Design and Synthesis of Some New <i>N</i>-(Thiazol-2-yl) Benzamides of Quinoxaline as DNA Topoisomerase II Targeting Anticancer Agents and ADMET

Bonakolluru, Yellaiah; Nukala, Satheesh Kumar; Dasari, Gouthami; Badithapuram, Vinitha; Manchal, Ravinder; Banala, Srinivas

doi:10.1080/10406638.2022.2117208

Cited by 7 publications

(4 citation statements)

References 48 publications

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“…Synthesis of 3‐(4‐methylpiperazin‐1‐yl) quinoxalin‐2(1 H )‐one (Nandikolla et al., 2022) and 3‐(4‐methylpiperazin‐1‐yl)‐1‐(prop‐2‐yn‐1‐yl) quinoxalin‐2(1 H )‐one was achieved from the previous reported methods (Bonakolluru et al., 2023; Vinitha et al., 2022).…”

Section: Methodsmentioning

confidence: 99%

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Design, synthesis, in silico molecular docking, and ADMET studies of quinoxaline‐isoxazole‐piperazine conjugates as EGFR‐targeting agents

Ali,

Thirukovela,

Kumar

et al. 2024

Chem Biol Drug Des

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In this paper, we report the synthesis of quinoxaline‐isoxazole‐piperazine conjugates. The anticancer activity was evaluated against three human cancer cell lines, including MCF‐7 (breast), HepG‐2 (liver), and HCT‐116 (colorectal). The outcomes of the tested compounds 5d, 5e, and 5f have shown more potent activity when compared to the standard drug erlotinib. In a cell survivability test (MCF‐10A), three potent compounds (5d, 5e, and 5f) were evaluated against the normal breast cell line, although neither of them displayed any significant cytotoxicity with IC50 values greater than 84 μM. Furthermore, the compounds 5d, 5e, and 5f were tested for tyrosine kinase EGFR inhibitory action using erlotinib as the reference drug and compound 5e was shown to be more potent in inhibiting the tyrosine kinase EGFR than sorafenib. In addition to this, molecular docking studies of compounds 5d, 5e, and 5f demonstrated that these compounds had more EGFR‐binding interactions. The potent compounds 5d, 5e, and 5f were subjected to in silico pharmacokinetic assessment by SWISS, ADME, and pkCSM. While the compounds 5d, 5e, and 5f followed Lipinski, Veber, Egan, and Muegge rules without any deviation.

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Section: Methodsmentioning

confidence: 99%

“…quinoxalin-2(1H)one was achieved from the previous reported methods (Bonakolluru et al, 2023;Vinitha et al, 2022).…”

Section: Chemistrymentioning

confidence: 99%

Design, synthesis, in silico molecular docking, and ADMET studies of quinoxaline‐isoxazole‐piperazine conjugates as EGFR‐targeting agents

Ali,

Thirukovela,

Kumar

et al. 2024

Chem Biol Drug Des

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“…Hence, in continuation of our work on developing some new biologically significant heterocycles [26a–n] and by keeping in mind the above mentioned medicinal applications of CA‐4, thiazolidine‐2,4‐dione and 1,2,3‐triazole we have designed the compounds (Figure 1) consisting of the three pharmacophores by taking the advantages of the pharmacophore hybridization approach [27,28] …”

Section: Introductionmentioning

confidence: 99%

Ring‐B Modification of Combretastatin A‐4 to Generate Thiazolidine‐2,4‐dione‐1,2,3‐triazole Hybrids as Tubulin Polymerization Inhibitors

Vanaparthy,

Bokkala,

Thirukovela

et al. 2023

ChemistrySelect

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In this work we have described the synthesis of thiazolidine‐2,4‐dione‐1,2,3‐triazole hybrids (7 a–n) via ring‐B modification of Combretastatin A‐4 involving reactions namely Knoevenagel condensation, O‐propargylation and finally copper (I) catalyzed azide‐alkyne cycloaddition (CuAAC). They were tested for the in vitro anticancer activity against A549, MCF‐7 and HeLa cell lines using MTT assay where some compounds were exhibited more potency than the Nocodazole. In vitro tubulin polymerization inhibition assay for the same compounds revealed that they were more potent in inhibiting tubulin with IC50 values ranging from 0.22 μM to 0.64 μM compared reference drug Combretastatin A‐4. Molecular docking studies of active compounds with α,β‐tubulin revealed that they compounds have more binding energies than that of combretastatin A‐4. Finally, in silico pharmacokinetic profile was achieved for the same compounds using SWISS/ADME and pkCSM, where some of them have followed Lipinski rule and Veber rule.

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“…They are increasingly acknowledged as a distinctive category of chemotherapeutic agents exhibiting notable efficacy against various types of tumors. 33 Quinoxaline-based compounds have shown signicant anticancer efficacy by selectively inhibiting many cellular targets, 34 including topoisomerase, 35 VEGFR2, 36 telomerase, 37 farnesyltransferase, 38 tyrosine kinase, 39 and protein kinase CK-11 (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Novel 2-substituted-quinoxaline analogs with potential antiproliferative activity against breast cancer: insights into cell cycle arrest, topoisomerase II, and EGFR activity

Salem,

Abu El-ata,

Elsayed

et al. 2023

RSC Adv.

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Design and Synthesis of Some New N-(Thiazol-2-yl) Benzamides of Quinoxaline as DNA Topoisomerase II Targeting Anticancer Agents and ADMET

Cited by 7 publications

References 48 publications

Design, synthesis, in silico molecular docking, and ADMET studies of quinoxaline‐isoxazole‐piperazine conjugates as EGFR‐targeting agents

Design, synthesis, in silico molecular docking, and ADMET studies of quinoxaline‐isoxazole‐piperazine conjugates as EGFR‐targeting agents

Ring‐B Modification of Combretastatin A‐4 to Generate Thiazolidine‐2,4‐dione‐1,2,3‐triazole Hybrids as Tubulin Polymerization Inhibitors

Novel 2-substituted-quinoxaline analogs with potential antiproliferative activity against breast cancer: insights into cell cycle arrest, topoisomerase II, and EGFR activity

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