Synthetic Communications最新文献

A series of 4-hydroxy-6-methyl-3-(1-(4-(aryl/methyl)thiazol-2-yl)-1H-pyrazol-3-yl)-2H-pyran-2-ones 3a–h have been synthesized from aryl/methyl halomethylketones and a key pyrazole intermediate 1 using a convenient one-pot synthesis method. All compounds were characterized by NMR and MS, and the structure of three of them (3a, 3b and 3f) was resolved by X-ray diffraction. These heteroatom-rich thiazole compounds were then evaluated as inhibitors of Mycobacterium tuberculosis InhA, a key enzyme involved in the type II fatty acid biosynthesis pathway of the mycobacterium. Although inhibitory activities were found to be rather weak, molecular docking studies were also been carried out to understand a possible mode of interaction with key residues in the enzyme’s active site.

The biocompatibility, specificity, and consistency of natural carbohydrate polymers in catalyzing organic processes have garnered significant interest. For the production of organic compounds, a variety of carbohydrate polymers have been employed as heterogeneous catalysts, including agarose, cellulose, chitosan, chitin, sodium alginate, carrageenan, dextrin, starch, and pectin. This article provides an overview of several straightforward and efficient techniques for the mild reaction conditions catalytic synthesis of organic compounds employing carbohydrate polymers as the source of heterogeneous catalytic species.

This study presents a novel and rare demethylation of 4-benzylidene-2-phenyloxazolones under NaOH/EtOH/H₂O conditions. The potential mechanism underlying the phenomenon was evaluated through control reactions.

Concise route for the synthesis of (-)-isoaltholactone and (±)-5-epi-OBn-Goniotriol were described. Key features for the (-)-isoaltholactone synthesis involved; a) diastereoselective and enantioselective aldol reaction between chiral pyrrolidine substituted γ-benzyloxy vinylogous urethane enolate and cinnamaldehyde afforded highly stereoselective syn δ-lactone, b) allylic 1,3-strain controlled epoxidation of styryl alkene following the stereospecific opening of the epoxide assisted by a proximal benzyloxy group completed the synthesis. Reaction of simple pyrrolidine substituted γ-benzyloxy vinylogous urethane enolate and cinnamaldehyde gave anti δ-lactone. Epoxidation and epoxide opening of the styryl alkene substrate of anti δ-lactone derivative was also investigated, which led to the synthesis of (±)-5-epi-OBn-Goniotriol.

With the ultimate goal of discovering new anticancer agents, this study involved the design and synthesis of fifteen novel Schiff bases 4a,b, 5, 6a–d, 7a–e, and 8–10 which contain 3-(2-oxo-2H-chromen-3-yl)-1-(4-phenylthiazol-2-yl)-1H-pyrazole moiety. The synthetic method depended on reaction of 3-(2-oxo-2H-chromen-3-yl)-1-(4-phenylthiazol-2-yl)-1H-pyrazole-4-carboxaldehyde (3) with a series of aromatic and heteroaryl amines under ultrasound irradiation to explore the influence of aromatic and heteroaryl rings on biological activity. The chemical structures of these Schiff bases were fully elucidated using various spectral and elemental analyses. The antiproliferative activities of the Schiff bases were studied by the standard SRB method. Among the new 15 Schiff bases, derivatives 4a,b, 5, and 7b have significant cytotoxic effects against PC3, HepG2, and HCT116 cancer cell lines. These four bioactive Schiff bases significantly increased the late apoptosis of all studied tumor cells. Also, both products 4a and 4b arrested the cell cycle at the G1 phase, while both compounds 5 and 7b arrested the S and G2 phases against PC3 cells. In addition, the products 4a, 4b, 5, and 7b have promising high abilities to arrest the cell cycle at the G2 phase against HepG2 and HCT116 cells. The different substitutions on the aryl ring were the basis for the structure–activity relationship study. The molecular docking study confirmed good binding interactions of these compounds with Cyclin-dependent kinase 8 (CDK-8) receptor, while the absorption, distribution, metabolism, excretion, and toxicity (ADMET) prediction supported that these bioactive products can be promising anticancer agents.

A concise and efficient synthetic protocol for the synthesis of furan-based bis-stilbene derivatives (BPBFCz1) was described, which is a very promising organic laser dye. Starting with 4,4’-diethynylbiphenyl, BPBFCz1 was prepared with a total yield of 40% through a three-step classical reaction of Sonogashira Coupling, intramolecular cyclization of 2-alkynyl phenol, and Buchwald Hartwig cross-coupling. The crystal structure of BPBFCz1 was presented for the first time. The synthesis strategy was applied to the synthesis of other three materials with similar structure and the yields of 28.6–36.6% were obtained.

An effective protocol for synthesis of some new pyrazolylbarbiturate derivatives is reported through a one-pot, three-component reaction between barbituric/thiobarbituric acid, aroylphenylhydrazones and arylglyoxal derivatives. All reactions were conducted in ethanol as solvent without using any catalyst and products were obtained by simple filtering of the precipitated solids in high yields. All products were characterized by ¹H and ¹³C NMR and IR spectral and elemental analysis data.

One-pot photo induced eosin-Y catalyzed, green approach for the synthesis of 5,5-diphenylimidazolidine-2,4-dione (Phenytoin) has been developed. The reaction proceeded smoothly, for a wide range of benzil and urea/thiourea derivatives as cheap and eco friendly reagents with high reactivity and good selectivity in DMSO as green solvent at room temperature in good to excellent yields. Biological studies such as drug-likeness and molecular docking have been conducted on the synthesized compounds, some of the compounds showed appreciable activity with least binding energy.

Aigialomycin D, a 14-membered benzannulated macrolactone, was synthesized in a simple, efficient and stereoselective approach using inexpensive and commonly accessible starting materials. The main steps in this convergent synthesis are Corey-Fuchs reaction, Yamaguchi esterification and ring closing metathesis (RCM).

We developed a new approach for the synthesis of flavanone from chalcones without electrical energy, such as stirring or heating, by using a cesium fluoride–crown ether complex. This “zero electrical energy reaction” is a new category of reaction that has the potential to replace the general organic reaction.