Synthesis and biological activity of uncondensed cyclic derivatives of piperidine (review)

Vartanyan, R. S.

doi:10.1007/bf00779895

Cited by 7 publications

(10 citation statements)

References 39 publications

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“…and loperamide (a synthetic piperidine derivative, effective against diarrhea resulting from gastroenteritis or inflammatory bowel disease). A review on the synthesis and biological activities of uncondensed cyclic derivatives of piperidine is reported (Vartanyan, 1984). The crystal structure of a related compound, 4-[(E)-(2,4-difluorophenyl) (hydroxyimino)methyl]piperidinium picrate (Jasinski et al, 2009) has been reported.…”

Section: Methodsmentioning

confidence: 99%

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4-(4-Chlorophenyl)-4-hydroxypiperidinium benzoate

et al. 2011

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In the title salt, C11H15ClNO+·C7H5O2 −, the dihedral angle between the mean planes of the chlorophenyl ring of the cation and the benzene ring of the anion is 74.4 (1)°. In the cation, the six-membered piperazine ring adopts a chair conformation. The crystal packing is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds, and weak intermolecular C—H⋯O, C—H⋯Cl and C—H⋯π interactions.

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Section: Methodsmentioning

confidence: 99%

“…For the synthesis and biological activity of uncondensed cyclic derivatives of piperidine, see: Vartanyan (1984). For puckering parameters, see: Cremer & Pople (1975) For related structures, see: Jasinski et al (2009).…”

Section: Related Literaturementioning

confidence: 99%

4-(4-Chlorophenyl)-4-hydroxypiperidinium benzoate

et al. 2011

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“…For background to the importance of piperidines, see: Vartanyan (1984). For related structures, see: Cygler et al (1980); Cygler & Ahmed (1984); Dutkiewicz et al (2010); Georges et al (1989); Jasinski et al (2009); Lisgarten & Palmer (1989); Tomlin et al (1996).…”

Section: Related Literaturementioning

confidence: 99%

Bis[4-(4-chlorophenyl)-4-hydroxypiperidinium] dipicrate dimethyl sulfoxide solvate

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Hemamalini

Siddaraju³

et al. 2010

Acta Cryst E

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The asymmetric unit of the title salt solvate, 2C11H15ClNO+·2C6H2N3O7 −·C2H6OS, contains two crystallographically independent 4-(4-chlorophenyl)-4-hydroxypiperidinium cations, two picrate anions and a dimethyl sulfoxide solvent molecule. In each cation, the piperidinium ring adopts a chair conformation. In the crystal structure, the cations, anions and solvent molecules are connected by intermolecular O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional network.

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“…Among these, heterocyclic moieties are quite common, covering a very wide range of pharmacological activities despite of their rather essential structure. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] In addition to the electronic effects exerted by groups substituting the heterocyclic moiety, the manifested biological activity can also derive from the particular stereochemistry 21 and structural rigidity characterizing the pharmacophoric portion that interacts with the target active site, [22][23][24][25] as observed, for example, for some classes of spiro-heterocycles. [26][27][28][29][30][31][32] Spiro-1,3,4-thiadiazoline derivatives, endowed with anti-inammatory, analgesic, antifungal and/or antimicrobial activities, [33][34][35][36] represent signicant examples of biologically active heterocyclic compounds in which the 1,3,4-thiadiazoline ring and the connected rigid spiro-structure act as a single 'hybrid pharmacophore' framework.…”

Section: Introductionmentioning

confidence: 99%

Elucidation of the mechanisms governing the thermal diastereomerization of bioactive chiral 1,3,4-thiadiazoline spiro-cyclohexyl derivatives towards their anancomeric stereoisomers

et al. 2016

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The kinetic of the thermal isomerization of some diastereomers of three chiral 1,3,4 thiadiazoline derivatives, selected as case studies of structures resulting by mono-alkyl substitution of the anancomeric 4-acetyl-2-acetamido-1,3,4- thiadiazolinyl-spiro-cyclohexane (TsC) framework has been investigated in order to elucidate the possible mechanistic pathways and the structural factors responsible for the observed spiro-junction lability. The insertion of a methyl or a tbutyl group on the C2 or C3 position with respect to the spiro junction generate two stereogenic centres, so that two pairs of enantiomers exist. The first-order rate constants for the isomerization of the less stable enantiomers into the most stable ones have been measured in different solvents and at different temperatures through batch-wise kinetic determinations. The obtained data have been successfully rationalizedby DFT calculations and Linear Solvation Energy Relationships (LSER) analyses. The achieved elucidation should make possible to plan a more rational synthesis of this kind of pharmacologically active compounds, thus affording a practical tool useful to control the involved stereochemistry and spiro-junctio

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Synthesis and biological activity of uncondensed cyclic derivatives of piperidine (review)

Cited by 7 publications

References 39 publications

4-(4-Chlorophenyl)-4-hydroxypiperidinium benzoate

4-(4-Chlorophenyl)-4-hydroxypiperidinium benzoate

Bis[4-(4-chlorophenyl)-4-hydroxypiperidinium] dipicrate dimethyl sulfoxide solvate

Elucidation of the mechanisms governing the thermal diastereomerization of bioactive chiral 1,3,4-thiadiazoline spiro-cyclohexyl derivatives towards their anancomeric stereoisomers

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