Synthetic Communications最新文献

The newly synthesized 1,2,3-triazole-thiazole hybrids were first evaluated for their antimicrobial activity against different microbial strains. Most of it showed a marked selectivity against Gram-positive and Gram-negative bacterial strains. The MIC assay was then assessed; for S. aureus, 4a was equipotent to the reference neomycin, while 3a, 3b, and 8b were 2-fold lower. For E. coli, compounds 3a, 4a, and 8c were equipotent to neomycin, while 5a was 8-fold higher, and 8d was 2-fold higher. Most of tested compounds showed superiority to the reference drug against C. albicans; 8a and 8e showed MIC value of 16-fold higher than neomycin, while 3a was 8-fold higher. Also, 3b and 8f were 4-fold higher; 8d was 2-fold higher, while 5a was equipotent to neomycin against the same microbe. Further biofilm formation inhibition assay was conducted to the most active compounds, 5a was the most active against the three types of bacterial strains.

Meglumine, an amino sugar alcohol compound, has recently emerged as a promising catalyst in various organic transformations due to its unique properties. This review provides a comprehensive overview of the applications of meglumine catalyst in organic synthesis, highlighting their efficiency, versatility, and mechanistic insights. Key examples of reactions catalyzed by meglumine, including aldol condensation, Michael addition, Mannich reaction, and other one-pot multicomponent condensation reaction are discussed along with mechanistic pathways and synthetic strategies. Additionally, recent advancements and future perspectives in the field are explored.

Two series of bis-thiazole derivatives (7a–f and 9a–j) were synthesized efficiently via two steps. First, the condensation of 3,3’-(alkane-diylbis(oxy)) dibenzaldehyde (3a,b) with hydrazinecarbothioamide (4) affording 2,2’-(((alkane-1,2-diylbis(oxy))bis(3,1-phenylene))bis(methaneylylidene))bis(hydrazine-1-carbothioamide) (5a,b). The formed 5a,b were then mixed with 2-bromo-1-arylethan-1-one 6a–c affording the corresponding thiazole derivatives 7a–f. Similarly, bis-thiazole derivatives 9a–j were synthesized through heating bis(hydrazine-1-carbothioamides) 5a,b with 2-oxo-N-arylpropanehydrazonoyl chloride 8a–i. Afterwards the synthesized bis-thiazoles 7a–f and 9a–j were evaluated for their in vitro-antibacterial activity against gram-positive and gram-negative bacterial strains. Among the tested candidates, compounds 7a, 7c, and 7d exhibited the highest antibacterial activity. Furthermore, a docking analysis showed that the most promising biologically active candidates under investigation are joined to the same amino acid (acids) as references supporting the biological activity of the tested compounds toward both gram-positive bacteria-protein and gram-negative bacteria-protein. DFT calculations were carried out to gain a better understanding of the target bis-thiazole-structures and their assembly mechanism.

Ylidineketonitrile 2 with chlorodifluoromethyl (A = Cl) demonstrated a strong solvent dependence reaction with primary amines to form either 1-N-alkylated-3,5-disubstituted-2-pyridones or 2-N-alkylated-3, 5-trisubstituted pyridines. The methodology was tested for its scope with primary amines and synthesized 29 derivatives in good to excellent yield. Ylidineketonitrile 2e preferrentially forms pyridone derivatives in the majority of the solvents screened except trifluoroethanol, where chemoselective formation of 2-aminopyridine derivatives was observed.

Imine-linked covalent organic frameworks (COFs) are highly ordered polymer networks that are more chemically stable compared to their boron-linked counterparts making them more attractive for a variety of applications, including as energy storage devices, proton-conductive membranes, and catalytic supports. Furthermore, these imines linked COFs may be synthesized using a diverse spectrum of monomers, providing tremendous design freedom and versatility. We report a general method for synthesizing Imine linked COFs based on the Schiff-base condensation reaction of anilines. The synthesis of 4,4′,4′′-(benzene-1,3,5-triyltris(ethyne-2,1-diyl) trianiline, 4,4′-dicarbaldehyde, 4,4′-(ethyne-1,2-diyl) dibenzaldehyde (BPDA), and terephthalaldehyde (PDA) monomers produced by multistep coupling processes.

The Mn(III)-based oxidation of 1,3-indanedione (1) with 1,1-diarylethenes 2a–c effectively proceeded in boiling AcOH to produce 2,2-bis(vinyl)indanediones 5a–c and 1,2’-spirobi[indene]-1’,3’-diones 6a–c via the formation of 2,2-bis(2-acetoxyethyl)indanedione 3 and acetoxyindeno[1,2-b]furan-4-one 4 intermediates. On the other hand, the Mn(III)-based aerobic oxidation of 1a with 2a at room temperature resulted in bis(endoperoxide) 8a and endoperoxypropellane 9a via the production of mono(endoperoxide) 7a. The plausible reaction pathways were also discussed.

One of the most serious future challenges to health care professionals is the emergence of multi-drug resistance pathogenic microbes that rapidly develop resistance to currently used antibiotics. So, as a way to overcome the antimicrobial drug-resistance problems, it is urgent need to synthesize several new lead molecules that are expected to have antibacterial and antifungal activities. So, some new thiazolidinone and methylthiazole derivatives incorporating benzodioxole nucleolus were constructed. Two different series of N-substituted thiosemicarbazones carrying a benzodioxole nucleus were synthesized through mutation reaction of the different aromatic and heterocyclic aldehydes with benzodioxolyl thiosemicarbazide. Cycloalkylation reaction of the latter thiosemicarbazones through with both of the ethyl chloroacetate or chloroacetone gave the thiazolidin-4-ones or 4-methylthiazoles, respectively. The antimicrobial activity of the thiazolidin-4-one and 4-methylthiazole derivatives was investigated. All of compounds showed from weak to moderate effects toward all tested bacteria.

A more efficient and environmentally friendly approach has been developed for synthesizing phosphonates through the Michaelis-Arbuzov reaction, catalyzed by nano-ZnO in a solvent-free environment, utilizing microwave irradiation. Before synthesis, each compound underwent in silico ADMET analysis and molecular docking to assess drug-like characteristics and their potential to inhibit α-amylase. The structure of the newly synthesized compounds was validated using spectroscopic analysis, and their in vitro inhibitory effects on α-amylase were assessed. Among the compounds, dimethyl 2-(anthracen-10-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6j), dimethyl 2-(naphthalen-1-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6h), and dimethyl 2-(1-methyl-1H-indol-3-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6e) displayed the highest inhibitory activity compared to the reference substance, acarbose. Additionally, compounds dimethyl 2-(benzo[d][1,3]dioxol-4-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6i), dimethyl 4-oxo-2-phenyl-4H-chromen-6-yl-6-phosphonate (6a), and dimethyl 2-(1H-indol-5-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6g) exhibited nearly equivalent effective inhibitory activity when compared to the standard. The remaining compounds demonstrated moderate to good enzyme inhibition.

Quinolines are very important materials in organic synthesis due to their wide range of biological activities as well as representing one of the most research area in medicinal chemistry. Quinolines have many applications in design and synthesis of multiple heterocyclic compounds with a wide variety of biological significance. Quinolines fused heterocycles at face b using different synthetic methodologies as well as variable precursors and reaction conditions were the aim of the current review.

Here we report the development of a concise and efficient synthetic protocol for the preparation of 1H-perimidin-2-amine derivatives that contain an N-(2,2,2-trichloroethyl)carboxamide substituent near the amino group. These compounds’ synthesis method is based on the interaction of naphthalene-1,8-diamine with N-(2,2,2-trichloro-1-isothiocyanatoethyl)carboxamides under reflux in acetonitrile medium for 15 minutes. This transformation is likely to pass through the stage of formation of the intermediate thiourea, which further eliminates hydrogen sulfide, which is accompanied by the closure of the perimidine cycle. Using the developed protocol, we synthesized nine new 1H-perimidin-2-amine derivatives. The yield of synthesized compounds was 67-82%. IR,¹H NMR,¹³C NMR, ¹H-¹H COSY, ¹H-¹³C HSQC, and ¹H-¹³C HMBC spectroscopy data proved their structures.