Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamides and N-[2-(2-{[2-(Acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides: New Antimicrobial Agents

Almutairi, Maha S.; Zakaria, Azza S.; Al-Wabli, Reem I.; Joe, I. Hubert; Attia, Mohamed I.

doi:10.3390/molecules23051043

Cited by 5 publications

(3 citation statements)

References 36 publications

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“…41 Subsequently, compound 2 was subjected to hydrazinolysis with hydrazine hydrate, thereby forming the acid hydrazide 3. 42 The target indole-isatin conjugates 5a-s were respectively prepared by reacting the acid hydrazide 3 with the appropriate isatin derivatives 4a-n in ethanol-containing drops of acetic acid. The stereochemistry of the title conjugates 5a-s was assigned the (Z)-configuration, based on the previously documented X-ray results of structurally related analogous compounds.…”

Section: Results and Discussion Chemistrymentioning

confidence: 99%

<p>New Isatin–Indole Conjugates: Synthesis, Characterization, and a Plausible Mechanism of Their in vitro Antiproliferative Activity</p>

Al-Wabli

Almomen

Almutairi

et al. 2020

DDDT

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Background: Cancer remains the leading cause of human morbidity universally. Hence, we sought to assess the in vitro antiproliferative activity of new isatin-based conjugates (5a-s) against three human cancer cell lines. Methods: The antiproliferative activities of compounds 5a-s were evaluated in vitro and their ADME (absorption, distribution, metabolism and excretion) was carried out using standard protocols. Subsequently, Western blot analysis was conducted to elucidate the potential antiproliferative mechanism of compounds 5a-s. Results: The in vitro antiproliferative activities of compounds 5a-s against the tested cancer cell lines ranged from 20.3 to 95.9%. Compound 5m had an IC 50 value of 1.17 µM; thus, its antiproliferative potency was approximately seven-fold greater than that of sunitinib (IC 50 = 8.11 µM). In-depth pharmacological testing was conducted with compound 5m to gain insight into the potential antiproliferative mechanism of this class of compounds. Compound 5m caused an increase in the number of cells in the G1 phase, with a concomitant reduction of those in the G2/M and S phases. Additionally, compound 5m significantly and dose-dependently reduced the amount of phosphorylated retinoblastoma protein detected. Compound 5m enhanced expression of B cell translocation gene 1, cell cycle-associated proteins (cyclin B1, cyclin D1, and phosphorylated cyclin-dependent kinase 1), and a pro-apoptotic protein (Bcl-2-associated X protein gene), and activated caspase-3. ADME predictions exposed the oral liability of compounds 5a-s. Conclusion: Herein, we revealed the antiproliferative activity and ADME predictions of the newly-synthesized compounds 5a-s and provided a detailed insight into the pharmacological profile of compound 5m. Thus, compounds 5a-s can potentially be exploited as new antiproliferative lead compounds for cancer chemotherapeutic.

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Section: Results and Discussion Chemistrymentioning

confidence: 99%

<p>New Isatin–Indole Conjugates: Synthesis, Characterization, and a Plausible Mechanism of Their in vitro Antiproliferative Activity</p>

Al-Wabli

Almomen

Almutairi

et al. 2020

DDDT

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“…On the basis of the antimicrobial activity shown in agar diffusion technique, three most active compounds were selected for MIC determination. Broth dilution method was employed in this study using 96 wells micro-titre plate [20][21][22]. Dilutions were made to obtain different concentrations of 600, 500, 400, 200, 100, 50, 25, 12.5, and 6.25 µg/mL.…”

Section: Determination Of Minimum Inhibitory Concentration and Minimumentioning

confidence: 99%

Synthesis and biological evaluation of triphenyl-imidazoles as a new class of antimicrobial agents

et al. 2018

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Newer triphenyl-imidazole derivatives (4a-h) were synthesized in good yields by the reaction of benzil and substituted benzaldehydes in equimolar quantities and refluxing the product with acetyl chloride thereafter. Structures were confirmed by using FT-IR, 1H NMR and 13C NMR spectroscopic methods. All the synthesized compounds were tested for their antimicrobial activity using agar diffusion technique against Gram positive (Staphhylococcus aureus and Bacillus subtilis), Gram negative (Escherichia coli and Pseudomonas aureginosa) as well as Fungal strain (Candida albicans). Interestingly compounds 4a, 4b, 4f and 4h showed significant antibacterial activity, whereas compound 4b was found to have remarkable activity against the fungal strain. The Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) of most active compounds were determined by broth dilution method and compound 4b emerged to have potent activities against most of the strains having MIC in the range of 25-200 µg/mL. To check the possible toxicities of the most active compounds, they were orally administered in rats and the concentration of liver enzymes serum glutamic-oxaloacetic transaminase (SGOT), serum glutamic pyruvic transaminase (SGPT) and alkaline phosphatase (ALKP) were determined. Compound 4h showed significant increase in the enzymes level depicting the hepatotoxicity. The structure-activity relationship studies showed the importance of electron withdrawing groups at the distant phenyl ring at ortho and para positions as the compounds having chloro or nitro at these positions tend to be more active than the compounds with electron releasing groups such as methoxy. These compounds may act as lead compounds for further studies and appropriate modification in their structure may lead to agents having high efficacy with lesser toxicity.

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“…Thus, a large number of publications are devoted to indole-containing glyoxylamides, which have a wide range of antitumor properties, [34][35][36][37] as well as antimicrobial, antiasthmatic, antiallergic, and immunomodulatory effects. 38 To our surprise, there are practically no examples of the synthesis of glyoxylamides containing a quinoline fragment in the literature. At the same time, the synthesis of new structurally different glyoxylamides is of undoubted interest for studying their properties, for instance by comparying them with their indole-containing glyoxylamides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a novel series of 1,2-dihydroquinoline-8-glyoxylamide derivatives

Novichikhina¹,

Ashrafova²,

Ledenyova³

et al. 2023

Arkivoc

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A series of new derivatives of 1,2-dihydroquinoline-8-glyoxylamides have been synthesized via nucleophilic opening of the pyrrolidine-2,3-dione ring of 4,4,6-trimethyl-4H-pyrrolo[3,2,1-ij]quinoline-1,2-diones by a variety of amines. This method is an efficient synthetic strategy for introducing substituents at the o-position of the amine function of the 1,2-dihydroquinolines. The obtained compounds are of interest as potentially physiologically active substances.

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Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamides and N-[2-(2-{[2-(Acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides: New Antimicrobial Agents

Cited by 5 publications

References 36 publications

<p>New Isatin–Indole Conjugates: Synthesis, Characterization, and a Plausible Mechanism of Their in vitro Antiproliferative Activity</p>

<p>New Isatin–Indole Conjugates: Synthesis, Characterization, and a Plausible Mechanism of Their in vitro Antiproliferative Activity</p>

Synthesis and biological evaluation of triphenyl-imidazoles as a new class of antimicrobial agents

Synthesis of a novel series of 1,2-dihydroquinoline-8-glyoxylamide derivatives

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