Current Organic Chemistry - Volume 29, Issue 1, 2025

Cesium carbonate is an alkali carbonate salt that has numerous applications and has been proven to be a mild inorganic base in organic synthesis. It has garnered significant attention due to its practicality in C-H functionalization and heteroatom-heteroatom bond formation reactions, in addition to its application in conventional synthetic transformations. In this six-year update, we have examined the most important applications of Cs2CO3 in organic synthesis from 2018 to the present, including the scope of the reaction and providing detailed explanations of the underlying mechanisms.

The complicated internal mechanical and structural qualities of normal bone tissue still prevent the development of effective therapeutic procedures for major bone lesions. It is still difficult to use tissue engineering to return damaged bones back to how they were originally intended. Due to recent advances in 3D printing, together with the introduction of new materials and technological assistance, the basis for BTE has been established. Biological 3D biomaterials have cells inside them, which allows for the creation of structures that mimic real tissues. Microextrusion, inkjet, and laser-assisted bioprinting are the three primary methods used in 3D bioprinting manufacturing. Hydrogels packed with cells, growth hormones, and bioactive ceramics are among the bioinks utilized in bone bioprinting. With the use of magnetic resonance imaging or computed tomography scanning, 3D printing offers substantial benefits for tailored treatment by enabling the creation of scaffolds with the right structural qualities, form, and dimensions. Three-dimensional (3D) bioprinting is a cutting-edge technique that has been utilized recently to create multicellular, biomimetic tissues with layers upon layers of intricate tissue microenvironment printing. We approached the use of hydrogels with great strength in 3D printing for BTE with an emphasis on first providing a thorough study about the development of 3D printing, printing techniques, and ink selection in this review. A brief prediction on how 3D printing would advance in the future was made.

N-arylated heterocycles are a significant class of core scaffolds in medicinal chemistry, materials science, and agrochemistry, highlighting their importance in various fields. The development of innovative methodologies for synthesizing these fundamental structures has been a central focus in organic synthesis. Over the past few decades, numerous approaches have been established to synthesize N-aryl heterocycles efficiently. Among these methods, the direct N-arylation of N-H heterocycles stands out as one of the most straightforward and robust strategies for accessing N-arylated heterocycles. This review provides a comprehensive review of the recent advances in the synthesis of N-arylated heterocycles, encompassing the relevant literature from the past decade. The review summarizes the N-arylation of N-H heterocycles using various catalytic systems, including palladium, nickel, copper, visible light-induced metal-catalyzed, and metal-free catalyzed methodologies. These advances highlighted the continuous evolution and optimization of synthetic strategies to create diverse and complex N-arylated heterocycles, which are pivotal for furthering research and development in multiple scientific domains.

A simple synthetic method was performed to design a novel series of polycyclic systems consisting of a coumarin-pyrazole-thiazole skeleton linked with a completed thiazole ring via hydrazone linkage. The methodology depended on the cyclization of the active precursor 2-[(3-(2-oxo-2H-chromen-3-yl)-1-(4-phenylthiazol-2-yl)-1H-pyrazol-4-yl)methy-lene]hydrazine-1-carbothioamide (2) by its reaction with a series of α-halocarbonyl reagents under Hantzsch reaction conditions. The spectral and analytical data confirmed the structures of all the synthesized compounds. The target compounds were screened for their in vitro anticancer activity. The cytotoxic effects of obtained compound were screened against cancer cell lines (MCF-7, HepG2, and HCT116) using the standard SRB method. Furthermore, products 4, 5, and 7b were the most active against all cancer cell lines, compared with Doxorubicin. These bioactive products effectively suppress the growth of cancer cells by activating the cell death program through late apoptosis. In addition, products 4 and 5 arrested the cell cycle at the S and G2 phases, while product 7b has the ability to arrest the cell cycle at the G2 phase against all three cancer cells. The molecular docking of the products 4, 5, and 7b showed good binding affinities with Cyclin-dependent kinase 8 (CDK-8), while the ADMET prediction supported that these bioactive products can be promising anticancer agents.

A one-pot three/two-component reaction of 3-acetyl-coumarin (1), 4/3-anisaldehyde (2a,b) and malononitrile or 3-acetylcoumarin (1) and 2-(4/3-methoxybenzylidene)malononitrile (5a,b) in glacial acetic acid/ammonium acetate under reflux afforded 2-amino-4-(4/3-methoxyphenyl)-6-(2-oxo-2H-chromen-3-yl)nicotinonitrile (4a,b). Spectral data helped establish the structures of the compounds. Subsequently, an antiproliferative evaluation against a selected line of tumorous cells (HepG-2, MDA-MB-231 and A549) was performed in-vitro for the novel 2-amino-4-(4/3-methoxyphenyl)-6-(2-oxo-2H-chromen-3-yl)nicotinonitrile (4a,b). Compound 4a exhibited good efficiency against the MDA-MB-231 and A549 cell lines compared with the reference drug (Vinblastine). Furthermore, the chemical reactivity of both compounds was discussed using DFT. Lastly, a molecular docking analysis was addressed and conducted for these desired molecules.