Bacterial Peptide deformylase inhibition of cyano substituted biaryl analogs: Synthesis, in vitro biological evaluation, molecular docking study and in silico ADME prediction

Khan, Firoz A. Kalam; Patil, Rajendra; Shinde, Devanand B.; Sangshetti, Jaiprakash N.

doi:10.1016/j.bmc.2016.05.051

Cited by 17 publications

(4 citation statements)

References 28 publications

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“…On the idea of the Lipinski “Rule of five,” all the final products have good membrane permeability (BBB/GI), log P (2.53–4.15) ≤5, number of hydrogen bond acceptors (4–6) ≤10, molecular weight ≤500, and also the number of hydrogen bond donors (1) ≤5. [ 48,49 ] The pharmacophoric properties of the compounds indicate that they all follow and satisfy Lipinski's rule, with all attributes falling within a tolerable range. These results are consistent with the activity potency of the compounds.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, density functional theory calculation, molecular docking studies, and evaluation of novel 5‐nitrothiophene derivatives for anticancer activity

Nuha

Evren

Çiyanci

et al. 2022

Archiv der Pharmazie

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Within the scope of this study, new 2-{2-[(5-nitrothiophen-2-yl)methylene] hydrazinyl}thiazole derivatives (2a-j) were synthesized and investigated for their potential anticancer and enzyme inhibition activities. Spectroscopic techniques were used to determine the structures of substances. The anticancer activities of compounds were detected in A549 human lung carcinoma and L929 murine fibroblast cell lines, determining cytotoxicity, apoptosis, mitochondrial membrane integrity, and caspase-3 activation. Compounds 2b bearing 4-nitrophenyl, 2c bearing phenyl, and 2d bearing 4-cyanophenyl moieties were specified with high anticancer activity, acting through an apoptotic pathway with an apoptosis ratio of 9.61%-15.59%. Mitochondrial membrane depolarization was determined to be 25.53% and 22.33% for compounds 2b and 2c, respectively. Furthermore, compound 2c exhibited excellent caspase-3 activation. A molecular docking study was realized with compound 2c on the caspase-3 enzyme. Furthermore, the electronic characteristics of the active compounds were investigated using density functional theory (DFT) at the B3LYP/6-31G (d, p) level. The frontier molecular orbital energy and atomic net charges were examined.

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Section: Resultsmentioning

confidence: 99%

Synthesis, density functional theory calculation, molecular docking studies, and evaluation of novel 5‐nitrothiophene derivatives for anticancer activity

Nuha

Evren

Çiyanci

et al. 2022

Archiv der Pharmazie

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“…Absorption (% ABS) was calculated by: % ABS = 109-(0.345 X TPSA) [47]. In the present study, the calculation of molecular volume (MV), molecular weight (MW), logarithm of partition coefficient (miLog P), number of hydrogen bond acceptors (n-ON), number of hydrogen bonds donors (n-OHNH), topological polar surface area (TPSA), number of rotatable bonds (n-ROTB), number of rigid bonds (Rig Bond), Rings, and Lipinski's rule of five [48]. All the synthesized compounds 6(a-j) were found to be nontoxic, as predicted by using mol-inspiration.…”

Section: In Silico Bioavailability Predictionsmentioning

confidence: 99%

Ultrasound-Assisted Synthesis and Docking Study of Novel Chromone-Thiadiazole Integrated Phosphonate Derivatives Targeting Topoisomerase Ii as Anticancer Agents

CHIVTE¹,

CHIVTE

2023

Int J Chem Res

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Objective: The present studies discuss the anticancer activity of different topoisomerase II inhibitors with docking study. Methods: The work reports the synthesis of novel diethyl (4-oxo-4H-chromen-3-yl)(5-substituted phenyl-1,3,4-thiadiazol-2-ylamino)methyl phosphonate derivatives 6(a-j). They were synthesized through one-pot three-component Kabachnik-Fields reaction by using ultrasonicator processor, at room temperature in presence of Zirconium oxychloride (ZrOCl2). Results: The structures of the synthesized compounds were confirmed by spectral analysis. The synthesized derivatives 6(a-j) were evaluated for their in vitro anticancer activity against human cancer cell lines such as DU 145 (Human Prostate Cancer) and MCF-7 (Breast cancer) and also on non-tumor cell lines such as MCF-10 (normal breast epithelial cell) by MTT assay. From the anticancer screening results data, compound 6e was found to be the most potent anticancer compound among the synthesized compounds against MCF-7 and DU 145 cancer cell lines with IC50 value of 2.97 µM and 3.11 µM, respectively. The compound 6h has shown cell cycle arrest at G2/M phase, along with the decrease of cells at G0/G1 phage. The compound 6h was able to induce apoptosis in DU 145 cell lines. The synthesized compounds 6(a-j) were further evaluated for their topoisomerase II inhibitory activity. Conclusion: The anticancer screening result and MTT assay, along with the docking study shows that the synthesised derivative are active anticancer agent against MCF-10, DU-145 and MCF-7 cell line.

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“…Infectious diseases caused by microorganisms are a major concern for human survival accounting for almost 50,000 deaths daily worldwide . These infections are generally caused by bacterial pathogens that have been resistant to one or more antibiotics due to which patients suffering from these infections do not respond to general antibiotic treatment.…”

Section: Introductionmentioning

confidence: 99%

New Quinoline Linked Chalcone and Pyrazoline Conjugates: Molecular Properties Prediction, Antimicrobial and Antitubercular Activities

et al. 2017

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Two novel series comprising of forty two compounds have been synthesized by conjugating quinoline scaffold with chalcone as well as pyrazoline motifs. All the synthesized conjugates were tested for their antibacterial, antifungal and anti‐tubercular activities. Several of these novel compounds exhibited good to appreciable antibacterial activity against the tested bacterial strains. Compounds 4 j and 7 b were found to be the promising candidates exhibiting MIC 4 μg/mL against B. subtilisMTCC 121 and M. luteus MTCC 2470. Moreover, several conjugates significantly inhibited growth of certain fungal organisms. Furthermore, some of the conjugates displayed moderate anti‐tubercular activity against both H37RV as well as RifR strains. The binding modes and effect of the C4 quinoline substitution on the activity have been studied using computational techniques. Methyl group enhances the antimicrobial activity upon replacement by aromatic phenyl group and this is supported by the experimental data.

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Bacterial Peptide deformylase inhibition of cyano substituted biaryl analogs: Synthesis, in vitro biological evaluation, molecular docking study and in silico ADME prediction

Cited by 17 publications

References 28 publications

Synthesis, density functional theory calculation, molecular docking studies, and evaluation of novel 5‐nitrothiophene derivatives for anticancer activity

Synthesis, density functional theory calculation, molecular docking studies, and evaluation of novel 5‐nitrothiophene derivatives for anticancer activity

Ultrasound-Assisted Synthesis and Docking Study of Novel Chromone-Thiadiazole Integrated Phosphonate Derivatives Targeting Topoisomerase Ii as Anticancer Agents

New Quinoline Linked Chalcone and Pyrazoline Conjugates: Molecular Properties Prediction, Antimicrobial and Antitubercular Activities

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