Cinnarizinium fumarate

Kavitha, C.; Yıldırım, Sema Öztürk; Jasinski, Jerry P.; Yathirajan, H. S.; Butcher, Ray J.

doi:10.1107/s1600536812051239

Cited by 4 publications

(4 citation statements)

References 11 publications

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“…zepin-11-yl)piperazinium hemifumarate (Ravikumar & Sridhar, 2005), Cinnarizinium fumarate (Kavitha et al, 2013). In view of the importance of the incorporated of heterocyclic ring compounds and derivative of pyrimidyl piperazines, this paper reports the crystal structure of the title salt.…”

Section: Methodsmentioning

confidence: 99%

“…For piperazine derivatives that have reached the stage of clinical application among the known drugs to treat anxiety, see: Tollefson et al (1991). For related structures, see: Betz et al (2011); Fun et al (2012); Jasinski et al (2010Jasinski et al ( , 2011; Kavitha et al (2013); Ravikumar & Sridhar (2005); Siddegowda et al (2011). For puckering parameters, see Cremer & Pople (1975).…”

Section: Related Literaturementioning

confidence: 99%

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4-(Pyrimidin-2-yl)piperazin-1-ium (E)-3-carboxyprop-2-enoate

Yamuna¹,

Kaur²,

Jasinski³

et al. 2014

Acta Cryst E

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In the cation of the title salt, C8H13N4 +·C4H3O4 −, the piperazinium ring adopts a slightly distorteded chair conformation. In the crystal, a single strong O—H⋯O intermolecular hydrogen bond links the anions, forming chains along the c-axis direction. The chains of anions are linked by the cations, via N—H⋯O hydrogen bonds, forming sheets parallel to (100). These layers are linked by weak C—H⋯O hydrogen bonds, forming a three-dimensional structure. In addition, there are weak π–π interactions [centroid–centroid distance = 3.820 (9) Å] present involving inversion-related pyrimidine rings.

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Section: Methodsmentioning

confidence: 99%

Section: Related Literaturementioning

confidence: 99%

4-(Pyrimidin-2-yl)piperazin-1-ium (E)-3-carboxyprop-2-enoate

Yamuna¹,

Kaur²,

Jasinski³

et al. 2014

Acta Cryst E

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“…In spite of this, only the crystal structures of the neutral free-base molecule (Cheng et al, 2005;Sharma et al, 2015) and the salt ebastinium 3,5-dinitrobenzoate (Shaibah et al, 2017) have been reported to date. By contrast, fumarates (di-anion fumarate and mono-anion hydrogen fumarate) are common counter-anions in compounds of pharmacological importance; examples include opipramolium fumarate (Siddegowda et al, 2011), cinnarizinium fumarate (Kavitha et al, 2013) (technically, both hydrogen fumarates), and the recently reported structure of bis(4-acetoxy-N,N-dimethyltryptammonium)fumarate, a new crystalline form of psilacetin (Chadeayne et al, 2019). As part of our studies in this area, we now report the synthesis and crystal structure of the title 1:1 salt ebastinium hydrogen fumarate, C 32 H 40 NO 2 + ÁC 4 H 3 O 4 À , (I), formed in the reaction between ebastine and fumaric acid.…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis and crystal structure of ebastinium hydrogen fumarate

Priyanka¹,

Jayanna²,

Kumar

et al. 2022

Acta Cryst E

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The structure of ebastinium hydrogen fumarate {systematic name: 1-[4-(4-tert-butylphenyl)-4-oxobutyl]-4-(diphenylmethoxy)piperidin-1-ium (E)-3-carboxy-1-hydroxyprop-2-en-1-olate}, C32H40NO2 +·C4H3O4 −, a 1:1 salt formed in the reaction between ebastine and fumaric acid is presented. All examined crystals were found to be twinned by pseudo-merohedry. The structure is extensively disordered, with over half (20 out of 35) its non-hydrogen atoms modelled as lying over two sets of sites. In the crystal, cation–anion pairs are linked by a strong N—H...O hydrogen bond [N...O = 2.697 (11) Å]. These units interact via weaker C—H...O and C—H...π contacts to form layers lying parallel to the bc plane. The hydrogen fumarate anions are linked by a very short O—H...O hydrogen bond [O...O = 2.5402 (17) Å], augmented by weak C—H...O contacts into pairs of R 2 2(6) ring motifs to form chains that extend parallel to the b-axis direction. Comparisons to similar crystal structures are presented.

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“…Its pharmacodynamic and pharmacokinetic properties and its therapeutic use have been reviewed (Holmes et al, 1984). Brief reports on the structures of several salts derived from flunarizine Shivaprakash et al, 2014) and from substituted piperazine derivatives closely related to flunarizine Kavitha, Yildirim et al, 2013) have been published recently, and we report here the molecular and supramolecular structures of flunarizinium nicotinate, (I) (Fig. 1), and flunarizinediium bis(4-toluenesulfonate) dihydrate, (II) (Fig.…”

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confidence: 99%

Three-dimensional hydrogen-bonded framework structures in flunarizinium nicotinate and flunarizinediium bis(4-toluenesulfonate) dihydrate

et al. 2014

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Author(s) of this paper may load this reprint on their own web site or institutional repository provided that this cover page is retained. Republication of this article or its storage in electronic databases other than as specified above is not permitted without prior permission in writing from the IUCr.For further information see http://journals.iucr.org/services/authorrights.html Acta Crystallographica Section C: Structural Chemistry specializes in the rapid dissemination of high-quality detailed studies of novel and challenging crystal and molecular structures of interest in the fields of chemistry, biochemistry, mineralogy, pharmacology, physics and materials science. The unique checking, editing and publishing facilities of the journal ensure the highest standards of structural reliability and presentation, while providing for reports on studies involving special techniques or difficult crystalline materials. Papers go beyond reporting the principal numerical and geometrical data, and may include the discussion of multiple related structures, a detailed description of non-routine structure determinations, placing the structure in an interesting scientific, physical or chemical context, or the discussion of interesting physical properties or modes of association. Reports of difficult or challenging structures, such as cases of twinning, severe disorder, or diffuse solvent regions are welcomed, provided the presented structures are correct and the difficulties and strategies used to treat them are scientifically discussed and properly documented. Section C readers have access to an extensive back archive of high-quality structural data.Crystallography Journals Online is available from journals.iucr.org Acta Cryst. (2014 Á2C 7 H 7 O 3 S À Á2H 2 O, (II), one of the anions is disordered over two sites with occupancies of 0.832 (6) and 0.168 (6). The five independent components are linked into ribbons by two independent N-HÁ Á ÁO hydrogen bonds and four independent O-HÁ Á ÁO hydrogen bonds, and these ribbons are linked to form a three-dimensional framework by two independent C-HÁ Á ÁO hydrogen bonds, but C-HÁ Á Á(arene) hydrogen bonds and aromatic -stacking interactions are absent from the structure of (II). Comparisons are made with some related structures.

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Cinnarizinium fumarate

Cited by 4 publications

References 11 publications

4-(Pyrimidin-2-yl)piperazin-1-ium (E)-3-carboxyprop-2-enoate

4-(Pyrimidin-2-yl)piperazin-1-ium (E)-3-carboxyprop-2-enoate

Synthesis and crystal structure of ebastinium hydrogen fumarate

Three-dimensional hydrogen-bonded framework structures in flunarizinium nicotinate and flunarizinediium bis(4-toluenesulfonate) dihydrate

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