Synthetic Communications最新文献

Seventeen new highly fluorinated phosphoramidates containing alkylamino moieties of the type (R_FO)₂P(O)NHR (R = CH₂CH₂CH₃, (CH₂)₃CH₃, (CH₂)₄-CH₃, CH(CH₃)₂, C₆H₁₁, CH₂CH₂-C₆H₅, CH₂-C₆H₅ or C₆H₅; R_F = CH₂CF₃, CH₂C₂F₅ or CH₂CH₂C₆F₁₃) were synthesized. These compounds were obtained through the reaction of primary amines with bis(polyfluoroalkyl)phosphites as phosphorylating agents, using molecular iodine as a mild catalyst and in the presence of H₂O_2.This method was chosen out of various literature common methods, which were thoroughly investigated using ³¹P NMR spectroscopy. In addition, the variation in reaction rates among different phosphites was studied and compared with previous research findings. The title phosphoramidates were fully characterized using multinuclear (¹H,¹³C,³¹P, and ¹⁹F) NMR, IR, and HRMS techniques.

Pyridines and its derivatives are an important class of heterocyclic compounds of low molecular weight. They have been used in the treatment of a various diseases like cardiovascular disease, antioxidant, antibacterial, anti-tubercular, anticancer, anticoagulant, etc. In 1882, Arthur Hantzsch reported pyridine derivative synthesis using different aldehydes, 2 molecules β-keto ester and ammonium acetate to give a Hantzsch ester or 1,4-dihydropyridine derivatives. This review article focuses on different protocols for Hantzsch reaction using different catalysts like β-cyclodextrin–polyurethane polymer (β-CDPU), chitosan nanoparticles (NPs), salicylic acid, p-toluenesulfonic acid (p-TSA), alginic acid, Fe-TUD-1, PdRuNi@GO, Ceric Ammonium Nitrate (CAN), sulfate polyborate, etc. for the synthesis of pyridine derivatives.

Sugar nucleotides are essential substrates used for synthesizing bioactive oligosaccharides in enzymatic reactions, however, their preparation via chemical and enzyme reactions is challenging. Therefore, we investigated the synthesis of sugar nucleotides under optimal conditions using a facile one-step reaction. Seven sugar nucleotides were synthesized via an optimized one-step reaction in 40–80% yield, exhibiting a preference for 1,2-trans glycoside. Moreover, a gram-scale synthesis of UDP-galactose resulted in a 46% (578 mg) yield.

Reaction of 9-fluorene propargylic alcohols and substituted-2-hydrazinopyridine using BF₃·OEt₂ as a Lewis acid catalyst afforded 9-fluorenlidene appended 2-hydrazinopyridine imine derivatives has been developed. The scope of the reaction is demonstrated by selecting a range of fluorene propargylic alcohols and substituted 2-hydrazinopyridine imines. All the synthesized molecules were characterized using various spectroscopic and analytical techniques including ¹H NMR,¹³C NMR, and Mass spectrometry. A plausible reaction mechanism for forming title compounds via propargylic allenyl carbocation is postulated. The synthetic utility of products thus formed is demonstrated by utilizing Suzuki coupling.

A simple and efficient route for the synthesis of a series of new mono/bis isoxazolines, and pyrroline linked chromone heterocyclic hybrids has been developed from 2-aminochromone via key intermediate mono and 2-(diallylamino)chromen-4-one. The intermediate subjected to the [1,3] dipolar cycloaddition with insitu generated nitrile oxides and ring-closing metathesis to generate the regio selective Isoxazolines and 3-pyrrolines. All the derivatives were screened for their anti-cancer activity (Cell viability), compared to the standard drug Imatinib. Compounds 13b and 13e, 14b and 14g showed good inhibition at 10 µM concentration.

Breast cancer and lung cancer causes a high rate of mortality all over the world. Pursuing our efforts toward searching for efficient anticancer agents herein a series of coumarin/piperazine hybrids 10a-f, 12a-d, 14 were synthesized and subsequently assessed for their potential In Vitro anticancer activity, against A549 (Lung cancer) and MCF-7 (breast cancer) cell lines using MTT assay. Encouragingly, all the synthesized compounds displayed varying degrees of effectiveness, ranging from good to moderate activity against these two cancer cell lines. However, amongst all the compounds synthesized, compound 12c exhibited notably higher potency against both A549 and MCF-7 cell lines, with an IC₅₀ of 0.40 µM and 0.51 µM, respectively. Additionally, the study delved deeper by conducting EtBr/AO assays, unveiling the induction of apoptosis. Furthermore, investigations into Reactive Oxygen Species (ROS) were conducted by using DCFH-DA dye. To understand the behavioral patterns and selectivity of the synthesized compounds, computational techniques were employed alongside experimental analysis. Utilizing density functional theory (DFT) calculations, electronic and structural characteristics were determined for compound 12c These calculations were then compared and associated with the observed biological effects. Additionally, molecular docking was utilized to investigate how compounds 12c interacted with crucial apoptotic genes, specifically targeting p53 and caspase 3. Compound 12c exhibited docking scores of −8.4 kcal/mol and −7.9 kcal/mol for p53 and caspase 3 respectively. Lastly, an in Silico ADME study was performed to evaluate the compounds’ potential as drug candidates.

Recently, photoredox catalysis using 9,10-phenanthrenequinone (PQ) has emerged as an efficient method for the transformation of various organic compounds. Low cost and good availability make it a promising alternate to typical transition metal complex-based photocatalysts. It has emerged as an alternative in photoredox catalysis highlighting recent advancement in organic transformation using (PQ) as photocatalyst.

A new method for the synthesis of 2-(phenyl)indole via the cyclization of 2-(phenylethynyl)aniline in the presence of K₂S was established, which was used to prepare 2-(phenyl)indole derivatives in high yields (66%-93%). Mechanistic studies have revealed that a trisulfur radical anion (S₃^•−) is generated from K₂S, which acts as an initiator for the intramolecular addition of the alkyne and the amino group in o-alkynylaniline, ultimately leading to the formation of the indole derivative. This method provides a new way to prepare 2-(phenyl)indoles and a novel application of S₃^•− in organic synthesis.

Reduction of styrene compounds was achieved by the simple method of adding more than 2.5 equivalents of an aqueous HI solution in chlorobenzene under refluxing conditions for 8 h to give the product in medium to excellent yields. There was no need to add further additional reagent and catalyst. HI was a specific reagent for this reduction reaction. Increment of the amount of HI was efficient to increase the yield rather than to elongate the reaction time. This reaction could be applied to compounds bearing halogen and sulfur atoms, which would act as reductive site and poisoning of the transition-metal catalyst, respectively. The yield was decreased in the case of the compounds bearing small substituent such as propyl and butyl groups on olefin. This reaction proceeded via the iodinated intermediate followed by the reduction of C-I bond. The reduction mechanism would contain the radical cleavage of the C-I bond.

Novel library of pyrazole derivatives (6a–k) from substituted 4-dioxaborolanyl-1H-pyrazole and halo benzaldehyde through simultaneous Suzuki reaction, nucleophilic addition, and hydrolysis under moderate reaction conditions. The desired compounds 6a–k have been formed in good to high yield. All the compound structures were characterized by analytical and spectral (¹H NMR,¹³C NMR and MS) studies. Furthermore, the evaluation of biological activity of synthesized molecules.