Mini-Reviews in Organic Chemistry - Volume 22, Issue 2, 2025

This review focuses on studying hydrogen bonds in triflamide derivatives, the supramolecular structures formed in a crystal, solution, and gas phase, and the relationship between structural, spectral and quantum chemical calculation data.

Heterocyclic compounds are the most common and diverse group of organic substances. Heterocyclic compounds are rapidly increasing in number as a result of intensive synthetic research as well as their value in other synthetic procedures. More than 90% of medications contain heterocyclic rings, and a wide range of medicinal chemistry applications make use of these substances. There are always unique characteristics of an efficient approach for creating newly discovered heterocyclic compounds and their moieties. Due to their biological effects, including those that are anti-cancer, anti-inflammatory, anti-fungal, anti-allergic, antibacterial, antiviral, and anticonvulsant, heterocyclic compounds are crucial to medicinal chemistry. Today's world population is generally suffering from various neurodegenerative diseases. Out of that, the most prevailing disease is Alzheimer's. There are many causes of Alzheimer's disease-like acetylcholinesterase enzyme, tau protein, amyloid aggregation, oxidative stress, phosphodiesterase, and others. In these cases, oxidative stress plays a very important role in the progression of this disease. To combat this oxidative stress various antioxidant-derived drugs have been used but the problem is that Alzheimer's progression cannot be targeted with a single target drug because of the other factors that are involved in its progression. So to overcome that, a drug targeting multiple targets has been synthesized by using the antioxidant in previous reports. These drugs are more potent and efficacious than single-target drugs. This review focused on various multi-target ligands to target oxidative stress.

2-(Arylidene)benzo[b]thiophen-3(2H)one 1,1-dioxides are oxidized form of thioaurones. Various methods have been reported for their synthesis, e.g., a) condensation of benzo[b]thiophen-3(2H)one 1,1-dioxides with aryl aldehydes under acidic or basic conditions, b) oxidation of thioaurones with hydrogen peroxide or sodium perborate tetrahydrate, c) from the catalytic reaction of iodonium ylides with (bis(trifluoroacetoxy)iodo) benzene in presence copper(II)acetoacetonate, d)by ring contraction of 1-thioflavones in the presence of ceric ammonium nitrate. The reports have shown addition reactions with p-thiocresol in the absence of any catalyst, conjugated addition product without hetero ring opening with Grignard reagent, forms corresponding oxime and hydrazone with hydroxyl amine and phenyl hydrazine, respectively, produces polycyclic compounds with enamines, shows contrasting behavior with NBS and gives addition products with organophosphorus compounds in both hydroxylic and non-hydroxylic solvents which depends on reaction medium. In the present mini-review, we have discussed the various synthetic strategies and reactions of 2-(arylidene)benzo[b]thiophen-3(2H)one 1,1-dioxides, along with their reported utilities.

The cinnoline nucleus is a bicyclic ring and is an isosteric precursor to quinolone or isoquinoline. Cinnoline analogs are aromatic heterocyclic compounds having diverse therapeutic activities, such as antimicrobial, analgesic, anti-inflammatory, anti-tuberculosis, antimalarial, anticonvulsant, antioxidant, anticancer, antihypertensive, anti-anxiety, and other activities. This heterocyclic nucleus is attracting a lot of attention in medicinal chemistry and is used as a structural subunit in various compounds with attractive medicinal and chemical properties. In this review, we focus on the biological activities of cinnoline analogs with various substitutions.

Asciminib, also known as ACP-196, is the FDA-approved low-molecular ABL kinase inhibitor. The ABL kinase is a non-receptor tyrosine kinase that helps in cell growth and survival and is a key player in the development of chronic myeloid leukemia (CML) and Philadelphia chromosome-positive acute lymphoblastic leukemia (Ph+ALL). The BCR-ABL fusion protein, which is formed by chromosomal translocation in CML and Ph+ ALL, results in the constitutive activation of ABL kinase, leading to uncontrolled cell growth and proliferation. To have a high binding affinity for the active site of the enzyme, structural biology and computer-aided drug design (CADD) concepts were applied to the design of asciminib so that it could specifically target the ABL kinase enzyme. The drug was synthesized and characterized in a laboratory. In its pharmacological studies, it has shown that asciminib is a potent and selective inhibitor of ABL kinase. Phase I clinical trials assessed its safety and efficacy, revealing that it is effective against tumors while causing minimal discomfort to patients. In addition to this, it was able to induce apoptosis and a cytogenetic response as well as inhibit the proliferation of CML and Ph+ALL cells in patients with CML. As this trial gave a positive response, phase II and III trials were conducted. In that sense, asciminib has shown to be highly effective, with response rates of over 90% in patients with these diseases. The safety and efficacy of asciminib were also evaluated in combination with other drugs, such as tyrosine kinase inhibitors and immunomodulatory drugs, and the results were promising. Overall, the discovery and development of asciminib showed that by using the concepts of pharmacology and CADD, a drug with a 90% positive rate response can be developed with a high tolerance level and lower side effects.

The secondary metabolites produced by fungi are an important resource for new drug development, and the biosynthesis of fungal secondary metabolites is closely related to the epigenetic status of the chromosomes in which their gene clusters are located. However, the induction of fungal silencing of gene expression is one of the challenges faced at this stage. Chemical epigenetic modification is a simple and effective method to regulate fungal metabolism by adding chemical epigenetic modifiers to the culture medium to activate silent metabolic pathways in the fungus, resulting in the production of cryptic natural products. This paper reviews the progress of research on increasing the chemical diversity of fungal secondary metabolites using chemical epigenetic modifications, with the aim of providing a reference for the in-depth study of fungal natural products.

The last decades have witnessed significant advances in the synthesis of bioactive carbohydrates. As in all fields of organic synthesis, the search for more environmentally friendly alternative synthetic methods is a current and expanding concern. Consequently, electrochemical organic synthesis has emerged as an efficient and sustainable methodology. Herein, we present recent developments in the synthesis of glycosides and other carbohydrate derivatives using electrochemical methods. Diverse natural and synthetic O-, S-, and C-glycosides were obtained using new approaches for the electrochemical activation of sugar precursors. The reported derivatives exhibited wide structural diversity on both the sugar moiety and the aglycone, revealing the great potential of the electrochemical methods.

Sea salt is a widely used ingredient in culinary practices around the world. Beyond its flavor-enhancing properties, sea salt has been recognized for its potential health benefits. This review aimed to explore the role of sea salt in food and its applications for promoting human health. We have discussed the composition and production of sea salt, its culinary uses, and its impact on various aspects of human health, including cardiovascular health, electrolyte balance, and digestion. Additionally, we have examined the potential risks associated with excessive sea salt consumption and highlight the importance of moderation in its usage. Overall, this review provides insights into the multifaceted role of sea salt, emphasizing its potential positive effects on human health when consumed in appropriate amounts. Ultimately, the review serves as a valuable resource for individuals seeking a comprehensive understanding of the role of sea salt in promoting human health.

Aurones are structural isomers of flavones and flavonols with the basic C6–C3–C6 skeleton arranged as (Z)-2-benzylidenebenzofuran-3(2H)-one, which contain an exocyclic carbon-carbon double bond bridging the benzofuranone and phenyl rings. In aurone, a chalcone-like group is closed into a 5-membered ring instead of the 6-membered ring more typical of flavonoids, which forms the core for a family of derivatives that are known collectively as aurones. As a kind of flavonoids, aurones are widely distributed in many plants which provide yellow color to some popular ornamental flowers. For a long time aurones had not got enough attention, while in recent years, finally this chemical is coming into researchers' view. As the secondary metabolite in the family of flavonoids, aurones displayed various biological activities, including antioxidant, antiparasitic, antitumor, antiviral, antibacterial, anti-inflammatory, anti-SARS-CoV-2 and neuropharmacological activities. Therefore, aurones have attracted the attention of more and more chemists and pharmaceutical chemists, who realized that it is possible to get lead compounds with better activities via structural modifications of aurones. In some research works, aurone and its derivatives have exhibited good activity, e.g., Xie discovered the heterocyclic variant of the (Z)-2-benzylidene-6-hydroxybenzofuran-3(2H)-one scaffold that possessed low nanomolar in vitro potency in cell proliferation assays using various cancer cell lines, in vivo potency in prostate cancer PC-3 xenograft and zebrafish models, and absence of appreciable toxicity, which proved that aurones are valuable compounds worthy of further study. Herein, the biological activities of aurone derivatives are reviewed, which covers the literature since 2000, in which the strategies to develop bioactive aurone derivatives and the structure-activity relationship are highlighted.

Primary photoreactions of riboflavin (Rf) are considered. The goal was to present data on the transients formed under photoexcitation of Rf: excited singlet and triplet states, triplet reactions with the formation of Rf neutral free radicals, and a radical anion. The absorption spectra of transients are presented, as are the rate constants of their decay. Special attention is devoted to Rf in water (aerobic and anaerobic reactions).