Abstract
(E)-1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline was synthesized via the cyclization reaction between the monocarbonyl curcuminoid (2E,6E)-2,6-bis(3,4-dimethoxybenzylidene)acetone and ethyl hydrazinobenzoate in high yield and purity (>95% by High-performance liquid chromatography (HPLC)). The compound has been fully characterized by 1H, 13C NMR, FTIR, UV-Vis and HRMS and its activity was evaluated in terms of its potential interaction with DNA as well as its cytotoxicity against resistant and non-resistant tumor cells. Both DNA thermal denaturation and DNA viscosity measurements revealed that a significant intercalation binding takes place upon treatment of the DNA with the synthesized pyrazoline, causing an increase in melting temperature by 3.53 ± 0.11 °C and considerable DNA lengthening and viscosity increase. However, neither re-sensitisation of Doxorubicin (DO X)-resistant breast cancer and multidrug resistance (MDR) reversal nor synergistic activity with DOX by potentially increasing the DOX cell killing ability was observed.
Highlights
Nitrogen‐containing heterocycles are important core structures found in many natural products [1] and synthetic compounds exhibiting a broad range of biological activities
Thiazolone containing pyrazoline 1 has been found to be selectively active against colon cancer cell lines, especially on HT‐29 [6]
Benzimidazole pyrazoline 2 has been reported by Shaharyar et al as the most active antitumor compound among a library of selected similar derivatives [7], whereas benzenesulfonamide pyrazoline 3 was shown by Rathish et al in in vitro and in vivo studies to be a Molbank 2020, 2020, M1114; doi:10.3390/M1114
Summary
Nitrogen‐containing heterocycles are important core structures found in many natural products [1] and synthetic compounds exhibiting a broad range of biological activities. Thiazolone containing pyrazoline 1 has been found to be selectively active against colon cancer cell lines, especially on HT‐29 [6]. 3,5‐divinylpyrazole 5 (Figure 1) which is a curcumin derivative, has been reported by Kolotova et al as a potent inhibitor of P‐glycoprotein, which is associated with the induction of multidrug resistance in cancer chemotherapy [17,18]. Such molecules have caused resensitisation of the resistant cells and reversal of the multidrug resistance phenomenon [18]. The product 6 is racemic, the relative configuration is shown for clarity and simplicity purposes to describe the AMX system and the assignments
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