Novel 3-fluoro-4-morpholinoaniline derivatives: Synthesis and assessment of anti-cancer activity in breast cancer cells

More, Namita A.; Jadhao, Nitin L.; Meshram, Rohan J.; Tambe, Prajkta; Salve, Rajesh; Sabane, Jagjivan K.; Sawant, Sanskruti N.; Gajbhiye, Virendra; Gajbhiye, Jayant M.

doi:10.1016/j.molstruc.2021.132127

Cited by 3 publications

(2 citation statements)

References 33 publications

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“…Heterocyclic compounds have attracted the attention of many researchers, as many of them are active against bacteria 23 , fungi 24 , inflammations 25 , 26 , and cancer 27 , 28 . Thiadiazole is one of the important heterocyclic compounds containing nitrogen and sulfur.…”

Section: Introductionmentioning

confidence: 99%

New thiadiazole modified chitosan derivative to control the growth of human pathogenic microbes and cancer cell lines

Ibrahim

Fouda

Elgammal

et al. 2022

Sci Rep

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The emergence of multidrug-resistant microbes and the propagation of cancer cells are global health issues. The unique properties of chitosan and its derivatives make it an important candidate for therapeutic applications. Herein, a new thiadiazole derivative, 4-((5-(butylthio)-1,3,4-thiadiazol-2-yl) amino)-4-oxo butanoic acid (BuTD-COOH) was synthesized and used to modify the chitosan through amide linkages, forming a new thiadiazole chitosan derivative (BuTD-CH). The formation of thiadiazole and the chitosan derivative was confirmed by FT-IR, 1H/13C-NMR, GC–MS, TGA, Elemental analysis, and XPS. The BuTD-CH showed a high antimicrobial effect against human pathogens Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus, and Candida albicans with low MIC values of 25–50 μg ml−1 compared to unmodified chitosan. The in-vitro cytotoxicity of BuTD-CH was evaluated against two cancer cell lines (MCF-7 and HepG2) and one normal cell (HFB4) using the MTT method. The newly synthesized derivatives showed high efficacy against cancerous cells and targeted them at low concentrations (IC50 was 178.9 ± 9.1 and 147.8 ± 10.5 μg ml−1 for MCF-7 and HepG2, respectively) compared with normal HFB4 cells (IC50 was 335.7 ± 11.4 μg ml−1). Thus, low concentrations of newly synthesized BuTD-CH could be safely used as an antimicrobial and pharmacological agent for inhibiting the growth of human pathogenic microbes and hepatocellular and adenocarcinoma therapy.

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Section: Introductionmentioning

confidence: 99%

New thiadiazole modified chitosan derivative to control the growth of human pathogenic microbes and cancer cell lines

Ibrahim

Fouda

Elgammal

et al. 2022

Sci Rep

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“…段, 广泛存在于活性分子中(如抗疟疾、抗癌、抑菌、抗肿瘤, 已上市的杀菌剂氟吗啉等) [19][20][21][22][23][24] . 综上, 为了获得结构新颖的、活性优良的脱落酸类似物, 本文保留硝基苯胺片段, 将吗啉片段替换苯环得到新型的吗啉磺酰胺化合物(4, 图 1), 并且以吗啉-4-磺酰胺( 5 时长(图 2, 方法一) [25] ; (2) Pd(dba) 3 与相应配体共同作用, 80 ℃反应 18 h 得化合物 4a, 该反应收率较低(42%), 需使用金属催化剂, 耗时较长(图 2, 方法二) [26] .…”

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Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination

Huang,

Yang,

et al. 2024

Chinese Journal of Organic Chemistry

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In order to obtain novel abscisic acid analogues, morpholine-sulfonamide compound was designed under the principle of active substructure combination. 14 target compounds were obtained through aromatic nucleophilic substitution (SNAr) when fluoride nitrobenzene and morpholine-4-sulfonamide were used as starting materials. The approach represents simple operation and broad substrate scope. Additionally, the soybean seed germination was inhibited overwhelmingly when treated with compounds 4a～4d, 4k, 4m and 4n at 50 μmol/L. Furthermore, the inhibition activity of compounds 4a～4d, 4k, 4m and 4n was higher than 95% at 25 μmol/L. Finally, the activity of 4m and 4n was much higher than that of ABA and lead compound (PM4) at 15 μmol/L. Moreover, the molecular docking study revealed that 4m and 4n could bind abscisic acid receptor strongly than ABA and PM4. These results are benefit to discovering novel ABA analogues.

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Design, Synthesis, Anti‐Cancer, Anti‐Inflammatory and In Silico Studies of 3‐Substituted‐2‐Oxindole Derivatives

Hublikar,

Kadu,

Edake

et al. 2024

Chemistry & Biodiversity

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This study focuses on the design and multistep synthesis of diverse structural and functional 3‐substituted‐2‐oxindole derivatives aimed at being dual‐active molecules with anti‐cancer and anti‐inflammatory properties. In vitro evaluations confirmed the dual activity of these derivatives. 4a exhibited GI50 value 3.00E‐05 against MDA‐MB‐231; 4b has shown GI50 value 2E‐05 against MDA‐MB‐231; 4c has shown GI50 value 6E‐05 against VERO; and 4d has shown GI50 value 8E‐05 each against both MDA‐MB‐231 and MCF‐7. 4e has shown GI50 values 2E‐05 and 5E‐05 each against both the MCF‐7 and VERO. The analysis indicates that compounds 3c (71.19%), 3e (66.84%), and 3g (63.04%) exhibited significant anti‐inflammatory activity. Additionally, in silico binding free energy analysis and interaction studies revealed significant correlations between in vitro and computational data, identifying compounds 4d, 4e, 3b, 3i, and 3e as promising candidates. Key residues such as Glu917, Cys919, Lys920, Glu850, Lys838, and Asp1046 were found to play critical roles in ligand binding and kinase inhibition, providing valuable insights for designing potent VEGFR2 inhibitors. The quantum mechanics‐based independent gradient model analysis further highlighted the electronic interaction landscape, showing larger attractive peaks and higher electron density gradients for compounds 4d and 4e compared to Sunitinib, suggesting stronger and diverse attractive forces.

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Novel 3-fluoro-4-morpholinoaniline derivatives: Synthesis and assessment of anti-cancer activity in breast cancer cells

Cited by 3 publications

References 33 publications

New thiadiazole modified chitosan derivative to control the growth of human pathogenic microbes and cancer cell lines

New thiadiazole modified chitosan derivative to control the growth of human pathogenic microbes and cancer cell lines

Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination

Design, Synthesis, Anti‐Cancer, Anti‐Inflammatory and In Silico Studies of 3‐Substituted‐2‐Oxindole Derivatives

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