10.2174/138620712800563909
The research aims to develop an efficient method for the synthesis of isoquinoline derivatives, specifically dialkyl pyrrolo[2,1-a]isoquinoline-2,3-dicarboxylates, pyrrolo[1,2-a]quinoline-1,2-dicarboxylates, and indolizines. The purpose of this study is to provide a simple, environmentally friendly, and cost-effective one-pot synthesis method that avoids the use of complex isolation procedures and hazardous solvents. The researchers concluded that they had successfully developed a convenient and one-pot method for preparing these stabilized heterocyclic compounds under solvent-free conditions at 50°C, which offers a significant advantage over traditional multi-step approaches. The chemicals used in the process include isoquinoline, quinoline, pyridine, phenacyl bromides, and dialkyl acetylenedicarboxylates or diaryloylacetylene. The reactions were carried out under mild conditions, and the products were obtained in high yields, demonstrating the synthetic advantage of these methods. The study also provides detailed characterizations of the synthesized compounds using various spectroscopic techniques, confirming the structure and composition of the products.
10.1002/jhet.205
The research focuses on the efficient synthesis of pyrrolo[2,1-a]isoquinolines and pyrrolo[1,2-a]quinolines, which are significant due to their potential applications as central nervous system depressants, calcium entry blockers, and anticancer agents, among others. The study aims to develop a more efficient and environmentally friendly method for synthesizing these compounds by conducting the reactions in aqueous media. The researchers successfully reported a one-pot procedure using quinoline or isoquinoline, phenacylbromide derivatives, and activated alkynes, which resulted in good to excellent yields of the desired heterocyclic compounds. The method offers the advantages of simple operation, mild reaction conditions, high product yields, and cost-effectiveness, demonstrating the potential of water as an efficient promoter in chemical transformations.
10.1021/jo00325a010
The research focuses on the synthesis and intramolecular reactions of Reissert compounds, which are known for their potential applications in the formation of complex organic molecules. The purpose of the study was to explore the possibility of using Reissert compounds with built-in halomethyl or aldehyde groups to undergo intramolecular reactions analogous to their intermolecular counterparts. The researchers synthesized various Reissert compounds, such as 2-(o-chloromethylbenzoyl)-1,2-dihydroisoquinoline and 2-(o-formylbenzoyl)-1,2-dihydroisoquinoline, using chemicals like isoquinoline, potassium cyanide, a-chloro-o-toluyl chloride, and a-bromo-o-toluyl chloride. They then treated these compounds with strong bases to induce cyclization and other intramolecular reactions. The study concluded that Reissert compounds with strategically placed functional groups can indeed undergo intramolecular reactions to form complex structures, such as 5,6,13,14-didehydro-8-oxoberbine and phthalideisoquinoline.
10.1016/j.bioorg.2018.09.033
This research presents the design, synthesis, and biological evaluation of N1-(isoquinolin-5-yl)-N2-phenylpyrrolidine-1,2-dicarboxamide derivatives, which are potent transient receptor potential vanilloid type 1 (TRPV1) antagonists. The researchers identified compound 3b, featuring a p-Br substituted phenyl, as a lead candidate due to its potent antagonism against capsaicin and protons in TRPV1 functional assays and its efficacy in capsaicin-induced and heat-induced pain models without causing hyperthermia. The synthesis involved a series of chemical reactions starting from 5-aminoisoquinoline urea, with key intermediates such as isoquinoline and pyrrolidine derivatives, ultimately leading to the target compounds like 3b. The study concluded that compound 3b has promising potential for further development as an antinociceptive drug.
10.1016/j.bmcl.2009.08.037
The research aimed at synthesizing and evaluating a series of berberine, phenantridine, and isoquinoline derivatives for their inhibitory activity against Rho GTPase nucleotide binding, with a focus on the isoform selective inhibitors of Rac1/1b GTPase. The study concluded that the insertion of 19 amino acids in the Rac1b splice variant introduces a conformational difference that allows certain compounds, such as 4, 21, 22, and 26, to selectively inhibit Rac1b over Rac1. The chemicals used in the process included protoberberine series compounds like berberine, (±)-canadine, tetrahydroxy berberine analogs, and demethylene berberine, as well as phenantridine alkaloids like chelerythrine and sanguinarine, and 3-aryl-isoquinolines. These compounds were tested for their ability to inhibit Rac1, Rac1b, and Cdc42, with some showing selective inhibition and potential as isoform-selective Rac1b nucleotide binding inhibitors.
10.1016/S0040-4020(01)86196-2
The study investigates the reactions of benzoylcyanate oxide (BZNO) with pyridine and isoquinoline. Pyridine reacts with BZNO to form a fragile zwitterionic adduct, which slowly reverts to the reactants and ultimately leads to benzoyl isocyanate and related products. In polar solvents, pyridine catalyzes the dimerization of BZNO to form the “abnormal” 1,4,2,3-dioxadiazine dimer, while in apolar solvents, site-specific biscycloadducts are obtained. The proposed mechanism involves two labile intermediates, a zwitterion and a monocycloadduct. The study also explores the stability of these intermediates through modifications of the reactants. The reaction of BZNO with isoquinoline yields a moderately stable cycloadduct, which can be converted to an isocarbostyril derivative through isomerization. The study provides insights into the solvent effects on product distribution and the stability of the intermediates involved in these reactions.
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