Synthesis Of Compounds Research Articles

Emerging Trends for the Direct Synthesis of Dithiocarbamates

Dithiocarbamates are common structural motifs in various bioactive compounds, attracting considerable attention due to their wide‐ranging applications in organic synthesis, material science, agrochemicals, and the pharmaceutical industry. Given the significant bioactivity and extensive applications of dithiocarbamates, the continuous pursuit of their efficient and diverse synthetic methods remains critical and urgent. Direct dithiocarbamation reactions can introduce ‐S‐C(S)NR2 group directly into parent molecules, providing shorter, greener, and more practical pathways for the synthesis of organodithiocarbamates. This article offers a comprehensive overview of the latest advancements in direct dithiocarbamation reactions, categorizing them based on the different sources of the ‐S‐C(S)NR2 group, with a particular emphasis on elucidating substrate scope and reaction mechanisms. Additionally, some synthetic limitations and applications of these methods are discussed. This review aims to provide the latest advancements in this field to both general readers and professional practitioners, inspiring innovative ideas for the synthesis of organosulfur compounds.

Comprehensive investigation of two substituted benzimidazoles: Design, synthesis, biological assessment, and characterization

Benzimidazole is a bicyclic molecule that is mostly used in medicinal chemistry. The 2-substituted benzimidazoles that are now on the market include omeprazole, flubendazole, mebendazole, and albendazole. Antioxidants are compounds that impede the oxidation process, which is the chemical process that produces free radicals. A computational technique called "in-silico screening" is used in drug discovery to effectively estimate a molecule's likelihood of interacting with a target of interest. Antihelminthics are a class of antiparasitic drugs that either kill or paralyze internal parasites like parasitic worms, all without endangering the host. A standard procedure was used to create the 2-substituted benzimidazole. PyRx software was used to do the in-silico screening for anthelmintic drugs. The DPPH and ABTS methods were used to measure the antioxidant activity. Melting point, TLC, and IR spectra were used to confirm the structures of the produced compounds. The binding affinity for sulphosalicylic acid in the anthelmentic in silico screening was -7.7. Salicylic acid demonstrated excellent antioxidant activity, as seen by its IC50 values of less than 5 mg/ml for the ABTS method and 37 mg/ml for the DPPH method. Overall, the combination of theoretical and practical yield data, along with melting points, ATR Spectra and Rf values, offers valuable insights into the synthesis and characterization of chemical compounds. The salicylic acid derivative exhibits good antioxidant activity by both the methods. The Sulphosalicylic acid derivative shows prominent In-silico anthelmintic activity result hence the synthesized compounds can be tested for anthelmintic activity in future.

Recent advances in fluorine chemistry using flow technology

Organofluorine compounds have proven to play an important role in pharmaceutical, agrochemical, and functional materials owing to their unique properties. However, the synthesis of these compounds is often challenging due to the difficulties in handling fluorinating agents and controlling their reactivity precisely. Recently, flow microreactor systems have attracted significant attention from chemists as a highly efficient synthetic methodology. In this review, we summarize recent advances in fluorine chemistry facilitated by continuous flow technology, highlighting its advantages and potential applications in streamlined synthesis of organofluorine compounds.

Synthesis, structure and photophysical properties of truxene and truxene-triindole compounds

Multi-branched π-conjugated organic molecules, due to their fascinating structures and unique optical properties, exhibit potential applications in optoelectronics. Herein, series of 4-N,N-diphenylaminostyryl substituted multi-branched truxene compounds (namely TN1, TN2 and TN3) and a truxene-triindole compound (namely N3T3) were synthesized. These compounds are characterized by effective π-extension and remarkably enhanced two-photon absorption (TPA) compared to their less π-conjugated analogues. For truxene compounds, the more the number of the branch, the large the TPA efficiency, and the C3-symmetric three-branched TN3 exhibit the largest TPA. The aromatic triindole unit proves to be a better two-photon fluorophore compared with truxene. The results conclude that the influence of π-conjugation, molecular planarity and intramolecular charge-transfer (ICT) to TPA is far more pronounced than to linear optical properties.

Molecular Design and DFT Analysis of High-performance Dyes Based on Pyrene with Different Donor Parts and Their Optoelectronic Applications.

The performance and efficacy of dyes, which are crucial photon-harvesting components in dye-sensitized solar cells (DSSCs), must be meticulously analysed at the molecular level. This research focuses on a theoretical investigation of dye characteristics rather than the synthesis of novel compounds. Using Density Functional Theory (DFT) and Time-Dependent DFT (TD-DFT), we have analysed six D-π-A structure dyes designed with pyrene as the π-bridge and various functional groups as donors. Our study examines their geometrical, electronic, optical, electronic localization, and electrochemical properties. The findings reveal that these theoretically designed D-π-A dyes show significant improvements in light-harvesting efficiency, open-circuit photovoltage, electron injection efficiency, and overall photovoltaic performance. The analysis indicates effective electron injection from each dye into the conduction band of TiO2, followed by efficient regeneration and enhanced intra- and intermolecular charge transfer properties. The incorporation of pyrene as a π-bridge and the use of different functional groups as donors are crucial for facilitating electron transfer from the donor to the acceptor region. Among the dyes studied, the D-π-D modified dye demonstrates superior theoretical performance, attributed to its higher energy levels of the lowest unoccupied molecular orbital and greater oscillator strengths for excited states. This results in improved intramolecular electron transfer and electron injection into the conduction band of TiO2, followed by effective regeneration. Overall, our study highlights the potential of these theoretically modeled dyes as highly promising sensitizers for DSSCs, due to their exceptional optical and electronic properties and impressive photovoltaic parameters. These findings position these molecular structures as strong candidates for future applications in organic DSSCs.

A comprehensive review on microbial diversity and anticancer compounds derived from seaweed endophytes: a pharmacokinetic and pharmacodynamic approach.

Seaweed endophytes are a rich source of microbial diversity and bioactive compounds. This review provides a comprehensive analysis of the microbial diversity associated with seaweeds and their interaction between them. These diverse bacteria and fungi have distinct metabolic pathways, which result in the synthesis of bioactive compounds with potential applications in a variety of health fields. We examine many types of seaweed-associated microorganisms, their bioactive metabolites, and their potential role in cancer treatment using a comprehensive literature review. By incorporating recent findings, we hope to highlight the importance of seaweed endophytes as a prospective source of novel anticancer drugs and promote additional studies in this area. We also investigate the pharmacokinetic and pharmacodynamic profiles of these bioactive compounds because understanding their absorption, distribution, metabolism, excretion (ADMET), and toxicity profiles is critical for developing bioactive compounds with anticancer potential into effective cancer drugs. This knowledge ensures the safety and efficacy of proposed medications prior to clinical trials. This study not only provides promise for novel and more effective treatments for cancer with fewer side effects, but it also emphasizes the necessity of sustainable harvesting procedures and ethical considerations for protecting the delicate marine ecology during bioprospecting activities.

Fe3O4@gC3N4@Thiamine: a novel heterogeneous catalyst for the synthesis of heterocyclic compounds and microextraction of tebuconazole in food samples

Graphite carbon nitride (g-C3N4) is a two-dimensional nano-sheet with electronic properties, which shows unique characteristics with high chemical and thermal stability in its structure. The functionalization of these compounds through covalent bonding is an important step towards significantly improving their properties and capabilities. To achieve this goal, a novel strategy for the covalent functionalization of Fe3O4@g-C3N4 with thiamine hydrochloride (vitamin B1) via cyanuric chloride (TCT), which is a divalent covalent linker, was presented. The efficiency of Fe3O4@gC3N4@Thiamine as a heterogeneous organic catalyst in the synthesis of spirooxindole-pyran derivatives and 2-amino-4H-pyran under solvent-free conditions was evaluated and the yields of high-purity products were presented. In addition, easy recycling and reuse for seven consecutive cycles without significant reduction in catalytic activity are other features of this catalyst. Moreover, the performance of the prepared sorbent in the microextraction technique (herein, magnetic solid phase extraction) was studied. The tebuconazole was selected as the target analyte. The target analyte was extracted and determined by HPLC–UV. Under the optimum condition, the linear range of the method (LDR) was estimated in the range of 0.2–100 μg L−1 (the coefficient of determination of 0.9962 for tebuconazole). The detection limit (LOD) of the method for tebuconazole was calculated to be 0.05 µg L−1. The limit of quantification (LOQ) of the method was also estimated to be 0.16 µg L−1. In order to check the precision of the proposed method, the intra-day and inter-day relative standard deviations (RSD%) were calculated, which were in the range of 1.5- 2.8%. The method was used for the successful extraction and determination of tebuconazole in tomato, cucumber, and carrot samples.

Sulfonated carbon–based heterogeneous acid catalysts in direct biomass redox flow fuel cell: A review

AbstractThis review focused on the potential applications of sulfonated carbon–based heterogeneous acid catalysts for the hydrolysis of lignocellulosic biomass (LCB) fuel feedstock and the development of membrane electrode assembly (MEA) for the direct biomass redox flow fuel cell (DBRFFC). LCBs are hydrolysed to yield simple sugars, which are subsequently oxidized over catalysts in the anode tank of the DBRFFC to generate electricity. Ferric chloride used as a catalyst in the DBRFFC is not efficient for glucose production from LCB, such that the power performance of the DBRFFC is affected during glucose oxidation due to low glucose yield from LCB for electron generation. Sulfonated carbon–based solid acid catalysts (SCSACs) have been established as efficient catalysts for the hydrolysis of LCB and as metal catalyst supports for the fabrication of MEA for further oxidation of glucose and its oxidation by‐products. These capabilities of SCSACs can be explored and applied to significantly improve the power output of the DBRFFC through efficient hybrid catalyst design. There is still a scarcity of literature on this subject and their combination with ferric chloride to enhance glucose yield and oxidation in DBRFFC. This gap was filled by discussing the various types of sulfonated carbon–based catalysts, highlighting their synthesis routes, and their applications in organic compound synthesis, and membrane electrode development in DBRFFC. The knowledge derived will certainly be beneficial to researchers willing to improve the performance of DBRFFC through molecular catalyst design and electrode membrane development for application in DBRFFC.

The ERF transcription factor SlERF7 promotes UV-C-induced biosynthesis of phenolic compounds in tomato

In this study, the molecular pathways of SlERF7 in regulating the synthesis and accumulation of phenolic compounds induced by postharvest UV-C in tomato fruit was deeply investigated by constructing transgenic plants. The findings revealed a pronounced induction of phenolic compounds accumulation following UV-C irradiation, coupled with heightened activities of PAL, 4CL, C4H, CHS, and CHI enzymes, alongside upregulated expression levels of SlPAL5, SlC4H, Sl4CL, SlCHS2, and SlCHI within SlERF7 overexpressed fruit. Conversely, SlERF7 knockout fruit exhibited diminished levels of phenolic compounds, enzyme activities, and gene expression after UV-C irradiation. Furthermore, subcellular localization analysis showed that SlERF7 was localized in the nucleus. Dual luciferase assay and electrophoretic mobility shift assay (EMSA) indicated that SlERF7 directly bound to the GCC-box in the SlPAL5 promoter and activated its transcriptional activity. Therefore, it was confirmed that SlERF7 might positively promote UV-C-induced phenolic biosynthesis in postharvest tomato fruit by targeting the promoter of SlPAL5.

Biocatalytic Desymmetrization for the Atroposelective Synthesis of Axially Chiral Biaryls Using an Engineered Imine Reductase.

The enzymatic atroposelective synthesis of biaryl compounds is relatively rare, despite considerable attention received by biocatalysis in academic and industrial sectors. Imine reductases (IREDs) are an important class of enzymes that have been applied in the asymmetric synthesis of chiral amine building blocks. In this work, two IREDs (IR140 and IR189) were identified to catalyze the efficient desymmetrization of biaryls utilizing various amine donors. Further protein engineering enabled the identification of variants (IR189 M8-M9 and IR189 M13-M14) that are able to catalyze the formation of both (R) and (S) atropisomers in excellent yields and atroposelectivities for up to 24 examples (up to 99% ee and yield). The absolute configuration and rotational barriers were confirmed, and the reactions were readily enlarged to allow isolation of the atropisomeric products in 99% ee and 82% isolated yields. The optically pure biaryl amines were further derivatized into various synthetically useful atropisomers. To shed light on the molecular recognition mechanisms, molecular dynamics (MD) simulations were performed, offering plausible explanations for the improved atroposelectivities and enzymatic activities. The current strategy expands the scope of IRED-catalyzed synthesis of axially chiral biaryl amines, contributing significantly to the field of atroposelective biocatalysis.

Palladium-Catalyzed [3 + 2] Cycloaddition of 4-Vinyl-4-Butyrolactones with Alkenes: Synthesis of Spirocyclopentane Compounds.

A palladium-catalyzed [3 + 2] cycloaddition of 4-vinyl-4-butyrolactones (VBLs) with alkenes has been developed to afford various spirocyclopentane products in high yields with excellent diastereoselectivities. The scale-up reaction and further derivations of the product worked well, demonstrating the potential application of the current reaction in organic synthesis.

Discovery of novel dihydro-pyrimidine hybrids: insight into the design, synthesis, biological evaluation and absorption, distribution, metabolism and excretion studies.

Aim: By keeping in aspects, the pharmacological potential of heterocyclic compounds, pyrimidine-based compounds were designed, synthesized and evaluated for α-amylase inhibitory potential.Materials & methods: Five new series 1a-l, 2a-d, 3a-d, 4a-d and 5a-d of 1,2,3,4-tetrahydroprimidine-5-carboxylate derivatives were designed by de novo method by taking Alogliptin as reference compound. Here in we describe synthesis and characterization of compounds as potential α-amylase inhibitor.Results: Structure activity relationship (SAR), in vitro analysis and molecular modelling approaches generate compounds 1h, 1i, 1k and 4c as potential lead with good α-amylase inhibitory selection. However, compound 1k failed the criteria of optimization as drug lead by ADME studies while all other compounds showed optimum range for all in silico ADME parameters.Conclusion: Therefore, these compounds can serve as potential lead candidate in developing anti-diabetic therapy.

Synthesis, Anti-TMV Activities, and Action Mechanisms of a Novel Cytidine Peptide Compound.

Cytidine has a broad range of applications in the pharmaceutical field as an intermediate of antitumor or antiviral agent. Here, a series of new cytidine peptide compounds were synthesized using cytidine and Boc group-protected amino acids and analyzed for their antiviral activities against tobacco mosaic virus (TMV). Among these compounds, the structure of an effective antiviral cytidine peptide SN11 was characterized by 1H NMR, 13C NMR, and high-resolution mass spectrometer. The compound SN11 has a molecular formula of C15H22N6O8 and is named 2-amino-N-(2- ((1- (3,4-dihydroxy-5-(hydroxymethyl) tetrahydrofuran-2-yl) -2-oxo-1,2-dihydropyrimidin-4-yl) amino) -2-oxyethyl) amino). The protection, inactivation, and curation activities of SN11 at a concentration of 500 μg/mL against TMV in Nicotiana glutinosa were 82.6%, 84.2%, and 72.8%, respectively. SN11 also effectively suppressed the systemic transportation of a recombinant TMV carrying GFP reporter gene (p35S-30B:GFP) in Nicotiana benthamiana by reducing viral accumulation to 71.3% in the upper uninoculated leaves and inhibited the systemic infection of TMV in Nicotiana tabacum plants. Furthermore, the results of RNA-seq showed that compound SN11 induced differential expression of genes involved in the biogenesis and function of ribosome, plant hormone signal transduction, plant pathogen interaction, and chromatin. These results validate the antiviral mechanisms of the cytidine peptide compound and provide a theoretical basis for their potential application in the management of plant virus diseases.

Synthesis and characterization of mixed aryl-alkyl organotin compounds

In an effort to develop new organotin compound, a series of organotin compounds containing mixed aryl-alkyl substituents have been synthesized. All prepared organotin (IV) compounds were characterized by IR, 1H, 13C, 119Sn NMR spectra, and the elemental analysis. In addition, the solid-state structures of 4–1a, 4–2a, 4–2b, 4–2c, 5–1b, 5–2a, 5–2b, and 5–1a’ were determined by the X-ray diffraction analysis. The Hirshfeld surface analysis shows that the complexes 5–1b and 5–2b have a similar contribution of different contacts to the Hirshfeld surfaces.

Integrated Analysis of the Transcriptome and Metabolome Reveals Genes Involved in the Synthesis of Terpenoids in Rhododendron fortunei Lindl.

Rhododendron, a globally popular ornamental flower, is nevertheless limited in our understanding of the mechanisms underlying its fragrance formation. Notably, terpenoids are the most prevalent volatile metabolite produced by plants. In this study, gas chromatography–mass spectrometry (GC–MS), liquid chromatography–mass spectrometry (LC–MS) and transcriptomics sequencing were conducted to analyze the synthesis mechanisms of terpenoid fragrance compounds of petals in fragrant R. fortunei Lindl. (YJ) and non-fragrant R. “Nova Zembla” (NW). The results identified that (-)-myrtenol, linalool, pinene, myrtenyl acetate, and terpineol were key floral aroma substances in YJ. Furthermore, an analysis of KEGG enrichment and differentially expressed genes (DEGs) revealed that the bud and decay stages exhibited the highest number of enriched DEGs among different aroma types, indicating these as critical stages for the synthesis of terpenoid floral compounds. In this study, a structural gene, denoted as RfFDPS, was identified as a negative regulatory gene for monoterpene accumulation and a positive regulatory gene for sesquiterpene accumulation in YJ. Utilizing subcellular localization technology, we determined that RfFDPS proteins are located in the cytoplasm. A functional analysis through transient expression and gene silencing of RfFDPS demonstrated its ability to regulate the accumulation of monoterpenes and sesquiterpenes. The overexpression of RfFDPS led to an increase in the expression of structural genes related to terpenoid synthesis, resulting in a decrease in monoterpenes and an increase in sesquiterpenes. Conversely, gene silencing had the opposite effect. In conclusion, RfFDPS plays a pivotal role in the synthesis and release of terpenoid volatile compounds in YJ petals, laying a solid theoretical foundation for the cultivation and enhancement of aromatic R. species.

Using Rigidity And Conjugation of Subunits to ModulateSupramolecular Topologies Constructed by Half-Sandwich Fragments.

The synthesis of supramolecular compounds with a high degree of controllability and the targeted modulation of their topological transitions pose significant challenges in situ. In this study, we have successfully constructed anarray ofdiscrete structures based ona series of bidentate pyridylligands (L1, L2, and L3), which were subsequently ligated with half-sandwiched (Cp*Irfragments)building blocks. Our further investigations elucidate a strategy for coordinating the relative lengths of the bidentate ligands with the building blocks, achieving specific concentrations that drive the transformation of tetranuclear metal macrocycles into Borromean rings. Notably, the distinct characteristics of the three pyridylligands markedly influence the efficiency of synthesis and the topological conversion of the supramolecular macrocycles. Detailed structural analyses reveal that π-πstacking interactions, the electron-donating capabilities of the ligands, and hydrogen-bonding interactions are pivotal in stabilizing these molecular macrocycles and in facilitating their transformationto Borromean rings. The analyses underscore the importance of the electron-rich effect induced by the sulfur atoms in the ligands and the regulation and modulation of the pyridine functional group in contributing to the structural stability and altered characteristics of the macrocycles.

Electro-photochemical Functionalization of C(sp3)-H bonds: Synthesis toward Sustainability.

Over the past several decades, there has been a surge of interest in harnessing the functionalization of C(sp3)-H bonds due to their promising applications across various domains. Yet, traditional methodologies have heavily leaned on stoichiometric quantities of costly and often environmentally harmful metal oxidants, posing sustainability challenges for C-H activation chemistry at large. In stark contrast, the emergence of electro-photocatalytic-driven C(sp3)-H bond activation presents a transformative alternative. This approach offers a viable route for forging carbon-carbon and carbon-heteroatom bonds. It stands out by directly engaging inert C(sp3)-H bonds, prevalent in organic compounds, without the necessity for prefunctionalization or harsh reaction conditions. Such methodology simplifies the synthesis of intricate organic compounds and facilitates the creation of novel chemical architectures with remarkable efficiency and precision. This review aims to shed light on the notable strides achieved in recent years in the realm of C(sp3)-H bond functionalization through organic electro-photochemistry.

Construction of Six-Membered Lactam and Lactone Structures via Ligand-Free Pd-Catalyzed C-H Activation/[5 + 1] Cyclization Carbonylation.

An approach for the ligand-free Pd-catalyzed C-H activation/[5 + 1] cyclization carbonylation by employing readily available ClCF2COONa as a carbonyl source via difluorocarbene transfer and hydrolysis has been developed. The current protocol enables us to obtain a series of carbonylation cyclization product benzopyranone and phenanthridinone derivatives in up to 91% yield with excellent functional group compatibility. This protocol has the advantages of mild reaction conditions, wide applicable substrates, and simple and safe operation and provides a new method for the synthesis of complex lactam and lactone compounds.

Efficient generation of novel phosphorus ylides via chemoselective and chemospecific reactions utilizing 2-(arylamino)-2-thioxoacetamide and methyl benzoylglycinates as precursors with activated acetylenic compounds

A chemospecific and chemoselective procedure has been developed for the efficient synthesis of novel phosphorus compounds, achieving moderate to excellent yields. This method involves the reaction of 2-(arylamino)-2-thioxoacetamide and methyl benzoylglycinate precursors with PPh3 in the presence of activated acetylenic esters. Notably, the reaction exhibits superior selectivity toward the NH2 group in 2-(arylamino)-2-thioxoacetamide, rather than the NH group. Moreover, when methyl benzoylglycinates are employed as a precursor, the reaction yields two distinct families of ylides, each with its own unique percentage yield.

Synthesis and characterization of a zinc-triazole coordination complex with potent antimicrobial and anticancer properties

The synthesis, characterization, and biological appraisement of a novel coordination compound [Zn(C4N4H5O)2(H2O)2]Cl have been comprehensively studied. The compound was synthesized using N-(1H-1,2,4-triazol-3-yl) acetamide and ZnCl2·6H2O, yielding a product characterized by FT-IR, elemental analysis, thermogravimetric analysis (TGA), and single crystal X-ray diffraction. FT-IR spectra confirmed the successful coordination of the ligand to the zinc ion, with significant shifts in characteristic absorption bands such as CO (1685 cm⁻¹), CN (1624 cm⁻¹), and NH (3394 cm⁻¹). Single crystal X-ray diffraction analyses revealed that the complex crystallized in the monoclinic system with space group P21/c and forms six-membered chelate rings. The unit cell parameters were a = 6.0595(3) Å, b = 14.2956(7) Å, c = 9.4762(4) Å, and β = 93.275(4)°. Thermal analysis showed that the complex undergoes stepwise decomposition with significant mass losses at various temperature intervals, including an overall mass loss of 71.09 % between 200 °C and 885 °C. Molecular docking studies indicated strong interactions between the [Zn(C4N4H5O)2(H2O)2]Cl complex and the 6QF6 cancer-related protein antigen A4, with low binding energy values (-9.32 to -8.44 kcal/mol) suggesting high binding affinity and potential biological activity. In vitro antimicrobial screening against several pathogenic microorganisms, viz. both gram-positive and gram-negative bacteria, demonstrated that the [Zn(C4N4H5O)2(H2O)2]Cl complex exhibited superior antibacterial activity, with inhibition zone diameters of 15.3 ± 0.47 mm for Bacillus subtilis and 24.17±0.56 mm for Agrobacterium tumefaciens, compared to N-(1H-1,2,4-triazol-3-yl) acetamide alone and some standard antibiotics. These findings highlight the [Zn(C4N4H5O)2(H2O)2]Cl complex as a promising candidate for developing new antimicrobial and anticancer agents, providing a foundation for further research and potential therapeutic applications.