Structure and Serotonin 5-HT2C Receptor Activity of ortho- and meta-Substituted Phenylpiperazines

Verdonk, Marcel L.; Voogd, J.; Kanters, J. A.; Kroon, Jan; Besten, R. Den; Брандсма, Л.; Leysen, Dirk; Kelder, J.

doi:10.1107/s0108768197009142

Cited by 9 publications

(9 citation statements)

References 13 publications

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“…In the CSD (Allen, 2002;Version 5.31 of Nov. 2009, updated August 2010 there are only a few picrates of simple piperazinium derivatives, for instance 4-(4-carboxybenzyl)-1-methylpiperazin-1-ium picrate (Li et al, 2009), 1-(2-methoxyphenyl)piperazinium picrate (Verdonk et al, 1997) or piperazine-1,4-diium-dipicrate piperazine complex (Wang & Jia, 2008). Also some more complicated structures were reported, for instance 4-(3-Carboxy-1-ethyl-6-fluoro-4-oxo-1,4dihydro-7-quinolyl)-1-methylpiperazinium picrate (Fun et al, 2010).…”

Section: Methodsmentioning

confidence: 99%

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1-Methylpiperazine-1,4-diium dipicrate

et al. 2011

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In the crystal structure of the title compound [systematic name: 1-methylpiperazine-1,4-diium bis(2,4,6-trinitrophenolate)], C5H14N2 2+·2C6H2N3O7 −, the ionic components are connected by relatively strong N—H⋯O hydrogen bonds into centrosymmetric six-membered conglomerates, which comprise two dications and four anions. Besides Coulombic interactions, only weak C—H⋯O interactions and some stacking between picrates (separation between the planes of ca. 3.4 Å but only a small overlapping) can be identified between these ‘building blocks’ of the crystal structure. The piperazine ring adopts a chair conformation with the methyl substituent in the equatorial position. In the picrate anions, the twist angles of the nitro groups depend on their positions relative to the phenolate O atom: it is much smaller for the NO2 groups para to the C—O− group [15.23 (9)and 3.92 (14)°] than for the groups in the ortho positions [28.76 (13)–39.84 (11)°].

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Section: Methodsmentioning

confidence: 99%

“…For examples of the biological activity of piperazines: Brockunier et al (2004); Bogatcheva et al (2006). For the crystal structures of simple piperidinium picrates, see: Fun et al (2010); Li et al (2009); Verdonk et al (1997); Wang & Jia (2008). For a description of the Cambridge Structural Database, see: Allen (2002).…”

Section: Related Literaturementioning

confidence: 99%

1-Methylpiperazine-1,4-diium dipicrate

et al. 2011

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“…Here we report the syntheses and structures of the salts (I)-(XI) formed between 2-MeOPP and eleven aromatic carboxylic acids, along with a redetermination of the salt (XII) ( Fig. 12) formed with 2,4,6trinitrophenol (picric acid) where the reported structure (Verdonk et al, 1997; CSD refcode NEBGIK) shows signs of unmodelled disorder, and we report here also the structures of three acid salts (XIII)-(XV) formed with some aliphatic dicarboxylic acids. All of the salts (I)-(XV) were straightforwardly prepared by the acid-base reactions and subsequent crystallizations of equimolar mixtures of 2-MeOPP with the appropriate organic acid.…”

Section: Chemical Contextmentioning

confidence: 95%

Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in zero, one, two and three dimensions

et al. 2020

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Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions have been prepared and structurally characterized. In the isostructural 4-chlorobenzoate and 4-bromobenzoate salts, C11H17N2O+·C7H4ClO2 − (I) and C11H17N2O+·C7H4BrO2 − (II), and the 4-iodobenzoate salt C11H17N2O+·C7H4IO2 − (III), the ions are linked by N—H...O hydrogen bonds, forming centrosymmetric R 4 4(12) four-ion aggregates; a similar aggregate is formed in the 2-chlorobenzoate salt (V), isomeric with (I). In the 2-fluorobenzoate salt C11H17N2O+·C7H4FO2 − (IV), and the isomorphous pair of salts, the 2-bromobenzoate (VI), isomeric with (II) and 2-iodobenzoate (VII), isomeric with (III), N—H...O and C—H...π(arene) interactions link the components into three-dimensional arrays. Four-ion R 4 4(12) aggregates are also found in the 2-methylbenzoate, 4-aminobenzoate and 4-nitrobenzoate salts, C11H17N2O+·C8H7O2 − (VIII), C11H17N2O+·C7H6NO2 − (IX) and C11H17N2O+·C7H4NO4 − (X), but those in (IX) are linked into complex sheets by an additional N—H...O hydrogen bond. In the 3,5-dinitrobenzoate salt, C11H17N2O+·C7H3N2O6 −·2H2O (XI), N—H...O and O—H...O hydrogen bonds link the components into a complex ribbon structure. In the picrate salt, C11H17N2O+·C6H2N3O7 − (XII), the four-ion aggregates are linked into chains of rings by C—H...O hydrogen bonds. In the hydrogen maleate salt, C11H17N2O+·C4H3O4 − (XIII), two- and three-centre hydrogen bonds link the ions into a ribbon structure while both anions contain very short but asymmetric O—H...O hydrogen bonds, having O...O distances of 2.4447 (16) and 2.4707 (17) Å. O—H...O Hydrogen bonds link the anions in the hydrogen fumarate salt (XIV), isomeric with (XIII), into chains that are linked into sheets via N—H...O hydrogen bonds. In the hydrogen (2R,3R)-tartrate salt, C11H17N2O+·C4H5O6 −·1.698H2O (XV), the anions are linked into sheets by O—H...O hydrogen bonds. Comparisons are made with the structures of some related compounds.

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“…In 4-(4-methoxyphenyl)piperazin-1-ium chloride, two N-HÁ Á ÁCl hydrogen bonds link the ions into C 1 2 (4) chains (Zia-ur-Rehman et al, 2009), and in the closely related 4-(4-nitrophenyl)piperazin-1-ium chloride monohydrate, a combination of N-HÁ Á ÁO, O-HÁ Á ÁCl and N-HÁ Á ÁCl hydrogen bonds links the components into complex ribbons in which each anion accepts three hydrogen bonds (Lu, 2007). The structure of 4-(3-methoxyphenyl)piperazin-1-ium maleate has been reported (Verdonk et al, 1997), as have those of the picrate (Verdonk et al, 1997) and 6-chloro-5-isopropyl-2,4-dioxopyrimidin-1-ide (Al-Omary et al, 2014) salts of the 4-(2-methoxyphenyl)piperazin-1-ium cation. Finally we note, in addition to the 1-aroyl-4-(4-methoxyphenyl)piperazines referred to in Section 1 above (Kiran Kumar et al, 2019), the structure of 1-acetyl-(4-hydroxyphenyl)piperazine (Kavitha et al, 2013), which is an N-acetylated derivative of 4-(4-hydroxyphenyl)piperazines, a metabolite of 4-(4-methoxyphenyl)piperazine.…”

Section: Figure 24mentioning

confidence: 99%

Twelve 4-(4-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in one, two and three dimensions

et al. 2019

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Twelve 4-(4-methoxyphenyl)piperazin-1-ium salts containing organic anions have been prepared and structurally characterized. The monohydrated benzoate, 4-fluorobenzoate, 4-chlorobenzoate and 4-bromobenzoate salts, C11H17N2O+·C7H5O2 −·H2O (I), C11H17N2O+·C7H4FO2 −·H2O (II), C11H17N2O+·C7H4ClO2 −·H2O (III), and C11H17N2O+·C7H4BrO2 −·H2O (IV), respectively, are isomorphous and all exhibit disorder in the 4-methoxyphenyl unit: the components are linked by N—H...O and O—H...O hydrogen bond to form chains of rings. The unsolvated 2-hydroxybenzoate, pyridine-3-carboxylate and 2-hydroxy-3,5-dinitrobenzoate salts, C11H17N2O+·C7H5O3 − (V), C11H17N2O+·C6H4NO2 − (VI) and C11H17N2O+·C7H3N2O7 − (VII), respectively, are all fully ordered: the components of (V) are linked by multiple N—H...O hydrogen bonds to form a chain of rings; those of (VI) are linked into a three-dimensional framework by a combination of N—H...O, C—H...O and C—H...N hydrogen bonds and those of (VII), where the anion has a structure reminiscent of the picrate anion, are linked into a three-dimensional array by N—H...O and C—H...O hydrogen bonds. The hydrogensuccinate and hydrogenfumarate salts, C11H17N2O+·C4H5O4 − (VIII) and C11H17N2O+·C4H3O3 − (IX), respectively, are isomorphous, and both exhibit disorder in the anionic component: N—H...O and O—H...O hydrogen bonds link the ions into sheets, which are further linked by C—H...π(arene) interactions. The anion of the hydrogenmaleate salt, C11H17N2O+·C4H3O3 − (X), contains a very short and nearly symmetrical O...H...O hydrogen bond, and N—H...O hydrogen bonds link the anions into chains of rings. The ions in the trichloroacetate salt, C11H17N2O+·C2Cl3O2 − (XI), are linked into simple chains by N—H...O hydrogen bonds. In the hydrated chloranilate salt, 2C11H17N2O+·C6Cl2O4 2−·2H2O (XII), which crystallizes as a non-merohedral twin, the anion lies across a centre of inversion in space group P21/n, and a combination of N—H...O and O—H...O hydrogen bonds generates complex sheets. Comparisons are made with the structures of some related compounds.

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Structure and Serotonin 5-HT_2C Receptor Activity of ortho- and meta-Substituted Phenylpiperazines

Cited by 9 publications

References 13 publications

1-Methylpiperazine-1,4-diium dipicrate

1-Methylpiperazine-1,4-diium dipicrate

Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in zero, one, two and three dimensions

Twelve 4-(4-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in one, two and three dimensions

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