Synonyms:quinaldic acid
≥99.0% *data from raw suppliers
2-?QuinolinecarboxylicAcid *data from reagent suppliers
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There total 86 articles about Quinoline-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
Reference yield: 98.0%
Reference yield: 98.0%
Reference yield: 95.0%
The study presents an efficient sequential reaction process for the synthesis of polysubstituted indolizidines and quinolizidines, which are important structural motifs found in a variety of natural products with biological activities such as neurological and antitumor functions. The process involves the reaction of iodides with δ-chloropropylamines in the presence of potassium carbonate (K2CO3) in acetonitrile (MeCN), resulting in a series of SN2/Michael addition/SN2/SN2 reactions. This method was used to synthesize indolizidine 223A, a specific alkaloid, from 2-ethyl-2-hexenoic acid in 12 linear steps with an overall yield of 14.5%. The chemicals used in the study include iodides 1, δ-chloropropylamines 5, and K2CO3, which serve as reactants and catalysts to facilitate the formation of the target compounds. The purpose of these chemicals is to enable a rapid and stereocontrolled evolution of molecular complexity, which is crucial for the total synthesis of natural products and for diversity-oriented synthesis in drug development and chemical biology.
The research investigates the development of new anti-tuberculosis (TB) compounds. The study aims to address the growing problem of drug-resistant TB strains by synthesizing and evaluating the antimycobacterial activity of two series of 4-(adamantan-1-yl) group containing quinolines conjugated to amino acids. The researchers synthesized these compounds using commercially available quinoline-2-carboxylic acid and various amino acids, and tested their efficacy against the M. tuberculosis H37Rv strain. The most potent analogs displayed in vitro antimycobacterial activity ranging between 1.00 and 3.125 mg/mL. The study also employed Comparative Molecular Field Analysis (CoMFA) to understand the structure-activity relationship (SAR) of these compounds. The results showed that quinolines conjugated with basic and heteroaromatic residues were more potent compared to hydrophobic ones. The most active compound, N2-[(1S)-4-amino(imino)methylamino-1-hydrazinocarbonylbutyl]-4-(adamantan-1-yl)-2-quinolinecarboxamide (57), exhibited 99% inhibition at 1.00 mg/mL against drug-sensitive M. tuberculosis H37Rv strain and 99% inhibition at 3.125 mg/mL against a drug-resistant strain. None of the compounds showed cytotoxic effects in mammalian Vero cells. The study concludes that amino acid derivatives of 4-(adamantan-1-yl)-2-substituted quinolines hold promise as anti-tuberculosis agents, and the 3D-QSAR models provide valuable insights for further optimization of these compounds.
The study presents a nine-step total synthesis of the quinolizidine alkaloid (+)-Epilupinine with an overall yield of 48%. The key step in this synthesis is the intramolecular nitrile oxide-alkene cycloaddition (INOC), which is used to construct the quinolizidine skeleton. The researchers developed a novel method to efficiently prepare the challenging intermediate (R)-(2-vinylpiperid-1-yl)propanal oxime (13a) from (R)-(2-vinylpiperid-1-yl)propanol (11a) using a two-step process involving Mitsunobu reaction and N-detosylation, avoiding the use of the highly unstable aldehyde intermediate. This method was further generalized to convert various 3-(N,N-dialkylamino)propanols into their corresponding oximes. The final steps of the synthesis involve a Raney nickel-promoted desulfurization to yield the target compound (+)-Epilupinine. The study not only provides a practical and scalable route to this biologically important alkaloid but also offers a new approach for the application of INOC in the total synthesis of other alkaloids.
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