Studies on 2(1H)-quinolinone derivatives as neuroleptic agents. I. Synthesis and biological activities of (4-phenyl-1-piperazinyl)-propoxy-2(1H)-quinolinone derivatives.

Banno, Kazuo; Fujioka, Tomoyuki; Kikuchi, Tetsuro; Oshiro, Yasuo; Hiyama, Takashi; Nakagawa, Kazuyuki

doi:10.1248/cpb.36.4377

Cited by 37 publications

(42 citation statements)

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“…The best compound was OPC-4392 ( Figure 2.12), which was found to be a dopamine autoreceptor agonist and a weak postsynaptic dopamine D 2 antagonist [39].…”

Section: Second-generation Atypical Antipsychotic Drugsmentioning

confidence: 99%

Standalone Drugs

Proudfoot

2010

Analogue‐Based Drug Discovery II

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In volume I of Analogue-Based Drug Discovery we focused on analogue drugs with a double similarity, that is, those that are similar to another drug from both chemical and pharmacological viewpoints. These were referred to as structural and pharmacological analogues or, alternatively, full analogues. One special class of these analogues is considered to be direct analogues if they have identical pharmacophores -that is, they can be described by a general structure that includes most of the chemical skeleton. The book also discussed some examples of structural analogues, in which the similarity is limited to their chemical structures since they possess different pharmacological properties. We also proposed the term pharmacological analogues for drugs that have completely different chemical structures but similar pharmacological properties.Analogues are based on following a lead compound, and if this compound were a drug that opened up a new therapeutic treatment then we use the term pioneer drug. Such a drug is often referred to as first in class. One can subdivide pioneer drugs into those that have analogues and those that do not. Thus, the latter group provides a special subclass called standalone drugs,

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“…The best compound was OPC-4392 ( Figure 2.12), which was found to be a dopamine autoreceptor agonist and a weak postsynaptic dopamine D 2 antagonist [39].…”

Section: Second-generation Atypical Antipsychotic Drugsmentioning

confidence: 99%

Standalone Drugs

Proudfoot

2010

Analogue‐Based Drug Discovery II

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“…Interestingly, a considerable enhancement of activity upon complexation has been observed, 6,7) which is certainly related to the increased lipophilicity upon complexation (which increases their permeability to the blood-brain barrier) and inertness of certain metal ligand linkages towards enzymatic degradation. 8,9) Quinoline derivatives have been known to possess a variety of biological activities such as antitumor, 10) antimalarial, 11) antidepressant, 12) antiulcer 13) and cardiac stimulant. 14) Along with these, there are reports suggesting that the quinolines have exhibited a very good anticonvulsant activity in the maximum electroshock method test.…”

Section: Regular Articlementioning

confidence: 99%

Anticonvulsant Activity and Toxicity Evaluation of Cu<sup>II</sup> and Zn<sup>II</sup> Metal Complexes Derived from Triazole-Quinoline Ligands

Kulkarni

Budagumpi

Kurdekar

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Epilepsy is an ever-present serious disease related to the neurological disorders. It is generally characterized by recurrent seizures that result from phasic changes in the firing properties of groups of neurons. The induction of a group of neurons into a pattern of burst-firing results in synchronized disruptive seizure discharge. The detailed studies reveals that, the excitatory and inhibitory neurotransmission as well as voltage-gated channels (that can be modulated selectively by natural or synthetic toxins) are the two major factors, that are found to be the crucial for seizure like activity.1,2) The antiepileptic drugs, which are in efficacious clinical practice, act by inducing prolonged inactivation of the Na ϩ channel, by blocking Ca 2ϩ channel currents or by enhancing inhibitory g-aminobutyrate (GABA)-ergic neurotransmission. Some of the other anticonvulsant agents act via a number of different mechanisms, which may include antagonism of glutamateergic neurotransmission.3) However it is seen that, the majorities of antiepileptic drugs do not provide satisfactory seizure control in all patients and typically cause notable adverse side effects. 4,5) It is hence becomes a crucial and challenging task in the field of medicinal chemistry to find more efficient and safer antiepileptic agents.In this regard, there are few attempts made, the organic moieties having anticonvulsant property were interacted with suitable metal ions and hence formed complexes are investigated for the anticonvulsant activity. Interestingly, a considerable enhancement of activity upon complexation has been observed, 6,7) which is certainly related to the increased lipophilicity upon complexation (which increases their permeability to the blood-brain barrier) and inertness of certain metal ligand linkages towards enzymatic degradation. 8,9) Quinoline derivatives have been known to possess a variety of biological activities such as antitumor, 10) antimalarial, 11) antidepressant, 12) antiulcer 13) and cardiac stimulant. 14)Along with these, there are reports suggesting that the quinolines have exhibited a very good anticonvulsant activity in the maximum electroshock method test. 15) In this regard, so many attempts are made by incorporating various hetero cyclic groups to the quinoline core, in order to obtain compounds with better anticonvulsant activity.16,17) Substitution of triazole or triazolone ring to the quinoline core has been found to increase receptor binding capacity and metabolic stability, which in turn enhances the anticonvulsant activity of the compound. 18,19) In the present research work, we have selected 2-hydroxy, 3-formyl quinoline as a precursor. The presence of oxygen functional groups in the quinoline core is expected to facilitate the elliptical activity 20) as well as complexation. Amino triazoles are incorporated to the precursor by means of Schiff base formation in the presence of Cu II and Zn II ions (these two are selected by considering the higher bioaccessiblity, as compared to the other transition met...

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“…Carbostyril derivatives are useful as blood platelet aggregation inhibitors, [107] cardiotonic agents, [108] and neuroleptic agents. [109] Several 6-substituted carbostyrils were shown to inhibit vascular smooth muscle phosphodiesterases that hydrolyze cAMP and cGMP and thus may find application as therapeutic agents, for example, in cardiovascular disease. [110] Procaterol-HCl (5-[1-hydroxy-2-isopropylaminobutyl]-8-hydroxycarbostyril hydrochloride hemihydrate) is a sympathomimetic amine used as bronchodilator.…”

Section: Future Prospects: Biotransformations Utilizing Molybdenum-comentioning

confidence: 99%

Bacterial Degradation of Quinoline and Derivatives—Pathways and Their Biocatalysts

Fetzner

Tshisuaka

Lingens

et al. 1998

Angewandte Chemie International Edition

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A series of interesting enzymes were discovered during investigations on the degradation of quinoline by microorganisms. These include the molybdenum-containing hydroxylases that catalyze the transformation 1→2 and the unusual 2,4-dioxygenases that catalyze the reaction 3→4. The application of the hydroxylases may even be interesting in industry, because several quinoline derivatives are used as pharmaceuticals or agrochemicals.

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Studies on 2(1H)-quinolinone derivatives as neuroleptic agents. I. Synthesis and biological activities of (4-phenyl-1-piperazinyl)-propoxy-2(1H)-quinolinone derivatives.

Cited by 37 publications

References 0 publications

Standalone Drugs

Standalone Drugs

Anticonvulsant Activity and Toxicity Evaluation of Cu<sup>II</sup> and Zn<sup>II</sup> Metal Complexes Derived from Triazole-Quinoline Ligands

Bacterial Degradation of Quinoline and Derivatives—Pathways and Their Biocatalysts

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