Benzoic Acid Derivatives Research Articles

Sulfonamidyl derivatives of sigmacidin: Protein-protein interaction inhibitors targeting bacterial RNA polymerase and sigma factor interaction exhibiting antimicrobial activity against antibiotic-resistant bacteria

RNA polymerase is an essential enzyme involved in bacterial transcription, playing a crucial role in RNA synthesis. However, it requires the association with sigma factors to initiate this process. In our previous work, we utilized a structure-based drug discovery approach to create benzoyl and benzyl benzoic acid compounds. These compounds were designed based on the amino acid residues within the key binding site of sigma factors, which are crucial for their interaction with RNA polymerase. By inhibiting bacterial transcription, these compounds exhibited notable antimicrobial activity, and we coined them as sigmacidins to highlight their resemblance to sigma factors and the benzoic acid structure. In this study, we further modified the compound scaffolds and developed a series of sulfonamidyl benzoic acid derivatives. These derivatives displayed potent antimicrobial activity, with minimum inhibitory concentrations (MICs) as low as 1 µg/mL, demonstrating their efficacy against bacteria. Furthermore, these compounds demonstrated low cytotoxicity, indicating their potential as safe antimicrobial agents. To ascertain their mechanism of action in interfering with bacterial transcription, we conducted biochemical and cellular assays. Overall, this study showcases the effectiveness of sulfonamidyl benzoic acid derivatives as antimicrobial agents by targeting protein–protein interactions involving RNA polymerase and sigma factors. Their strong antimicrobial activity and low cytotoxicity implicate their potential in combating antibiotic-resistant bacteria.

Analgesic Activity of 5-Acetamido-2-Hydroxy Benzoic Acid Derivatives and an In-Vivo and In-Silico Analysis of Their Target Interactions.

The design, synthesis, and evaluation of novel non-steroidal anti-inflammatory drugs (NSAIDs) with better activity and lower side effects are big challenges today. In this work, two 5-acetamido-2-hydroxy benzoic acid derivatives were proposed, increasing the alkyl position (methyl) in an acetamide moiety, and synthesized, and their structural elucidation was performed using 1H NMR and 13C NMR. The changes in methyl in larger groups such as phenyl and benzyl aim to increase their selectivity over cyclooxygenase 2 (COX-2). These 5-acetamido-2-hydroxy benzoic acid derivatives were prepared using classic methods of acylation reactions with anhydride or acyl chloride. Pharmacokinetics and toxicological properties were predicted using computational tools, and their binding affinity (kcal/mol) with COX-2 receptors (Mus musculus and Homo sapiens) was analyzed using docking studies (PDB ID 4PH9, 5KIR, 1PXX and 5F1A). An in-silico study showed that 5-acetamido-2-hydroxy benzoic acid derivates have a better bioavailability and binding affinity with the COX-2 receptor, and in-vivo anti-nociceptive activity was investigated by means of a writhing test induced by acetic acid and a hot plate. PS3, at doses of 20 and 50 mg/kg, reduced painful activity by 74% and 75%, respectively, when compared to the control group (20 mg/kg). Regarding the anti-nociceptive activity, the benzyl showed reductions in painful activity when compared to acetaminophen and 5-acetamido-2-hydroxy benzoic acid. However, the proposed derivatives are potentially more active than 5-acetamido-2-hydroxy benzoic acid and they support the design of novel and safer derivative candidates. Consequently, more studies need to be conducted to evaluate the different pharmacological actions, the toxicity of possible metabolites that can be generated, and their potential use in inflammation and pain therapy.

Investigation of Structure-Activity Relationships for Benzoyl and Cinnamoyl Piperazine/Piperidine Amides as Tyrosinase Inhibitors.

Melanin is a substance that plays important roles in several organisms. Its function as an antioxidant and metal-complexing agent makes tyrosinase, the key enzyme that controls melanogenesis, an interesting target for designing inhibitors. In this article, we report a set of piperazine/piperidine amides of benzoic and cinnamic acid derivatives as tyrosinase inhibitors with improved potency and drug-likeness. The most potent compound 5b showed a pIC50 of 4.99 in the monophenolase assay, and only compound 3a showed reasonable potency in the diphenolase assay (pIC50, 4.18). These activities are not correlated to antiradical activity, suggesting that the activity is dependent on competition with the substrates. Molecular docking studies indicated that the benzyl substituent of 5b and other analogues perform important interactions in the enzyme that may explain the higher potency of these compounds. Moreover, the compounds present adequate lipophilicity and skin permeability and no relevant cytotoxicity (CC50 > 200 μM) to mammalian cells.

Spectroscopic investigations and electronic transitions, topology studies, and biological assay of a potent antimicrobial compound: 2-amino-pyrimidine benzoic acid

The derivatives of benzoic acid, a claimed anti-fungal agent, are physiologically active components of vitamin B-complex. Signals in a heavily deshielded area is found using nuclear magnetic resonance analysis. In optimized geometry, the result reveals that nitrogen and oxygen are responsible for transfer of charge within the ring system wherein increases the bond length. Broadening and red shifting, which result from vibrational assignments, show the strength of intermolecular hydrogen bonds. Topological analysis like atoms in molecules, reduced density gradient graph that demonstrates favorable findings The electron localized function and localized orbital locator analysis are helpful when a site displays a strong distribution of electrons as a result of having the presence of a covalent bond, a lone pair of electrons, or a nuclear shell there. Findings of in vitro tests for antimicrobial activity clearly show that all two strains’ activity and inhibition both rise as compound concentrations climb. The title chemical may be verified to block antimicrobial activity and be a pesticide using molecular docking, in vitro antimicrobial activity, and qualities of a drug’s resemblance.

Short chiral pitch and blue phase stability in cholesteric liquid crystal mixtures by adding achiral benzoic acid derivative

ABSTRACT Cholesteric liquid crystal (CLC) is anticipated to have applications such as blue light and ultraviolet (UV) light blocking for human skin owing to its selective wavelength reflection against incident sunlight through several hundred nanometres of a periodic helical twist structure. In this study, we investigated short chiral pitch control and enlargement of the blue phase (BP) temperature range by adding an achiral constituent of 4-n-octylbenzoic acid (8 BA) into CLC mixtures composed of three kinds of cholesteryl compounds: cholesteryl chloride, cholesteryl pelargonate and cholesteryl palmitate. Hydrogen bonding dependence of chiral pitch and BP temperature range were also investigated for achiral dopant (8 BA) and CLC mixture through temperature-dependent Fourier-transform infrared analysis. It was found that 40 wt% of 8 BA within the CLC mixture selectively reflected UV and blue light over 360–400 nm with a decrease of chiral pitch. It was also found that the BP temperature range increased by 15.6°C owing to hydrogen bond dimers composed of 8 BA molecules in the CLC mixture.

Silica-Based Stationary Phase with Surface Bound N-Acetyl-glucosamine for Hydrophilic Interaction Liquid Chromatography.

A hydrophilic silica-based stationary phase with surface bound N-acetylglucosamine (GlcNAc-silica) was prepared in house and characterized physically via Fourier transform infrared (FTIR) analysis and thermogravimetric analysis (TGA) and chromatographically over a wide range of mobile phase compositions. While both FTIR and TGA confirmed the attachment of the GlcNAc ligands to the silica surface, the chromatographic evaluation of GlcNAc-silica with polar and slightly polar standard solutes (e.g., sugars, nucleic acid fragments, phenolic, and benzoic acid derivatives) yielded the typical hydrophilic interaction liquid chromatography (HILIC) behaviors in the sense that retention increased with increases in solute polarity and the organic content (i.e., acetonitrile) of the hydro-organic mobile phase (i.e., ACN-rich mobile phase). Sugars derivatized with 1-naphthylamine (1-NA) and 2-aminoanthrcene (2-AA) such as xylose, glucose, and short chains maltooligosaccharides constituted the most polar species for HILIC retention evaluation, and in addition, the maltooligosaccharides offered a polar homologous series for gauging the hydrophilicity of GlcNAc-silica in analogy with alkylbenzene homologous series and other nonpolar homologues for evaluating the hydrophobicity of non-polar stationary phases. On the other hand, the benzoic acid and phenolic acid derivatives were the probe solutes for evaluating the HILIC retention dependence of ionizable solutes on the pH of the mobile phase. Similarly, the nucleobase and nucleoside weak basic solutes as well as some typical cyclic nucleotide acidic solutes allowed for the examination of the dependence of solute retention on the pH of the mobile as well as the polarity of the species.

PusALDH1 gene confers high levels of volatile aroma accumulation in both pear and tomato fruits

Aroma is an important commercial trait that determines fruit quality and has an important influence on the overall flavor of fruits. Plant ALDH genes have been implicated in diverse pathways and play crucial roles in physiological activities. In this study, via genome resequencing we identified one gene PusALDH1 (Pbr034873.1) related to aroma biosynthesis that can respond to the induction of methyl jasmonate. Transient transformation of pear fruits and heterologous stable transformation of tomato further confirmed the function of PusALDH1 in aroma accumulation. The content of ALDH precursor substance, benzaldehyde, was reduced in the overexpressing pear and tomato fruits, and the content of ALDH product, benzoic acid and benzoic acid derivatives, was increased in the pear fruits. Meanwhile, transgenic tomato fruits with PusALDH1 overexpression exhibited a greater area of yellow placenta, indicating that the gene may be related to the growth and development of the fruit. Taken together, PusALDH1 could act as a strong candidate gene in aroma synthesis.

Development and Antibacterial Properties of 4-[4-(Anilinomethyl)-3-phenylpyrazol-1-yl]benzoic Acid Derivatives as Fatty Acid Biosynthesis Inhibitors.

A number of novel pyrazole derivatives have been synthesized, and several of these compounds are potent antibacterial agents with minimum inhibitory concentrations as low as 0.5 μg/mL. Human cell lines were tolerant to these lead compounds, and they showed negligible hemolytic effects at high concentrations. These bactericidal compounds are very effective against bacterial growth in both planktonic and biofilm contexts. Various techniques were applied to show the inhibition of biofilm growth and eradication of preformed biofilms by lead compounds. Potent compounds are more effective against persisters than positive controls. In vivo studies revealed that lead compounds are effective in rescuing C. elegans from bacterial infections. Several methods were applied to determine the mode of action including membrane permeability assay and SEM micrograph studies. Furthermore, CRISPRi studies led to the determination of these compounds as fatty acid biosynthesis (FAB) inhibitors.

Evaluation of the Chemical Profile and Antioxidant Capacity of Green, Brown, and Dark Propolis.

The chemical composition of propolis varies between different types, due to the specific vegetation found near the hives and the climatic and soil conditions worldwide. Green propolis is exclusive to Brazil, produced by bees, with the resin of the plant Baccharis dracunculifolia. Brown propolis is a specific variety produced mainly in Northeast Brazil from the plant Hyptis divaricata, also known as "maria miraculosa". Dark propolis is a variety of propolis produced by bees from the resin of the plant known as Jurema Preta (Mimosa hostilis benth). In this study, the aqueous extracts of green, brown, and dark propolis were analyzed for their antioxidant capacity using ABTS, FRAP, and DPPH, and their chemical profiles were determined using paper spray mass spectrometry. Among the three extracts, green propolis had the highest content of total phenolic compounds (2741.71 ± 49.53 mg GAE. 100 g-1), followed by brown propolis (1191.55 ± 36.79 mg GAE. 100 g-1), and dark propolis had the lowest content (901.79 ± 27.80 mg GAE. 100 g-1). The three types of propolis showed high antioxidant capacity, with green showing the highest antioxidant capacity for the three methods used. Using paper spray mass spectrometry, it was possible to suggest the presence of 116 substances, including flavonoids (56), phenylpropanoids (30), terpenes (25), carboxylic acids (1), benzoic acid derivatives (1), fatty acids (1), amino acids (1) and alkaloids (1). The compounds in the green, brown, and dark propolis extracts reinforce the bioactive potential for application in these tree extracts' food and pharmaceutical products.

EFFECT OF MECHANOCHEMICAL PROCESSING PARAMETERS ON ETHOXYLATION OF BENZOIC ACID DERIVATIVES

The regularities of ethoxylation of benzoic acid derivatives during interaction with polyethylene glycol through mechanochemical solid-phase synthesis in a vibrating apparatus have been studied. The conditions for carrying out mechanochemical reactions to increase the conversion degree of initial reagents into reaction products are analysed. The products of ethoxylation are characterized by IR spectroscopy, acid-base potentiometric titration, tensiometry, and dilatational rheology. It has been established that the degree of starting reagents conversion into ethoxylation products depends on the nature of the substituent and its position in the benzene ring. The degree of conversion into reaction products is higher for ortho-substituted derivatives of benzoic acid. It is shown that the salts of ethoxylated derivatives of benzoic acid exhibit pronounced surfactant properties at the air - solution interface.

Enzymatic degradation and metabolic pathway of phenanthrene by manglicolous filamentous fungus Trichoderma sp. CNSC-2

Manglicolous filamentous fungi release extracellular lignolytic enzymes that can readily degrade polycyclic aromatic hydrocarbons (PAHs). The present study emphasizes the role of the extracellular enzyme in phenanthrene degradation by the manglicolous fungus Trichoderma sp. CNSC-2 isolated from the Indian Sundarban mangrove ecosystem. The removal efficiency reached 64.05 ± 0.75 % in 50 mg l−1 phenanthrene-amended mineral salt medium at pH 5.6 after 10 days of incubation. Phenanthrene removal was optimized at different pH, nutrient sources, and Cu2+ concentrations. The degradation significantly increased to 67.75 ± 4.32 % at pH 6 (P < 0.0001). The addition of Cu2+ (30 mg l−1) increased the degradation to 78.15 ± 0.36 % (P < 0.0001). The validation experiment confirmed the increase in phenanthrene degradation up to 79.9 ± 1.67 % under optimized conditions. The Lac1 and CytP450 genes encoding for extracellular and intracellular enzymes, respectively, were identified. The GC-MS derived phenanthrene degradation metabolites, i.e., phthalic acid, isobutyl 2-pentyl ester derivative, 1, 2 benzene dicarboxylic acid, butyl 2-methyl propyl ester derivative, TMS derivative of benzoic acid and 3,5 dihydroxy benzoic acid determined two possible metabolic pathways. The laccase enzyme activity was higher in the presence of Phe+Cu2+ (P < 0.0001), indicating the enzyme induction potential of PAH and Cu2+ ions. Purified laccase had a molecular weight of 45 kDa and was highly stable at pH 4–6 and temperature 20–50 °C. The enzyme retained 47 %, 87 %, and 63 % of enzyme activity at 30 mg l−1 concentration of Pb2+, Cd2+, and Hg2+. However, laccase activity was induced by 1.37 folds in the presence of 30 mg l−1 Cu2+ concentration. Thus, the study suggests the potential role of Trichoderma sp. CNSC-2 in phenanthrene degradation.

Phytochemical Properties of Silk Floss Tree Stem Bark Extract and Its Potential as an Eco-Friendly Biocontrol Agent against Potato Phytopathogenic Microorganisms

In the current study, the ethanolic extract of the stem bark of Ceiba speciosa, the silk floss tree (SFSB), was evaluated against various phytopathogenic microorganisms, including Ralstonia solanacearum, Dickeya solani, Pectobacterium atrosepticum, P. carotovorum, Fusarium oxysporum, and Rhizoctonia solani. At 300 µg/mL concentration, the SFSB extract exhibited the highest inhibition percentages of 83.33 and 86.67 for R. solani and F. oxysporum, respectively. In addition to its antimicrobial activity, SFSB extract exhibited strong antioxidant activity (IC50 value of 140.88 g/mL). HPLC analysis of the extract revealed the presence of various phenolic acids and flavonoids. Among these compounds, naringenin (18,698.83 µg/g), chlorogenic acid (2727.49 µg/g), ferulic acid (1276.18 µg/g), syringic acid (946.26 µg/g), gallic acid (812.34 µg/g), and methyl gallate (651.73 µg/g) were found to be the most abundant constituents. GCMS analysis showed that there were antimicrobial compounds like terpenoids, benzoic acid derivatives, phthalate esters, and different fatty acids. Isopropyl myristate was the most common compound, with a relative abundance of 55.61%. To our knowledge, this is the first investigation on the phytochemical composition and antimicrobial properties of SFSB extract. Consequently, utilizing SFSB extract could hold significant potential as a sustainable and natural approach for controlling and mitigating plant diseases.

Synthesis, crystal growth and supramolecular chemistry of 4-dimethylaminopyridinium salts of benzoates and a phenolate ion

Abstract Seven novel molecular salts were synthesized from the commonly available 4-dimethylaminopyridine organic base and benzoic acid derivatives contain additional functional groups. Benzoic acids with additional hydroxyl, nitro, amino, and bromo functional groups, were successfully employed and investigated their role in non-covalent interactions within the supramolecular chemistry of heterosynthons solid-state architecture. The collection of all 4-dimethylamopyrinium salts of benzoates and phenolate was accomplished through the utilization of conventional solvent evaporation technique. The resulting molecular salts were afforded by deprotonation of the acidic moiety such as COOH, or OH to the ring N of 4-dimethylaminopyridine, establishing a strong charged-assisted hydrogen bond between the deprotonated group (benzoate or phenolate) and protonated ring N. The structure of compounds was fully elucidated by single X-ray diffraction, powder X-ray diffraction, 1H NMR, FT-IR, and thermogravimetric analysis. The crystal packing is interpreted by the strong charge-assisted N–H⋯O hydrogen bond between the NH+ and the corresponding deprotonated group and O–H⋯O, N–H⋯N hydrogen bonding. The analysis concluded that C–H⋯O, CH3⋯O, C–H⋯π, CH3⋯π, π–π, C–H⋯Br, and CH3⋯Br contacts contribute significantly to stabilizing and expanding the high-dimensionality (2D–3D framework) of the structures. The structures were thoroughly explored for their various bonding and nonbonding interactions, as well as their supramolecular chemistry in detail. The antimicrobial activities of all compounds were evaluated using the Oxford cup method.

Antarctic Soil Metabolomics: A Pilot Study.

In Antarctica, ice-free areas can be found along the coast, on mountain peaks, and in the McMurdo Dry Valleys, where microorganisms well-adapted to harsh conditions can survive and reproduce. Metabolic analyses can shed light on the survival mechanisms of Antarctic soil communities from both coastal sites, under different plant coverage stages, and inner sites where slow-growing or dormant microorganisms, low water availability, salt accumulation, and a limited number of primary producers make metabolomic profiling difficult. Here, we report, for the first time, an efficient protocol for the extraction and the metabolic profiling of Antarctic soils based on the combination of NMR spectroscopy and mass spectrometry (MS). This approach was set up on samples harvested along different localities of Victoria Land, in continental Antarctica, devoid of or covered by differently developed biological crusts. NMR allowed for the identification of thirty metabolites (mainly sugars, amino acids, and organic acids) and the quantification of just over twenty of them. UPLC-MS analysis identified more than twenty other metabolites, in particular flavonoids, medium- and long-chain fatty acids, benzoic acid derivatives, anthracenes, and quinones. Our results highlighted the complementarity of the two analytical techniques. Moreover, we demonstrated that their combined use represents the "gold standard" for the qualitative and quantitative analysis of little-explored samples, such as those collected from Antarctic soils.

Identification of a herbicide-resistant biotype of Echinochloa crus-galli in Ukraine

Ukraine is one of the world’s guarantors of food security and has the potential to further increase agricultural production. However, the vast majority of herbicides used on crops are acetolactate synthase (ALS) inhibitors, which poses a threat of herbicide-resistant weed species. The emergence and spread of herbicide-resistant weed biotypes can significantly increase the cost of growing crops to the point of loss of profitability. Herbicide resistance in barnyardgrass (Echinochloa crus-galli var. crus-galli) has been studied in long-term field and greenhouse experiments. Resistance of E. crus-galli to the ALS herbicide triazolopyrimidine derivative ‒ penoxsulam was identified. Expressed resistance was observed in weed plants grown from seeds collected under production conditions in Kherson region in 2015–2016 and 2020–2021. Cross resistance was observed for imidazolinone and sulfonylurea derivatives. It should be noted that the level of cross resistance to ALS herbicides was slightly higher for plants derived from weed seeds harvested in 2020–2021 compared to those harvested in 2015–2016. The introduction of a herbicidal composition of a herbicide mixture ‒ an inhibitor of 4-hydroxyphenylpyruvate dioxygenase (HPPD) (an enzyme in plants in the chain of carotenoid synthesis) ‒ mesotrione with an ALS-inhibitor (nicosulfuron) allowed effective control of the weed, which indicates the absence of multiple resistance to herbicides ‒ inhibitors of carotenoid synthesis. The high efficiency of E. crus-galli control was established by the application of herbicides ‒ inhibitors of fatty acid synthesis (graminicides). The highest level of efficiency in the experiments was observed with the application of fluazifop-butyl and somewhat less ‒ with pinoxaden. A tendency to reduce phytotoxicity to barnyardgrass from the south of Ukraine was observed with the introduction of tepraloxydim and quizalofop-ethyl. A lower level of phytotoxicity of fenoxaprop-p-ethyl on E. crus-galli should be noted compared to the effect of pinoxaden. No multiple resistance was observed with glyphosate (5-enolpyruvylshikimate-3-phosphate synthase inhibitor) and reglone (photosystem I inhibitor), allowing control of vegetative weeds at the beginning and end of the growing season. It has been established that monocot weed species have significantly increased their presence and harmfulness in agrophytocenoses in Ukraine and in the world since the 1950s with the widespread introduction of selective dicotyledonous species control with aryloxyphenoxyacetic, propionic and benzoic acid derivatives. This trend has been maintained until recently ‒ barnyardgrass is one of the dominant weed species in modern agrophytocenoses of Ukraine. Therefore, the identification of the ALS-resistant biotype of barnyardgrass complicates weed control in the following crops in rotations in the southern regions of the country: in maize crops with cross resistance to nicosulfuron, in sunflower ‒ to imidazolinones (imazamox, imazapyr), and also makes it impossible to use penoxsulam in rice production. Traditionally, the use of synthetic auxins, phenoxyacetic acid derivatives, etc. is used to control ALS-resistance. However, in Kherson region of Ukraine, already in the third year of application of rinskor (florpyrauxifen-benzyl), some weed plants were found on rice fields affected by ALS-resistant barnyardgrass, which recovered after the use of synthetic auxin. Therefore, the control of ALS-resistance (penoxsulam, etc.) in E. crus-galli with the application florpyrauxifen-benzyl in the Kherson region of Ukraine is already limited. An obvious and economically feasible preventive measure against the emergence of resistant weed biotypes is the implementation of GAP (Good Agricultural Practice, FAO) approaches: in particular, the use of high quality seeds without weed impurities, increasing the proportion of agrotechnical weed control measures, restoring and expanding crop rotations with mandatory rotation of herbicides with different modes of action, introducing dicotyledonous/leguminous crops into rotations, and using herbicides with different modes of action in crops separately or in mixtures. At the same time, agrotechnical measures and the preservation of biodiversity in agrophytocenoses should be the main factor in controlling resistance in weeds. The use of herbicides and their mixtures with different modes of action is of secondary importance. The identification of highly damaging ALS-resistant E. crus-galli in southern Ukraine indicates the insufficient effectiveness of weed control exclusively with herbicides with a single mechanism of action and requires a significant revision of the principles of crop rotation and ways of weed control in the country to maintain high levels of profitability and productivity of agrophytocenoses. Solving this problem is urgent for the preservation of Ukraine's potential as one of the guarantors of global food security.

Benzoic acid derivatives as potent antibiofilm agents against Klebsiella pneumoniae biofilm

Klebsiella pneumoniae is responsible for a significant proportion of human urinary tract infections, and its biofilm is a major virulence. One potential approach to controlling biofilm-associated infections is targeting the adhesin MrkD1P to disrupt biofilm formation. We employed Schrodinger's Maestro tool with the OPLS 2005 force field to dock compounds with the target protein. Two benzoic acid derivatives, 3-hydroxy benzoic acid and 2,5-dihydroxybenzoic acid, had strong binding free energies (-55.57 and-18.68kcal/mol) and were the most potent compounds. The in-vitro experiments were conducted to validate the in-silico results. The results showed that both compounds effectively inhibited biofilm formation at low concentrations (4 and 8mg/mL, respectively) and had antibiofilm activity, restricting cell attachment. Both compounds demonstrated a strong biofilm inhibitory effect, with 97% and 89% reduction in biofilm by 3-hydroxy benzoic acid and 2,5-dihydroxybenzoic acid, respectively. These findings suggest that natural compounds can be a potential source of new drugs to combat biofilm-associated infections. The study highlights the potential of targeting adhesin MrkD1P as an effective approach to controlling biofilm-associated infections caused by K.pneumoniae. The results may have implications for the development of new therapies for biofilm-associated infections and pave the way for future research in this area.

Dehydrative Coupling of 1,1-Diarylalkenes and Cyclohexa-2,5-diene-1-carbaldehyde Derivatives Induced by a B(C6F5)3-Initiated [1,2]-Alkyl Migration.

A four-step formal ipso allylation of benzoic acid derivatives involving a B(C6F5)3-initiated and proton-catalyzed [1,2]-alkyl shift as part of a dehydrative coupling of cyclohexa-2,5-diene-1-carbaldehyde derivatives and 1,1-diarylalkenes is reported. By this, a series of allyl arenes can be regioselectively obtained from readily available benzoic acids in good yields.

Physical properties of hydrogen bonded nematic liquid crystals and electro-optical properties in terahertz waves [Invited

4-m-alkyl cyclohexane carboxylic acids and 4-n-alkylbenzoic acids were mixed to form hydrogen bonded liquid crystals (HBLCs), which exhibited a nematic phase at room temperature. Dielectric constants and three elastic constants of HBLC mixtures were investigated. Benzoic acid derivatives with some polar groups were added to the HBLC and the dielectric anisotropy was successfully enhanced. Considering the absorption loss of HBLCs in the terahertz wave region, the electro-optical properties of the homogeneous and twisted nematic cells were numerically evaluated using measured physical properties, and the transmitted polarization state was compared with that of conventional nematic LCs.

Evolution of the Polyphenolic Content of Moravian White Grape Variety Wines of Different Vintages During Storage

Wine is known as a source of bioactive compounds and is one of the alcoholic beverages with the highest phenolic content. There has been growing interest in the composition of wine due to its beneficial properties for human health. This work focuses on biologically active and sensory attributes of white wine and presents research on wine chemical profiles in relation to their geographical origin, varieties and storage. The aim of this study was to investigate the phenolic compound evolution of 35 selected white wine varieties from the Moravian region in the Czech Republic. To separate and identify individual phenolic compounds in the wines, the high-performance liquid chromatographic method was used. A spectrophotometric method was applied for the determination of total polyphenol and total flavonoid content. This research presents results for the total benzoic and cinnamic acid derivatives, flavonols, flavanols and stilbene content of Moravian white grape varieties. Differences were found in the content of these compounds, and the results show that the phenolic concentrations depend on grape variety and storage time.

Synthesis, Characterization, 'ADMET-SAR' Prediction, DPPH Assay, and Anti-Mycobacterium Study of 4-[(substituted benzyl) amino]benzo hydrazides and its Hydrazones as the Acyl-CoA Carboxylase, AccD5 Inhibitors.

Hydrazide-hydrazone derivatives have shown diverse biological activities, such as antitubercular (anti-TB), antibacterial, antifungal, anticancer, anti-inflammatory, antiviral, and antiprotozoal actions. Hydrazide-hydrazones contain azomethine (-NH-N=CH-) group connected with carbonyl group and are believed to be responsible for various pharmaceutical applications. They aid in the synthesis of different five-membered heterocyclic systems, such as oxadiazole, triazoles, etc. Methods: In the present study, various hydrazines/hydrazones were synthesized starting from 4- amino benzoic acid derivatives. Structures of all 9 newly synthesized compounds (6a-6d and 8a- 8e) were further characterized by using various spectroscopic methods, such as 1H-NMR (Nuclear Magnetic Resonance), FT-IR (Fourier-transform infrared spectroscopy), Gas chromatographymass spectrometry (GC-MS), etc. Furthermore, molecular docking analysis against the acyl-CoA carboxylase, AccD5 (PDB ID: 2A7S), was also carried out using the Glide module, which depicted good binding scores than standard drugs. The anti-tuberculosis activity of all the hydrazides and hydrazones (6a-6d and 8a-8e) were evaluated against the Mycobacterium tuberculosis H37 RV strain using the Alamar-Blue susceptibility (MABA) test. The activity was expressed as the minimum inhibitory concentration (MIC) in μg/mL values. The antioxidant activity was also carried out using a DPPH assay. Our findings demonstrated highly encouraging in-vitro results (MABA assay, MIC: 1.2 μg/mL) of hydrazones as depicted by good antimycobacterial activity. The antioxidant results showed a moderate to a good percentage of DPPH inhibition. Our in-silico ADMET analysis further suggested good pharmacokinetic and toxicity-free profiles of synthesized analogues (6a-6d and 8a-8e). Our results signify hydrazones/hydrazines as potential hit candidates against the future developments of potent and safer anti-TB agents.