Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

Giardina, Giuseppe; Artico, Marco; Cavagnera, Stefano; Cerri, Alberto; Consolandi, Emanuela; Gagliardi, Stefania; Graziani, Davide; Grugni, Mario; Hay, Douglas W. P.; Luttmann, Mark A.; Mena, Ramon; Raveglia, Luca F.; Rigolio, Roberto; Sarau, Henry M.; Schmidt, Dulcie B.; Zanoni, G; Farina, Carlo

doi:10.1016/s0014-827x(99)00043-9

Cited by 20 publications

(11 citation statements)

References 21 publications

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“…In contrast, replacing the 6-bromo with a chloro atom as in 7c directed the activity, unexpectedly, towards the agonistic side (increase in response 18.39-2.5%) ( Table 1). The data also revealed that the carboxylate derivatives exerted appreciable antagonistic properties especially the aminoethyl carboxylate analog 9d (reduction in response 60.7-4.3%) ( Table 1).and its arylidene derivative 15b (reduction in response 55.28-6.5 %) ( These findings coincided with those of Giardina et al [18,20], who suggested that the 2-arylquinoline backbone would be considered as an essential pharmacophore for optimal fitting to the hNK-3 receptor. Based on the results of the biological screening of the carboxamide and ester candidates, one can conclude that the occurrence of an acidic amide is not important for their activities.…”

Section: Methodssupporting

confidence: 83%

“…Recently, they proved that the 3-substituted-2-phenylquinoline-4-carboxamides 3 (Chart 1) were the most potent hNK-3 receptor antagonists [19]. Furthermore, they explored the effect of replacing the quinoline nucleus with a naphthalene ring, which appeared to be suitable for further modifications as it offers the option of introducing an electron-withdrawing group at position 2 or 4, conferring on the ring an overall electron-deficiency similar to that of quinoline [20].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 2‐(4‐Biphenylyl)quinoline‐4‐carboxylate and Carboxamide Analogs. New Human Neurokinin‐3 (hNK‐3) Receptor Antagonists

Saudi

Rostom

Fahmy

et al. 2003

Archiv der Pharmazie

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The 2-phenylquinoline-4-carboxamide 1 (Chart[TH]1) has been found to possess moderate affinity for human neurokinin-3 (hNK-3) receptor. In the present work, and in a trial to investigate the effect of the lipophilic moiety at C-2 of the quinoline ring on the antagonistic activity, an enlargement of the aromatic area at this position was suggested. In this respect, two series of 2-(4-biphenylyl)quinoline-4-carboxylates and carboxamides have been synthesized with certain modifications at the quinoline-2 and 4-position in order to study their effect on the anticipated hNK-3 receptor antagonistic activity. Fifteen compounds were screened for such activity using guinea-pig isolated ileum longitudinal muscle preparation and senktide as selective hNK-3 receptor agonist. Some compounds showed considerable antagonistic effect. Compound 7b, 6-bromo-2-(4-biphenylyl)quinoline-4-carboxylic acid, was the most prominent hNK-3 receptor antagonist in this study. Unexpectedly, some compounds were agonists.

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Section: Methodssupporting

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐(4‐Biphenylyl)quinoline‐4‐carboxylate and Carboxamide Analogs. New Human Neurokinin‐3 (hNK‐3) Receptor Antagonists

Saudi

Rostom

Fahmy

et al. 2003

Archiv der Pharmazie

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“…This process is commonly referred to as Guareschi‐Thorpe condensation [54]. An account of its application to benzoylpyruvates has been reported, involving reaction with nitroacetamidine 71 to afford pyridine 72 (Scheme ) [55]. Subsequent elaboration via reduction of the nitro group can then be used to furnish fused pyridines.…”

Section: Cn‐dinucleophilesmentioning

confidence: 99%

Benzoylpyruvates in heterocyclic chemistry

Nolsöe

Weigelt

2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).The present review covers the utility of benzoylpyruvates as a vehicle for the preparation of highly functionalized heterocycles. Regio-and chemoselective features are discussed with reference to the application of different nucleophilic species. In this context, the preparation of such rings as pyrazoles, isoxazoles, primidines, and pyridines are presented. As the means to establish a distinct functional pattern, the rendered strategy can be seen as an alternative to cross-coupling protocols.

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“…The N ‐heterocyclic compounds such as N‐ arylindole and N‐ arylimidazole are widely used as antipsychotic agent,, anti‐allergic, cyclooxygenase (COX)‐1 inhibitors, COX‐2 inhibitors, antiestrogen, analgesic, melatonin receptor MT1 agonists, and anti HIV‐1 agents . Traditionally N ‐arylation is carried out by using Ullmann‐type cross coupling reaction . This method requires severe reaction conditions such as elevated temperature and the use of stoichiometric amounts of copper catalyst.…”

Section: Introductionmentioning

confidence: 99%

Hydrothermal Synthesis of CuFe₂O₄ Magnetic Nanoparticles as Active and Robust Catalyst for N‐arylation of Indole and Imidazole with Aryl Halide

Nakhate

Yadav

2017

ChemistrySelect

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Spinel ferrite magnetic nanoparticles are superior to the conventional catalysts. Here we report the synthesis of different types of spinel ferrite nanoparticles, MFe 2 O 4 (M = Cu, Mn, Mg, Co, Ni), by a hydrothermal method. The prepared spinel ferrite nanoparticles were used for the N-arylation reaction of indole with iodobenzene. Among these CuFe 2 O 4 nanoparticles exhibited the best activity and selectivity for N-arylation under ligand free condition. The prepared spinel ferrite microspheres were well characterised by using various characterization techniques such as TEM, XRD, XPS, SEM, EDXA, FT-IR, N 2 adsorption desorption measurements and TGA. The effect of various parameters were studied such as solvent, base, speed of agitation, mole ratio, catalyst loading and temperature in the reaction of indole with iodobenzene. Best conversion and yield were achieved at 110 8C and 1 3 10 -3 g/cm 3 catalyst loading. Notably, CuFe 2 O 4 magnetic nanoparticles were completely recovered and could be reused six times without any noticeable loss of activity. Reaction mechanism and kinetics are also presented.[a] Dr.

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Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

Cited by 20 publications

References 21 publications

Synthesis of 2‐(4‐Biphenylyl)quinoline‐4‐carboxylate and Carboxamide Analogs. New Human Neurokinin‐3 (hNK‐3) Receptor Antagonists

Synthesis of 2‐(4‐Biphenylyl)quinoline‐4‐carboxylate and Carboxamide Analogs. New Human Neurokinin‐3 (hNK‐3) Receptor Antagonists

Benzoylpyruvates in heterocyclic chemistry

Hydrothermal Synthesis of CuFe₂O₄ Magnetic Nanoparticles as Active and Robust Catalyst for N‐arylation of Indole and Imidazole with Aryl Halide

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Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

Cited by 20 publications

References 21 publications

Synthesis of 2‐(4‐Biphenylyl)quinoline‐4‐carboxylate and Carboxamide Analogs. New Human Neurokinin‐3 (hNK‐3) Receptor Antagonists

Synthesis of 2‐(4‐Biphenylyl)quinoline‐4‐carboxylate and Carboxamide Analogs. New Human Neurokinin‐3 (hNK‐3) Receptor Antagonists

Benzoylpyruvates in heterocyclic chemistry

Hydrothermal Synthesis of CuFe2O4 Magnetic Nanoparticles as Active and Robust Catalyst for N‐arylation of Indole and Imidazole with Aryl Halide

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Product

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Hydrothermal Synthesis of CuFe₂O₄ Magnetic Nanoparticles as Active and Robust Catalyst for N‐arylation of Indole and Imidazole with Aryl Halide