Current Organic Chemistry - Volume 27, Issue 21, 2023

Deoxycholic and cholic acid-based receptors 6, 13, and 16 containing imidazolium groups were synthesized, and their properties as anion receptors have been evaluated. Cholaphanes 13 and 16 exhibited moderate binding selectivity and affinity for fluoride ions, while cholapod 6 showed low binding selectivity and affinity for chloride ions due to the presence of a nitro group in the imidazolium ring. The H-bonding interactions involve C-2 protons of imidazolium ring with anion. The detection of halide ions is revealed by the binding constant through the 1H NMR titration experiment.

Boesenbergia rotunda (the family Zingiberaceae) is a well-known medicinal plant from Southeast Asia and China. Its parts, especially the roots, were used as an alternative in cuisine, and flavoring. Many attempts tend to explore its phytochemistry and pharmacological values. The ultimate goal of this review is to critically offer the pharmacological values and mechanisms of action of B. rotunda crude extracts and their isolated compounds. Phytochemical investigation and pharmacokinetics were also discussed.On the basis of the most effective keyword "Boesenbergia rotunda", the relevant data have been gathered from international electronic sources, including Sci-Finder, Google Scholar, PubMed, and reputation publishers. B. rotunda species was reported to contain two main chemical classes of phenolics and terpenoids. Its constituents have great biological values and spread out to drug development, including anticancer, anti-inflammatory, antimicrobacterial, antioxidative, ani-viral, anti-insect, antidiabetic, anti-allergic, anti-obesity, hepatoprotective, neuroprotective, rhenoprotective, gastroprotective, skin protective, vasorelaxant, and aphrodisiac activities. Various pharmacological actions were successfully proven by the underlying mechanisms. (–)-Panduratin A seems to be the most active compound with an oral bioavailability of 7-9%. B. rotunda plant extracts are safe in use with LD50 > 4.0 g/kg. Pharmacokinetic studies indicated that the metabolism of B. rotunda constituents may be related to the oxidation and glucuronidation of its phenolic compounds. Further phytochemical and pharmacological studies are expected, as well as clinical applications are urgently needed.

Tribe Delphineae in the family Ranunculaceae is composed of the genera Aconitum and Delphinium and is a resource plant group with important medicinal value. Alkaloids are the main active ingredients in these two genera, with previous studies primarily focusing on diterpenoid alkaloids. Recent comprehensive studies of the chemical components have uncovered numerous non-diterpenoid alkaloids of diverse structural types, such as amides, isoquinolines, pyridines, phenethylamines, and diazines. These compounds exhibit various biological activities, including cardiotonic, antitumor, and antibacterial effects. In this paper, the structural characteristics and biological activities of 156 non-diterpenoid alkaloids reported in Aconitum and Delphinium are reviewed for the first time to provide references for the efficient utilization of plant resources of these two genera.

A topological index is a quantitative measure of molecular structure and connection. It also estimates the toxicological, structural, biological, and physicochemical characteristics of a chemical molecule. The use of nano-structured graphs in the study of chemistry is very extensive. Melem, one of the most significant tri−s−triazine compounds, is a nucleophilic reagent that may be employed in reactions with derivatives of phthalic acid. Materials with borophene nanostructures are also exploited in cross-disciplinary research. In comparison to carbon hexagonal nanotubes, boron triangular nanotubes are thought to be a superior conductor. The goal of computing the multiplicative Zagreb connection indices for Chemical graphs is to understand the complexity, connectedness, and chemical activity of molecules. Information is useful in a number of applications, including drug design, chemical synthesis, and property prediction. In this paper, we compute the first, second, third, fourth, and fifth multiplicative Zagreb connection indices (ZCIs) of the melem chain MC(s), the borophene chain B36(s), and the boron triangular sheet BTS(m,s).

The synthesis and biological properties of molecules simultaneously comprising various heterocycles, such as fused 2-quinolones and 1,2,3-triazoles, have been evaluated as a part of our ongoing research in medicinal and organic chemistry. We were successful in developing a synthetic procedure for 1,2,3-triazole substituted quinolone derivatives. Infrared, proton, and carbon nuclear magnetic resonance, mass spectroscopy and elemental analysis were used to characterise the structures of the recently synthesised triazole derivatives. From screening results, all the compounds demonstrated increased antibacterial action against both Gram-positive and Gram-negative bacteria. Moreover, 1,2,3-triazoles linked to tert-butyl benzyl (3a), trifluoromethyl benzyl (3b), 3-chlorobenzyl (3c), 4- hydroxy-3-nitrobenzyl (6b), 4-hydroxy-4-trifluoromethylbenzyl (6d), and 4-hydroxy-2,4- difluorobenzyl (6e) compounds showed promising antibacterial and antifungal activities with MICs values of 1.07-4.33 μg/mL. The prepared ligand 4-hydroxy-2,4-difluoro benzyl-1,2,3-triazole (6e) exhibited the highest docking score of -6.34 kcal/mol and showed interacting amino acid residues ArgB:¹¹²², MetB:¹¹²¹, AspB:¹⁰⁸³, TryB:¹⁰⁸⁷, AlaB:¹¹¹⁸, AlaB:¹¹²⁰, GluB:¹⁰⁸⁸, GlyB:¹¹¹⁷, SerB:¹⁰⁸⁴, and AlaB:¹¹¹⁹ within the active site of 2XCT. Final scaffolds were further evaluated for their ADMET and physicochemical properties by using ADMETlab2.0 and SwissADME web servers as good oral bioavailability drugs.

Warfarin containing a 4-hydroxycoumarin moiety possesses excellent anticoagulant activity, with the (S) enantiomer being the eutomer. The present work is designed to synthesize warfarin based derivatives enantioselectivity to explore their anticoagulant potential. The substituted chalcones were reacted with 4-hydroxycoumarin in the presence of the chiral organocatalyst 9-amino-9-deoxyepiquinine to afford warfarin-based analogues 5a- 5k. The structures of synthesized compounds 5a-5k were confirmed by Fourier transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance spectroscopy (¹H NMR), carbon-13 nuclear magnetic resonance spectroscopy (¹³C NMR) and electron ionization mass spectroscopy (EIMS) data. The enantiomeric excess (ee) has been found in the range of 16-99% as determined by chiral high-performance liquid chromatography (HPLC) analysis. The in vitro anticoagulant activity of the products 5a-5k was evaluated by plasma recalcification time (PRT) method, and it was found that most of the derivatives showed good anticoagulant activity, specifically compound 5b exhibited excellent results compared to that of warfarin. Compound 5b displayed an IC50 value of 249.88 μM, which is better than that of warfarin (IC50 408.70 μM). The molecular docking studies have been performed against vitamin K epoxide reductase with PDBID 3kp9. The synthesized compounds bind well in the active binding site of the target enzyme. The derivative 5b showed π-π stacking interactions with the amino acid phenylalanine (Phe 114). The antimicrobial activity of synthesized compounds has also been evaluated, and results showed moderate antimicrobial activity. Based on our results, it is proposed that derivative 5b may act as a lead compound to design more potent anticoagulant derivatives.

The activation and thermodynamic parameters of the Diels-Alder reaction of cyclopentadiene, anthracene and tetracene with C60 fullerene are estimated at the DFT level using PBE0, B3LYP and CAM-B3LYP functionals and the effect of accounting for dispersion interactions in various semi-empirical Grimme models on these parameters. Structural characteristics of the reagents, products, pre-reaction van der Waals complex, and transition state are obtained. Taking into account dispersion corrections have practically no effect on the geometric characteristics of structures with the covalent type of the bond, as well as on the structure of the transition state. Still, it has a noticeable effect only on the structure of the pre-reaction complex, in which the interparticle interaction has a van der Waals character. At the same time, taking into account dispersion corrections plays a significant role in assessing the thermodynamic and activation parameters of the reaction. An analysis of the performed calculations showed that the combination of PBE0/def2-TZVP with the D4 model for dispersion interactions could be recommended for the Diels-Alder reaction considered above.