ChemInform Abstract: THE NITRATION OF SOME 4‐PHENYL SUBSTITUTED 1,8‐NAPHTHYRIDINES

Carboni, S.; Settimo, A. Da; Bertini, D.; Ferrarini, Pier Luigi; Livi, Oreste; Tonetti, I.

doi:10.1002/chin.197441259

Cited by 2 publications

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“…7-Methyl-2-phenyl-1,8-naphthyridin-4(1 H )-one (12). 1 H NMR: δ 11.18 (brs, OH), 8.34 (d, 1H, H 5 ), 7.84 (m, 2H, Ar), 7.35 (m, 3H, Ar), 7.27 (d, 1H, H 6 ), 6.36 (s, 1H, H 3 ), 2.59 (s, 3H, CH 3 ). 13 C NMR: δ 176.02 (C 4 ), 162.59 (C 7 ), 150.92 (C 2 ), 150.92 (C 8a ), 134.66 (C 5 ), 133.64 (C 1 ‘ ), 130.53 (C 4 ‘ ), 128.85 (C 3 ‘ ), 127.66 (C 2 ‘ ), 120.12 (C 6 ), 117.25 (C 4a ), 108.51 (C 3 ), 24.33 (7 st ).…”

Section: Methodsmentioning

confidence: 99%

“…7-Methyl-2-phenyl-1,8-naphthyridine (33). 1 H NMR: δ 8.44 (d, 1H, H 5 ), 8.30 (m, 2H, Ar), 8.13 (d, 1H, H 4 ), 8.12 (d, 1H, H 3 ), 7.54 (m, 3H, Ar), 7.45 (d, 1H, H 6 ), 2.72 (s, 3H, CH 3 ).…”

Section: Methodsmentioning

confidence: 99%

“…The compounds described in this study are shown in Tables −3, and their synthetic methods are outlined in Schemes −4. Alkylation in position 1 of 12 was achieved by means of EtI and KOH in a hydro-alcoholic solution to give 13 (Scheme ). When the 4-hydroxy-7-methyl-2-phenyl-1,8-naphthyridine 12 21 was refluxed in toluene with Lawesson's reagent, the corresponding mercapto derivative 14 was obtained.…”

Section: Chemistrymentioning

confidence: 99%

“…When the 4-hydroxy-7-methyl-2-phenyl-1,8-naphthyridine 12 21 was refluxed in toluene with Lawesson's reagent, the corresponding mercapto derivative 14 was obtained. Treatment of the 4-chloronaphthyridine 15 , prepared with POCl 3 as described in the literature, with MeONa in MeOH under reflux led to the methoxy derivative 16 . Compound 17 was obtained when 15 21 was allowed to react with PhONa in DMF at reflux temperature (Scheme ).…”

Section: Chemistrymentioning

confidence: 99%

“…Selective reduction of the 4-azido derivative 18 , obtained by reaction of 15 with NaN 3 as described in the literature, was performed in MeOH, in the presence of Pd/C as a catalyst, to give the 4-amino derivative 19 (Scheme ). Reaction of 4-chloro-7-methyl-2-phenyl-1,8-naphthyridine 15 21 with an excess of the appropriate amine in a sealed tube at 140 °C gave 20 − 22 (Scheme ).…”

Section: Chemistrymentioning

confidence: 99%

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A Novel Class of Highly Potent and Selective A₁ Adenosine Antagonists: Structure−Affinity Profile of a Series of 1,8-Naphthyridine Derivatives

et al. 2000

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A series of 1,8-naphthyridine derivatives (12-36), bearing a phenyl group in position 2 and various substituents in positions 4 and 7, were synthesized in an attempt to obtain potent, selective antagonists for the A1 adenosine receptor subtype. The compounds were tested to evaluate their affinity for A1 compared with A2A and A3 adenosine receptor subtypes. In binding studies in bovine brain cortical membranes, most of the compounds showed an affinity for A1 receptors in the low nanomolar range and two in the subnanomolar range with an interesting degree of A1 versus A2A and A3 selectivity. Comparison of the 4-substituted derivatives indicated that 4-OH substitution, with a 4-quinoid structure, causes an increase in the A1 and A2A affinity and generally also in A1 selectivity. The kind of substitution in position 7 can greatly modulate the affinity: the most interesting substituents in this position seemed to be electron-withdrawing groups; in particular the 7-chloronaphthyridine 25d showed a remarkable selectivity (A2A/A1 ratio of 670, A3/A1 ratio of 14,000) associated with a higher A1 affinity (Ki = 0.15 nM). NMR studies on these compounds 12-36 indicated that the 4-OH-substituted ones prefer the tautomer in which the oxygen in position 4 is in the quinoid form and the nitrogen in position 1 is protonated. Theoretical calculations are in agreement with the NMR data.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

See 3 more Smart Citations

A Novel Class of Highly Potent and Selective A₁ Adenosine Antagonists: Structure−Affinity Profile of a Series of 1,8-Naphthyridine Derivatives

et al. 2000

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Study on Affinity Profile toward Native Human and Bovine Adenosine Receptors of a Series of 1,8-Naphthyridine Derivatives

et al. 2004

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A new series of 1,8-naphthyridine derivatives (29-44 and 46-52) bearing various substituents in different positions on the heterocyclic nucleus were synthesized in order to analyze the effects produced on the affinity toward the bovine adenosine receptors. These derivatives represent an extension of our previous work on this class of compounds with high affinity toward A(1) adenosine receptors.(19) The results of radioligand binding assays indicate that a large number of the 1,8-naphthyridine derivatives proved to be A(1) selective, with a high affinity toward bovine adenosine receptors in the low nanomolar range, and one (29) in the subnanomolar range. Furthermore, the new series of 1,8-naphthyridine derivatives (29-44 and 46-52), together with the analogous derivatives 1-28 previously studied,(19) were tested to evaluate their affinity toward human cortical A(1) receptors and human striatal A(2A) receptors. The results indicate that all the 1,8-naphthyridine compounds generally possess a higher affinity toward the bovine A(1) receptor compared with the human A(1) receptor. As regards the affinity toward the A(2A) bovine receptor, only a few compounds possess a moderate affinity, which for some compounds remained approximately the same toward the A(2A) human receptor. A molecular modeling study of the docking of the 1,8-naphthyridine compounds with both the bovine and the human A(1) adenosine receptors was carried out with the aim of explaining the marked decrease in the affinity toward human A(1) adenosine receptors in comparison with bovine A(1) adenosine receptors. This study indicated that the structural differences, albeit small, of the active sites of the two receptors make differences in the dimensions of the site and this influenced the ability of the title compounds to interact with the two A(1) receptors.

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ChemInform Abstract: THE NITRATION OF SOME 4‐PHENYL SUBSTITUTED 1,8‐NAPHTHYRIDINES

Abstract: Die Nitrierung der Naphthyridine (I) in Schwefelsäure ergibt je nach verwendetem HNO3‐Überschuß die Mononitroderivate (II) und (III) (Naphthyridin: HNO3 = 1: 1,1) oder die Trinitroderivate (IV) und (V) (1:6).

Cited by 2 publications

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A Novel Class of Highly Potent and Selective A₁ Adenosine Antagonists: Structure−Affinity Profile of a Series of 1,8-Naphthyridine Derivatives

A Novel Class of Highly Potent and Selective A₁ Adenosine Antagonists: Structure−Affinity Profile of a Series of 1,8-Naphthyridine Derivatives

Study on Affinity Profile toward Native Human and Bovine Adenosine Receptors of a Series of 1,8-Naphthyridine Derivatives

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ChemInform Abstract: THE NITRATION OF SOME 4‐PHENYL SUBSTITUTED 1,8‐NAPHTHYRIDINES

Abstract: Die Nitrierung der Naphthyridine (I) in Schwefelsäure ergibt je nach verwendetem HNO3‐Überschuß die Mononitroderivate (II) und (III) (Naphthyridin: HNO3 = 1: 1,1) oder die Trinitroderivate (IV) und (V) (1:6).

Cited by 2 publications

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A Novel Class of Highly Potent and Selective A1 Adenosine Antagonists: Structure−Affinity Profile of a Series of 1,8-Naphthyridine Derivatives

A Novel Class of Highly Potent and Selective A1 Adenosine Antagonists: Structure−Affinity Profile of a Series of 1,8-Naphthyridine Derivatives

Study on Affinity Profile toward Native Human and Bovine Adenosine Receptors of a Series of 1,8-Naphthyridine Derivatives

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A Novel Class of Highly Potent and Selective A₁ Adenosine Antagonists: Structure−Affinity Profile of a Series of 1,8-Naphthyridine Derivatives

A Novel Class of Highly Potent and Selective A₁ Adenosine Antagonists: Structure−Affinity Profile of a Series of 1,8-Naphthyridine Derivatives