10.1007/s10593-010-0647-2
The study focuses on the intramolecular cyclization of 1-[1-alkylsulfanyl-2-phenyl-2-(phenylhydrazono)ethylidene]pyrrolidinium salts, which are synthesized by the alkylation of thioamide with benzyl, allyl, and propargylsulfanyl groups in the presence of cesium carbonate in DMF at room temperature. These pyrrolidinium salts can be efficiently converted into 1,3-diphenyl-6,7,8,8a-tetrahydro-1H-pyrrolo[2,1-c]-1,2,4-triazine-4-thione derivatives in good yields. The research demonstrates that this cyclization method is general for alkyl derivatives of arylhydrazonothioacetamides, expanding the scope of this reaction type. The synthesized pyrrolotriazines are of practical interest due to their potential high antitumor activity, making them promising candidates for biological investigation. The study was financially supported by the Russian Basic Research Fund and includes detailed experimental procedures, characterization data, and comparison of the reaction outcomes with different bases and solvents.
10.1016/S0040-4039(00)73243-6
The research aimed to develop an efficient route to optically pure key intermediates of dihydromevinolin, which are biologically active compounds known for their ability to inhibit HMG CoA reductase, a rate-limiting enzyme in cholesterol synthesis in humans. The researchers focused on the intramolecular Diels-Alder (MDA) reaction as the most promising approach for constructing the decalin system present in mevinic acids. They successfully synthesized the key intermediate through a series of chemical reactions starting from (R)-5-methyl-2-cyclohexanone, involving vinylmagnesium bromide, MnO2, LiAlH4, propargyl bromide, t-BuOK, 10-camphorsulphonic acid (CSA), BH3*THF, NaOH, H2O2, Jones reagent, and other reagents.
10.1016/S0040-4020(01)88723-8
The research focuses on the synthesis of 5-propynyloxycycloalkane pyrimidines (IIIA, IIIB, IIIC, and IIID) and their selective and reactive behavior in intramolecular Diels-Alder reactions with inverse electron demand, followed by a retro Diels-Alder reaction. The compounds IIIA and IIIB favor the extrusion of X-CH2CN, yielding 3-(3-cyanopropyl)-1,3-dihydro-6-phenyl-R1-R2-furo[3,4-c]pyridines (29-36), while compounds 17 and 21 also yield 4-phenyl-6,7,8,8a-tetrahydro-furo[4,3,2-d]quinoline (38) by expelling HCN or MeCN, respectively. For compounds IIIC and IIID, HCN expulsion is favored over X-CH2CN, leading to the formation of 2H-1,6,7,8,9,9a-hexahydro-4-phenyl-9a-R1-5-aa-l-oxo-benz[~~azulenes (39, 40). The reactivity of these compounds towards cycloaddition is significantly influenced by the nature of the substituent R2 when R1 = H, but less so when R1 = Me. The ratio of products V and VI mainly depends on the nature of -X-. The synthesis of these pyrimidines involves starting from their keto precursors (I) and using various reagents such as NaBH4, Grignard reagents, and propargyl bromide in the presence of sodium hydride. The intramolecular Diels-Alder reactions are performed by heating the compounds III in nitrobenzene at 140°C, and the products are analyzed using 1H-NMR spectroscopy.
10.1021/ol3015804
The research presents a one-pot, three-step method for synthesizing triazolotriazepinoindazolones from oxazolino-2H-indazoles, aiming to generate a library of structurally complex and diverse small molecules for high-throughput screening in drug discovery. The process begins with a propargyl bromide-initiated ring opening of the oxazolino-2H-indazole, followed by a bromide-to-azide displacement, and concludes with an uncatalyzed intramolecular azide-alkyne 1,3-dipolar cycloaddition. Propargyl bromide plays a pivotal role as the initiating reagent for the ring-opening step of the oxazolino-2H-indazole. Specifically, in the first step of the one-pot, three-step synthesis, propargyl bromide is used to open the oxazolino-2H-indazole ring, forming an intermediate N1-(propargyl)-N2-(2-bromoethyl)-disubstituted indazolone. The synthesized triazolotriazepinoindazolones have drug-like properties, aligning with Lipinski’s rule-of-five, making them suitable for high-throughput biological screening.
10.1002/jhet.4167
The study focuses on the synthesis, characterization, and evaluation of novel 1,5-benzodiazepine derivatives (compounds 2-7) for their potential applications in corrosion inhibition and antibacterial activities. The chemicals used in the study include 1-ethyl-4-phenyl-1,5-benzodiazepine-2-thione, phosphorus pentasulfide, hydrazine hydrate, carbon disulfide, and various alkylating agents such as propargyl bromide, benzyl chloride, and ethyl bromoacetate. These chemicals served the purpose of synthesizing the target benzodiazepine derivatives through a series of reactions including sulfurization, condensation, and alkylation. The synthesized compounds were then characterized using spectroscopic techniques and single-crystal X-ray crystallography. The study aimed to determine the molecular and crystal structures of these compounds, analyze their intermolecular interactions through Hirshfeld surface analysis, and evaluate their potential as corrosion inhibitors for aluminum, copper, and iron in acidic media using Monte Carlo simulations. Additionally, the antibacterial activity of these compounds against Gram-positive and Gram-negative bacteria was assessed, with the results indicating their potential as antibacterial agents.
10.1021/ol702370m
The research describes the synthesis of monofunctional curcumin derivatives, a "clicked" curcumin dimer, and a PAMAM dendrimer-curcumin conjugate for therapeutic applications. The purpose of this study was to overcome the poor water and plasma solubility of curcumin, a bioactive compound found in turmeric, which possesses antioxidant, anticancer, anti-inflammatory, and anti-Alzheimer's disease properties. The researchers developed a synthetic methodology to produce curcumin conjugates with water-soluble polymers and targeting proteins, potentially enhancing curcumin's therapeutic efficacy. Key chemicals used in the process include curcumin, glutaric anhydride, amino-PEG azide, 1,3-dicyclohexylcarbodiimide (DCC), propargyl bromide, K2CO3, and copper(II) sulfate with sodium ascorbate for the "click" reaction. The study concluded that the monofunctional curcumin derivatives retained biological activity, efficiently labeled and dissolved amyloid fibrils, and the curcumin dimer selectively destroyed human neurotumor cells, making it a promising drug candidate. The conjugates were also expected to exhibit the EPR effect, enhancing their potential therapeutic applications.
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