One-Pot Regioselective Synthesis of 7-Bromo-2H-Benzo[b][1,4]Oxazin-3(4H)-One Linked Isoxazole Hybrids as Anti-Cancer Agents and Their Molecular Docking Studies

Karthik, B.; Swamy, T. Narasimha; Kumar, Abdhesh; Ravinder, M.; Nukala, Satheesh Kumar

doi:10.1134/s1068162021060091

Cited by 3 publications

(1 citation statement)

References 28 publications

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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

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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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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

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Synthesis of Quinoline‐Morpholine‐Coupled 1,2,3‐Triazole Hybrids as In vitro EGFR inhibitors

Mamidala

Bokkala²,

Thirukovela³

et al. 2022

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Herein we described the synthesis of some new quinolinemorpholine coupled 1,2,3-triazole hybrids (6 a-n) from 5chloroquinolin-8-ol using well known reactions like Mannich reaction, O-propargylation, and finally copper (I) catalyzed azide-alkyne cycloaddition (CuAAC). The structures of all newly synthesized hybrids were confirmed by 1 H-NMR, 13 C-NMR, and Mass spectra. All of them were screened for their in vitro cytotoxicity towards three human cancer cell lines including MCF-7, A549 and HepG2 by MTT assay where four compounds (6 c, 6 j, 6 m and 6 n) exhibited more potency than the reference erlotinib against all the three cell lines. In vitro tyrosine kinase EGFR inhibition assay for the same four compounds revealed that 6 m has triple inhibiting power with IC 50 value of 0.14 μM and 6 j has nearly double inhibiting power with IC 50 value of 0.22 μM compared to erlotinib. Molecular docking studies with EGFR have shown that all the above four compounds have more binding energies (À 9.09 kcal/mol to À 9.96 kcal/mol) than that of erlotinib (-7.69 kcal/mol). Finally, in silico pharmacokinetic profile was achieved using SWISS/ADME and pkCSM, where all the four compounds followed Lipinski rule, Veber rule, Egan rule and Muegge rule and the lipophilicity (ClogP) was found to be ranging from 2.98 to 3.69.

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Synthesis, antiproliferative evaluation and in silico studies of a novel steroidal spiro morpholinone

et al. 2023

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One-Pot Regioselective Synthesis of 7-Bromo-2H-Benzo[b][1,4]Oxazin-3(4H)-One Linked Isoxazole Hybrids as Anti-Cancer Agents and Their Molecular Docking Studies

Cited by 3 publications

References 28 publications

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

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

Synthesis of Quinoline‐Morpholine‐Coupled 1,2,3‐Triazole Hybrids as In vitro EGFR inhibitors

Synthesis, antiproliferative evaluation and in silico studies of a novel steroidal spiro morpholinone

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