Synthetic Communications最新文献

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.

Ten novel 4-esterchalcones, licochalcone analogues, were strategically synthesized to study the effect of electro-donating or electro-withdrawing substituents in the aryl enone moiety on their pharmacological and photoprotective properties. 4-Esterchalcones had their drug-like character evaluated, which demonstrated positive characteristics for the development of novel drug candidates. In the in vitro antimicrobial evaluation, isovaleryl 4-esterchalcones showed activity against strains of Staphylococcus aureus, Candida albicans and C. tropicalis with minimum inhibitory concentration (MIC) in the range of 2.64-3.32 µmol mL⁻¹, and the isobutyryl 4-esterchalcone 5d (4’-Br) presented antimicrobial activity against all strains tested, with a MIC of 2.74 µmol mL⁻¹. In the UV-Vis study, λ_max were observed at 312-327 nm, the UVB range, mainly. The best SPF-UVB results ranged from 18.04 to 21.06, with high ε_max values, indicating that 4-esterchalcones have the potential to act as sunscreens. Furthermore, along with the environmental concern, halogenated compounds demonstrated slightly toxic on Artemia salina.

2-Chloro-5-[(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)carbonyl]pyridine-3-carbonitrile (3) was synthesized and its chemical reactivity was investigated toward a diversity of binucleophiles. Treatment of compound 3 hydrazine hydrate and phenylhydrazine produced pyrazolo[3,4-b]pyridines while isoxazolo[5,4-b]pyridine was obtained from reacting compound 3 with hydroxylamine. A diversity of pyrido[2,3-d]pyrimidines was synthesized from treatment of staring substrate 3 with some 1,3-N,N-binucleophiles. Treating compound 3 with some 1,4-binucleophiles including ethylenediamine, o-phenylenediamine, 2-aminophenol and 2-aminothiophenol furnished pyrido[2,3-e][1,4]diazepine 12 and pyrido[2,3-b][1,5] benzodiazepine 13, pyrido[2,3-b][1,5]benzoxazepine 14 and pyrido[2,3-b][1,5] benzothiazepine 15, respectively. The synthesize compounds shown remarkable effect against yeast and fungus, while compounds 4 and 7–11 exhibit excellent efficacy against all types of Gram + and Gram - bacteria. Structures of the produced compounds were established using analytical and spectroscopic tools.

A new library of tetrazole rings with oxazole-pyrimidine derivatives (9a–j) has been developed and synthesized. All of the compounds were characterized using spectral data. These were then tested for in vitro anticancer activity against four human cancer cell lines: prostate cancer (PC3 & DU-145), lung cancer (A549), and breast cancer (MCF-7) using an MTT assay. Etoposide was chosen as the positive control. Most of the compounds demonstrated moderate to good activity. These compounds (9a, 9b, 9d, 9g, and 9h) demonstrated the most powerful action. Particularly, one chemical 9h had exceptional antitumor efficacy.

Benzoxazoles and benzothiazoles are a class of aromatic heterocyclic compounds having similar ring structures, in which a benzene ring is fused to the 4 and 5 positions of the 1,3-oxazole and 1,3-thiazole rings respectively. They constitute an interesting class of organic compounds due to their powerful and significant biological, agrochemical, pharmaceutical and physicochemical activities. Indeed, benzoxazole and benzothiazole derivatives possess a wide range of applications, such as: anticancer, anti-inflammatory, antioxidant, anticonvulsant, antitubercular, antifungal, pesticidal, anticorrosive, complexing properties and so on. The synthesis of benzoxazole and benzothiazole derivatives has attracted much attention from several researchers across the world and numerous synthetic methods have been developed to access these compounds over the past decades. In this review, we present new and recent synthetic strategies, as well as some biological properties of benzoxazole and benzothiazole derivatives.