Arene- and quinoline-sulfonamides as novel 5-HT7 receptor ligands

Zajdel, Paweł; Marciniec, Krzysztof; Maślankiewicz, Andrzej; Paluchowska, Maria H.; Satała, Grzegorz; Partyka, Anna; Jastrzębska-Więsek, Magdalena; Wróbel, Dagmara; Wesołowska, Anna; Duszyńska, Beata; Bojarski, Andrzej J.; Pawłowski, Maciej

doi:10.1016/j.bmc.2011.09.044

Cited by 42 publications

(37 citation statements)

References 34 publications

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“…The 7-v-chloroalkyl-8-alkoxy-1,3-dimethyl-purine-2,6-diones 5-9 were obtained in a reaction of 2, 3, or 4 with the appropriate sodium alcoholate in a corresponding alcohol medium [15]. The designed derivatives 10-24 were synthesized by nucleophilic substitution of 5-9 with the appropriate arylpiperazines in the presence of K 2 CO 3 in toluene (10)(11)(12)(13)(14)(15)(16)(17)(18) and in 1-propanol (19)(20)(21)(22)(23)(24). Compounds 10-24 were separated by column chromatography as free bases.…”

Section: Chemistrymentioning

confidence: 99%

“…The multireceptor strategy has also been explored in a series of isoquinoline-and quinolineamide-and sulfonamide-derivatives of long chain arylpiperazines (LCAPs) exemplified by structures A and B ( Fig. 1) with potential antipsychotic, antidepressant, and anxiolytic properties [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, the potential antidepres- Figure 1. Structures of mixed 5-HT/D receptor agents: SLV313 (adoprazine) [8], bifeprunox [6], and isoquinoline-amide (A) [9] and quinoline-sulfonamide (B) [10] LCAPs derivatives. Results and discussion…”

Section: Introductionmentioning

confidence: 99%

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New Arylpiperazinylalkyl Derivatives of 8‐Alkoxy‐purine‐2,6‐dione and Dihydro[1,3]oxazolo[2,3‐f]purinedione Targeting the Serotonin 5‐HT_1A/5‐HT_2A/5‐HT₇ and Dopamine D₂ Receptors

Chłoń-Rzepa

Zagórska

Bucki

et al. 2015

Archiv der Pharmazie

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To obtain potential antidepressants and/or antipsychotics, a series of new long-chain arylpiperazine derivatives of 8-alkoxy-purine-2,6-dione (10-24) and dihydro[1,3]oxazolo[2,3-f]purinedione (30-34) were synthesized and their serotonin (5-HT1A , 5-HT2A , 5-HT6 , 5-HT7 ) and dopamine (D2 ) receptor affinities were determined. The study allowed the identification of some potent 5-HT1A /5-HT7 /D2 ligands with moderate affinity for 5-HT2A sites. The binding mode of representative compounds from both chemical classes (11 and 31) in the site of 5-HT1A receptor was analyzed in computational studies. In functional in vitro studies, the selected compounds 15 and 16 showed antagonistic properties for the evaluated receptors. 8-Methoxy-7-{4-[4-(2-methoxyphenyl)-piperazin-1-yl]-butyl}-1,3-dimethyl-purine-2,6-dione (15) showed a lack of activity in terms and under the conditions of the forced swim, four plate and amphetamine-induced hyperactivity tests in mice, probably as a result of its high first pass effect in the liver.

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Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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New Arylpiperazinylalkyl Derivatives of 8‐Alkoxy‐purine‐2,6‐dione and Dihydro[1,3]oxazolo[2,3‐f]purinedione Targeting the Serotonin 5‐HT_1A/5‐HT_2A/5‐HT₇ and Dopamine D₂ Receptors

Chłoń-Rzepa

Zagórska

Bucki

et al. 2015

Archiv der Pharmazie

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“…Within the framework of our studies on serotonin receptor ligands, 11 this Letter reports the binding properties on human cloned 5-HT 1A R and 5-HT 7 R of new derivatives (14,(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29), and 35-45) bearing, with the exception of compound 14, a thienopyrimidinone or quinazolinone as terminal fragment (Fig. 2).…”

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confidence: 99%

Synthesis and binding properties of new long-chain 4-substituted piperazine derivatives as 5-HT1A and 5-HT7 receptor ligands

Modica

Intagliata

Pittalà

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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Preparation of 3-Cyano-1-(2-Pyridyl)Isoquinolines by Using Aryne Intermediates

Kopchuk

Nikonov

Zyryanov

et al. 2014

Chem Heterocycl Comp

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While the isoquinoline system serves as a structural foundation of many natural product molecules, such as certain alkaloids [1], isoquinolines also have intrinsic biological activity [2] and play an important role as fragments in natural and synthetic drugs. Besides that, 1-(2-pyridyl)isoquinolines present interest as ligands for transition metal cations [3]. The introduction of a cyano group at position 3 of isoquinoline ring in such compounds opens a broad range of possibilities for obtaining various derivatives through subsequent functionalization. Unfortunately, no effective methods are currently known for the synthesis of 3-cyanoisoquinolines. For example, direct cyanation of isoquinoline N-oxides occurs exclusively at position 1, while the few cases of direct 3-cyanation of isoquinolines gave low yields [4] or required special reaction conditions [5]. Besides, 3-cyanoisoquinolines can be obtained through various variants of heterocyclization [6,7] and by the decomposition of 2,3-substituted diazidonaphthaline -in that case 3-cyanoisoquinoline was formed in mixture with by-products [8]. Finally, the 3-cyano group in isoquinoline may be created by chemical transformations of other functional groups, such as substitution of a chlorine atom [9].In this report, we propose a convenient method for the synthesis of 3-cyano-1-(2-pyridyl)isoquinolines based on the available 5-cyano-3-(2-pyridyl)-1,2,4-triazines 1а-с [10] by using a known effective method for the synthesis of various pyridine derivatives from 1,2,4-triazine analogs [11]. It has been established that the interaction of 1,2,4-triazines with enamines followed by oxidation [12], or with in situ generated arynes [13] allows to obtain substituted isoquinolines effectively, even avoiding the aromatization step in the case of arynes [14]. We have previously demonstrated that 3-(2-pyridyl)-1,2,4-triazines substituted with aryl groups at positions 5 and/or 6 [15] react with 1,2-dehydrobenzene forming 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles. However, 5-cyano-3-(2-pyridyl)-1,2,4-triazines have never before been used as starting materials in these reactions.

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Arene- and quinoline-sulfonamides as novel 5-HT7 receptor ligands

Cited by 42 publications

References 34 publications

New Arylpiperazinylalkyl Derivatives of 8‐Alkoxy‐purine‐2,6‐dione and Dihydro[1,3]oxazolo[2,3‐f]purinedione Targeting the Serotonin 5‐HT_1A/5‐HT_2A/5‐HT₇ and Dopamine D₂ Receptors

New Arylpiperazinylalkyl Derivatives of 8‐Alkoxy‐purine‐2,6‐dione and Dihydro[1,3]oxazolo[2,3‐f]purinedione Targeting the Serotonin 5‐HT_1A/5‐HT_2A/5‐HT₇ and Dopamine D₂ Receptors

Synthesis and binding properties of new long-chain 4-substituted piperazine derivatives as 5-HT1A and 5-HT7 receptor ligands

Preparation of 3-Cyano-1-(2-Pyridyl)Isoquinolines by Using Aryne Intermediates

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Arene- and quinoline-sulfonamides as novel 5-HT7 receptor ligands

Cited by 42 publications

References 34 publications

New Arylpiperazinylalkyl Derivatives of 8‐Alkoxy‐purine‐2,6‐dione and Dihydro[1,3]oxazolo[2,3‐f]purinedione Targeting the Serotonin 5‐HT1A/5‐HT2A/5‐HT7 and Dopamine D2 Receptors

New Arylpiperazinylalkyl Derivatives of 8‐Alkoxy‐purine‐2,6‐dione and Dihydro[1,3]oxazolo[2,3‐f]purinedione Targeting the Serotonin 5‐HT1A/5‐HT2A/5‐HT7 and Dopamine D2 Receptors

Synthesis and binding properties of new long-chain 4-substituted piperazine derivatives as 5-HT1A and 5-HT7 receptor ligands

Preparation of 3-Cyano-1-(2-Pyridyl)Isoquinolines by Using Aryne Intermediates

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New Arylpiperazinylalkyl Derivatives of 8‐Alkoxy‐purine‐2,6‐dione and Dihydro[1,3]oxazolo[2,3‐f]purinedione Targeting the Serotonin 5‐HT_1A/5‐HT_2A/5‐HT₇ and Dopamine D₂ Receptors

New Arylpiperazinylalkyl Derivatives of 8‐Alkoxy‐purine‐2,6‐dione and Dihydro[1,3]oxazolo[2,3‐f]purinedione Targeting the Serotonin 5‐HT_1A/5‐HT_2A/5‐HT₇ and Dopamine D₂ Receptors