Molbank — Open Access Journal

The 3,5-bis((E)-4-methoxybenzylidene)-1-(2-morpholinoethyl)piperidin-4-one (3) compound was synthesized by a two-step reaction with 92% yield. The chemical structure of compound 3 was confirmed by IR, NMR, and mass spectrometry. The title compound was screened for its anti-dengue activity against DENV2 NS2B-NS3 protease and showed 39.09% inhibitory activity at 200 µg/mL. Full article

A new onoceranoid triterpenes, namely 3-hydroxy-8,14-secogammacera-7,14-dien-21-one (1), has been isolated from the fruit peels of Lansium domesticum Corr. cv kokossan. The structure of 1 was determined on the basis of spectroscopic data including infrared, 1D and 2D-NMR, as well as high resolution mass spectroscopy analysis. Compound 1 showed a weak activity against MCF-7 breast cancer cell lines. Full article

Pyridazinone derivatives are a great template for developing cyclooxygenase-2 (COX-2) inhibitors. The 2-butyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one was prepared by reacting 6-phenyl-4,5-dihydropyridazin-3(2H)-one with n-butyl bromide in the presence of potassium carbonate. The structure of the compound was confirmed based on its FTIR, ¹H-NMR, ¹³C-NMR, and Mass data. The molecular docking studies assessed the COX-2 binding capability of the synthesized compound. The in silico physicochemical and pharmacokinetic parameters of this compound concerning selected drugs were also calculated. The COX-2/COX-1 analysis revealed the synthesized compound as a novel potent COX-2 inhibitor, in comparison to indomethacin, with a promising physicochemical and pharmacokinetic profile. Full article

As ferulic acid was reported to be involved in novel potential mechanisms associated with Alzheimer’s disease (AD) therapy, five closely related phenethyl esters and amide of this natural product were synthesized and screened for their free radicals scavenging activity. Ferulic acid and its analogue′s absorption, distribution, metabolism, and excretion (ADME) properties were predicted. All compounds obey Lipinski′s rules. Moreover, all evaluated compounds seem to present a high oral bioavailability and blood–brain barrier (BBB) permeation which is crucial for Alzheimer′s disease drug candidates. Molecular docking of analogues 4 and 8 with acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) showed interactions with the residues of the catalytic triad of AChE and BChE. In addition to their interactions with the anionic subsite, hydroferulic acid phenethyl ester 4 and homovanillic acid phenethyl ester 8 may have potential as inhibitors of AChE and BChE, respectively. Full article

The 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine heterocyclic system has been used in the construction of heteropropellanes, which attracted much attention not only on the possible modification of drugs, but also for novel materials with unusual and important physical properties. In this communication, the reaction of ethyl 2-(hydroxyimino)propanoate 1 with disulfur dichloride and o-aminophenol, which gave ethyl 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine-5a(6H)-carboxylate in moderate yield, was described. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C NMR and IR spectroscopy, mass-spectrometry and X-ray analysis. Full article

The development of the methods for amide bond formation is important for various uses in the laboratory and industrial applications. The compounds combined in their structures 1,4-dihydroisonicotinic acids and amino acids linked with an amide bond can be considered as “privileged structures” due to their broad range of biological activities. Herein, the formation of amide bond between 1,4-dihydroisonicotinic acid and l-methionine is reported. The coupling of l-methionine with pentafluorophenyl active ester of 1,4-dihydroisonicotinic acid appears to be a convenient and effective method for amide bond formation. Sodium N-(3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate has been successfully synthesized via a procedure where the key step is amide formation from 5-diethyl 4-(perfluorophenyl) 2,6-dimethyl-1,4-dihydropyridine-3,4,5-tricarboxylate and l-methionine. Sodium salt formation was performed to improve physicochemical properties, such as solubility of the l-methionine-derived 1,4-dihydroisonicotinamide. The obtained target compound was fully characterized by UV, IR, ¹H NMR, ¹³C NMR, MS, and microanalysis. Full article

γ-Glutamyl derivatives of sulfur amino acids have been prepared in multigram scale starting from readily available starting materials. The synthesis comprises two one-pot operations, both consisting of two reactions. In the first operation, N-phtaloyl-l-glutamic acid anhydride is obtained from l-glutamic acid and phtalic anhydride. In the second one, N-phtaloyl-l-glutamic acid anhydride is used to acylate amino acids and the N-phtaloyl protecting group is removed. The described approach offers a viable entry to γ-glutamyl derivatives of sulfur-containing amino acids with flavor-enhancer and nutraceutical properties. Full article

On the basis of the knowledge from traditional herbal and folk medicine, flavonoids are among the most studied chemical classes of natural compounds for their potential activity as phosphodiesterase 5 (PDE5) inhibitors. We here describe the preparation of a semi-synthetic hydrazone derivative of quercetin, 2-(3,4-dihydroxyphenyl)-4-(2-(4-nitrophenyl)hydrazono)-4H-chromene-3,5,7-triol, that was obtained via a single-step modification of the natural compound. The product was characterized by NMR, mass spectrometry and HPLC. Preliminary molecular modeling studies suggest that this compound could efficiently interact with PDE5. Full article

6-Hydroxy-2-methylbenzofuran-4-carboxylic acid was synthesized in two steps, starting from 3,5-dihydroxybenzoate. The product was obtained through a direct thermal one-pot cyclization with propargyl bromide, followed by a base-catalyzed hydrolysis. Its molecular structure was elucidated by means of mono- and bidimensional NMR techniques, ESI-MS, FT-IR and single-crystal X-ray diffraction. Full article