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This work demonstrates the optimization of an efficient, mild, and environmentally friendly synthetic approach to access a diverse library of -naphthoyl thioureas. These derivatives could be exploited as precursor scaffolds for designing valuable heterocycles with anticipated biological activities. Additionally, the utilization of a copper complex derived from the newly synthesized -naphthoyl thiourea ligand in the photodegradation of methyl orange (MO) dye was explored. The antiproliferative effect of the synthesized derivatives was examined against MCF-7, HCT116, and A549 cancer cell lines. Most of the assembled derivatives revealed a significant cytotoxic effect, in some cases, greater than doxorubicin. Of these, the copper complex demonstrated significant antitumor activities (IC < 1.3 μM) and lesser cytotoxic impact (IC > 76 μM), indicating its possibility as a pioneering candidate for future carcinogenic pharmaceutics. Relations between the structure and activity also have been addressed.
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http://dx.doi.org/10.1021/acsomega.1c06718 | DOI Listing |
BMC Chem
July 2025
Department of Physics, Hacettepe University, Beytepe-Ankara, 06800, Turkey.
Naphthyl Thiourea based derivative N-(ethylcaramothbioyl)-1-naphthamide (NA-MT) was synthesized by freshly prepared 1-naphthoyl isothiocyanate with ethyl amine to afford the products (NA-MT) high purity and characterized via spectroscopic techniques including FTIR, H-NMR, C-NMR, elemental and HRMS analysis and single crystal X-ray diffraction. In-vitro analysis showed that the compound (NA-MT) possesses potent inhibitory effect with IC = 9.875 ± 0.
View Article and Find Full Text PDFChembiochem
May 2025
Centre for Organometallic Chemistry, School of Chemistry, Bharathidasan University, Tiruchirappalli, Tamil Nadu, 620 024, India.
Herein, the synthesis, characterization, and anticancer activity of ruthenium(II) p-cymene complexes comprising naphthoyl thiourea-based ligands are described. The synthesized N^O and N^S chelating ruthenium(II) complexes (1-3) are fully characterized by elemental analysis and spectral (fourier transform-infrared, Ultraviolet-visible, nuclear magnetic resonance, mass) methods. The structure of complex 2 has been elucidated by employing single-crystal X-ray diffraction, which verifies the two bidentate N^O and N^S coordination of the thiourea ligand to two Ru(II) centers.
View Article and Find Full Text PDFMed Chem Res
April 2023
International Research Center for Food Nutrition and Safety, Jiangsu University, Zhenjiang, 212013 China.
Naphthalene ring is present in a number of FDA-approved, commercially available medications, including naphyrone, terbinafine, propranolol, naproxen, duloxetine, lasofoxetine, and bedaquiline. By reacting newly obtained 1-naphthoyl isothiocyanate with properly modified anilines, a library of ten novel naphthalene-thiourea conjugates () were produced with good to exceptional yields and high purity. The newly synthesized compounds were observed for their potential to inhibit alkaline phosphatase (ALP) and scavenge free radicals.
View Article and Find Full Text PDFACS Omega
February 2022
Chemistry Department, Faculty of Science, Fayoum University, P.O. Box 63514, Fayoum 63514, Egypt.
This work demonstrates the optimization of an efficient, mild, and environmentally friendly synthetic approach to access a diverse library of -naphthoyl thioureas. These derivatives could be exploited as precursor scaffolds for designing valuable heterocycles with anticipated biological activities. Additionally, the utilization of a copper complex derived from the newly synthesized -naphthoyl thiourea ligand in the photodegradation of methyl orange (MO) dye was explored.
View Article and Find Full Text PDFSpectrochim Acta A Mol Biomol Spectrosc
November 2015
CEQUINOR (UNLP, CONICET-CCT La Plata), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, C.C. 962, 1900 La Plata, Argentina. Electronic address:
Two novel 1-(1-naphthoyl)-3-(halo-phenyl) substituted thioureas, namely 1-(1-naphthoyl)-3-(2,4-di-fluoro-phenyl)-thiourea (1) and 1-(1-naphthoyl)-3-(3-chloro-4-fluoro-phenyl)-thiourea (2), were synthesized and fully characterized. The X-ray crystal and molecular structures have been determined resulting in a planar acylthiourea group, with the C=O and C=S adopting a pseudo-antiperiplanar conformation. An intramolecular N-H⋯O=C hydrogen bond occurs between the thioamide and carbonyl groups.
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