Synthesis, antimicrobial activity, and molecular docking study of fluorine-substituted indole-based imidazolines

Mendoza-Figueroa, Humberto L.; Serrano-Alva, Maria Trinidad; Aparicio-Ozores, Gerardo; Martínez-Gudiño, Gelacio; Suárez‐Castillo, Oscar R.; Pérez-Rojas, Nadia A.; Morales‐Ríos, Martha S.

doi:10.1007/s00044-018-2177-x

Cited by 8 publications

(4 citation statements)

References 32 publications

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“…First, reduction of commercially available indole-2-carboxylate with lithium aluminum hydride in dry tetrahydrofuran gave (1H-indole-2-yl)methanol (10) in 89% yield. The obtained alcohol was exposed to benzoyl chloride and triethylamine to furnish benzoate 11, which was further reacted with potassium cyanide to yield nitrile 12 [27]. Saponification of the nitrile was performed by exploiting the Pinner reaction with saturated HCl gas in methanol.…”

Section: Resultsmentioning

confidence: 99%

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

Kuznetcova¹,

Bacher²,

Vegh³

et al. 2022

Beilstein J. Org. Chem.

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Paullone isomers are known as inhibitors of tubulin polymerase and cyclin dependent kinases (Cdks), which are potential targets for cancer chemotherapy. Herein we report an efficient and clean pathway to the fourth isomer, which remained elusive so far, namely 7,8-dihydroindolo[2,3-d][1]benzazepin-6(5H)-one. Moreover, we demonstrate the generality of our pathway by synthesizing two closely related analogues, one containing a bromo substituent and the other one incorporating an 8-membered instead of a 7-membered ring. The key transformation in this four-step synthesis, with an overall yield of 29%, is the Fischer indole reaction of 2-nitrophenylacetyl acetoacetate with 1-benzyl-1-phenylhydrazine in acetic acid that delivers methyl 2-(1-benzyl-3-(2-nitrophenyl)-1H-indol-2-yl)acetate in 55% yield.

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Section: Resultsmentioning

confidence: 99%

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

Kuznetcova¹,

Bacher²,

Vegh³

et al. 2022

Beilstein J. Org. Chem.

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“…The lowest MICs 90 were within the range 1.5 µM and 12.5 µM. It has been shown in literature that compounds containing fluorine and chlorine incorporated in them generally show high antimicrobial activity [27,28]. Here, we examined whether the inclusion of fluorine and chlorine can enhance the antimicrobial activity of our peptoids.…”

Section: Antibacterial Activitymentioning

confidence: 94%

Novel tetrameric cell penetrating antimicrobial peptoids effective against mycobacteria and drug-resistant Staphylococcus aureus

Fleck¹,

Mukherjee²,

Tram³

et al. 2022

Front. Biosci. (Landmark Ed)

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Background: Antimicrobial peptides (AMPs) are short, cationic, amphipathic molecules that have gained tremendous popularity as alternatives to traditional antibiotics due to their lower propensity to develop bacterial resistance. However, the clinical developability of AMPs remains impeded due to shortcomings such as proteolytic instability and poor penetration leading to low bioavailability. Aims: To improve the access of AMPs to cells and subsequent bacteria killing, we evaluated the cell-penetrating and antimicrobial properties of three novel libraries of synthetic peptoids using Minimum Inhibitory Concentration, killing efficacy and membrane permeabilization assays against mycobacteria and Staphylococcus aureus. In addition, we investigated cell selectivity using mammalian cells to assess peptoid toxicity. Results: We showed that short tetrameric Rhodamine B-labeled peptoids composed of a balance of aromatic and lipophilic residues have potent selective antimicrobial activity against a range of microorganisms. The most potent candidates were active against drug-resistant S. aureus isolates as well as mycobacterial strains, with cell penetrating capabilities reported in HeLa and RAW 264.7 macrophage cells. Conclusions: These data suggest that peptoids with novel dual functionalities may potentially be an interesting class of therapeutics and/or molecular delivery agents for anti-infective purposes.

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“…Before simulation, constructions of prepared derivatives were structure and save as the 3D conformation via Discovery Studio 4.0 Client. The geometry optimization of synthesized compounds execute utilizing density functional theory (DFT) in the B3LYP hybrid selected the criterion 6-31G+(d,p) basis set by utilizing Gaussian 09W program package [20] , with the MMFF94 force-field minimization was employed for prepared compounds. Furthermore, for aim protein was protonated, charged and minimized energy via MOE 2009.…”

Section: Docking Studymentioning

confidence: 99%

Preparation, Antimicrobial Evaluation and Molecular docking of New 2,3-Substituted [1,3] Benzooxazin-4-one derivatives

Al-Naseeri¹,

Saleh²,

Jassim³

2022

JUAPS

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New 2, 3-substituted benzooxazin-4-one derivatives were prepared by means of a altered step by step proceedings in which Schiff bases were substituted with salicylic acid for a ring forming reaction. The compositions of the synthesized compounds were certain via methods spectrometry as elemental analysis, FT-IR, 13 C-NMR & 1 H-NMR spectral analysis. The bioactivities for the prepared compounds in-vitro as antibacterial and antifungal were estimated as opposed to two races of gram-positive & two races of gram-negative bacteria as parallel to Cefotaxime sodium as regular drug and assessed versus two types of fungi. The prepared compounds were got to have antimicrobial activities spreading from middling to perfect against of the bacteria strains with good percentage mycelial growth inhibition activity against fungi. Molecular docking displays the critical part while effect of variety of substituents on biological activity while mark the disadvantageous constitutional parameters in drawing medication: A different substitution does ensure additional efficiency in bioactivity.

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Synthesis, antimicrobial activity, and molecular docking study of fluorine-substituted indole-based imidazolines

Cited by 8 publications

References 32 publications

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

Novel tetrameric cell penetrating antimicrobial peptoids effective against mycobacteria and drug-resistant Staphylococcus aureus

Preparation, Antimicrobial Evaluation and Molecular docking of New 2,3-Substituted [1,3] Benzooxazin-4-one derivatives

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