Current Organic Chemistry - Volume 27, Issue 17, 2023

A heterocyclic scaffold-like benzodiazepine (BZD) has shown a wide variety of medicinal values and utmost importance in pharmaceutical industries. BZDs are sevenmembered heterocyclic molecules and have many structural isomers, such as 1,2; 1,3; 1,4; 1,5; 2,4; and 2,3. Among these BZDs, 1,5-BZDs play a significant role in pharmacological activities like anti-anxiety, anti-convulsion, antimicrobial, sedative, and hypnotics. These moieties have been the subject of extensive research with the development of synthetic methods, leading to the generation of numerous useful molecules over the last few decades. Therefore, we have further explored the recent literature on the 1,5-BZDs synthesis and associated biological activities to expand the role and utility of newer 1.5-BZDs. This review article gives a recent and insightful thought about the synthetic methods and therapeutic applications of 1,5-BZDs.

This review describes recent advances that are commonly applied in the synthesis of dialkyl (aryl) α-aminophosphonates containing heterocyclic compounds. The target structures are divided into three categories, which include α-aminophosphonic acids and their diesters bearing a heterocyclic or heteroaryl system at the α-carbon, nitrogen atom, or both. The synthetic protocols based on the Kabachnik-Fields and Pudovik reactions as the main pathways for the construction of these features, besides other miscellaneous methods. This review may be a useful resource for researchers and it will help them to work in this emerging research area.

Dess-Martin periodinane (DMP) is one of the hypervalent iodines that is most frequently utilized as an oxidizing agent in organic chemistry. The authors of this septennial review have critically and methodically presented representative applications of DMP in organic synthesis from 2015 to the present, including oxidations, dehydrogenations, hetero and homo-dimerizations, aromatizations, thiocyanations, halogenations, dearylations, ring expansions, cyclizations, heterocyclic ring formation, and other miscellaneous reactions. This review discusses the range and constraints of these transformations.

The Annona muricata L. leaves have been long employed in the traditional remedy of diabetes mellitus (DM) and its comorbidities. Different analytical techniques were used to evaluate the methanol extract of this plant part. In vitro antidiabetic assays of A. muricata extract were analysed using α-glucosidase and α-amylase inhibition tests. Employing gas chromatography-mass spectrometry (GC-MS), the primary bioactive components of the methanol extract were identified. Additionally, molecular docking experiments regarding the identified compounds were performed by silicification of UCFS Chimera, Autodock Vina, and BIOVIA Discovery Studio software. The total phenolic content of the A. muricata leaf extract was 14.83 mg GAE/g and the total flavonoids 34.22 mg QE/g. The plant extract showed concentration-dependent ferric reducing antioxidant power (FRAP) when compared with the standard ascorbic acid whereas significant radical scavenging activity was exhibited through the 2,2-Diphenyl-1-picrylhydrazyl (DPPH128;¢) assay with IC50 of 0.202 μg/mL. Ten compounds were revealed by GC-MS analysis, and they exhibited a favourable quantity (area %). The extract inhibited α-amylase enzymes with a range of 36.52% - 67.30% as well as α-glucosidase enzymes with a range of 42.68 - 72.80% at different doses (15 μg/mL - 240 μg/mL) and performed well compared to the conventional drug acarbose. The high binding affinity of plant phytochemicals to α-amylase and α-glucosidase and their acceptable pharmacokinetic characteristics further suggested a prospective therapeutic relevance. According to our investigations, the leaves of A. muricata can be used to develop drugs with high antioxidant potential. However, adequate scientific data is needed for A. muricata's therapeutic use, as well as further clinical and in vivo research both for toxicological and pharmacological evaluation.

Tetrahydrobenzo[b]pyrans are fused oxygen-containing heterocycles that are found in many biologically active compounds. Therefore, researchers in organic synthesis are searching for suitable, efficient, and useful methods for their synthesis. In this contribution, a series of tetrahydrobenzo[b]pyran derivatives was synthesized using aryl aldehydes, malononitrile, and cyclohexane-1,3-dione or dimedone as the available starting materials. The three-component reactions were catalyzed by 1,3-dibenzyl-1H-benzo[d]imidazol-3-ium chloride as the N-heterocyclic carbene precursor. The heterocyclic oxygen-containing products were obtained in good to excellent isolated yields within relatively shorter reaction times. Optimizing the reaction conditions was performed from the point of view of various parameters of the reaction. The results of these experiments showed that the best solvent system includes water-ethanol, the most suitable reaction temperature is 60ºC, and the optimal amount of the imidazolium catalyst loading is 5 mol%. Operational simplicity, no need for chromatographic methods for purification, simple work-up for pure products, and avoiding hazardous solvents are remarkable features of this three-component reaction. Moreover, in these multicomponent cyclo-condensations, no by-products were observed.

A total of eleven ortho-carboxamidostilbene derivatives were synthesized through Heck coupling with a different type of amide derivatives. These compounds were characterized by FTIR, 1D- and 2D-NMR as well as mass spectroscopy analysis (HRESIMS). The synthesized compounds were tested for their cytotoxic potential against four human cancer cell lines (MCF-7, MDA-MB-231, MCF-7/TAMR-1, and A549), as well as two human normal cell lines (MCF-10A and BEAS-2B) using tamoxifen and cisplatin as a positive control. The active compound has proceeded with molecular docking on the colchicine binding site of tubulin protein using AutoDock Vina and Biovia Discovery Studio. Compounds 6a, 6d-6k exhibited selective cytotoxic activity against A549 cells rather than breast cancer cell lines. Compounds 6d, 6f, and 6g showed moderate cytotoxicity to A549 cells after 72 hours, with IC50 values of 10.4 μM, 6.47 μM, and 8.99 μM, respectively. Interestingly, these compounds had a high selective index (SI) value against A549 lung cancer cells, ranging from 8.87 to 15.4 μM. Molecular docking studies for compounds 6d, 6f, and 6g on the colchicine binding site of tubulin protein, α- and β-subunits were done to comprehend and research ligand-receptor interactions.