Synthesis and preliminary biological evaluations of (+)-isocampholenic acid-derived amides

The synthesis of two novel (+)-isocampholenic acid-derived amines has been realized starting from commercially available (1S)-(+)-10-camphorsulfonic acid. The novel amines as well as (+)-isocampholenic acid have been used as building blocks in the construction of a library of amides using various aliphatic, aromatic, and amino acid-derived coupling partners using BPC and CDI as activating agents. Amide derivatives have been assayed against several enzymes that hold potential for the development of new drugs to battle bacterial infections and Alzheimer’s disease. Compounds 20c and 20e showed promising selective sub-micromolar inhibition of human butyrylcholinesterase \((h\hbox {BChE})\) (\(\hbox {IC}_{50}\) values \(0.80\,\pm 0.05\) and \(0.25\,\pm 0.02\,{\upmu }\hbox {M}\), respectively).     

Molecular imprinted membrane biosensor for pesticide detection: Perspectives and challenges

Polymers are crucial component for modern sensor devices. However, comprehensive research on polymer sensor technology is still going strong. Molecular imprinted membrane (MIM) is a great design that demonstrates acceptable recognition ability when integrated with a sensing transducer. Generally, the detection technique that has been widely and sparingly used for pesticide is mass spectrometry merged with gas and/or liquid chromatography. Nevertheless, this review focuses not on these common methods but on the specific methodology of MIM biosensor for the analysis of pesticides. Finally, the transduction schemes of the MIM sensor are reviewed. The interest of this article is sketched to the trends and challenges present in this field of study.     

High-affinity pyrophosphate receptor by a synergistic effect between metal coordination and hydrogen bonding in water

We have developed the tightest binding PPi receptor reported to date by a combination of metal coordination and hydrogen bonding interaction in water.     

Entropically driven self-assembly of a strained hexanuclear indium metal-organic macrocycle and its behavior in solution

The self-assembly of a polyprotic pentadentate ligand, N-cyclopentanoylaminobenzoylhydrazide (H(4)L(4)), and an In(III) nitrate hydrate in methanol led to a strained hexanuclear indium metal-organic macrocycle (In-MOM), [In(III)(6)(H(2)L(4))(6)(NO(3))(x)(solvent)(6-x)](NO(3))(6-x) (where, the solvent is either methanol or a water molecule and x is the number of the nitrate anions ligated). The ligand in the doubly deprotonated state serves as an unsymmetric linear ditopic donor and the alternating indium ions in two different chelation modes serve as two different bent ditopic metal acceptors, which led to a D(3)-symmetric hexanuclear In-MOM. Although the hexanuclear In-MOM is enthalpically unfavorable because of the ring strain, the combination of the soft coordination characteristic of the indium ion and the slight ligand deformation from the conjugated planar conformation allows the formation of the entropically favored hexanuclear In-MOM rather than the enthalpically favored octanuclear In-MOM. While the hexanuclear In-MOM is stable in acetonitrile, it partially dissociates into its components in dimethylsulfoxide, and then slowly reaches a new equilibrium state with several different indium species yet to be identified in addition to the free ligand.     

The continuous differential ant-stigmergy algorithm for numerical optimization

Many promising optimization algorithms for solving numerical optimization problems come from population-based metaheuristics. A few of them are based on Swarm-Intelligence Algorithms, which are inspired by the collective behavior of social organisms. One of the most successful of such algorithms is the Differential Ant-Stigmergy Algorithm (DASA), which uses stigmergy, a method of communication in emergent systems where the individual parts (artificial ants) of the system communicate with one another by modifying their local environment (pheromone intensity). The main characteristic of the DASA is its underlying structure (pheromone graph) that uses discrete steps to move through a continuous search space. As a consequence of this the search-space movement is in some way limited and the algorithm’s time/space complexity is increased. In order to overcome the problem an improved algorithm called the Continuous Differential Ant-Stigmergy Algorithm (CDASA) is proposed and then benchmarked on standard benchmark functions. This benchmarking showed that the CDASA performs better than the DASA, especially at lower dimensions, that its time/space complexity is decreased, and that the algorithm code is simplified. As such, the CDASA is more suitable for parallel implementations on General-Purpose Graphic Processing Units. Compared to the Swarm-Intelligence Algorithms presented in this paper, the CDASA is the best-performing algorithm and competitive to the state-of-the-art algorithms belonging to different metaheuristic approaches.     

Determination of folates in foods by high-performance liquid chromatography with fluorescence detection after precolumn conversion to 5-methyltetrahydrofolates

A liquid chromatographic-fluorimetric determination of folates in foodstuffs including their extraction, without or with deconjugation, chemical conversion to 5-CH3-H4PteGlu(n) and purification of the extract by affinity chromatography is reported. The conversion enables the analysis of total folates and also of the contents of the different mono- and polyglutamate forms of the folates. The method has a satisfactory day-to-day repeatability (never,more than 10%) and a very low detection limit (0.02 pmol per injection). Depending on the folate studied, the recovery rates varied from 78% (10-CHO-PteGlu) to 98% (5-CHO-H4PteGlu). Furthermore it has been possible to show that the deconjugation of the folates by rat plasma conjugase was incomplete in foodstuffs whereas chicken pancreas conjugase effectively converted the different folate polyglutamates into folate diglutamates. It could not be demonstrated that prior hydrolysis with a protease and amylase was useful for the analysis of the different foodstuffs studied (yeast, spinach, beef liver, beef fillet and peas) when deconjugation was performed with the chicken pancreas conjugase.     

The synthesis of 5-substituted 3-benzoylamino-6-(2-substituted amino-1-ethenyl)-2H-pyran-2-ones and their transformations into 2H-pyrano[3,2-c]pyridine derivatives

A new approach to the 2H-pyrano[3,2-c]pyridine system is described. 5,6-Disubstituted 3-benzoylamino-2H-pyran-2-ones 3a,b , prepared from the corresponding 1,3-dicarbonyl compounds 1a,b and methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate ( 2 ), were converted into 3-benzoylamino-6-(2-dimethylamino-1-ethenyl)-5-ethoxycarbonyl-2H-pyran-2-one ( 4a ) and 5-acetyl derivative 4b . The exchange of the dimethylamino group in 4a,b with aromatic amines 5a-f,m , héteroaromatic amines 5g-i , and benzylamines 5j-l produced 5-ethoxycarbonyl-3-benzoylamino-6-(2-arylamino- or heteroarylamino-or benzylamino-1-ethenyl)-2H-pyran-2-ones 6a-l , and its 5-acetyl analog 6m . The compounds 6 were cyclized in basic media into 2H-pyrano[3,2-c]pyridine derivatives 7a-h . Analogously react also α-amino acid derivatives 8a-c and 11 as nitrogen nucleophiles producing 9a-c, 10 and 12 .     

Unusually Stable Triazine‐based Organic Superstructures

Solid‐state reactions have been rapidly gaining popularity in organic chemistry owing to their simplicity, efficiency, and selectivity compared to liquid‐phase reactions. Herein, we describe the formation of superstructures through the solid‐state reaction of an organic single‐crystal. The superstructure of 5,5′,5′′‐(1,3,5‐triazine‐2,4,6‐triyl)triisophthalonitrile (TIPN) can be formed by cyclotrimerization of 1,3,5‐tricyanobenzene (TCB) single crystals. The TIPN superstructure was confirmed by single crystal X‐ray diffraction and visualized by transmission electron microscopy. The superstructure has hexagonally packed 1‐dimensional (1D) channels along the crystal axis. Furthermore, the superstructure arises from interdigitated nitrile interactions in the crystal lattice, and thus has electron‐beam tolerance and very high thermal stability.