Using an in silico method, seven analogs bearing hydrophobic substituents (8a: Me, 8b: Et, 8c: n-Pent, 8d: n-Hept, 8e: n-Tridec, 8f: isoBu and 8g: neoPent) at the 3'-O-position in salacinol (1), a highly potent natural α-glucosidase inhibitor from Ayurvedic traditional medicine 'Salacia', were designed and synthesized. In order to verify the computational SAR assessments, their α-glucosidase inhibitory activities were evaluated in vitro. All analogs (8a-8g) exhibited an equal or considerably higher level of inhibitory activity against rat small intestinal α-glucosidases compared with the original sulfonate (1), and were as potent as or higher in potency than the clinically used anti-diabetics, voglibose, acarbose or miglitol. Their activities against human maltase exhibited good relationships to the results obtained with enzymes of rat origin. Among the designed compounds, the one with a 3'-O-neopentyl moiety (8g) was most potent, with an approximately ten fold increase in activity against human maltase compared to 1.
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http://dx.doi.org/10.1016/j.bmc.2016.06.013 | DOI Listing |
J Chromatogr B Analyt Technol Biomed Life Sci
January 2025
University of Belgrade-Institute of Chemistry, Technology and Metallurgy, Department of Chemistry, Njegoševa 12, 11000 Belgrade, Republic of Serbia. Electronic address:
The lipophilicity of thirteen tacrine/piperidine-4-carboxamide derivatives was assessed using reversed-phase thin-layer chromatography (RP-TLC) with MeOH and acetonitrile (ACN) as organic modifiers. Among the parameters evaluated, the R and C values obtained using MeOH were identified as the most reliable for characterizing the lipophilicity of the investigated compounds. The observed differences in lipophilicity among the derivatives resulted from a delicate interplay of substituent effects (hydrophobicity, polarity, steric hindrance, and electronic effects), positional influence, and characteristics of the organic modifier.
View Article and Find Full Text PDFJ Pestic Sci
November 2024
Graduate School of Agriculture, Ehime University.
The enantiospecific anti-phytopathogenic fungal activity of a new type of coumarin bearing a phenylpropanoid unit at the 3-position was found. ()-3-[1-Methoxy-3-(4-methoxyphenyl)prop-2-yl]coumarin (()-: EC=16.5 µM) was 30 times more effective than the ()-form against the Japanese pear pathotype.
View Article and Find Full Text PDFRSC Adv
January 2025
Institute of Chemistry, Vietnam Academy of Science and Technology Hanoi Vietnam
In this paper, a series of novel quinazoline-4(3)-one-2-carbothioamide derivatives (8a-p) were designed and synthesized the Wilgerodt-Kindler reaction between 2-methylquinazoline-4-one 10 and amines using S/DMSO as the oxidizing system. Their characteristics were confirmed by IR, NMR, HRMS spectra, and their melting point. These novel derivatives (8a-p) were evaluated for their anti-inflammatory activity by inhibiting NO production in lipopolysaccharide (LPS)-activated RAW 264.
View Article and Find Full Text PDFNanotechnology
January 2025
Institute of Nano Science and Technology, Knowledge City, Sector 81, Mohali, 140306, INDIA.
This study investigates simple acetylenes substituted with phenylurea as a constant H-bonding unit (Alk-R) and varied hydrophobic units (R = H, Phenyl (Ph), Phenylacetylene (PA), Ph-NMe2) to understand self-assembly properties driven by synergistic non-covalent interactions. Our observations reveal hierarchical self-assembled fibrillar networks with luminescent needles, fibers, and flowers on nano- to micro-meter scales. Subtle changes in substituents led to significant differences: H, Ph, PA, and Ph-NMe2 produced needle-like crystals, dendritic nanofibers, microflakes, and no self-assembly, respectively.
View Article and Find Full Text PDFRSC Med Chem
January 2025
Department of Chemistry, The State University of New York at Buffalo Natural Sciences Complex Buffalo NY 14260 USA
Small molecules targeting activating mutations within the epidermal growth factor receptor (EGFR) are efficacious anticancer agents, particularly in non-small cell lung cancer (NSCLC). Among these, lazertinib, a third-generation tyrosine kinase inhibitor (TKI), has recently gained FDA approval for use in combination with amivantamab, a dual EGFR/MET-targeting monoclonal antibody. This review delves into the discovery and development of lazertinib underscoring the improvements in medicinal chemistry properties, especially in comparison with osimertinib.
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