Fluorinated Imines and Hydrazones as Antibacterial Agents

Sztanke,

Wilk,

Sztanke

2024

IJMS

View full text Add to dashboard Cite

show abstract

“…The results show that the bacterium S. aureus is resistant to the compounds SBPC, FCPC and FCFF with MIC at 12.5 mg.mL -1 (>200 μg/mL) and completely resistant to SBFF. Similarly, the bacterium S. epidermidis is resistant to the Schiff's bases SBPC, SBFF with MIC at 12.5 mg.mL -1 and completely resistant to the benzimidazole derivatives FCPC and FCFF [38].…”

Section: Antibacterial Evaluationmentioning

confidence: 99%

Synthesis, Cytotoxicity, Antibacterial and Antioxidant Activity of New 2-Substituted Benzimidazole Containing 1,2,4-Triazoles

Aryal

Shakya

2023

J. Nepal Chem. Soc.

View full text Add to dashboard Cite

The development of a potent new drug with high biological activity is a challenge in drug design and is of strategic importance. Due to the increasing resistance of pathogens on the available drugs, there is always a demand for designing a potent drug with high biological activity. The pharmacological effects have been observed in compounds containing different moieties of pharmaceutical importance such as triazole, Schiff’s base, benzimidazole.Triazole thione, Schiff’s bases, and two new compounds containing three pharmacophores viz. triazole, benzimidazole, and Schiff base incorporated in a single compound were prepared by applying different synthetic reactions. Different spectroscopic methods, including FT-IR, UV-vis, 1H-NMR, and 13C-NMR, were used to confirm the structure of the prepared compounds. All compounds exhibited moderate antibacterial activity against Staphylococcus aureus (ATCC 6538P) and Staphylococcus epidermidis (ATCC 1228). Antioxidant activity was carried out by DPPH radical scavenging test and among the tested five compounds, the IC50 value of 4-amino-3-(2-hydroxyphenyl)-1H-1,2,4-triazole-5(4H)-thione was found to be 32.364 μg.mL-1 which is closer to the ascorbic acid that was found to be 28.546 μgmL-1. All tested compounds were toxic against brine shrimp where 2-(5-((1H-benzo[d]imidazol-2-yl)thio)-4-((4-chlorobenzylidene) amino)-4H-1,2,4-triazol-3-yl) was comparatively more toxic (LC50= 26.827 μgmL-1).

show abstract

“…An important class of hydantoins consists of the derivatives of 1-aminohydantoin. The compounds are usually prepared from 1-aminohydantoin hydrochloride, which synthesis on solid-support has been described recently (Scheme ), and the aldehyde or ketone corresponding to the desired substitution on the hydrazide moiety. − …”

Section: Aminohydantoinsmentioning

confidence: 99%

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

et al. 2017

View full text Add to dashboard Cite

The review highlights the hydantoin syntheses presented from the point of view of the preparation methods. Novel synthetic routes to various hydantoin structures, the advances brought to the classical methods in the aim of producing more sustainable and environmentally friendly procedures for the preparation of these biomolecules, and a critical comparison of the different synthetic approaches developed in the last twelve years are also described. The review is composed of 95 schemes, 8 figures and 528 references for the last 12 years and includes the description of the hydantoin-based marketed drugs and clinical candidates.

show abstract

Synthesis and antibacterial activity of Schiff bases of 5-substituted isatins

Cited by 65 publications

References 28 publications

An Insight into Fluorinated Imines and Hydrazones as Antibacterial Agents

An Insight into Fluorinated Imines and Hydrazones as Antibacterial Agents

Synthesis, Cytotoxicity, Antibacterial and Antioxidant Activity of New 2-Substituted Benzimidazole Containing 1,2,4-Triazoles

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

Contact Info

Product

Resources

About