We summarize the challenges to design and synthesize self-assembled molecules, discussing their synthetic routes and structural features in relationship to the efficiency of perovskite-based solar cells where they are applied as selective contacts.
Chemical and pharmacological information on cantharidin‐based small molecules was analyzed. The review summarizes new facts about blister beetles' metabolites for the period 2006–2012. General synthetic approaches to cantharidin‐based small molecules as well as their chemical transformations and biological activities related to cantharidin, norcantharidin, cantharidimide, and norcantharimide analogs, especially their inhibitory activity of phosphoprotein phosphatases in cancer treatment, were discussed in this mini review, which could help to design new small molecule modulators for other biological models.
30 August 2013 in Organic & Biomolecular Chemistry
A highly regio- and stereoselective method has been developed and expanded for the synthesis of a 20-membered library of spirooxindole 1′-nitro pyrrolizidines via 1,3-dipolar cycloaddition of azomethine ylides, generated in situ by a decarboxylative route from a common set of diverse isatins and L-proline derivatives, with substituted β-nitrostyrenes under aqueous medium. Among various reaction conditions, water proved to be necessary for the interaction of the reagents as well as heating the reaction at 90 °C for one hour, during which time the desired products were obtained in good yields and with excellent regio- and stereoselectivities. We subsequently applied in silico drug discovery computational methods to (i) identify the ADME properties, based on Lipinski's rule, (ii) screen the toxicological profile, and (iii) predict the penetration through the blood brain barrier (BBB) of the synthesized compounds. Next, the LC50 values of all these spirocyclic oxindoles were determined in zebrafish embryos cultured individually in buffer solutions of each compound and, finally, the phenotypes induced by these molecules in the zebrafish embryos at concentrations below their LC50 were analyzed at 48, 72 and 96 hours post fertilization.
Functionalized quinolines are an important group of heterocyclic molecules with diverse, different, and interesting biological and pharmacological activities. Traditionally, several methods have been developed for the construction of this N-heterocyclic ring, but nowadays the functionalization of the quinoline scaffold has gained great interest and it is highly demand for the synthesis of quinoline derivatives. In this context, quinoline N-oxides have attracted considerable attention as a starting material for different transformations in organic chemistry, such as oxidations, deoxygenations, nucleophilic reactions, cycloadditions, aminations, etc. However, with the current need to extend the quinoline framework through the formation of new C–C bonds, in this review we will survey the recent developments in the direct alkenylation of quinoline N-oxides via the C(sp2)–H bond activation process, discussing metal-free and transition-metal catalysed protocols, and the regioselectivity during the synthesis of promising antiparasitic drugs.
7 August 2019 in Journal of Agricultural and Food Chemistry
The synthesis of 6H-benzo[c]chromenes from unactivated 2-bromo aryl benzyl ethers was studied through two approaches: (i) the transition-metal-free intramolecular dehydrohalide coupling via intramolecular homolytic aromatic substitution; and (ii) the intramolecular cyclization via direct C–H arylation catalysed by PdCl2(MeCN)2. Having developed the most efficient method, a 17-membered chromene library was prepared in good yields and in shorter reaction times starting from commercially available phenol derivatives and phenol-rich essential oils (Eugenia caryophyllys and Plectranthus amboinicus) as raw materials, proving how sustainable and eco-friendly our protocol is. Additionally, the ruggedness of the optimized reaction conditions was evaluated with N-benzylanilines, giving the respective phenanthridone as an unexpected product, while the metal-free oxidation of the obtained 6H-benzo[c]chromenes was also performed to furnish the benzocoumarins.