Refernces
10.1002/kin.20745
The study investigates the charge-transfer (CT) complex formation between the donor antipyrine, a drug used as an analgesic and anti-inflammatory, and the acceptor 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), a quinone with potential biological relevance. The research was conducted spectrophotometrically in various halocarbon and acetonitrile solvents to explore the molecular interaction, kinetics, and thermodynamics of the complex. The purpose of using these chemicals was to understand the formation of an electron donor-acceptor complex, assess the activation parameters such as activation energy, enthalpy, entropy, and free energy of activation, and determine the stoichiometry and formation constants of the resulting complexes. This information is crucial for understanding drug action, enzyme catalysis, and ion transfer in biological systems, as well as for developing analytical methods for drug detection and estimation.
10.1021/jo952083l
The research focuses on the synthesis of the C1-C21 fragment of the serine/threonine phosphatase inhibitor tautomycin, a novel secondary metabolite with significant biological activity. The purpose of this study was to develop a synthetic route to this complex natural product, which could potentially lead to the development of new therapeutic agents. The researchers successfully synthesized compound 40, which contains the C1-C21 region of tautomycin, using a series of chemical reactions that included the Matteson’s chloromethylene insertion reaction to construct stereocenters and Cr/Ni-mediated coupling to form the spirocyclic structure. Key chemicals used in the synthesis process included various organometallic reagents, protecting groups like PMB (para-methoxybenzyl), and reagents for oxidation and reduction steps such as DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) and lithium aluminum hydride. The conclusions of the research detailed the successful synthesis of the target fragment with a high degree of stereoselectivity, setting the stage for further extension to the natural product tautomycin and potential applications in the study of serine/threonine phosphatases.
10.1016/0223-5234(87)90275-3
The research focuses on the synthesis of a series of nitro-naphtho[1,2-b]furans with methoxy groups on the external homocycle. The purpose of this study is to synthesize and characterize these compounds, which are of interest due to their potential mutagenic and carcinogenic properties, similar to the previously studied methoxy-7 nitro-2 naphtho[2,1-b]furane (R 7000). The researchers used methoxy-tetralones as starting materials, converting them into ortho-hydroxylated naphthaldehydes via a series of chemical reactions involving ethyl formate, sodium methoxide, and dichlorodicyanobenzoquinone. These intermediates were then treated with bromonitromethane and potassium carbonate, followed by dehydration in acetic anhydride to yield the desired nitro-naphtho[1,2-b]furans. The study concludes that this synthetic method is efficient, with overall yields ranging from 40% to 70% for the different compounds. The synthesized compounds are obtained in sufficient quantities for further biological testing, which will be detailed in subsequent studies.
10.1002/chem.202001450
The study presents the enantioselective synthesis of polycyclic aromatic hydrocarbon (PAH)-based planar chiral bent cyclophanes using rhodium-catalyzed [2+2+2] cycloaddition. The researchers achieved this by intramolecular regio- and enantioselective cycloaddition of tethered diyne benzofulvenes, followed by stepwise oxidative transformations. The synthesized planar chiral bent cyclophanes, featuring bent p-terphenyl and 9-fluorenone cores, were converted into 9-fluorenol-based cyclophanes with excellent enantiomeric excess (ee) values of over 99%. These cyclophanes exhibited high fluorescence quantum yields, significantly higher than an acyclic reference molecule, due to reduced flexibility and suppressed radiationless deactivation. The study also found that the anisotropy factors for electronic circular dichroism (ECD) increased as the tether length became shorter, enhancing the bending effect and reducing twist. The work demonstrates the utility of rhodium-catalyzed [2+2+2] cycloaddition for constructing PAH-based planar chiral bent cyclophane structures with high enantioselectivity and unique optoelectronic properties.
10.1016/j.bmcl.2013.01.054
The study focuses on the design, synthesis, and in vitro evaluation of a series of pyrazole-based fatty acid binding protein (FABP) 3 ligands. The researchers aimed to develop subtype-selective FABP ligands, specifically targeting heart fatty acid binding protein (FABP3), which is involved in lipid homeostasis and the uptake and transport of fatty acids towards mitochondrial β-oxidation systems. The study utilized a structure-guided approach, comparing the X-ray crystallographic structures of adipocyte FABP (FABP4) with the selective inhibitor BMS309403 and FABP3 with elaidic acid. Key chemicals used in the study include chalcone derivatives, substituted phenylhydrazines HCl, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) for oxidation, BBr3 for demethylation, and various alkyl bromo alkanoates for alkylation. These chemicals were used to synthesize 1,3,5-trisubstituted pyrazole derivatives, which were then tested for their binding-inhibitory activity towards FABP3 and FABP4. The purpose of these chemicals was to create ligands that could selectively bind to FABP3, potentially leading to the discovery of new drugs for the treatment of conditions related to lipid metabolism.
T
