ABSTRACT
A new series of cationic gold(i) pyrazole complexes were prepared in excellent yields as their perchlorate salts. Results of cell viability assays show that these novel complexes have good cytotoxic properties against the human HepG2 cancer cell line. These complexes showed promising anti-cancer activities and to our knowledge, pyrazoles have never been tested against this cell line. The regioselectivity of the complexation is also discussed in regards to the substitution pattern of the pyrazoles.
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Gold/chemistry , Organogold Compounds/chemical synthesis , Organogold Compounds/pharmacology , Pyrazoles/chemistry , Antineoplastic Agents/chemistry , Cell Survival/drug effects , Chemistry Techniques, Synthetic , Drug Design , Hep G2 Cells , Humans , Organogold Compounds/chemistryABSTRACT
A rapid and easy entry into λ(3)-phospholes and λ(4)-phosphole oxides derived from BINAP is reported herein featuring a variety of C and Si substituents and functional groups, as well the investigative work on the mechanistic pathway. DFT calculations using B3LYP functionals have been carried out to rationalize the mechanism. The observed experimental (31)P resonance shifts were compared with the calculated shifts of the proposed intermediates after calibration of the shielding tensors. The calculations included the use of polarizable continuum models to take into account solvent effects and were found to be in excellent agreement, providing further evidence for the proposed mechanism.
Subject(s)
Naphthalenes/chemistry , Organophosphorus Compounds/chemical synthesis , Models, Molecular , Molecular Structure , Organophosphorus Compounds/chemistry , Oxidation-Reduction , Quantum TheoryABSTRACT
Modular gold amide chemotherapeutics: Access to modern chemotherapeutics with robust and flexible synthetic routes that are amenable to extensive customisation is a key requirement in drug synthesis and discovery. A class of chiral gold amide complexes featuring amino acid derived ligands is reported herein. They all exhibit in vitro cytotoxicity against two slow growing breast cancer cell lines with limited toxicity towards normal epithelial cells.
Subject(s)
Amides/chemistry , Antineoplastic Agents/pharmacology , Gold/chemistry , Organogold Compounds/pharmacology , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Epithelial Cells/drug effects , Humans , Molecular Structure , Nigericin/pharmacology , Organogold Compounds/chemical synthesis , Organogold Compounds/chemistry , Structure-Activity RelationshipABSTRACT
We report the synthesis and activity of new mononuclear and dinuclear gold amide complexes 1-7. The dinuclear complexes 6b and 7 were characterised by single crystal X-ray analysis. We also report solution NMR and freezing point depression experiments to rationalise their behaviour in solution and question the de-ligation process invoked in gold catalysis.
ABSTRACT
Caught in the middle: The ionomycin calcium complex (see structure; O red, Ca green) was the target of an approach featuring the efficient asymmetric synthesis of an allene by a copper(I)-mediated anti-selective S(N)2' reaction, a highly stereoselective gold(III)-catalyzed cycloisomerization of an alpha-hydroxyallene, and a Rh-catalyzed rearrangement of an alpha-diazo-beta-hydroxyketone.
Subject(s)
Calcium/chemistry , Ionomycin/chemistry , Anti-Bacterial Agents/chemistry , Catalysis , Cyclization , Gold/chemistry , StereoisomerismABSTRACT
[reaction: see text]. A novel intermolecular nitrile oxide cycloaddition sequence has been developed for the formation of highly substituted heterocyclic rings. Reaction of trimethylsilyl cyanide with epoxides generates isonitriles which can react with nitroalkenes to form N-(isoxazolylidene)alkylamines. After fragmentation to nitrile oxides, the dipoles can undergo intermolecular 1,3-dipolar cycloadditions with electron deficient dipolarophiles to generate substituted isoxazolines in one synthetic operation.
