Design, synthesis and biological evaluation of 3,5-diaryl isoxazole derivatives as potential anticancer agents

Aktaş, Derya; Akinalp, Gökçen; Şanli, Fatma; Yucel, Mehmet Ali; Gambacorta, Nicola; Nicolotti, Orazio; Karataş, Ömer Faruk; Algül, Öztekin; Burmaoğlu, Serdar

doi:10.1016/j.bmcl.2020.127427

Cited by 16 publications

(10 citation statements)

References 21 publications

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“…Moreover, 4,5,6,7-tetrahydro-isoxazole-[4,5-c]-pyridine derivatives showed significant antiproliferative and pro-apoptotic effects inducing both the early and late apoptosis of leukemic cell line K562 [17]. On the other hand, compounds containing 3,5-diarylisoxazole as the core of the structure showed antitumor activity against PC3 neoplastic cells of prostate cancer [18]. In addition, isoxazole-based chalcones and their dihydropyrazole derivatives bearing 2-fluoro-3,4-dimethoxyphenyl and 3,4-dimethoxyphenyl substituents showed excellent antitumor activity against the prostate cancer cell line (DU-145) [19].…”

Section: Discussionmentioning

confidence: 99%

Preclinical Study of Immunological Isoxazole Derivatives as a Potential Support for Melanoma Chemotherapy

Jęśkowiak

Wiatrak

Szeląg

et al. 2021

IJMS

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(1) Background: Melanoma is an aggressive neoplasm derived from melanocyte precursors with a high metastatic potential. Responses to chemotherapy and immunotherapy for melanoma remain weak, underlining the urgent need to develop new therapeutic strategies for the treatment of melanoma. (2) Methods: The viability of NHDF and A375 cell cultures after the administration of the tested isoxazole derivatives was assessed after 24-h and 48-h incubation periods with the test compounds in the MTT test. ROS and NO scavenging analyses, a glycoprotein-P activity analysis, a migration assay, a test of apoptosis, and a multiple-criteria decision analysis were also performed. (3) Results: All compounds that were tested resulted in a slower migration of melanoma neoplastic cells. The mechanism of the antitumor activity of the tested compounds was confirmed—i.e., the pro-apoptotic activity of the compounds in A375 cell cultures. Compound O7K qualified for further research. (4) Conclusions: All the tested compounds inhibited the formation of melanoma metastases and demonstrated the ability to reduce the risk of developing drug resistance in the tumor. The MCDA results showed that O7K showed the strongest antitumor activity.

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Section: Discussionmentioning

confidence: 99%

Preclinical Study of Immunological Isoxazole Derivatives as a Potential Support for Melanoma Chemotherapy

Jęśkowiak

Wiatrak

Szeląg

et al. 2021

IJMS

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“…Remarkably, compounds 116a displayed the lowest IC 50 value with the value of 3.40 ± 0.52 and 2.66 ± 0.22 for PNT1a and PC3, respectively. 40 …”

Section: Metal-free Synthesis Of Isoxazoles Via Mi...mentioning

confidence: 99%

“…Remarkably, compounds 116a displayed the lowest IC 50 value with the value of 3.40 AE 0.52 and 2.66 AE 0.22 for PNT1a and PC3, respectively. 40 Later, Chitneni and his group accomplished the synthetic methodology as well as the antibacterial activity of unique cinnoline-isoxazole hybrid scaffolds. Initially, anthranilic acid derivatives 117 were reacted with methyl lithium in anhydrous THF solvent for 3 h at À78 C to produce the corresponding oamino acetophenones 118.…”

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confidence: 99%

An overview of metal-free synthetic routes to isoxazoles: the privileged scaffold

Das

Chanda

2021

RSC Adv.

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“…Microbial diseases are becoming global threat because of the effective decrease in the potential activity of anti-microbial therapies and also bacteria's like Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumonia, Acinetobacter baumannii, Pseudomonas aeruginosa, Enterobacter theses families of organism becomes serious threat to the society because of change in the pathology of these organisms [3,4].…”

Section: Introductionmentioning

confidence: 99%

Design, Binding Affinity Studies and in Silico Admet Predictions of Novel Isoxazoles as Potential Anti-Bacterial

SAI

JAYS

Madriwala

2022

Int J Curr Pharm Sci

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Objective: The objective of the study is to design novel isoxazole derivatives, predicting their interactions with the selected target proteins and determining the ADMET properties of potent molecules using recent computational methods. Methods: With the intent to discover potent novel antibacterial, we have designed a set of compounds containing the isoxazole nucleus by using software tools like Discovery studios, PyRx, PyMOL, SWISSPDB. ADMET studies were carried out by using SWISS ADMET and pkCSM. Molecular docking studies were carried out on the target proteins of both gram-positive and gram negative bacteria in order to assesses binding affinity for the proteins. Results: Designed scaffold was designed by Benzene Derivatives Tethered with 5(4-chloro-3-nitro phenyl-1-yl) isoxazole. All the derivatives were docked against the three proteins, namely DNA Ligase (PDB ID: 3PN1), Topoisomerase (PDB ID: 3TTZ), Sterol demethylase (PDB ID: 5FSA), The compound JJC3F has shown best binding score against DNA ligase, sterol demethylase protein. Further, compound JJC3A has shown a better binding affinity towards topoisomerase than the standard drugs. Conclusion: Molecular Docking study indicates that isoxazole derivatives may be effective inhibitors for the different microbial proteins. Additionally, in silico ADMET studies predicts drug-like features. Hence, these compounds may be considered as leads and further investigation of their analogues may help in development of novel drugs for the treatment of microbial diseases.

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Design, synthesis and biological evaluation of 3,5-diaryl isoxazole derivatives as potential anticancer agents

Cited by 16 publications

References 21 publications

Preclinical Study of Immunological Isoxazole Derivatives as a Potential Support for Melanoma Chemotherapy

Preclinical Study of Immunological Isoxazole Derivatives as a Potential Support for Melanoma Chemotherapy

An overview of metal-free synthetic routes to isoxazoles: the privileged scaffold

Design, Binding Affinity Studies and in Silico Admet Predictions of Novel Isoxazoles as Potential Anti-Bacterial

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