831235-64-4

Upstream product

• 612-62-4 2-Chloroquinoline 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 1613-37-2 Quinoline N-oxide 
• 2005-43-8 2-bromoquinoline 

Downstream Products

• 119-91-5 2,2'-biquinoline 
• 40176-78-1 2-ethynyl-quinoline 

Relevant academic research and scientific papers

Sonogashira-Hagihara and Buchwald-Hartwig cross-coupling reactions with sydnone and sydnone imine derived catalysts

Seven different palladium complexes of sydnones and sydnone imines and a co-catalyst system consisting of lithium sydnone-4-carboxylate and Pd(PPh3)4 catalyzed Sonogashira-Hagihara reactions between (hetero)- aromatic bromides and 2-methylbut-3-yn-2-ol (52 examples, up to 100% yield). The co-catalyst system and a sydnone Pd complex were also tested in Buchwald-Hartwig reactions (9 examples, up to 100% yield). (Equation Presented).

Design, synthesis, and protein crystallography of biaryltriazoles as potent tautomerase inhibitors of macrophage migration inhibitory factor

Optimization is reported for biaryltriazoles as inhibitors of the tautomerase activity of human macrophage migration inhibitory factor (MIF), a proinflammatory cytokine associated with numerous inflammatory diseases and cancer. A combined approach was taken featuring organic synthesis, enzymatic assaying, crystallography, and modeling including free-energy perturbation (FEP) calculations. X-ray crystal structures for 3a and 3b bound to MIF are reported and provided a basis for the modeling efforts. The accommodation of the inhibitors in the binding site is striking with multiple hydrogen bonds and aryl-aryl interactions. Additional modeling encouraged pursuit of 5-phenoxyquinolinyl analogues, which led to the very potent compound 3s. Activity was further enhanced by addition of a fluorine atom adjacent to the phenolic hydroxyl group as in 3w, 3z, 3aa, and 3bb to strengthen a key hydrogen bond. It is also shown that physical properties of the compounds can be modulated by variation of solvent-exposed substituents. Several of the compounds are likely the most potent known MIF tautomerase inhibitors; the most active ones are more than 1000-fold more active than the well-studied (R)-ISO-1 and more than 200-fold more active than the chromen-4-one Orita-13.

Synthesis of sugar-derived triazole- and pyridine-based metal complex ligands

A series of 30 bi- and tridentate ligands for metals were prepared by copper-catalyzed coupling (CLICK reaction) of 2-ethynylpridine, 2-ethynyl-5-nitropyridine, 2-ethynylquinoline, and 2,6-diethynylpyridine with 12 protected glycosyl azides in the gluco a

2-(Substituted ethynyl)quinoline Derivatives as mGLUr5 Antagonists

Provided is a 2-(substituted ethynyl)quinoline derivative having an mGluR5 antagonistic activity and pharmaceutically acceptable salts thereof. The compound of the present invention can be useful as a medicament for treating and preventing mGluR5 receptor

Luminescence modulations of rhenium tricarbonyl complexes induced by structural variations

Octahedral d6 low-spin Re(I) tricarbonyl complexes are of considerable interest as noninvasive imaging probes and have been deeply studied owing to their biological stability, low toxicity, large Stokes shifts, and long luminescence lifetimes. We reported recently the bimodal IR and luminescence imaging of a Re(I) tricarbonyl complex with a Pyta ligand (4-(2-pyridyl)-1,2,3-triazole) in cells and labeled such metal-carbonyl complexes SCoMPIs for single-core multimodal probes for imaging. Re(I) tricarbonyl complexes have unique photophysical properties allowing for their unequivocal detection in cells but also present some weaknesses such as a very low luminescence quantum yield in aqueous medium. Further optimizations would thus be desirable. We therefore developed new Re(I) tricarbonyl complexes prepared from different ancillary ligands. Complexes with benzothiadiazole- triazole ligands show interesting luminescent quantum yields in acetonitrile and may constitute valuable luminescent metal complexes in organic media. A series of complexes with bidentate 1-(2-quinolinyl)-1,2,3-triazole (Taquin) and 1-(2-pyridyl)-1,2,3-triazole (Tapy) ligands bearing various 4-substituted alkyl side chains has been designed and synthesized with efficient procedures. Their photophysical properties have been characterized in acetonitrile and in a H 2O/DMSO (98/2) mixture and compared with those of the parent Quinta- and Pyta-based complexes. Tapy complexes bearing long alkyl chains show impressive enhancement of their luminescent properties relative to the parent Pyta complex. Theoretical calculations have been performed to further characterize this new class of rhenium tricarbonyl complexes. Preliminary cellular imaging studies in MDA-MB231 breast cancer cells reveal a strong increase in the luminescence signal in cells incubated with the Tapy complex substituted with a C12 alkyl chain. This study points out the interesting potential of the Tapy ligand in coordination chemistry, which has been so far underexploited.

Synthesis and biological evaluation of 2-(arylethynyl)quinoline derivatives as mGluR5 antagonists for the treatment of neuropathic pain

We described here the synthesis and biological evaluation of mGluR5 antagonists containing a quinoline ring structure. Using intracellular calcium mobilization assay (FDSS assay), we identified compound 5n, showing high inhibitory activity against mGluR5. In addition, it was found that compound 5n has excellent stability profile. Finally, this compound exhibited favorable analgesic effects in spinal nerve ligation model of neuropathic pain, which is comparable to gabapentin.

Synthesis of 2-alkynylquinolines from 2-chloro and 2,4-dichloroquinoline via Pd/C-catalyzed coupling reaction in water

The Pd/C-CuI-PPh3 catalyst system facilitated Sonogashira coupling of 2-chloroquinoline and 2,4-dichloroquinoline with terminal alkynes in water without generating any significant side products. A variety of 2-alkynylquinolines were prepared from 2-chloroquinoline in good to excellent yields and the 2,4-dichloroquinoline afforded monosubstituted product i.e., 2-alkynyl-4-chloro quinoline with high regioselectivity. The methodology was found to be effective for the alkynylation of 1-chloroisoquinoline and 3-methyl-2-chloroquinoline.

Synthesis of n-chloroquinolines and n-ethynylquinolines (n=2, 4, 8): Homo and heterocoupling reactions

The n-(ethynyl)quinolines were satisfactorily prepared by heterocoupling reaction between the appropriate n-chloroquinoline and 2-methyl-3-butyn-2-ol, catalyzed by palladium, followed by treatment with a catalytic amount of powdered sodium hydroxide in toluene. The n-(ethynyl)quinolines were transformed in the corresponding conjugate 1,4-bis[n′-(quinolyl)]buta-1,3-diynes by oxidative dimerization, catalyzed by cuprous chloride, with excellent yields. Moreover, the heterocoupling between n′-haloquinoline and n′-(ethynyl)quinoline (n′, 2′ or 3′), catalyzed by palladium, gives 2′,2′-bis(quinoline) or 1,2-di(3′-quinolyl) ethyne, respectively. The same coupling reaction with zerovalent nickel complexes, gives a mixture of 1,2,4- and 1,3,5-tri(n′-quinolyl)benzene.