10.1016/j.tet.2007.11.036
The study presents a two-step synthesis method for benzo-fused 2,8-dioxabicyclo[3.3.1]nonane derivatives, utilizing a domino Knoevenagel condensation/intramolecular hetero-Diels-Alder reaction sequence. The process involves an initial intermolecular Knoevenagel condensation of a compound with active methylene compounds to form a heterodiene, which then undergoes intramolecular hetero-Diels-Alder cycloaddition. The research successfully optimized the reaction conditions, including the choice of catalyst and solvent, to achieve high yields of the desired products. The method demonstrates a novel route for constructing complex heterocycles with potential applications in medicinal chemistry.
10.1016/j.bmcl.2006.11.020
The research focuses on the design and synthesis of a novel class of furan-based molecules as potential 20S proteasome inhibitors, aiming to develop new anti-tumor agents. The purpose of this study is to create compounds that can inhibit the activity of the 20S proteasome, a protein complex involved in the degradation of proteins, which is often dysregulated in pathological conditions such as cancer. The researchers synthesized a series of furan-based compounds, including nine peptide derivatives and six statine peptidomimetics, with the C-terminal furanyl moiety introduced as furan-based amino acids to target the proteasome. The synthesis involved the use of various chemicals such as Boc-protected α-amino acids, isobutyl chloroformate (IBCF), N-methylmorpholine (NMM), trifluoroacetic acid (TFA), and others in a series of reactions including methylation, coupling, and hydrolysis. The study concluded that compound 12 emerged as a selective and moderate potent proteasome peptidomimetic inhibitor, effectively inhibiting the proliferation of HepG2 (human hepatoma) and HL-60 (acute human myeloid leukemic) cell lines. The research provides insights into the potential of these furan-based inhibitors as anti-tumor agents by targeting the 20S proteasome and offers a detailed synthetic route for the development of these compounds.
10.1023/A:1011656605605
The research aimed to resolve inconsistencies in the literature regarding the synthesis of 5-acetyl-3-cyano-6-methylpyridine-2(1H)-thione and to explore new biologically active compounds. The study successfully developed a new method for synthesizing the target compound through the reaction of ethoxymethyleneacetylacetone with cyanothioacetamide in the presence of N-methylmorpholine. The researchers further investigated the alkylation and bromination properties of the synthesized compound and its derivatives. The study concluded that the synthesized compounds and their properties were consistent with physicochemical data and literature values, contributing to the understanding of the chemistry of heterocyclic compounds with potential biological activity.
10.1002/jccs.199600014
The study focuses on the synthesis of novel triazole, sulfur-containing diazole, and N-phenylthiatriazole biphenyltetrazole derivatives as potential angiotensin II receptor antagonists. This research was inspired by the success of the angiotensin II receptor antagonist losartan (DuP 753) and aimed to explore alternative heterocycles that could maintain or enhance its efficacy. Chemicals such as methyl valerimidate hydrochloride, thionyl chloride, N-methylmorpholine, cesium carbonate, and Lawesson's reagent were used in the synthetic processes. Among the synthesized compounds, 5-butyl-3-[(2-trifluoromethyl)phenyl]-2,1,3,4-1H-thiatriazole-2-one biphenyltetrazole demonstrated promising in vitro activity, suggesting its potential for further pharmaceutical development?.
C,
F
