4 research outputs found
Synthesis, Characterization and Molecular Docking of New Naphthalene-Based Chalcone and Pyrazoline Compounds
No full textMost chemotherapeutic drugs are unable to distinguish between healthy and cancerous cells, resulting in the risk of side effects and drug resistance. There is a continuous effort to find new agents to help bring this disease under control. Compounds with bioactive natural product scaffolds have been of great interest due to their low toxicity and high efficacy. In this study, new naphthalene-based chalcone 1 and pyrazoline 1A compounds were synthesized via a Claisen-Schmidt condensation and cyclo-condensation reaction, respectively. These compounds were characterized using the Fourier Transform Infrared (FT-IR),1 H, and13 C Nuclear Magnetic Resonance (NMR) spectroscopy. The molecular docking activities were performed to study the interactions between these new compounds with breast cancer protein, 3ERT as estrogen receptor-α (ERα). Chalcone 1 and pyrazoline 1A compounds obey Lipinski's rule whereby pyrazoline 1A showed the lowest binding energy of-9.47 kcal/mol, inhibition constant of 113.93 µM and log P of 2.30. Interaction of pyrazoline 1A with 3ERT protein exhibited the hydrogen bonding with GLY521 amino acid, while the hydrophobic interactions were observed with LEU346, LEU384, LEU391, LEU525, LEU387, MET343, ALA350, and MET421 amino acids. Pyrazoline 1A is expected to show promising activities as an anticancer agent. © 2022 Trans Tech Publications Ltd, Switzerland
Molecular Docking Study, Synthesis and Characterization of New Hybrid Anthracene-Thiophene Compounds with Chalcone and Pyridine Scaffolds
No full textBreast cancer is a major health problem with an increasing number of cases over the years. Few classes of anticancer agents have been developed, but they established toxic effects on normal cells. In this study, a new hybrid anthracene-thiophene chalcone 1 has been synthesized via a Claisen-Schmidt condensation of substituted anthracene aldehyde and a thiophene ketone. The cyclo-condensation reaction of chalcone 1 formed a new anthracene-thiophene pyridine 2. The synthesized compounds were structurally characterized by Fourier Transform Infrared (FT-IR) and Nuclear Magnetic Resonance (NMR) spectroscopy. The molecular docking activities using AutoDock 4.2 software were performed to study the intermolecular interactions between these compounds with breast cancer protein, 3ERT as the estrogen receptor-α. Chalcone 1 showed free binding energy of -9.81 kcal/mol, while pyridine 2 exhibited better free binding energy of -10.45 kcal/mol against 3ERT protein. The interactions in pyridine 2 include one hydrogen bonding with MET343 amino acid and several hydrophobic interactions such as π-σ interaction with LEU384, π-anion interaction with ASP351, π-alkyl interactions with ALA350, LEU346, LEU391, LEU525, and MET388 and also a π-sulfur interaction with MET343. Chalcone 1 has only noncovalent interactions such as π-σ interaction with THR347 and π-alkyl interactions with ALA350, LEU346, LEU349, LEU387, LEU391, LEU525, and MET388. The molecular docking study of these compounds indicated that chalcone 1 and pyridine 2 showed a promising anticancer effect
Synthesis, characterization, cytotoxicity evaluation and molecular docking study of new bis-chalcone, fused-pyrimidine and fused-pyrazoline derivatives
No full text251-264Chemotherapeutic drug resistance and high-risk side effects are common limitations in cancer treatment. Thus, the
continuous development of new drugs that target only the cancer cell without affecting the normal cells is needed. The simple
structure of the chalcone and the ease of its synthesis showed promising functions. Such compounds have been reported to
exhibit diverse pharmacological activities, particularly anticancer. This study involves the design of chalcones 1 and 2 which
have been synthesized via Claisen-Schmidt condensation. Further cyclo-condensation reactions of these chalcone compounds
has formed five pyrazoline and three pyrimidine derivatives. All the desired derivatives are characterised by FT-IR, 1H-NMR,
and 13C-NMR. These derivatives are tested for cytotoxicity against breast cancer cell lines (MCF-7 and MD-MB-231) and
normal breast cell lines (MCF-10A). The results emphasized that pyrazoline compounds 1Aii and 1Aiii are showing the
minimum inhibition against MCF-7 with the IC50 values of56.73±3.3 μM and 37.74±1.32 μM, respectively, after 24 h of
exposure, which are comparable to Tamoxifen, as reference anticancer drug (IC50 = 42.66±2.19 μM)
Synthesis, characterization, cytotoxicity evaluation and molecular docking study of new bis-chalcone, fused-pyrimidine and fused-pyrazoline derivatives
Get PDFChemotherapeutic drug resistance and high-risk side effects are common limitations in cancer treatment. Thus, the continuous development of new drugs that target only the cancer cell without affecting the normal cells is needed. The simple structure of the chalcone and the ease of its synthesis showed promising functions. Such compounds have been reported to exhibit diverse pharmacological activities, particularly anticancer. This study involves the design of chalcones 1 and 2 which have been synthesized via Claisen-Schmidt condensation. Further cyclo-condensation reactions of these chalcone compounds has formed five pyrazoline and three pyrimidine derivatives. All the desired derivatives are characterised by FT-IR, 1H-NMR, and 13C-NMR. These derivatives are tested for cytotoxicity against breast cancer cell lines (MCF-7 and MD-MB-231) and normal breast cell lines (MCF-10A). The results emphasized that pyrazoline compounds 1Aii and 1Aiii are showing the minimum inhibition against MCF-7 with the IC50 values of56.73±3.3 µM and 37.74±1.32 µM, respectively, after 24 h of exposure, which are comparable to Tamoxifen, as reference anticancer drug (IC50 = 42.66±2.19 µM)
