A novel class of antiulcer agents. 4-Phenyl-2-(1-piperazinyl)quinolines.

Hino, Ken‐ichi; Kawashima, Katsuyoshi; Oka, Makoto; Nagai, Yasutaka; Uno, Hitoshi; Matsumoto, Junichi

doi:10.1248/cpb.37.110

Cited by 37 publications

(25 citation statements)

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“…(CmHmFNOj) C, H, N. l-Amino-2-(2'-fluorobenzoyl)naphthalene (32). 1 -(IV-Benzoylamino)-2-(2'-fluorobenzoyl)naphthalene (31) (3.05 g, 8.3 mmol) was treated according to procedure d to afford 32 (2.2g, 95%) as light green-yellow crystals: mp 119-121 °C; IR (KBr) 3499, 3377 (NH2), 3058,1612 (C=0), 1520,1483, 913, 815, 741 cm-1; >H NMR (CDCls) S 6.94 (d, 1H, J = 8.3 Hz), 7.11-7.30 (m, 3H), 7.41-7.51 (m, 3H), 7.57 (dt, 1H, J = 1.2, 8.1 Hz), 7.70 (br s, 2H, NH2), 7.71 (dd, 1 H, J = 1.2,8.3 Hz), 7.96 (34) (1.3 g, 5 mmol) was treated as described in procedure c with 2 equiv of (o-fluorophenyl)lithium, and this was followed by treatment analogous to procedure d to afford 36 (0.93 g, 71 %) as light brown crystals (hexane/EtOAc): mp 98-99 °C; XH NMR (CDCls) & 5.60 (br s, 2H, NH2), 6.90 (d, 1H, J = 9 Hz), 6.98-7.17 (m, 4H), 7.17-7.40 (m, 2H), 7.26 (d, 1H, J =9 Hz), 7.62 General Procedure e To Prepare Bromoacetyl Amides. l-[/V-(Bromoacetyl)amino]-2-benzoylnaphthalene (16).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of benzo-fused benzodiazepines employed as probes of the agonist pharmacophore of benzodiazepine receptors

Zhang

Koehler²,

Harris³

et al. 1994

J. Med. Chem.

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The synthesis and in vitro evaluation of benzo-fused benzodiazepines 1-6 are described. These "molecular yardsticks" were employed to probe the spatial dimensions of the lipophilic pocket L2 in the benzodiazepine receptor (BzR) cleft and to determine the effect of occupation of L2 with respect to agonist activity. Of the new analogs synthesized, the 7,8-benzo-fused benzodiazepine 6 displayed moderately high affinity for the BzR (IC50 = 55 nM) and exhibited both anticonvulsant (ED50 approximately 15 mg/kg) and muscle relaxant (ED50 approximately 15 mg/kg) activity. As expected, 2 and 4 interacted with the repulsive regions of interaction, S1 and S2, and exhibited low affinities for BzR. The rigid nature of these molecular yardsticks (especially 6, Figure 7) has been employed to probe the depth of L2. Moreover, in the case of 6 full occupation of L2 has resulted in an increase in the muscle relaxant effect at the expense of the anticonvulsant/anxiolytic effect.

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Section: Methodsmentioning

confidence: 99%

Synthesis of benzo-fused benzodiazepines employed as probes of the agonist pharmacophore of benzodiazepine receptors

Zhang

Koehler²,

Harris³

et al. 1994

J. Med. Chem.

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“…The attempted cyclization of the benzoyl acetanilides ( 1 ) to the 2‐hydroxy 4‐phenyl quinolines ( 2 ) in acid medium by the Combes process gave average yields in sulfuric acid, while maximum yields was obtained through in situ prepared and activated polyphosphoric acid. Literature reveals that K. Hino and co‐workers have prepared the 2‐hydroxyl‐4‐(4′‐methoxy)phenyl quinoline ( 2g ) by the Camps quinoline syntheses route and found them to be antiulcer agents. Their reported yields were 67%.…”

Section: Resultsmentioning

confidence: 99%

A Facile Synthesis of 5‐Phenyl‐Dibenzo[b, g][1,8]Napthyridines

Sampathkumar

Murugesh

Rajendran

2015

Journal of Heterocyclic Chem

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“…13 tert-Butyl 5-Phenylimidazo[1,5-a]quinoline-3-carboxylate (8b). This compound was prepared from 28 61 (1.0 g, 4.17 mmol), tertbutyl isocyanoacetate (1.8 mL, 12.4 mmol), and potassium tertbutoxide (1.4 g, 12.5 mmol) according to the general procedure described for the synthesis of 7a−i,k−m,o−y and purified by flash chromatography with n-hexane−ethyl acetate (1:1) as the eluent to obtain 8b as a white solid (1.0 g, yield 70%, mp 231−233 °C). 1 H NMR (400 MHz, CDCl 3 ): δ 1.66 (s, 9H), 7.37−7.55 (m, 6H), 7.67 (t, J = 7.5, 1H), 7.79 (d, J = 8.0, 1H), 8.04 (s, 1H), 8.11 (d, J = 8.1, 1H), 8.68 (s, 1H).…”

Section: Journal Of Medicinal Chemistrymentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Imidazo[1,5-a]quinoline as Highly Potent Ligands of Central Benzodiazepine Receptors

et al. 2016

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A series of imidazo[1,5-a]quinoline derivatives was designed and synthesized as central benzodiazepine receptor (CBR) ligands. Most of the compounds showed high CBR affinity with K i values within the submicromolar and subnanomolar ranges with interesting modulations in their structure−affinity relationships. In particular, fluoroderivative 7w (K i = 0.44 nM) resulted in the most potent ligand among the imidazo[1,5-a]quinoline derivatives described so far. Overall, these observations confirmed the assumption concerning the presence of a large though apparently saturable lipophilic pocket in the CBR binding site region interacting with positions 4 and 5 of the imidazo[1,5-a]quinoline nucleus. The in vivo biological characterization revealed that compounds 7a,c,d,l,m,q,r,w show anxiolytic and antiamnestic activities without the unpleasant myorelaxant side effects of the classical 1,4-BDZ. Furthermore, the effect of 7l,q,r, and 8i in lowering lactate dehydrogenase (LDH) release induced by ischemia-like conditions in rat brain slices suggested neuroprotective properties for these imidazo[1,5-a]quinoline derivatives.

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A novel class of antiulcer agents. 4-Phenyl-2-(1-piperazinyl)quinolines.

Cited by 37 publications

References 0 publications

Synthesis of benzo-fused benzodiazepines employed as probes of the agonist pharmacophore of benzodiazepine receptors

Synthesis of benzo-fused benzodiazepines employed as probes of the agonist pharmacophore of benzodiazepine receptors

A Facile Synthesis of 5‐Phenyl‐Dibenzo[b, g][1,8]Napthyridines

Design, Synthesis, and Biological Evaluation of Imidazo[1,5-a]quinoline as Highly Potent Ligands of Central Benzodiazepine Receptors

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