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From the well-known 1,3,5-triaza-phosphaadamantane (PTA, ), the novel N-allyl and N-benzyl tetrafuoroborate salts 1-allyl-1-azonia-3,5-diaza-7-phosphaadamantane (APTA(BF), ) and 1-benzyl-1-azonia-3,5-diaza-7-phosphaadamantane (BzPTA(BF), ) were obtained. These phosphines were then allowed to react with (Pt(μ-Cl)(CF)(tht)) (tht = tetrahydrothiophene) affording the water soluble Pt(II) complexes (PtCl(CF)(PTA)) () and its bis-cationic congeners (PtCl(CF)(APTA))(BF) () and (PtCl(CF)(BzPTA))(BF) (). The compounds were fully characterized by multinuclear NMR, ESI-MS, elemental analysis and (for ) also by single crystal X-ray diffraction, which proved the configuration of the phosphine ligands. Furthermore, in order to evaluate the cytotoxic activities of all complexes the normal human dermal fibroblast (NHDF) cell culture were used. The antineoplastic activity of the investigated compounds was checked against the human lung carcinoma (A549), epithelioid cervix carcinoma (HeLa) and breast adenocarcinoma (MCF-7) cell cultures. Interactions between the complexes and human serum albumin (HSA) using fluorescence spectroscopy and circular dichroism spectroscopy (CD) were also investigated.
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http://dx.doi.org/10.3390/ma12233907 | DOI Listing |
Molecules
February 2025
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi 274-8510, Chiba, Japan.
A spherical amide with symmetry was synthesized by a one-step cyclization reaction using triphenylphosphine and hexachloroethane as coupling reagents. This method enabled synthesis of -benzyl and -allyl derivatives, which could not be obtained by the previously reported method. The optical resolution of each compound was measured, and their electronic circular dichroism spectra revealed that they were mirror images.
View Article and Find Full Text PDFACS Chem Neurosci
January 2024
Designer Drug Research Unit, National Institute on Drug Abuse, Intramural Research Program, Baltimore, Maryland 21224, United States.
Primary metabolites of mushroom tryptamines, psilocybin and baeocystin (i.e., psilocin and norpsilocin), exhibit potent agonist activity at the serotonin 2A receptor (5-HT) but differ in their 5-HT-mediated effects .
View Article and Find Full Text PDFFront Microbiol
January 2023
Department of Immunobiology, University of Arizona College of Medicine - Tucson, Tucson, AZ, United States.
Despite the availability of several vaccines against multiple disease-causing strains of , the rise of antimicrobial resistance and pneumococcal disease caused by strains not covered by the vaccine creates a need for developing novel antimicrobial strategies. (DMDC) was found to be a potent copper-dependent antimicrobial against several pathogens, including . Here, DMDCs efficacy against pathogens , , and was tested using bactericidal and inductively coupled plasma - optical emission spectrometry.
View Article and Find Full Text PDFMaterials (Basel)
November 2019
Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383 Wrocław, Poland.
From the well-known 1,3,5-triaza-phosphaadamantane (PTA, ), the novel N-allyl and N-benzyl tetrafuoroborate salts 1-allyl-1-azonia-3,5-diaza-7-phosphaadamantane (APTA(BF), ) and 1-benzyl-1-azonia-3,5-diaza-7-phosphaadamantane (BzPTA(BF), ) were obtained. These phosphines were then allowed to react with (Pt(μ-Cl)(CF)(tht)) (tht = tetrahydrothiophene) affording the water soluble Pt(II) complexes (PtCl(CF)(PTA)) () and its bis-cationic congeners (PtCl(CF)(APTA))(BF) () and (PtCl(CF)(BzPTA))(BF) (). The compounds were fully characterized by multinuclear NMR, ESI-MS, elemental analysis and (for ) also by single crystal X-ray diffraction, which proved the configuration of the phosphine ligands.
View Article and Find Full Text PDFJ Org Chem
July 2017
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, U.K.
The asymmetric syntheses of all eight tetraponerine alkaloids (T1-T8) were achieved using the diastereoselective conjugate additions of lithium amide reagents in the key stereodefining steps. Conjugate addition of either lithium (R)-N-allyl-N-(α-methylbenzyl)amide or lithium (R)-N-(but-3-en-1-yl)-N-(α-methylbenzyl)amide to tert-butyl sorbate was followed by ring-closing metathesis of the resultant N-alkenyl β-amino esters, reduction to the corresponding aldehydes, and reaction with tert-butyl (triphenylphosphoranylidene)acetate. Subsequent conjugate addition of the requisite antipode of lithium N-benzyl-N-(α-methylbenzyl)amide to the resultant α,β-unsaturated esters gave a range of diamines for elaboration to T1-T8 via a sequence involving reduction of the ester moiety to give the corresponding aldehyde, olefination, tandem hydrogenation/hydrogenolysis, and cyclization upon reaction with 4-bromobutanal to give the tricyclic skeleton.
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