The Novel 4-Phenyl-2-Phenoxyacetamide Thiazoles modulates the tumor hypoxia leading to the crackdown of neoangiogenesis and evoking the cell death

Mohammed, Yasser Hussein Eissa; Malojirao, Vikas H.; Thirusangu, Prabhu; Al‐Ghorbani, Mohammed; Prabhakar, B.T.; Khanum, Shaukath Ara

doi:10.1016/j.ejmech.2017.10.082

Cited by 31 publications

(17 citation statements)

References 29 publications

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“…From both the theoretical and a practical perspective, their great results are highly encouraging to study these compounds in deeply [ 8 ]. The natural and synthetic compounds with acetamide nucleus exhibited diverse pharmacological activities such as anti-cancer [ 9 ], anti-angiogenic [ 10 ], anti-oxidant [ 11 ], anti-metastasis [ 12 ], anti-inflammatory [ 13 ], anti-microbial [ 14 ], tranquilizer [ 15 ], analgesic, anti-convulsant etc. [ 16 ] and the acetamide residue is found in many proteins [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization, and DFT studies of anti-cancer drug N-(2-Aminophenyl)-2-(4-bromophenoxy)acetamide

Chandana¹,

Al-Ostoot

Mohammed

et al. 2021

Heliyon

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Drug design is an integrated and developing system that portends an era of a novel and safe tailored drugs. It involves studying the effects of biologically active synthetic, semi-synthetic, and natural compounds based on molecular interactions in terms of molecular structure with activated functional groups or its unique physicochemical properties involved. The title compound, N -(2-aminophenyl)-2-(4-bromophenoxy) acetamide ( c ), was synthesized in a good yield and characterized by different spectroscopic techniques ( 1 H, 13 CNMR, and LC-MS) and finally, the structure was confirmed by X-ray diffraction (XRD) studies. The XRD data confirms that the cryatal structure is orthorhombic with space group of Pca2 1 . The intermolecular interactions (N–H … O and N–H … Cg) inside the molecule stabilizes the crystal structure. The existence of this intermolecular interactions are computed by the Hirshfeld surfaces (HS) and two-dimensional (2D) fingerprints plot analysis. In addition to this, Energy frame work analysis is performed to quantify the interaction energies between the molecular pairs in a crystal by incorporating new version of CrystalExplorer17 using the energy model of HF/3-21G. Also to calculate the HOMO and LUMO energies, DFT calculations were carried out.

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Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization, and DFT studies of anti-cancer drug N-(2-Aminophenyl)-2-(4-bromophenoxy)acetamide

Chandana¹,

Al-Ostoot

Mohammed

et al. 2021

Heliyon

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“…Compounds which contain benzophenone pharmacophores are known to be pharmacologically active molecules which are utilized against several pathological conditions including cancer. 16,19,20 A multistep synthesis of benzophenone containing imidazole and pyrone analogues is involved in our current study. It is apparent that compound 9d, which contains the same backbone structure of benzophenone with an aceto moiety and N-methyl imidazole ring as other members of the same series but with a methyl group in the benzophenone moiety, has shown good activity compared to others in the same series.…”

Section: Biologymentioning

confidence: 99%

“…Then the cells were viewed under the 40× objective of a microscope (Biolux, Bresser Germany) and mounted with MagCam (Magnus Analytics); finally, the images were analyzed with ImageJ software. 14,19,30 4.3.11. Endonuclease assay.…”

Section: Chemistry: Plan Of the Synthesismentioning

confidence: 99%

The critical role of novel benzophenone analogs on tumor growth inhibition targeting angiogenesis and apoptosis

Mohammed

Shaukath

2018

Med. Chem. Commun.

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In modern biology, one of the major topics of importance is progress in anti-cancer drugs with specific targets. The angiopreventive and tumor inhibition activities of novel synthetic benzophenone analogs have been investigated intensively and explored in a very systematic way. Novel benzophenone analogs ( and ) substituted with methyl, chloro and fluoro groups at different positions on an identical chemical backbone and incorporating variations in the number of substituents have been synthesized in a multistep process and characterized. In this study, we further evaluate the newly synthesized compounds for their cytotoxic and anti-proliferative effects against A549, HeLa and MCF-7 cells. The potent lead compound was further assessed for anti-angiogenic effects. Through the structure-activity relationship, we found that an increase in the number of methyl, chloro and fluoro groups in a benzophenone ring on compound resulted in higher potency compared to other compounds. Tumor inhibition was notably promoted, and this was reflected in effects on neovessel formation in systems, such as the CAM. Compound interacts with rVEGF through hydrogen bonds , thereby down-regulating the expression of VEGF in angiogenesis. From our investigation, it is suggested on the basis of clonogenesis and cell migration assays that compound has the potency to exhibit prolonged activity against cancer progression, through cell cycle arrest at the G2/M phase. In addition, compound inhibits A549 cells through caspase-activated DNase-mediated apoptosis.

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“…Therefore, oxidative stress prevails when the reactive oxygen species (ROS) production in the target cell exceeds the antioxidant capacity. This may alter in the target cell function leading to cell death . Such process plays a significant role in developing chronic as well as degenerative illness including cancer, autoimmune disorders, ageing, cataract, rheumatoid arthritis, cardiovascular and neurodegenerative diseases .…”

Section: Introductionmentioning

confidence: 99%

“…However, the antioxidant supplements or medicinal plants‐based foods plays a major role in reducing oxidative damage caused by the free radicals and active oxygen species. But, in the animals, ROS are much conspicuous because of the antioxidant enzymes and antioxidant compounds, which are working as defence systems …”

Section: Introductionmentioning

confidence: 99%

Molecular Structure, DFT, Vibrational Spectra with Fluorescence Effect, Hirshfeld Surface, Docking Simulation and Antioxidant Activity of Thiazole Derivative

et al. 2019

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2‐(4‐methylphenoxy)‐N‐(4‐(4‐bromophenyl) thiazol‐2‐yl) acetamide compound was obtained via a multistep synthesis sequence processes, which is characterized by 1H NMR, 13C NMR and its three‐dimensional structure has been confirmed by single crystal X‐ray diffraction method. The supramolecular structure of the molecule revealed the stability of crystal packing with diverse intermolecular interactions. Density functional theory calculations (DFT) at B3LYP 6–311++G(d,p) level has been used to predict the molecular geometry and were in good agreement with the experimental data. Moreover, the theoretical calculations were carried out to appraise the electronic structure, vibrational spectra, natural bond orbital analysis, molecular electrostatic potential, frontier molecular orbitals and global reactivity descriptors. Raman spectra with fluorescence effect was examined with visible and near IR excitation wavelengths. Hirshfeld surface and energy framework analysis revealed the important intermolecular contacts and interaction energies. The antioxidant activity of this synthesized compound was predicted by in silico docking study on human peroxiredoxin 5 protein. The potential antioxidant activity was investigated by 1,1‐diphenyl‐1‐picrylhydrazyl (DPPH) free radical screening and compared with standard drug ascorbic acid.

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The Novel 4-Phenyl-2-Phenoxyacetamide Thiazoles modulates the tumor hypoxia leading to the crackdown of neoangiogenesis and evoking the cell death

Cited by 31 publications

References 29 publications

Synthesis, structural characterization, and DFT studies of anti-cancer drug N-(2-Aminophenyl)-2-(4-bromophenoxy)acetamide

Synthesis, structural characterization, and DFT studies of anti-cancer drug N-(2-Aminophenyl)-2-(4-bromophenoxy)acetamide

The critical role of novel benzophenone analogs on tumor growth inhibition targeting angiogenesis and apoptosis

Molecular Structure, DFT, Vibrational Spectra with Fluorescence Effect, Hirshfeld Surface, Docking Simulation and Antioxidant Activity of Thiazole Derivative

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